We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Sheffield, MA and nearby

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Change Dates
    Price
    per night
    |||
    |||
    $0
    $332 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Payment
    Book Online
    View Map
    More filters
    loading...
    Don't let other travellers get your favourite Sheffield area vacation rental. You're so close to securing your perfect getaway. Book today.
    Applied filters:
    Nearby
    Clear All
    1 / 10
    5 of 5 stars (2) Excellent
    Sheffield
    3 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    1 / 14
    5 of 5 stars (1) Excellent
    Sheffield
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection

    The following rentals are within 15 kilometres of Sheffield, Massachusetts.

    1 / 22
    5 of 5 stars (1) Excellent
    Copake, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    1 / 12
    5 of 5 stars (3) Excellent
    Alford
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Mountain Views
    • Satellite TV
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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... View all property information
    Location Information
    Alford, Massachusetts 01266
    5 of 5 stars Reviewed 2 May 2013
    The Smith Homestead is a fantastic get-away for those looking to get peace and quiet in the picturesque Berkshire community of alford. The drive up to alford was both easy and...
    5 of 5 stars Reviewed 10 April 2013
    Set back in the Berkshires, Alford Ma is a stone's throw from New York State. The small town borders Great Barrington, which is rich in activity. Many famous americans have...
    See all reviews
    1 / 10
    5 of 5 stars (2) Excellent
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Mountain Views
    • DVD Player
    • Washer
    • Porch
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Please note that this property is not winterized so it's not available this winter of 2012. I am winterizing this spring & the property will be available on a year around basis stating on 5/15/2013. Please go to VRBO.com listing #219964 to see my reviews, I am new to flipkey. Located in South... View all property information
    Location Information
    Great Barrington, Berkshires 33304
    5 of 5 stars Reviewed 20 May 2013
    This was a perfect weekend for us. I am very picking when choosing a cabin rental because I want it to be "just right--" to fit into all of my ideal visions of the quintessential...
    5 of 5 stars Reviewed 18 May 2012
    This cabin was shared by re-uning nearby Berkshire School graduates and was perfect. It had all the needed amenities, WiFi, Hdtv with a dish, beautiful fireplace, nice kitchen...
    See all reviews
    Copake Falls, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Washer
    • Central Heating
    • Porch
    • Outdoor Dining Area
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Ski the Berkshires at Catamount 10 minutes away and Butternut 30 minutes away. Beautifully renovated cottage in walking distance to Taconic State Park. Enjoy farm to table dining nearby. Hike to Birkshires' Bash Bish Falls, bike on the Harlem Valley Bike Trail, and swim in the spring fed iron ore... View all property information
    Location Information
    Copake Falls, New York 12517
    Great Barrington
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Grill
    • Washer
    • DVD Player
    • Air Conditioning
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This home is uniquely and magnificently furnished by a retired couple that spent 18 years traveling and living abroad. Even local real estate agents have called the house “special”. It has 7,000 sf of living space (3 floors) with plenty of places to be together or to be alone (as one so chooses).... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 23
    Great Barrington
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Hot Tub
    • Satellite TV
    • Patio
    • Air Conditioning
    • Internet Access
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This Elegant Luxury Estate offers 6000+ SF of Living Space on 13+ park-like, sunny acres located within only minutes from the downtown Great Barrington. This fantastic home offers 5 Bedrooms, 4.5 bathrooms, sweeping dual staircase ending with the magnificent open gallery, the kitchen offers the... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 11
    5 of 5 stars (2) Excellent
    Hillsdale, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Parking
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    We found a great circa 1845 house in the Berkshire/Taconic Mtn area and fully renovated the entire building creating retail shops and a sophisticated but casually comfortable 2 BR apt. saving many of the original building features. Fully equipped efficiency kitchen with a W/D, marble bath, sleeps 6... View all property information
    Location Information
    Hillsdale, New York 12529
    5 of 5 stars Reviewed 4 November 2015
    C'était tellement bien, que j'ai déjà envie d'y retourner!! As a French citizen, I can affirm that my stay at Lynne and Bill's loft was perfect! No noise, comfortable and with...
    5 of 5 stars Reviewed 27 September 2015
    Bill and Lynne, the proprietors were wonderful. Very accommodating and helpful. Although located on highway 23, there is very little road noise as the apartment is brand new...
    See all reviews
    1 / 12
    1 of 5 stars (1) Terrible
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Satellite TV
    • Internet Access
    • Mountain Views
    • Grill
    • DVD Player
    • Waterfront
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    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... View all property information
    Location Information
    Great Barrington, Berkshires 01236
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    New Marlborough
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Balcony
    • Central Heating
    • Wi-Fi
    • Grill
    • Washer
    • Terrace
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Welcome to Mill River, and our 1905 Queen Anne style Victorian backing onto hundreds of acres of woods, deep in the heart of the Berkshires. Step in and enjoy the peace of sitting on the porch of an old house on a quiet country lane, the wind in the trees and the babble of the nearby stream. The... View all property information
    Location Information
    New Marlborough, Berkshires 01230
    1 / 6
    Copake, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Parking
    • DVD Player
    • Air Conditioning
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Well appointed comfortable 4 season home short walk to lake beach and dock. Large deck with lake views. TV with VCR/DVD Washer/dryer/dishwasher Beds: 1 Queen Bed, 4 Twin Beds View all property information
    Location Information
    Copake, New York 12529
    Copake, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Terrace
    • Washer
    • Balcony
    • Central Heating
    • Patio
    • Grill
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A single storey house with a large basement less than 100 yards from the boat launch to the lake. Swimming, fishing, boating, walking, climbing, cycling and skiing all within 20 minutes ride from the house. A perfect location for all of these activities, plus a quiet location if you just want to... View all property information
    Location Information
    Copake, New York 12516
    Great Barrington
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Outdoor Dining Area
    • Parking
    • DVD Player
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Charming get-a-way in a friendly residential neighborhood in Great Barrington. Our home is sunny and bright, with an eat-in-kitchen, casual living room and dining area with beautiful picture windows, three comfortable bedrooms, and 1.5 bathrooms. Fully furnished with an eclectic mix of modern and... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 19
    5 of 5 stars (1) Excellent
    North Egremont
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Grill
    • Balcony
    • Parking
    • DVD Player
    • Air Conditioning
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    About this property
    Enjoy beautiful Prospect Lake while staying at our comfortable home. Full kitchen with almost anything you can think of. Farm table seats 8 and is perfect for family meal. Cozy living spaces with enough seating for all to gather. Sunny bright deck in private rear yard . Covered porch is perfect... View all property information
    Location Information
    North Egremont, Berkshires 01230
    5 of 5 stars Reviewed 12 October 2015
    It's my first time booking through flipkey. Zoe, the hostess, helped me a lot during the process. She is warm, kind, and patient. Her email was in details and we checked in...
    See all reviews
    1 / 11
    5 of 5 stars (15) Excellent
    Falls Village, CT
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Balcony
    • Grill
    • Satellite TV
    • Mountain Views
    • Central Heating
    • Hot Tub
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Rare property available for vacation rental in Falls Village Ct Originally dating to 1800 's this highly unique property was purchased in 1999 by artist and master craftsman Mario Genova. The interior features plaster throughout, stone, marble and terra cotta mosaic flooring and wonderful... View all property information
    Location Information
    Falls Village, Connecticut 06031
    5 of 5 stars Reviewed 29 May 2015
    My husband and I stayed here for a recent visit on a trip to New England. We chose this Falls Village cottage and it was truly wonderful. Everything from the location, right up...
    5 of 5 stars Reviewed 9 April 2015
    I have been traveling to the northwest of Connecticut since my teens, spending a lot of weekends at Lime Rock and Sharon where my daughters spent their summers in a camp. There...
    See all reviews
    1 / 14
    5 of 5 stars (1) Excellent
    Copake, NY
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Grill
    • Outdoor Dining Area
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Beautifully restored 2 bedroom (plus attic loft) home brings contemporary living to this hidden gem just 2 hours from NYC. We gutted the house completely incorporating modern amenities like a brand new stainless steel kitchen with granite countertops, hardwood bamboo flooring and a large deck to... View all property information
    Location Information
    Copake, New York 12516
    5 of 5 stars Reviewed 6 February 2014
    The home fit all 5 of my guests comfortably. It was centrally located to skiing and was a wonderful home and a very cozy experience
    See all reviews
    Monterey
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Skiing: Property Is...
    • Patio
    • DVD Player
    • Internet Access
    • Washer
    • Grill
    • Central Heating
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This is a beautiful Berkshire, post and beam private house nestled in the woods just off the Appalachian trail. Set on one of the Berkshires most coveted roads close to fresh water swimming in Lake Garfield, boating, fishing, classical outdoor concerts at Tanglewood & Skiing are all close by. The... View all property information
    Location Information
    Monterey, Berkshires 01245
    1 / 42
    5 of 5 stars (3) Excellent
    Lakeville, CT
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Porch
    • Washer
    • Satellite TV
    • Outdoor Dining Area
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This newly renovated 4 bedroom, 3 bath house is fully furnished and available for short or long term rentals. This house has a new kitchen, air conditioning, cable TV and wireless internet. It is located approximately 200 feet from the entrance to the Town Grove which offers many recreational... View all property information
    Location Information
    Lakeville, Connecticut 06068
    5 of 5 stars Reviewed 26 May 2014
    My friends and I stayed at this house for a race weekend at Lime Rock Park. The location of this house is perfect - 15 minutes from the track, walking distance from a small lake...
    5 of 5 stars Reviewed 6 May 2014
    We rented this sweet home in Lakeville for the bride and bridesmaids for my son's wedding. The bridal party came from far and wide and this was the perfect destination for the...
    See all reviews
    1 / 13
    4.5 of 5 stars (16) Very good
    Monterey
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Washer
    • DVD Player
    • Waterfront
    • Mountain Views
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Charming house with the feeling of a cottage, set on a knoll with adjacent cathedral-like pine forest. ** Stone fireplace, woodstove, beautiful kitchen with modern appliances (gas stove, microwave, refrigerator with water/ice dispenser, dishwasher, breadmaker, crockpot, blender, etc.) **... View all property information
    Location Information
    Monterey, Berkshires 01245 0933
    5 of 5 stars Reviewed 18 November 2015
    I took my wife and three young children up to this house for columbus day week. We had a blast. The house has a real cabin in the woods feel and is just a short walk to the...
    4 of 5 stars Reviewed 9 November 2015
    When looking for a house to rent in the Berkshires I began with spots in the towns. However we chose this place due to the reasonable price. As it turned out we liked the remote...
    See all reviews
    Get the List
    1 / 9
    Copake, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 17 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Balcony
    • Grill
    • DVD Player
    • Central Heating
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Completely furnished kitchen, bedrooms and bathrooms. Master bedroom has full bath, large window overlooking lake, secondary bedroom has 1/2 bath. Downstairs area, has two curtained rooms with king beds, two bunk beds and a 1/2 bath. Dock on property gives access to lake within 30 feet of house,... View all property information
    Location Information
    Copake, New York 12516
    1 / 4
    4 of 5 stars (1) Very good
    Copake, NY
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Porch
    • DVD Player
    • Washer
    • Grill
    • Central Heating
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This cottage with a view of Copake Lake has 3 bedrooms and a loft. The master bedroom contains a queen bed, a second bedroom contains a double bed, and the third bedroom contains two bunk beds. The recently-renovated bathroom has a washer/dryer and a whirlpool tub. There is also a sunroom and the... View all property information
    Location Information
    Copake, New York 12529
    4 of 5 stars Reviewed 14 November 2012
    My husband and I drove up from NYC and stayed here for a weekend in april. The lake community was just waking up for spring and we loved the feeling of getting away from it all...
    See all reviews
    1 / 12
    5 of 5 stars (19) Excellent
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Satellite TV
    • Shared Outdoor Pool...
    • Grill
    • DVD Player
    • Central Heating
    • Mountain Views
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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..... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    5 of 5 stars Reviewed 25 October 2015
    My husband and I stayed at this very charming cottage for 3 nights in the beginning of October and we very much enjoyed our stay. The furniture and decor were very french...
    5 of 5 stars Reviewed 27 August 2015
    I stayed in the cottage with my girlfriend and our small dog and we had a fantastic time! The cottage had everything we needed (wifi, large bathroom, dining table, cable TV) and...
    See all reviews
    Great Barrington
    4 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Parking
    • Washer
    • Shared Garden
    • Outdoor Dining Area
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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,... View all property information
    Location Information
    Great Barrington, Berkshires 01236
    1 / 8
    Hillsdale, NY
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Central Heating
    • Washer
    • Outdoor Dining Area
    • Balcony
    • Mountain Views
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Glorious views across meadows to distant mountains. Open-plan living/dining/kitchen with fireplace, and soaring ceiling. Many glass doors lead to decks where you may drink in the view. Great master bedroom suite with state of the art bathroom, two guest rooms, family room, media room and two guest... View all property information
    Location Information
    Hillsdale, New York 12529
    1 / 11
    4 of 5 stars (1) Very good
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Shared Garden
    • Grill
    • DVD Player
    • Parking
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Welcome to our School House Cottage located in the heart of the Berkshires. Set in front of the ledges of Warner Mountain, this historic home was originally a three room schoolhouse. An addition in the 1960's transformed it into a private home which it remained for many years. Now updated, the... View all property information
    Location Information
    Great Barrington, Berkshires 01237
    4 of 5 stars Reviewed 10 September 2015
    I spent a delightful month at the Schoolhouse cottage. It's comfortably furnished, and while I was by myself most of the time it didn't feel crowded when friends or family stopped...
    See all reviews
    Great Barrington
    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor...
    • Waterfront
    • Satellite TV
    • Washer
    • DVD Player
    • Wi-Fi
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Welcome to my dream come true! Pick from your own orchards, vegetable gardens and perennial beds. Swim in your own Green River or your beautiful heated swimming pool. And of course, SKI, SKI, SKI!! This home is beautiful four seasons of the year. Major highlights include a fireplace in the kitchen... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 37
    5 of 5 stars (1) Excellent
    Salisbury, CT
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Grill
    • Waterfront
    • Mountain Views
    • Outdoor Dining Area
    • DVD Player
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    For the price of a motel room, enjoy a cabin on a lake. Great casual summer-fall vacation place for a small family with room for guests. MINIMUM 14 DAY STAY. THOUGH DAILY AND WEEKLY RATES MUST BE SHOWN, WE DO NOT RENT FOR THESE SHORT PERIODS. SEE NOTE BELOW. Great room, master bedroom, and... View all property information
    Location Information
    Salisbury, Connecticut 06079
    5 of 5 stars Reviewed 7 September 2014
    My wife and I and two small children stayed at the cabin for one month after a big road trip adventure across the country from California. It was exactly what we needed! Our pace...
    See all reviews
    Monterey
    5 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Satellite TV
    • Patio
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Get away from it all at our beautiful Berkshire lakefront wooded retreat. Swim, canoe, kayak, sunbathe, play tennis during the day, then enjoy the evening a short drive away at Tanglewood, Jacobs Pillow, or perhaps go to the movies in Great Barrington. Have dinner at the Red Lion Inn, or one of the... View all property information
    Location Information
    Monterey, Berkshires 01245
    Copake, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Grill
    • Skiing: Property Is...
    • DVD Player
    • Parking
    • Patio
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This house had extensive renovations in 2014 and has free wifi throughout. The kitchen and living room were combined for a large open family area. The kitchen was completely renovated with high end cabinets, granite countertops, a huge center island that seats five, and a beautiful large mission... View all property information
    Location Information
    Copake, New York 12521
    Hillsdale, NY
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This extremely private luxury home is situated on 48-acres at the end of a cul de sac and is located two miles from NY Route 22 in Columbia County just 10 minutes from the Massachusetts boarder and 30 minutes from the Vermont border. Recently renovated, this contemporary home with 5 bedrooms... View all property information
    Location Information
    Hillsdale, New York 12529
    1 / 10
    4 of 5 stars (1) Very good
    Great Barrington
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • DVD Player
    • Parking
    • Porch
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    4 of 5 stars Reviewed 2 February 2015
    My cousin and I thoroughly enjoyed our stay. The house was cozy and very convenient for our needs. Having a laundry room just off the kitchen was great when we came back from the...
    See all reviews
    1 / 26
    5 of 5 stars (7) Excellent
    Hillsdale, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Mountain Views
    • Central Heating
    • Washer
    • Grill
    • Satellite TV
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    3 bedrooms, 2 full baths, living room, dining room, kitchen, loft area. Private and secluded log cabin chalet is situated on three picturesque acres overlooking tall pines and forests with heartwarming winter mountain views. The chalet was built in 2003 and has gorgeous stone countertops and two... View all property information
    Location Information
    Hillsdale, New York 12529
    5 of 5 stars Reviewed 21 December 2015
    Owners were delightful to deal with. House was clean and well equipped. Would definitely rent again for a ski weekend! Really enjoyed family dinner at "The Gypsy Joint" in nearby...
    5 of 5 stars Reviewed 8 November 2015
    My family and I spent 4 nights in the chalet. We enjoyed our time there. The chalet is equipped with everything you need. It even has a basement with bycicles, an air hockey...
    See all reviews
    1 / 18
    5 of 5 stars (1) Excellent
    Hillsdale, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 13 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Satellite TV
    • DVD Player
    • Porch
    • Parking
    • Internet Access
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Cozy modern log cabin nestled in the Berkshires in a large wooded area with landscaped yard on a small river. The cabin has a full service kitchen and a great room with dining and lounging space. There is a full entertainment center with furnished recorded music and movies. Bedrooms and bath are... View all property information
    Location Information
    Hillsdale, New York 12529
    5 of 5 stars Reviewed 9 November 2010
    It's a Beautiful home that has all the modern conveniences. It's quiet, quaint and had just what I needed to get away from it all. I enjoyed morning coffee on the back deck among...
    See all reviews
    Monterey
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    You'll love our hand-hewn post & beam beauty on 13 acres in the Berkshire Mountains of Western Mass located near the Monterey/Great Barrington line, close to everything. Great for summer and winter ski season. Rich in both outdoor and cultural attractions, shopping and antiquing. Located adjacent... View all property information
    Location Information
    Monterey, Berkshires 01245
    1 / 50
    5 of 5 stars (7) Excellent
    North Egremont
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Grill
    • Satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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,... View all property information
    Location Information
    North Egremont, Berkshires 01230
    5 of 5 stars Reviewed 7 October 2015
    My husband and I were looking for a relaxing getaway for a long weekend. We chose the River Song and were not disappointed. The suite is beautifully and comfortably furnished...
    5 of 5 stars Reviewed 8 July 2015
    This suite is located in a beautiful serene setting. Barbara keeps the suite very clean, and her attention to every detail is unmatched. We had a wonderful stay, and only wish...
    See all reviews
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • DVD Player
    • Parking
    • Washer
    • Wi-Fi
    • Balcony
    • Air Conditioning
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Sweet cozy house with plenty of room for large groups coming to enjoy the treasures of the Berkshires. Nestled behind Monument Mountain in Great Barrington. 4 bedrooms, 2.5 bathrooms, a spacious kitchen, living room, TV room, & two cars garage. Located within a neighborhood friendly to children.... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    • Mountain Views
    • Private Garden
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf. The Space: Quaint cottage with wood burning stove. Ideal base for enjoying... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 27
    3.5 of 5 stars (2) Average
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Grill
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • DVD Player
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    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,... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    3 of 5 stars Reviewed 11 September 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...
    See all reviews
    1 / 15
    5 of 5 stars (7) Excellent
    Copake, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Porch
    • Grill
    • Washer
    • Satellite TV
    • Parking
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Rustic 3 Bedrooms vacation home 1500 sq ft sleeps 9+ There are 6 beds (1 queen bed, 3 single beds (two beds have a trundle bed underneath) and 1 double sofa-bed, a pack & play and high chair for the little one! Full kitchen, 2 baths and large living and dining space. Wrap around deck, BBQ grill,... View all property information
    Location Information
    Copake, New York 12516
    4 of 5 stars Reviewed 10 August 2015
    Comfortable, well equipped house that's ideal for a family or group of friends outing. Roomy with yard, deck and BBQ. Close to Copake, the local lake and the sights of the area...
    5 of 5 stars Reviewed 5 September 2014
    a great location tucked away yet close to all activities. The house is super comfortable and clean. Includes everything you might want, wifi internet is free and easy to access
    See all reviews
    1 / 16
    5 of 5 stars (4) Excellent
    Copake, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    About this property
    House, 3 Bedrooms + Loft, 2 Baths (Sleeps 7) BE SURE TO CLICK ON THE LINK BELOW TO SEE MORE OF OUR BEAUTIFUL PHOTOS. This three bedroom , two living rooms with flate screen home theater system, 2 Baths, plus sleeping loft(or office) has it all. Our deeded lake access on a clean freshwater lake... View all property information
    Location Information
    Copake, New York 12516
    5 of 5 stars Reviewed 6 January 2015
    I'm sorry for not responding sooner. Your home was the best vacation rental in which I have stayed today and I rent frequently in the Berkshires. I am going to want to stay there...
    5 of 5 stars Reviewed 20 October 2014
    We spent seven days at this house in the New York side of the Berkshires. I'd never rented in this way before so I was a little nervous. When we got there, we were really wowed...
    See all reviews