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.

Holiday Rentals in Great Barrington, MA

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.
Check In Check Out
    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}
    View Map
    Price
    per night
    ₹ 22,230 Average
    ₹ 0₹ 65,000+
    Suitability
    More filters
    All 15 Rentals in Great Barrington
    Sort by:
    Default
    Travellers to Great Barrington are booking May dates now. Secure your holiday home today, and have the perfect trip.
    Great Barrington
    21 Reviews
    1 BedroomSleeps 3Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Great Barrington
    3 Reviews
    5 BedroomsSleeps 12Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Great Barrington
    2 Reviews
    5 BedroomsSleeps 10Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Great Barrington
    1 Review
    1 BedroomSleeps 4Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • DVD Player
    • Internet Access
    • Mountain Views
    • Washer
    • Satellite TV
    • Balcony
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Elegant, contemporary one bedroom house sleeps 4. Great central location. Peace, beauty and convenience. Perfectly located for all Berkshires activities, while still maintaining privacy and quiet. All new construction. This is my mother-in-law's property (I handle her online reservations) and...
    View all property information
    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Great Barrington
    1 BedroomSleeps 2Quick View
    other traveller has booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    • Mountain Views
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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.<BR><BR>The Space:<BR><BR>Quaint cottage with wood burning stove. Ideal base for...
    View all property information
    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Great Barrington
    2 BedroomsSleeps 5Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Balcony
    • Mountain Views
    • Washer
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Restored 1940's log cabin, amazing undisturbed 30 mile, 180 degree views. Hilltop location, walking distance to the village of South Egremont, ideal for hiking, Appalachian trail nearby, minutes to all major Berkshire attractions, very private & quiet, abundant wildlife, deer, fox, hawks, turkey....
    View all property information
    Location Information
    Great Barrington, Berkshires
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Great Barrington
    4 BedroomsSleeps 12Quick View
    other traveller has booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Grill
    • Outdoor Dining Area
    • Air Conditioning
    • Washer
    • Internet Access
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
    Make Enquiry
    Great Barrington
    1 Review
    4 BedroomsSleeps 10Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Satellite TV
    • Internet Access
    • Mountain Views
    • Grill
    • DVD Player
    • Waterfront
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Great Barrington
    1 Review
    2 BedroomsSleeps 4Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • DVD Player
    • Parking
    • Porch
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Great Barrington
    6 BedroomsSleeps 12Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Patio
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 6,700 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
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    Make Enquiry
    List your property for free!
    List your holiday home where TripAdvisor travellers can find it.
    Add a Listing
    Great Barrington
    9 BedroomsSleeps 16Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • Wi-Fi
    • Washer
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is by far one of the nicest homes that you will come across in the area (or this site for that matter!). The estate comes complete with 7 bedroom, 7 bathroom main house, a guest house with 2 bedrooms and one bath, several fire places, a pool table, ping pong table, pool, jacuzzi, several TV's...
    View all property information
    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 9 Bedrooms, 8 Bathrooms, Sleeps 16
    Make Enquiry
    The following rentals are within 10 kilometres of Great Barrington.
    North Egremont
    10 Reviews
    1 BedroomSleeps 2Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Grill
    • Satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2017
    I was very skeptical about staying somewhere other than a "chain hotel or resort". That is until I met Barbara and Phil. They were a very gracious, humble and warm couple who...
    Reviewed 16 November 2016
    River Song is a wonderfully private and relaxing place to hang your hat before heading out to visit Great Barrington and all the beauty that the Berkshires offers in any season...
    See all reviews
    About this property
    Located in the Berkshire mountains on more than 5 acres <BR>surrounded by 29 acres of conservation land. Featuring<BR>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,...
    View all property information
    Location Information
    North Egremont, Berkshires 01230
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Alford
    5 Reviews
    1 BedroomSleeps 2Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Mountain Views
    • Satellite TV
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 February 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 16 October 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...
    See all reviews
    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, Berkshires 01266
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    North Egremont
    1 Review
    3 BedroomsSleeps 8Quick View
    other traveller has booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Grill
    • Balcony
    • Parking
    • DVD Player
    • Air Conditioning
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Alford
    3 BedroomsSleeps 8Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wonderful Alford upscale family home with in ground heated pool; art barn, acreage; lush view & privacy. Private tranquil getaway vacation home.Delightful tri-level saltbox which has been completely, thoughtfully & tastefully renovated with every comfort in mind. Main floor: Enters into a breath...
    View all property information
    Location Information
    Alford, Berkshires 01266
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    List your property
    Owner log in