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Berkshires Cheap Vacation Rental Deals

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    Travellers to Berkshires are booking October dates now. Secure your vacation rental today, and have the perfect trip.
    31 Matching Rentals in BerkshiresView all 126 rentals
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    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    Berkshire House Share-The Blue Room1 / 10
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    the garden room is a small room with a full sized bed. everything is floral, even the closet walls. it 's a sweet room with even a wood stove. it has an entrance to the courtyard just outside in the hall, the bath may be shared depending on the situation. bath has shower and lovely old sink. bath...
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    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Parking
    • Shared Outdoor Pool (Unheated)
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    • Grill
    • Air Conditioning
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bentley Brook The town of Hancock is off the beaten path near the Taconic Mountains, which are part of the Appalachians. Hancock is 14 miles northwest of Pittsfield, MA, and 28 miles east of Albany, NY. Bentley Brook is tucked away in a peaceful rural setting with a cozy lobby fireplace and...
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    The guest suite is within 'Keyes House,' a quintessential 19th century Greek Revival colonial. It is conveniently located in a small, bucolic village in Southern Berkshire County that is on the National Register of Historic Districts. The entire home, including the two-room suite, has been...
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    New Marlborough, Berkshires 01230
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
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    • Mountain Views
    • Grill
    • Sauna
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury Condo in Beaver Pond, Hancock, Mass. Three bedrooms, loft, 2 baths, living room, kitchen with dining area, deck w/grill. Near Clark Art Museum, MassMoca. Williams College with schedule of sports open to the public: swimming, tennis, squash, basketball, skating and fitness room. Indoor...
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    Hancock, Berkshires 01237
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Whitman Woods - A Berkshire Vacation1 / 26
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed 5 weeks ago
    Whitman Woods is an amazing house for families to get away from it all. We did an overnight in this house while visiting Pittsfield to watch a couple musicals. The house is...
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    About this property
    The vacation house at Whitman Woods offers privacy with proximity to excellent skiing at Jiminy Peak and to many cultural attractions of the Berkshires, 'America's Premier Cultural Resort', including Williamstown Theater Festival, the Clark Art Museum, Hancock Shaker Village and Tanglewood. For...
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    Hancock, Berkshires 01237
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Sauna
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    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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Nestled in the woods of East Otis, you’ll have a peaceful stay in the Berkshires at this cozy 2-bedroom, 1-bathroom vacation rental cabin. Comfortably accommodating up to 5 guests, this retreat is perfect for a memorable family vacation. With miles of hiking trails to explore and the Otis Reservoir...
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    Otis, Berkshires 01029
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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
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    Pet friendly
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    Smoking allowed
    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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    West Stockbridge, Berkshires 01266
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have a two bedroom downstairs apartment and a three bedroom upstairs apartment (all of the rooms are available to rent). I also rent out the full apartments but I also rent out rooms (please ask for information). The house is located on a dead end street with a huge wooded backyard that...
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    North Adams, Berkshires 01247
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    Lake House in Berkshires1 / 21
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 4, 2017
    Robert was so thoughtful and courteous to make sure we had the best birthday weekend ever! He literally thought of everything such as bug spray, flash lights, birthday candles...
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    About this property
    Charming studio cottage on Windsor Lake, North Adams, MA. Great spot from which to explore MASS MoCa, attend Solid Sound or Fresh Grass, Clark Art Museum, Massachusetts College of Liberal Arts, Williamstown Theater Festival, Williams College, the Berkshires, and Southern Vermont. Hike, bike, swim...
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    North Adams, Berkshires 01247
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    Bring your loved one along on a Berkshires getaway in this 1-bedroom, 1-bathroom vacation rental cottage in New Marlborough that sleeps 2. Nestled under the pine trees on the edge of Lake Buel, you'll have unbeatable views of the picturesque landscape, framed by the large windows throughout the...
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    New Marlborough, Berkshires 01230
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
    • Hot Tub
    • Parking
    • Wi-Fi
    • Grill
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the beautiful Berkshires. Watch the horses roam. Have a guided trail ride (additional fee) or have a camp fire only feet away from the horses. Within steps from your accommodations, enjoy the largest recreational lake in Massachusetts. Bring your boat or jetski. Or use our row boat. Go...
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    East Otis, Berkshires 01029
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bentley Brook Surround yourself with the natural beauty of Massachusetts at Bentley Brook. Situated at the bottom of Jiminy Peak in the stunning Berkshires, Bentley Brook is the ski enthusiast dream come true. Ski out your door and straight to the resorts ski lift. Spend a day out on the world...
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This 1400 square foot, three bedroom home has all amenities including washer and dryer in basement. Electric heat and oven. Front porch and back deck. First floor is open floor plan with kitchen, dining area and living room flowing from one to the other. Skylights in the living/dining area and...
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    Lee, Berkshires 01240
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lakefront Berkshires Ski/Summer House, Great Views1 / 17
    (4)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Mountain Views
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    • Waterfront
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 16, 2017
    The house was cozy. The lake was beautiful. The surrounding towns offer great restaurants. The host was very helpful.
    Reviewed November 16, 2017
    We rented this lovely home on the lake (or maybe it's a pond... Long Pond I think) last year and loved every minute of our visit. The house is well equipped and has all one...
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    About this property
    Located in a wooded area overlooking a pristine lake, this woodsy style contemporary is a sportsman's paradise. It's a short drive to skiing (Jiminy Peak, Butternut, Catamount) and cultural attractions, (Tanglewood, National Music Center, Aston Magna, etc.) or you can fish, swim, boat, hike, or...
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    Great Barrington, Berkshires 01236
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    • Waterfront
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    • Private Garden
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely house on pond, Beautiful views of pond from every room, except one. Lounge on the deck with a glass of wine watch the Great Blue Heron has he stalks his fish, see the beavers swim lazily across the pond, flapping their tails to let you know they are there. Every room but one has a water...
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    Becket, Berkshires 01223
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 2
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    Unique People & Pet-Welcoming Country Haven1 / 37
    (173)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Outdoor Dining Area
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    • Shared Garden
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    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    A cute cottage off the beaten trackDefinitely in the country but close enough to lovely cities. The scones and juice every morning were a treat.. the kitchen came in...
    Reviewed July 27, 2018
    We like to travel with our dogs, and it was so easy to stay with them at Cavalier Cottage. Comfortable and charming for humans and canines alike. We loved the quiet woodsy area...
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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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    Enjoy the Appalachians At Bentley Brook!1 / 21
    (1)Terrible
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bentley Brook Surround yourself with the natural beauty of Massachusetts at Bentley Brook. Situated at the bottom of Jiminy Peak in the stunning Berkshires, Bentley Brook is the ski enthusiast dream come true. Ski out your door and straight to the resorts ski lift. Spend a day out on the world...
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    • Private Garden
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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • DVD Player
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    • Balcony
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    • Outdoor Dining Area
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on 19 acres of forest and a creek, mixing modern and traditional with a charming two story wall of windows overlooking a back deck. This comfortable furnished home has two bedrooms with an additional open loft area for a third bedroom, two baths, all hardwood floors, and contains a large...
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    Hinsdale, Berkshires 01235
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    PanoramicView1000 sq ft Guest Quarters Berkshires1 / 16
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Mountain Views
    • Washer
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    Pet friendly
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    Reviewed July 30, 2015
    This is a lovely rental in the heart of the Berkshires. Each morning you wake up to aview of Jiminy Peak and the sounds of bird life. Tom and Susan are wonderful innkeepers and...
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    About this property
    Low long term rates. Call $2500/mo for 3 months. Free Electric Vehicle Charging Station! (240V 40A no J1772) Thanksgiving Special - Nov 24 - Dec 1 - $500 Christmas Special - Dec 20 - Dec 27 - $800 Ski Season Dec 1 - Mar 31 $8000 April $50/nt Summer Cultural May 26, 2014 - Seot 2, 2014 $7500 Summer...
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    Hancock, Berkshires 01237
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    chestnut lodge Queens Room1 / 2
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Reviewed August 16, 2015
    I had the pleasure of staying at the Chestnut Lodge in the Queen's room. From the moment you step into the foyer you are taken back to a simpler time in this historic lodge. The...
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    About this property
    Sunny, light , bright and wide! the queens room is one of the biggest rooms and has private ensuite bathroom with tub/shower. 2 big closets, large writing desk, comfy conversation area, 2 dressers full sized bed. a section of the room has original ceilings so persons taller than 6'2' would be...
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    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The Smith Farm Homestead1 / 12
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Hot Tub
    • Mountain Views
    • Cable/satellite TV
    • Waterfront
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    • Air Conditioning
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 4, 2017
    Cozy and pretty room and bathroom suite that I shared with my teenaged daughter. Susan is very welcoming and friendly. We loved our stay here and would return!
    Reviewed October 16, 2016
    This is a terrific B&B. Lovely, spacious, comfortable room looking out over rolling pastures and forest. Fabulous breakfasts delivered to your room in a basket: fresh baked...
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    About this property
    The Smith Homestead in Alford Massachusetts has been homesteaded and farmed by our family for the past two centuries. Located on one of the nicest settings in the Berkshires, with 30 acres of fields and woods, and the crystal clear Alford Brook running through, we are central to all the cultural...
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    Alford, Berkshires 01266
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 19, 2017
    The location was easy to get to (even in the dead of winter).The place was clean, spacious and exactly as described. The wood stove was a great heat source as it was really cold...
    Reviewed October 25, 2016
    A charming cozy cottage in a quiet setting with all you need for comfort included. We hiked, canoed and visited farms and museums close by. It was a lovely fall getaway!
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    About this property
    Remember the simple pleasures of a country, lakeside vacation where you can spend the day swimming or boating, exploring new towns and attractions, or just spending a lazy afternoon reading on the screened-in porch? Get back to those simple pleasures in our cabin, which is located in a beautiful,...
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    Becket, Berkshires 01223
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Waterfront
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    • Mountain Views
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cozy, converted, modernized barn sits on 171 acres. The wooded location is private and quiet, yet easily accessible. It's a quick drive to all the gems in the Berkshires. Spend a weekend, a week, or more, unwinding. A converted horse barn, 'The Barn' has been used by our family as a...
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    Hancock, Berkshires 01237
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Cozy and clean in Gt Barrington- available for October1 / 14
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    Our home is located in Great Barrington, given the title of the #1 Best Small Town in America by Smithsonian Magazine. There are many great restaurants, shopping, the Mahaiwe theater, a cineplex, golf, natural foods Co-op, a State Forest, yoga studio, and more. There are about twelve (12!) hiking...
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    This farmhouse has 3 bedrooms available so guests may bring their family, several friends, or overlap with new ones. The Iris Room is bright and airy with 4 windows; the Nasturtium Room has a Full bed with a half bath and the Horse room has a full and single bed across from the community...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    The 1762 farmhouse has 3 bedrooms available to bring your family and friends enjoy the close proximity to Tanglewood, Norman Rockwell Museum, and several lakes, many hiking areas, great restaurants. Larry makes a fresh egg breakfast which is included in your stay. You can join us for horseback...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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