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Berkshires Vacation Rentals

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    All 146 Rentals in Berkshires
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    Escape to the Berkshires!1 / 20
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Quiet Comfortable Cabin 5 Min. Walk to Lake1 / 13
    (13)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Waterfront Cottage - 10 Mins to Great Barrington!1 / 24
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Stone School Cottage1 / 10
    (17)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Mountain Views
    • Private Garden
    • Grill
    • Shared Garden
    • Outdoor Dining Area
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 20, 2018
    Lovely, memorable spot 20 mins from Williams College. The cottage is full of history, comfortable and well equipped. Even the one bathroom setup exceeded our expectations...
    Reviewed January 1, 2018
    this is a one of a kind experience. we loved it. Owners are super nice and were always promptly available. Location is perfect: a silent road, yet close to skiing, excellent...
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    About this property
    If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room schoolhouse – a function it served until 1950 -- this charming and historic building has been given new life as a vacation getaway. We are about 8 minutes away from Jiminy Peak and...
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    Lanesboro, Berkshires 01237
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Berkshires Waterfront Lakehouse Sanctuary1 / 31
    (6)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • DVD Player
    • Hot Tub
    • Mountain Views
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 4, 2019
    Rented the Lakehouse for a few days to get away. It was a perfect place to unplug. The house is updated, clean and comfortable and the kitchen was the perfect place to gather...
    Reviewed January 11, 2019
    We thoroughly enjoyed our escape from nyc to the lake house. It was everything we hoped for: peaceful and secluded with gorgeous views of the lake. The house was fully...
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    About this property
    Beautiful private peninsula like setting surrounded by a cove , stream and lake adorn this location. Waterfowl and birds are everywhere in this quiet spot just a few minute walk from the 11 mile Ashuwilticook Rail Trail. The house has undergone a total renovation and all the furnishings are new...
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    Lanesboro, Berkshires 01224
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Unique People & Pet-Welcoming Country Haven1 / 37
    (180)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Outdoor Dining Area
    • Air Conditioning
    • Shared Garden
    • Cable/satellite TV
    • Washer
    • Secure Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Short drive to all local amenities, welcoming to all pets (with cat-loving friends and family who don’t like to leave their kitties for long, what’s not to love about that...
    Reviewed July 14, 2019
    We brought our 2 dogs Ellie and Emma for the weekend. Pat is by far the best hostess I've ever met. She is so pleasant and we didn't need to bring anything. She had everything...
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    About this property
    Discover Cavalier Cottage B&B, a pet-friendly home away from your home and an attractive alternative to conventional hotels, motels and B&B’s. We warmly welcome visitors who come to this beautiful area of Western Massachusetts with or without their companion animals. Now in its sixth year,...
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    Charlemont, Berkshires 01339
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Restored 1886 Eyebrow Colonial1 / 17
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Washer
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 4, 2017
    Our family of four absolutely loved our stay in Melanie and Henry's home. After communicating with Melanie before our arrival, we felt welcome before we stepped into the house...
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    About this property
    Explore the culture and natural beauty of the Berkshires while vacationing in a completely restored colonial home with modern amenities. You will be central to all the wonderful cultural attractions and outdoor activities in the area. Walk to the quaint town of Stockbridge and the Norman Rockwell...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    RiverSong Suite In The Berkshires1 / 52
    (15)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 22, 2019
    We were visiting friends in Great Barrington and found this wonderful place.It is right on a small river with lovely grounds. The hosts were very helpful.
    Reviewed August 19, 2018
    We eagerly anticipated our stay at RiverSong. Based on the plethora of five-star reviews we expected near-perfection. While we loved the atmosphere, fabulous comfortable bed...
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    About this property
    Located in the Berkshire mountains on more than 5 acres surrounded by 29 acres of conservation land. Featuring beautiful views of meadows, mountains and farm land bordering the crystal clear Green River (great trout fishing).Only 10 minutes from Great Barrington's Main Street stores, resturaunts,...
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    North Egremont, Berkshires 01230
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Berkshires: Romantic Cottage with spectacular view1 / 18
    (24)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Central Heating
    • Mountain Views
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 13, 2018
    First of all, the area where this house is is AMAZING. My husband and I have been coming to the Berkshires for years but we had never driven in this particular neighborhood. The...
    Reviewed August 3, 2018
    The picture is real (except we didn't see the rainbow). It's a lovely first floor studio cottage with a kitchenette; very comfortable, well stocked, and beautifully decorated...
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    About this property
    Berkshires: Romantic Berkshires Cottage with Stunning Views (Great Barrington) The Berkshires in spring, summer and fall are alive with beauty, and now is the time to plan your restoring getaway in this idyllic studio cottage with its glorious views of the rolling hills and verdant meadows.....
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Stockbridge Bowl - Beach Lake Cottage near Tanglewood (1.8 miles) & Kripalu1 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Mountain Views
    • Balcony
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 26, 2018
    Great location, 2 minute walk to the beach with a view of the mountains and a very short drive to Tanglewood, Norman Rockwell Museum and all local attractions.Cindy and Paul are...
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    About this property
    Central Berkshire location! Walk across street to Stockbridge Bowl Beach Lake! Kripalu around the corner, Tanglewood only 1.8 miles to South Gate. Open layout, vaulted ceilings, exposed rafters, ceiling fans, fully equipped kitchen and amenities, washer & dryer. New hypoallergenic Mellanni...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Comfortable Farmhouse in the Berkshires1 / 10
    (4)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 6, 2017
    Nice house, great spot for our family reunion. Convenient to many of the Berkshires attractions. Nice kitchen for cooking and eating in for a group.
    Reviewed June 5, 2017
    House was comfortable and well furnished. The Berkshires are beautiful with lots of activities, galleries, shopping and restaurants. Our hosts were helpful and responsive to...
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    About this property
    Rent a comfortable 1840 farmhouse with 26 acres in the Berkshire mountains. Walk to the village of West Stockbridge or a short drive to all the Berkshire attractions. Close to the ski resorts of Butternut, Bousquet, Catamount and Jiminy Peak. The house sleeps 10 to 12 people and is fully equipped....
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    West Stockbridge, Berkshires 01266
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our nearly new home we call RiverSong is on 5.5 acres surrounded by almost 30 more conservation land of meadow and farmland. The pristine Green River is right in our back yard with a wonderful swimming hole. Our Penthouse room is on the upper level of our home. A Bright and spacious king size...
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    North Egremont, Berkshires 01230
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Berkshire Farmhouse Vacation1 / 20
    (40)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 15 Quick View
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    Amenities & Details
    • Central Heating
    • Grill
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Great farmhouse in a great location. The house is very clean, comfortable and well equipped especially the kitchen. Convenient to Tanglewood, Stockbridge and Lenox. Perfect...
    Reviewed February 13, 2019
    This was my second time staying at Elaine's and I will certainly be going back for a third. My friends and I had a great time ringing in the new year. The farm house is cozy...
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    About this property
    Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16' floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer,...
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    West Stockbridge, Berkshires 01266
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 15
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living room, fall foliage and scenic atmosphere in the area, and soak in the...
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    West Stockbridge, Berkshires 01266
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    To Ski or Not to Ski?  Great conditions Great fireplace.Your Choice.1 / 18
    (7)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Wi-Fi
    • Balcony
    • Patio
    • Grill
    • Washer
    • Porch
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 4, 2018
    The house was so comfortable; the location was perfect -- close to so many beautiful places and Berkshires attractions, especially Tanglewood!; Cassandra was so helpful when I...
    Reviewed August 27, 2016
    We had a wonderful stay in this large, lovely house that contained everything we needed for comfort and convenience. We were impressed with the degree to which details were...
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    About this property
    Enjoy this perfectly located home to pursue what brings you to the Berkshires. Ski and warm up next to the fire in the winter. Go to Kripalu but enjoy all the comforts of this home just 8 minutes away. Enjoy fabulous foods, and make new friends. Located in West Stockbridge minutes from everything ....
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    West Stockbridge, Berkshires 01266
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Family-friendly Cottage Near Lake, Tanglewood1 / 16
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Porch
    • Parking
    • Washer
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 21, 2017
    Location was fantastic. Sarah (the owner) provided some great advice on local farmers markets and hikes. The beach was a quick walk from the cottage where we could paddle on...
    Reviewed July 31, 2015
    This was a wonderful place to spend a family vacation. The house is immaculate, functional and well furnished. The proximity to all of the many venues and activities the area...
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    About this property
    Located a short walk to the town beach on the Stockbridge Bowl, and 1.5 miles from Tanglewood's Hawthorn entrance, this casual summer cottage is a great get away for the whole family. The master bedroom is equipped with a queen bed; two twins in the 2nd bedroom, and a full-size bed in the 3rd...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Country Elegance in the Berkshires1 / 44
    (2)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Grill
    • Outdoor Dining Area
    • Air Conditioning
    • Washer
    • Internet Access
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 30, 2018
    We rented this house for our family coming together in celebration of my Brice getting married.mu sister showed up to the Home first but she was sure she was at the wrong place...
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    About this property
    This immaculate home is the place for relaxing, entertaining and sharing great times with family and friends. The house sets over 4 beautifully wooded acres. We call it the 'illision of seclusion,' as it is very private and yet is 5 minutes from the town as well as lakes, hiking, movies, theater,...
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    Great Barrington, Berkshires 01236
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    Lake House1 / 18
    (4)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Wi-Fi
    • DVD Player
    • Sauna
    • Air Conditioning
    • Grill
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 2, 2016
    My family and I traveled to the Berkshires from Boston and stayed in this gorgeous lake house. We had booked vacation rentals in the past and had a whole range of experiences...
    Reviewed September 1, 2016
    We stayed at the Lake House on beautiful Laurel Lake with my family of 5 (two daughters, son, and my wife). We had an awesome time. The owners Marjorie and Frank were wonderful...
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    About this property
    Custom designed Furnished Lake House in The Berkshires in Massachusetts on the Lee/Lenox line. Gorgeous western sunsets ! The home has 4/5 bedrooms and one is equipped as a nanny suite or teen haven. It is close to skiing, golf, outdoor sports, shopping, and all cultural venues. It is located...
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    Lee, Berkshires 01238
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 9
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    • DVD Player
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The lakeside house is built on a 1.1 acre lot with view of Lake Garfield. It is only three minute walk to the public beach with life guards on site. In the summer, Jacob’s Pillow Dance Center and Tanglewood Music Center are about 25 to 30 minutes away. In the winter, Ski Butternut resort is about...
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    Monterey, Berkshires 01245
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Great Vacation House in the Berkshires by Richmond Pond1 / 10
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Grill
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 31, 2018
    Being Tanglewood lovers, this was the perfect vacation spot to enjoy the area's concerts, plays, art galleries and restaurants as well as the lovely Richmond Pond and the...
    Reviewed August 27, 2017
    This comfortable, breezy house was perfect! We loved being able to walk to the lake and canoe, play frisbee on the lawn, walk in the woods, eat on the deck, and gaze at the...
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    About this property
    Beautiful two bedroom house sits just steps from Richmond Pond. Enjoy a day on the water swimming and fishing followed by an evening enjoying the symphony at Tanglewood (ten scenic minutes away). Yoga enthusiasts will love the proximity to Kripalu (again, ten minutes away). Leaf peepers and skiers...
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    Richmond, Berkshires 01254
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Gartner House, a charming home in Lenox1 / 21
    (30)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Porch
    • Washer
    • Parking
    • Internet Access
    • Central Heating
    • Grill
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 17, 2018
    If you are looking to stay in the Berkshire’s and especially in the Lenox area the charming Gartner House, is great option. The location is perfect for exploring Lenox and is...
    Reviewed November 20, 2018
    The perfect place for six girlfriends to catch up. We stayed in Lenox because we all had a day pass at Kripalu for some R&R. The house is so convenient to shopping...
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    About this property
    Located on a quiet side street in the charming Berkshire town of Lenox, Gartner House is a great place to call home while exploring this scenic, historical, and culturally rich area of Western Massachusetts. Walk to breakfast, lunch or dinner at one of the town's many charming restaurants, explore...
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    Lenox, Berkshires 01240
    Condo/Apartment - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, your luxury resort home at Vacation Village will also serve as your gateway to all that the Berkshires has to offer. The area has been a center for dance and the fine arts since the turn of the century. Hear the Boston Symphony at their summer...
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, your luxury resort home at Vacation Village will also serve as your gateway to all that the Berkshires has to offer. The area has been a center for dance and the fine arts since the turn of the century. Hear the Boston Symphony at their summer...
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Balcony
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, your luxury resort home at Vacation Village will also serve as your gateway to all that the Berkshires has to offer. The area has been a center for dance and the fine arts since the turn of the century. Hear the Boston Symphony at their summer...
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Balcony
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, your luxury resort home at Vacation Village will also serve as your gateway to all that the Berkshires has to offer. The area has been a center for dance and the fine arts since the turn of the century. Hear the Boston Symphony at their summer...
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    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Hot Tub
    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, your luxury resort home at Vacation Village will also serve as your gateway to all that the Berkshires has to offer. The area has been a center for dance and the fine arts since the turn of the century. Hear the Boston Symphony at their summer...
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    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
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    • Balcony
    • Shared Outdoor Pool (Unheated)
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, your luxury resort home at Vacation Village will also serve as your gateway to all that the Berkshires has to offer. The area has been a center for dance and the fine arts since the turn of the century. Hear the Boston Symphony at their summer...
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Terrace
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    • Air Conditioning
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, your luxury resort home at Vacation Village will also serve as your gateway to all that the Berkshires has to offer. The area has been a center for dance and the fine arts since the turn of the century. Hear the Boston Symphony at their summer...
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, your luxury resort home at Vacation Village will also serve as your gateway to all that the Berkshires has to offer. The area has been a center for dance and the fine arts since the turn of the century. Hear the Boston Symphony at their summer...
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Hot Tub
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, your luxury resort home at Vacation Village will also serve as your gateway to all that the Berkshires has to offer. The area has been a center for dance and the fine arts since the turn of the century. Hear the Boston Symphony at their summer...
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Terrace
    • Balcony
    • Cable/satellite TV
    • Parking
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, your luxury resort home at Vacation Village will also serve as your gateway to all that the Berkshires has to offer. The area has been a center for dance and the fine arts since the turn of the century. Hear the Boston Symphony at their summer...
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    Hancock, Berkshires 01237
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, your luxury resort home at Vacation Village will also serve as your gateway to all that the Berkshires has to offer. The area has been a center for dance and the fine arts since the turn of the century. Hear the Boston Symphony at their summer...
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, your luxury resort home at Vacation Village will also serve as your gateway to all that the Berkshires has to offer. The area has been a center for dance and the fine arts since the turn of the century. Hear the Boston Symphony at their summer...
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, your luxury resort home at Vacation Village will also serve as your gateway to all that the Berkshires has to offer. The area has been a center for dance and the fine arts since the turn of the century. Hear the Boston Symphony at their summer...
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    Hancock, Berkshires 01237
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • Parking
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, your luxury resort home at Vacation Village will also serve as your gateway to all that the Berkshires has to offer. The area has been a center for dance and the fine arts since the turn of the century. Hear the Boston Symphony at their summer...
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Terrace
    • DVD Player
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, your luxury resort home at Vacation Village will also serve as your gateway to all that the Berkshires has to offer. The area has been a center for dance and the fine arts since the turn of the century. Hear the Boston Symphony at their summer...
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    Hancock, Berkshires 01237
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, your luxury resort home at Vacation Village will also serve as your gateway to all that the Berkshires has to offer. The area has been a center for dance and the fine arts since the turn of the century. Hear the Boston Symphony at their summer...
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    Hancock, Berkshires 01237
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Gem of the Berkshires, walk to downtown & lake.1 / 30
    (4)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Patio
    • Grill
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 15, 2018
    This home is a wonderfully appointed home, conveniently located just outside of town. It was perfect for our multiple family ski getaway. The owner is thorough in helping...
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    About this property
    This sparkling, newly renovated 3 floors house is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions, such as Tanglewood, Butternut ski, etc The house has an open floor plan, making each room flow into another....
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Shaker Hill1 / 27
    (2)Average
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Porch
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • DVD Player
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 11, 2014
    This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
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    About this property
    Shaker Hill is a quirky rambling farmhouse located less than 3 hours from NYC and Boston. Hidden away down a 400’ unpaved driveway on 30 acres of fields and forest in the heart of the Berkshires, Shaker Hill is totally private and surrounded by 30 acres of rolling fields, diverse wetlands,...
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Sauna
    • Wi-Fi
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Complete your Berkshires retreat with a stay in the spacious Studios, perfect for romantic couples and small families. Suites feature plush bedding, additional sleeper sofa and fully equipped kitchen for all your dining needs. Minimum age to check in is 21 Daily housekeeping is not included and...
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    Hancock, Berkshires 01237
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
    • Terrace
    • Balcony
    • Private Garden
    • Grill
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large home in wooded area of the Berkshires. Ideal for all the summer events such as visiting Great Barrington, Lenox, Lee, Stockbridge. Many mountain areas for picnics, biking, hiking in the summer and winter events such as skiing and snowboarding. Near Center pond where there are many boating...
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    Becket, Berkshires 01223
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    Apartment walking distance to Mass MoCa!!1 / 39
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Patio
    • Skiing: Property Is In A Ski Resort
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 11, 2015
    Owners were very friendly and helpful. We enjoyed our stay very much. this is the place for a quiet vacation.
    Reviewed July 6, 2014
    Stephanie was helpful and accommodating of us and our last minute request . Sheafs it easy to stay, come and go and we found the location convenient yet private and remote from...
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    About this property
    I have a 2 to 3 bedroom first floor apartment located in a dead end street. This spacious 8 room apartment is surrounded by woods and minutes from downtown North Adams or Williamstown!! It is also walking distance to Mass MoCa (about a 10 minute walk)!!! Animals are welcome if needed. The master...
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    North Adams, Berkshires 01247
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 10
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    Berkshires Spacious Comfortable Charming Farmhouse1 / 12
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 17, 2013
    This property was a great home base for our brief visit to the Berkshires. Plenty of space and well equipped. We especially enjoyed the beautiful property, whether sitting on...
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    About this property
    Experience a little of old New England. Our vacation rental is a charming historic family farmhouse apartment with lots of room and comfort,2100Sq.ft., situated on 22 acres. Built in 1782, our farm was famous for breeding Plymouth Barred Rock chickens. In the 1800's, one of these barred rock...
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    Lee, Berkshires 01238
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Outdoor Dining Area
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Washer
    • Patio
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lots of space, great yard, walk to everything: restaurants, museums, Williams College, theater, night life, etc. Plus, nearby ski and tubing areas. This beautifully maintained historic House On Main Street was known as the Victorian Tourist & Antique House in a by-gone era. It was originally...
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    Williamstown, Berkshires 01267
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 16
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    3 Bedrooms, 1 Bathroom, Sleeps 15 Quick View
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    • Patio
    • DVD Player
    • Air Conditioning
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is located at the end of a dead end street. It has a huge, private backyard with 2 firepits, hammock, portable bar, grill and ample seating. Under one mile to downtown North Adams and about a 5 minute drive to Williamstown. This is a 3 bedroom, upstairs apartment (one bedroom has a...
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    North Adams, Berkshires 01247
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 15
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Grill
    • Wi-Fi
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    • Washer
    • DVD Player
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE ESCAPE at Stockbridge. Enjoy our Open & Spacious Newly built house in the Berkshires, Complete Privacy! No Visible Neighbors. -1 1/2 miles to downtown Stockbridge, -just minutes to Norman Rockwell museum, Chesterwood, Naumkeag, Tanglewood & Kripalu. -Housatonic River just across the street,...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
    • Grill
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated contemporary house on 2 acres in Stockbridge. Great space surrounding house for outdoor sports and sitting around the fire at night. 3 bedrooms, 3 bathrooms, indoor fireplace, wood floors, many windows and closets. Large kitchen. WiFi. Master bedroom has king bed and master...
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    Stockbridge, Berkshires 01238
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Cozy & Modern Home -mins from Tanglewood & Kripalu1 / 8
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 days ago
    Great location - quiet, private, and felt like our own little home. Close to the lake with the beach. Only 4 minutes drive to Tanglewood.Next time I visit I will sure look to...
    Reviewed December 18, 2013
    We stayed at this home in Housatonic, which is part of Great Barrington, the Smithsonian pic for best small town in the USA. I hope you all don't however as one of the best...
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    About this property
    Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living...
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    Location Information
    West Stockbridge, Berkshires 01266
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Wyndham Bentley Brook Resort Rents-Hancock,MA -Jiminy Peak1 / 10
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Shared Indoor Pool
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 25, 2018
    Staying in a ski in/out cannot be topped. This place was family friendly, so easy to navigate and the staff was SUPER helpful throughout the entire weekend. We have a 3 year old...
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    About this property
    Lodging at the highest rated resort at Jiminy Peak Mountain--Wyndham Bently Brook Resort-Mountainside What is Jiminy Peak Known For---The Best Skiing in the Berkshire Mountains tucked away in Hancock, Ma. 2 Bedroom Unit consisting of-King bed master, 2 doubles 2nd bedroom and a queen sleep...
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Romantic Berkshire Cottage on Storybook Estate1 / 10
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Terrace
    • Cable/satellite TV
    • Outdoor Dining Area
    • Internet Access
    • DVD Player
    • Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2017
    What a wonderful, magical place, heaven on earth! From the moment we were greeted warmly by Denise and entered our Tiny House, we knew this was such a special place.The sound of...
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    About this property
    Charming, One Bedroom Cottage, former sculpting studio on the Santarella Estate in Tyringham, MA. Known as the 'Silo Studio', there is a bedroom with queen bed upstairs, sitting room, wet bar with Micro/Fridge and bath downstairs. Fall asleep to sounds of babbling brook and views to pond and forest...
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    Location Information
    Tyringham, Berkshires 01264
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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