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.

Apartments and cabins in Berkshires, MA

About Berkshires
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.
mm/dd/yyyy mm/dd/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}
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 103 Rentals in Berkshires
    loading...
    Sort by
    From
    $120
    / Night
    Payment Protection
    View Details
    1 / 10
    5 of 5 stars (1) Excellent
    North Adams
    2 Bedrooms / 1 Bathroom / Sleeps 8
    traveler have booked this property
    Overview Reviews (1) Make Inquiry
    From
    $275
    / Night
    Payment Protection
    View Details
    1 / 32
    5 of 5 stars (1) Excellent
    Becket
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    From
    $120
    / Night
    Payment Protection
    View Details
    1 / 35
    5 of 5 stars (108) Excellent
    Charlemont
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Reviews (108) Make Inquiry
    From
    $1,700
    / Week
    Payment Protection
    View Details
    1 / 10
    4 of 5 stars (1) Very good
    Great Barrington
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • 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
    Make Inquiry
    4 of 5 stars Reviewed February 2, 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
    From
    $200
    / Night
    Payment Protection
    View Details
    1 / 8
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 2
    traveler have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The Writer's Room is at the top of the stairs on the right. This handsome room is made completely of wood. Ceilings are higher and there's a sitting area in the big dormer. dormer faces east and get the morning sun! The floors are wide plank cherry milled from the property. the walls are pine.... View all property information
    Make Inquiry
    5 of 5 stars Reviewed June 17, 2014
    We have taken the Writer's Room each Summer for about three years now. We find the Lodge to be authentic New England... our natural wood room to the rest of the house. It is...
    See all reviews
    From
    $189
    / Night
    Payment Protection
    View Details
    1 / 16
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Sauna
    • Shared Indoor Pool
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    A fully furnished and nicely appointed 2br/2ba suite. There's a full kitchen, living room with sofa sleeper, king bed in master bedroom, 2nd bedroom has either a king bed or two queen size beds(varies), washer/dryer, private balcony with mountain or valley views. Everything you need on your... View all property information
    Make Inquiry
    4 of 5 stars Reviewed October 25, 2014
    Lovely place with pool, spa, gym, and movie theater. Units are a bit noisy between floors but otherwise nice and quiet. We had the unfortunate experience of having three small...
    See all reviews
    From
    $300
    / Night
    Payment Protection
    View Details
    1 / 25
    5 of 5 stars (2) Excellent
    Lee
    3 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Dryer
    • Fireplace
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    ** Rental is only available for 2 week minimum during the summer (July - August) Special Summer Deal -- Rent for the Season (July and August) and get either the last week in June OR the first week in September for half price! This adorable cottage has all the ingredients for the ultimate retreat... View all property information
    Make Inquiry
    From
    $300
    / Night
    Payment Protection
    View Details
    1 / 12
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 1
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Gym
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • x
    About this property
    Wyndham Bentley Brook Ski-In Ski Out Wyndham Bentley Brook Resort Ski-In Ski-Out at Jiminy Peak at Wyndham Bentley Brook Resort. Beginners or Experts, we have -programs designed for all levels. After a couple days of skiing, you want to venture out and hit local attractions like, Barrington... View all property information
    Make Inquiry
    4 of 5 stars Reviewed July 21, 2014
    The condo was great - clean, roomy, stocked with expected items (towels, linens, shampoos, etc.) - my kids felt that it was very hotel-like. Location was perfect for us, although...
    See all reviews
    From
    $140
    / Night
    Payment Protection
    View Details
    1 / 11
    Hinsdale
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Internet Access
    • Safe
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    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... View all property information
    Make Inquiry
    From
    $450
    / Night
    Payment Protection
    View Details
    1 / 17
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 2
    traveler have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    handsome and welcoming, this authentic Berkshire lodge will make you feel like you`re in an old fashioned Christmas card! fireplace blazing, wood floors post and beam, hand planed planks. in the kitchen the floor is marble slabs from the famous lee marble quarry. Daniel Chester French, the designer... View all property information
    Make Inquiry
    5 of 5 stars Reviewed June 12, 2014
    I had several summer months here, it never disappoints. Full of nature's bounty, hospitable host, friendly vacationers. Very close to all the best of the Berkshires, Tanglewood...
    See all reviews
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    From
    $150
    / Night
    Payment Protection
    View Details
    1 / 4
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 2
    traveler have booked this property
    Overview Reviews (1) Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    first floor queensized bed, bath with shower. floors are wood ceiling has exposed beams and is furnished with oak antiques and a big wingbacked chair.built in bookshelf was from a companionway on a wooden sailing vessel owned by a sea captain that owned and ran the lodge back at the turn of the... View all property information
    Make Inquiry
    5 of 5 stars Reviewed June 17, 2014
    And I hope to stay here again in the future. I feel very comfortable here - good privacy, the house is huge, rustic charm, generally very quiet. The property is massive - and the...
    See all reviews
    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 19
    5 of 5 stars (12) Excellent
    West Stockbridge
    5 Bedrooms / 2 Bathrooms / Sleeps 12
    travelers have booked this property
    Overview Reviews (12) Make Inquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    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,... View all property information
    Make Inquiry
    5 of 5 stars Reviewed February 24, 2015
    We just spent a wonderful week staying at the Berkshire Farmhouse. The house was exactly as pictured, and Elaine was a warm and friendly host. She gave us a lot of great...
    5 of 5 stars Reviewed January 25, 2015
    We were a group of three family with 7 kids under the age of 8 (including two infants). The Farmhouse was a perfect place for us to gather. We equipped kitchen, open floor plan...
    See all reviews
    From
    $229
    / Night
    Payment Protection
    View Details
    1 / 4
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Cozy ranch home 3 miles away from Jiminy Peak Ski Resort. Near MASS MOCA, Clark Art Institute, Williams College Contemperary Museum of Art, Williamstown Theatre Festival, Tanglewood, shopping, golf courses. Wrap around deck with beautiful mountain views. Family room with full wet bar & flat screen... View all property information
    Make Inquiry
    4 of 5 stars Reviewed August 11, 2013
    Aside from the excessive amount of men's shirts in the closets (closets and drawers had not been emptied so storage space was minimal), the full trash bins and dirty dishes...
    See all reviews
    From
    $325
    / Night
    Payment Protection
    View Details
    1 / 21
    Lee
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Enjoy all the Berkshires has to offer in our new (2014) restoration and outstanding renovation of the historic South Lee Schoolhouse. Perched on a hillside just across the road from the Housatonic River and Beartown State Forest in the hamlet of South Lee, just outside of Stockbridge, the 1892... View all property information
    Make Inquiry
    From
    $135
    / Night
    Payment Protection
    View Details
    1 / 11
    5 of 5 stars (4) Excellent
    Richmond
    3 Bedrooms / 1 Bathroom / Sleeps 6
    travelers have booked this property
    Overview Reviews (4) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Fantastic spot for families and for those looking for a quiet getaway. Come have some summer fun, enjoy the autumn colors or play in the snow. This year round cottage is the perfect spot for those who enjoy outdoor activities. The house is on a private dead end road, has a wonderful lake view... View all property information
    Make Inquiry
    From
    $130
    / Night
    Payment Protection
    View Details
    1 / 16
    Stockbridge
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    One bedroom air conditioned apartment with private entrance in 18th century house in Historic District of Stockbridge. Wonderful views of the river, 18th green of Stockbridge Golf Club and the Berkshire Hills. 5 minutes walk to the famous Red Lion Inn/town center. Self contained and private. You... View all property information
    Make Inquiry
    From
    $200
    / Night
    Payment Protection
    View Details
    1 / 24
    Stockbridge
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This 1600 sq. ft. cottage boasts everything you would need for your visit to the Berkshires whether it be for a full summer / winter season to explore this beautiful area or a quick getaway to Tanglewood, The recently added master suite features a queen size bed, en-suite bathroom and a bonus... View all property information
    Make Inquiry
    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 6
    Hancock
    2 Bedrooms / 1 Bathroom / Sleeps 6
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Two Bedroom Ski Condo at base of Jiminy Peak. Renovated kitchen, fireplace, deck and a large livingroom with vaulted ceilings. Rent from the owner and save. View all property information
    Make Inquiry
    From
    $200
    / Night
    Payment Protection
    View Details
    1 / 7
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 6
    traveler have booked this property
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    sleeps 4 can combine with writer's room for large suite, private entrance. fireplace or windowed woodstove, ceiling fans cathedral ceiling, terrace with seating, pasture and forest views. windows line both sides of room and feels like a treehouse. beautiful wood floors and soft carpets make you... View all property information
    Make Inquiry
    From
    $99
    / Night
    Payment Protection
    View Details
    1 / 13
    5 of 5 stars (8) Excellent
    Becket
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Reviews (8) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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,... View all property information
    Make Inquiry
    5 of 5 stars Reviewed November 3, 2014
    This was exactly what we were looking for in a getaway rental! The place was exactly as described and every bit of the transaction went by without a hitch. The house was cozy...
    5 of 5 stars Reviewed June 28, 2014
    The Becket cabin is a great getaway for young families. Our 4- and 2-year-old happily played about in and around the cabin and we spent a lot of time building fires in the fire...
    See all reviews
    Get the List
    From
    $157
    / Night
    Payment Protection
    View Details
    1 / 9
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 1
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    This is an amazing 2 Bedroom Condo located in the heart of Berkshires.. On site amenities include, Pool and Game Room. Full Kitchen, 2 Baths and a large Living Room. Western Mass known for its rich culture, which will allow to enjoy close by Jaunts like, Norman Rockwell Museum, Tanglewood etc..... View all property information
    Make Inquiry
    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 5
    Granville
    5 Bedrooms / 3 Bathrooms / Sleeps 12
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    4 Bedrooms, 3 Baths, 3 Guest Rooms, Open Floor Plan Kitchen, Living, Dining Lakefront, 4 bedrooms, 3 baths, 3 guest rooms, open floor plan with kitchen, living and dining areas, family room, sports room, deck, two balconies and patio. The house has a unique setting in the heart of a nature... View all property information
    Make Inquiry
    From
    $495
    / Night
    Payment Protection
    View Details
    1 / 17
    Williamstown
    5 Bedrooms / 3 Bathrooms / Sleeps 16
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • ?
    • x
    About this property
    Lots of space, great yard, plus you can walk to everything: restaurants, museums, Williams College, theater, night life, etc. This beautifully maintained historic House On Main Street was known as the Victorian Tourist & Antique House in a by-gone era. It was originally constructed in the mid... View all property information
    Make Inquiry
    From
    $175
    / Night
    Payment Protection
    View Details
    1 / 12
    Windsor
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Peaceful, mountain hideaway. Rural, yet easily accessible to all major Berkshire County and Pioneer Valley attractions. Recently renovated, this charming 2-bedroom cottage can comfortably accommodate 4-6 people or could be a romantic retreat for two. Full kitchen with all appliances gives you... View all property information
    Make Inquiry
    From
    $225
    / Night
    Payment Protection
    View Details
    1 / 16
    5 of 5 stars (4) Excellent
    Stockbridge
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    travelers have booked this property
    Overview Reviews (4) Make Inquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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... View all property information
    Make Inquiry
    4 of 5 stars Reviewed October 24, 2013
    Some friends and I wanted to have a reunion as we are spread out along the east coast, and we were debating between camping or renting. I heard no end of the gratitude from my...
    5 of 5 stars Reviewed September 30, 2013
    We rented this cabin originally for 5: 2 adults and 3 children (6,11,13). At the last minute our older daughter (18) decided to join us. The cabin is very spacious and...
    See all reviews
    From
    $200
    / Night
    Payment Protection
    View Details
    1 / 12
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    cute cozy cottage, screened porch with views, close to everything, sleeps 4 . nice yard with big old trees and soft grass. gas bbq, just one mile to stockbridge center , Berkshire theatre festival. 5 miles to tanglewood, lenox , kripalu. 10 minutes to great barrington. bath has shower. full... View all property information
    Make Inquiry
    From
    $125
    / Night
    Payment Protection
    View Details
    1 / 10
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 2
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Balcony
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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... View all property information
    Make Inquiry
    From
    $175
    / Night
    Payment Protection
    View Details
    1 / 2
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    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... View all property information
    Make Inquiry
    From
    $499
    / Night
    Payment Protection
    View Details
    1 / 32
    5 of 5 stars (2) Excellent
    Stockbridge
    4 Bedrooms / 4 Bathrooms / Sleeps 12
    travelers have booked this property
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Fishing...
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    We call this house ‘South Sedgwick’ because of its location on a piece of land formerly used by the Sedgwick family for picnicking–an ideal spot for relaxation with stunning views of Monument Mountain and Ice Glen. The house is newly constructed with ash hardwood floors, custom white pine trim and... View all property information
    Make Inquiry
    5 of 5 stars Reviewed December 3, 2014
    What a great place! Teva was wonderful to work with, communication was incredible, and he is very welcoming. The house was spacious, very comfortable with 9 people! Teva came by...
    5 of 5 stars Reviewed July 18, 2014
    Our family of 5 rented this home over July 4th weekend and we couldn't have been more pleased. The home has just been newly renovated, is very tastefully appointed and looks and...
    See all reviews
    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 21
    Monterey
    5 Bedrooms / 3 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • 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
    Make Inquiry
    From
    $170
    / Night
    Payment Protection
    View Details
    1 / 45
    5 of 5 stars (5) Excellent
    North Egremont
    1 Bedroom / 1 Bathroom / Sleeps 2
    travelers have booked this property
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Private Fishing...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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
    Make Inquiry
    5 of 5 stars Reviewed September 11, 2014
    I had a wonderful stay! The property is gorgeous and serene. The suite is clean, very nicely decorated and private. Absolutely lovely!
    5 of 5 stars Reviewed September 4, 2014
    Lovely haven in the bucolic Berkshire countryside . Our suite had everything we could want- privacy, beautiful restful decor, comfort , all in a gorgeous setting. Short drive to...
    See all reviews
    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 16
    5 of 5 stars (1) Excellent
    North Adams
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    • Grill
    • Mountain Views
    • Private Fishing...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Windsor Cottage is a beautiful, newly renovated lakeside retreat located on Windsor Lake in North Adams, MA. where you can enjoy your own private water access from your front lawn. You will feel like you are in the middle of the forest, yet you are in walking distance to the town, Mass MoCA and... View all property information
    Make Inquiry
    5 of 5 stars Reviewed August 16, 2014
    The cottage is well located, seemingly remote, but with nearby access to local attractions and restaurants. I enjoyed sitting on the deck, looking out over the water in the...
    See all reviews
    From
    $150
    / Night
    Payment Protection
    View Details
    1 / 12
    South Lee
    1 Bedroom / 2 Bathrooms / Sleeps 4
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    RIght off the Mass Pike Exit 2, Berkshire family vacation condo with full kitchen and all amenities.Take in Boston Symphony at Tanglewood and dance at Jacob's Pillow, theatre at Shakespeare & Company, Yoga at Kripalu, a spa day at Canyon Ranch, the Norman Rockwell Museum, Hancock Shaker Village,... View all property information
    Make Inquiry
    From
    $145
    / Night
    Payment Protection
    View Details
    1 / 16
    5 of 5 stars (1) Excellent
    Hancock
    1 Bedroom / 1 Bathroom / Sleeps 6
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    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... View all property information
    Make Inquiry
    5 of 5 stars Reviewed October 16, 2014
    This property is perfect for people with pets. Serene setting with a gorgeous view. The hosts, Tom and Susan, were gracious and very helpful. Highly recommended if your travels...
    See all reviews
    From
    $200
    / Night
    Payment Protection
    View Details
    1 / 6
    Savoy
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Located in a quiet corner of the northern Berkshires, this lovely two-bedroom home has a combined living room/kitchen with cathedral ceilings and a spacious bathroom complete with a 2-person jacuzzi tub. The house is located about a mile from beautiful Tannery Falls in the Savoy State Forest and... View all property information
    Make Inquiry
    From
    $360
    / Night
    Payment Protection
    View Details
    1 / 33
    4 of 5 stars (8) Very good
    Lee
    5 Bedrooms / 3 Bathrooms / Sleeps 11
    travelers have booked this property
    Overview Reviews (8) Make Inquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Beautiful house surrounded by protected woodland and a small beaver pond behind your backyard. All kinds of birds and wildlife. 5 Bedrooms, 2.5 baths, brand new kitchen, open living/dining room, laundry room. Wood stove that can function as a fireplace. 3 heating zones for comfort. All new... View all property information
    Make Inquiry
    4 of 5 stars Reviewed September 27, 2014
    We went there for a golf buddy trip and it was the perfect place for us in the Berkshires. Place was very clean, and had all the comforts of home. Robin is super friendly and...
    5 of 5 stars Reviewed September 3, 2014
    This is a wonderful home! Robin has taken care with the furnishing and finishings, which are a nice blend of antique and modern. Her love of the home and region is apparent...
    See all reviews
    From
    $350
    / Night
    Payment Protection
    View Details
    1 / 11
    5 of 5 stars (1) Excellent
    Great Barrington
    4 Bedrooms / 2 Bathrooms / Sleeps 9
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    The perfect house for friends and family to share! Bright,uncluttered, and inviting, with privacy and views just minutes to town. There are two fireplaces,a sunken living room, dining room with seating for 10, 4 bedrooms, 2 full bathrooms, and a cozy hang out area in the basement. There is a washer... View all property information
    Make Inquiry
    5 of 5 stars Reviewed February 5, 2015
    This was the first time we had a rental cottage, but it surpassed all of our expectations. The cottage was clean and well arranged. Kitchen was spacious enough for more than a few...
    See all reviews
    From
    $225
    / Night
    Payment Protection
    View Details
    1 / 10
    Tyringham
    1 Bedroom / 1 Bathroom / Sleeps 2
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Balcony
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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... View all property information
    Make Inquiry
    From
    $4,500
    / Week
    Payment Protection
    View Details
    1 / 25
    Great Barrington
    6 Bedrooms / 6 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • 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
    Make Inquiry
    From
    $500
    / Night
    Payment Protection
    View Details
    1 / 23
    5 of 5 stars (1) Excellent
    Stockbridge
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    A home for the family: SKIING, SNOWSHOEING, AND SLEDDING. Fall and Winter availability. Behind the house, on the property is a HUGE hill that is great for sledding. 12 mins to Butternut. 25 mins to Jiminy. Across the road is a park that is great fun to hike, snowshoe, CC ski, and explore. A... View all property information
    Make Inquiry
    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 9
    Tyringham
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Santarella Estate and Gardens in Tyringham, MA is a magical destination in the heart of one of the Berkshires' most beautiful valleys, located 3 miles from Interstate 90 and 15 minutes from most of the principal attractions (Tanglewood, Jacob's Pillow, Norman Rockwell museum, etc.) Pictures are... View all property information
    Make Inquiry
    From
    $500
    / Night
    Payment Protection
    View Details
    1 / 15
    Tyringham
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Located on the Santarella Estate, an historic site located in the the Massachussetts' Berkshires. The colonial home is the former residence of sculptor Sir Henry Hudson Kitson. The estate includes the landmark, iconic storybook style 'Gingerbread House,' designed by Kitson to look like an English... View all property information
    Make Inquiry
    From
    $300
    / Night
    Payment Protection
    View Details
    1 / 23
    Great Barrington
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Beautifully furnished, updated 3,000 square foot house. 3 bedrooms, 2 full baths; large sun room with great windows and sky-lights, comfortable seating area for 6 plus cafe table; dining room with table for 6 to 8 people; reading room with a wood-burning stove; living room with a fireplace;... View all property information
    Make Inquiry
    From
    $143
    / Night
    Payment Protection
    View Details
    1 / 15
    5 of 5 stars (1) Excellent
    Sandisfield
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Home on 2.5 wooded acres in a private lake community, with vacant wooded acres on both sides. Amenities of the community include non-motor boat lake, outdoor heated swimming pool, tennis courts, exercise facility, clubhouse and walking trails. The home is located in the Berkshires, a popular year... View all property information
    Make Inquiry
    5 of 5 stars Reviewed February 1, 2015
    We stayed at this beautiful house in a lovely lake community. The house is open and bright and very comfortable. We spent most of our time on the large screened back porch...
    See all reviews
    From
    $432
    / Night
    Payment Protection
    View Details
    1 / 8
    Charlemont
    5 Bedrooms / 3 Bathrooms / Sleeps 14
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Mountain Views
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Hawk Mountain Lodge offers a year-round New England vacation experience! Enjoy comfortable accommodations conveniently located in Charlemont in the northern Berkshires, just 2.5 hours from Boston and 3.5 to 4 hours from New York City. Overlooking the Deerfield River Valley and Berkshire East Ski... View all property information
    Make Inquiry
    From
    $465
    / Night
    Payment Protection
    View Details
    1 / 33
    5 of 5 stars (3) Excellent
    Great Barrington
    4 Bedrooms / 3 Bathrooms / Sleeps 12
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    This sparkling, newly renovated cottage is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions. The house has been renovated by a contemporary designer. It has an open floor plan, making each room flow into... View all property information
    Make Inquiry
    From
    $200
    / Night
    Payment Protection
    View Details
    1 / 15
    Great Barrington
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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, game room with pool/Ping-Pong table & two cars garage. Located within a... View all property information
    Make Inquiry
    From
    $450
    / Night
    Payment Protection
    View Details
    1 / 20
    Richmond
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed... View all property information
    Make Inquiry
    From
    $375
    / Night
    Payment Protection
    View Details
    1 / 5
    Lee
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    I have a corner unit first floor 2-bed resort presidential suite in beautiful Berkshires! Just 2 hours drive down the Mass Pike from Boston. It's July 4th week and James Taylor will be playing at Tanglewood. This is one of the most sought after concerts every year and you wouldn't want to miss it!... View all property information
    Make Inquiry
    From
    $400
    / Night
    Payment Protection
    View Details
    1 / 24
    Lenox
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Private Indoor Pool
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    220+ Acres W\ Tennis Cts, Indoor / Outdoor Pool, Canoe, Fishing Boat, Hot Tub. New first time rental of 4 BR, 2BA, Cape Cod style, sleeps 10-12. New fully equipped kitchen w/ center island, indoor and outdoor barbecues, wine cooler, 2 fireplaces, large deck with 8 person hot tub and super seating... View all property information
    Make Inquiry