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 Colebrook, CT 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.
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}
    List your property
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price range
    ($307 Average)
    $0per night $1,000+
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    loading...

    The following rentals are within 20 miles of Colebrook, Connecticut.

    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 5
    5 of 5 stars (1) Excellent
    Granville, MA
    5 Bedrooms, 3 Bathrooms, Sleeps 12
    other travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    From
    $375
    / Night
    Payment Protection
    View Details
    West Cornwall
    3 Bedrooms, 3 Bathrooms, Sleeps 10
    other travelers have booked this property
    Overview Make Inquiry
    Overview
    From
    $199
    / Night
    Payment Protection
    View Details
    1 / 10
    5 of 5 stars (15) Excellent
    Great Barrington, MA
    1 Bedroom, 1 Bathroom, Sleeps 3
    other travelers have booked this property
    Overview Reviews (15) Make Inquiry
    Overview Reviews (15)
    From
    $350
    / Night
    Payment Protection
    View Details
    1 / 27
    3.5 of 5 stars (2) Average
    Great Barrington, MA
    5 Bedrooms, 4 Bathrooms, Sleeps 10
    other travelers have booked this property
    Overview Reviews (2) Make Inquiry
    Overview Reviews (2)
    Amenities & Details
    • Deck
    • Stereo System
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • DVD Player
    • Grill
    • 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
    Make Inquiry
    Location Information
    Great Barrington, Berkshires 01230
    3 of 5 stars Reviewed September 11, 2014
    This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
    4 of 5 stars Reviewed January 4, 2015
    MAにあるSki Butternut というスキー場を利用するため、クリスマスからお正月にかけて、6泊7日で滞在しました。4家族(大人7人、子供5人・子供は5歳と7歳)というグループでしたが部屋の広さは十分で、非常に快適に過ごすことができました。 【ロケーション】 Butternut...
    See all reviews
    From
    $250
    / Night
    Payment Protection
    View Details
    Tyringham, MA
    1 Bedroom, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Tyringham, Berkshires 01264
    From
    $500
    / Night
    Payment Protection
    View Details
    Tyringham, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 8
    other traveler has booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Central Heating
    • Satellite TV
    • Staffed Property
    • Wi-Fi
    • DVD Player
    • Watersports Nearby
    • Mountain Views
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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
    Location Information
    Tyringham, Berkshires 01264
    From
    $275
    / Night
    Payment Protection
    View Details
    Monterey, MA
    5 Bedrooms, 3 Bathrooms, Sleeps 12
    other traveler has booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Mountain Views
    • Water Park Nearby
    • Central Heating
    • Watersports Nearby
    • TV
    • DVD Player
    • Playground
    • Internet Access
    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
    Make Inquiry
    Location Information
    Monterey, Berkshires 01245
    From
    $595
    / Night
    Payment Protection
    View Details
    Barkhamsted
    6 Bedrooms, 8 Bathrooms, Sleeps 12
    other traveler has booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Fireplace
    • Air Conditioning
    • Deck
    • Waterfront
    • Skiing: Property Is...
    • Patio
    • Satellite TV
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Nestled on the banks of the Farmington River, Legends offers comfortable rooms in a lodge setting with river views, breakfast Thursday -Sunday, healthy afternoon snacks and a special homemade juice of the day. All rooms offer AC, private bath, TV and internet. Fly-fishing,hunting kayaking, hiking,... View all property information
    Make Inquiry
    Location Information
    Barkhamsted, Connecticut 06063
    From
    $750
    / Night
    Payment Protection
    View Details
    Cornwall Bridge
    3 Bedrooms, 3 Bathrooms, Sleeps 7
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Mountain Views
    • DVD Player
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Private Indoor Pool
    • Air Conditioning
    • Sauna
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Prana Residence-Spa creates an environment for relaxation and the rejuvenation of vital life (prana). If you appreciate tranquility in the pursuit of personal happiness and are inspired by unique surroundings, personal spa facilities and select services, Prana Residence-Spa is waiting for you.... View all property information
    Make Inquiry
    Location Information
    Cornwall Bridge, Connecticut 06754
    From
    $2,450
    / Week
    Payment Protection
    View Details
    Great Barrington, MA
    5 Bedrooms, 3 Bathrooms, Sleeps 10
    other traveler has booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Mountain Views
    • Deck
    • Satellite TV
    • Waterfront
    • Internet Access
    • DVD Player
    • Water Views
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Attractive year-round lakefront house in a wooded area on a pristine Round Pond in the Berkshires. Relax and enjoy the view from your deck or dock. Fish from the dock or take the boat out onto the lake. Ideal family retreat in Great Barrington and only a short drive to cultural attractions... View all property information
    Make Inquiry
    Location Information
    Great Barrington, Berkshires 01236
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    From
    $675
    / Night
    Payment Protection
    View Details
    Great Barrington, MA
    4 Bedrooms, 6 Bathrooms, Sleeps 12
    Overview Make Inquiry
    Overview
    Amenities & Details
    • TV
    • Washer
    • Dryer
    • Internet Access
    • Air Conditioning
    • Fireplace
    • Grill
    • Deck
    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
    Make Inquiry
    Location Information
    Great Barrington, Berkshires 01236
    From
    $200
    / Night
    Payment Protection
    View Details
    Great Barrington, MA
    2 Bedrooms, 1 Bathroom, Sleeps 4
    other travelers have booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • DVD Player
    • Grill
    • Satellite TV
    • Linens Provided
    • Stove
    • Refrigerator
    • Air Conditioning
    • Internet Access
    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
    Make Inquiry
    Location Information
    Great Barrington, Berkshires 01237
    From
    $350
    / Night
    Payment Protection
    View Details
    1 / 11
    5 of 5 stars (1) Excellent
    Great Barrington, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 9
    other travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Hot Tub
    • Washer
    • Internet Access
    • Satellite TV
    • Stereo System
    • Fireplace
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Great Barrington, Berkshires 01230
    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
    $90
    / Night
    Payment Protection
    View Details
    1 / 12
    5 of 5 stars (1) Excellent
    Torrington
    1 Bedroom, 1 Bathroom, Sleeps 2
    other travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Porch
    • Balcony
    • Refrigerator
    • Patio
    • Stove
    • Wi-Fi
    • Central Heating
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Large apartment, windows on 3 sides, new appliances, Wi-Fi, Conveniently situated on Main street downtown Torrington, from one to ten minutes away from restaurants, ten minutes away from movies theater, ten minutes away from the Post office, and all this is walking time to these locations, one... View all property information
    Make Inquiry
    Location Information
    Torrington, Connecticut 06790
    5 of 5 stars Reviewed August 14, 2015
    Stayed in this splendid apartment for 2 weeks in July- August 2015. Not only Denis was a great host. But he did install air conditioning in our bedroom, after I asked if there...
    See all reviews
    From
    $4,500
    / Week
    Payment Protection
    View Details
    Great Barrington, MA
    6 Bedrooms, 6 Bathrooms, Sleeps 12
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Playground
    • Internet Access
    • Mountain Views
    • Fireplace
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Stereo System
    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
    Make Inquiry
    Location Information
    Great Barrington, Berkshires 01230
    From
    $300
    / Night
    Payment Protection
    View Details
    1 / 19
    5 of 5 stars (3) Excellent
    Lakeville
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    other travelers have booked this property
    Overview Reviews (3) Make Inquiry
    Overview Reviews (3)
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Washer
    • Deck
    • Grill
    • Internet Access
    • Dryer
    • Water Views
    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
    Make Inquiry
    Location Information
    Lakeville, Connecticut 06068
    5 of 5 stars Reviewed May 26, 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 May 6, 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
    From
    $1,100
    / Week
    Payment Protection
    View Details
    1 / 17
    4 of 5 stars (1) Very good
    Goshen
    5 Bedrooms, 4 Bathrooms, Sleeps 12
    other travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Internet Access
    • Stereo System
    • Fireplace
    • Satellite TV
    • Deck
    • Air Conditioning
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in the heart of northwestern Connecticut's elegant Litchfield County. The house is a fully furnished, newly constructed 5 bedroom / 4 bathroom home complete with a beautiful kitchen, fireplace, deck, state-of-the-art home theater system and all the amenities of Woodridge Lake. You will... View all property information
    Make Inquiry
    Location Information
    Goshen, Connecticut 06756
    From
    $250
    / Night
    Payment Protection
    View Details
    Great Barrington, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    other traveler has booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Stereo System
    • Satellite TV
    • Washer
    • Mountain Views
    • Deck
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Surrounded by one of the most beautiful gardens in the Berkshires, Maya's Garden House is an outstanding example of an 18th century barn converted into a modern, comfortable, semi-secluded home. Located less than a mile from Great Barrington, it is close to everything the Berkshires are famous for;... View all property information
    Make Inquiry
    Location Information
    Great Barrington, Berkshires 01230
    From
    $500
    / Night
    Payment Protection
    View Details
    1 / 20
    5 of 5 stars (8) Excellent
    Sheffield, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 15
    Overview Reviews (8) Make Inquiry
    Overview Reviews (8)
    Amenities & Details
    • Deck
    • Hot Tub
    • Shared Outdoor Pool...
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    The Race Mountain House is set high on the slopes of the Taconic Mountains in Southern Berkshire County. Large, east-facing windows look out over a sweeping view of the Housatonic River Valley. In the early hours, the house floods with warm morning light and sunrises are spectacular. The inviting,... View all property information
    Make Inquiry
    Location Information
    Sheffield, Berkshires 01257
    5 of 5 stars Reviewed August 6, 2014
    Casey's place was really lovely - just exactly as described! WONDERFUL central great room/dining room for our large group to gather and relax - and beautiful decks for reading...
    5 of 5 stars Reviewed February 23, 2014
    Racebrook Lodge is our "home away from home", and Casey and Dave (the owners) are so incredibly hospitable. This house, their most recent addition to the property, is the GEM of...
    See all reviews
    From
    $175
    / Night
    Payment Protection
    View Details
    1 / 13
    4.5 of 5 stars (14) Very good
    Monterey, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 7
    other traveler has booked this property
    Overview Reviews (14) Make Inquiry
    Overview Reviews (14)
    Amenities & Details
    • Mountain Views
    • Playground
    • Water Views
    • Satellite TV
    • Internet Access
    • Waterfront
    • 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
    Make Inquiry
    Location Information
    Monterey, Berkshires 01245 0933
    4 of 5 stars Reviewed July 19, 2015
    What a relaxing, quiet getaway! The cabin was rustic, roomy and secluded. Fully stocked with just about everything you could possibly need to enjoy your stay. We saw two bears...
    See all reviews
    Get the List
    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 10
    5 of 5 stars (2) Excellent
    Great Barrington, MA
    2 Bedrooms, 1 Bathroom, Sleeps 5
    other travelers have booked this property
    Overview Reviews (2) Make Inquiry
    Overview Reviews (2)
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Mountain Views
    • DVD Player
    • Stereo System
    • Washer
    • 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
    Make Inquiry
    Location Information
    Great Barrington, Berkshires 33304
    5 of 5 stars Reviewed May 20, 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...
    See all reviews
    From
    $175
    / Night
    Payment Protection
    View Details
    South Lee, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    other traveler has booked this property
    Overview Make Inquiry
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Two Bedroom two bathroom condo located on beautiful resort in the Berkshires. Oak and Spruce Resort located 15 minutes to Tanglewood is the summer home in the Berkshires of the Boston Symphony Orchestra. Condominium sleeps 6 with an eat in kitchen and living area. Recreational activities, ample... View all property information
    Make Inquiry
    Location Information
    South Lee, Berkshires 01260
    From
    $425
    / Night
    Payment Protection
    View Details
    1 / 33
    5 of 5 stars (1) Excellent
    Simsbury
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Watersports Nearby
    • Hot Tub
    • Deck
    • Air Conditioning
    • There Are Tennis...
    • Horse Riding Nearby
    • Wi-Fi
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    New Nantucket Style Home ~ Summer June 15th-Sept 7th-$39k, $13,000mo, $3,300wkSpacious NEW 4 Bedroom, home, French Doors Galore! Light Bright & Open! Large Gourmet Kitchen, Nice Deck for relaxing! Situated on 4+ private acres, in a park like setting. Master suite + 1st floor bedroom suite. Private... View all property information
    Make Inquiry
    Location Information
    Simsbury, Connecticut 06070
    5 of 5 stars Reviewed July 7, 2015
    My three friends and I (two couples) are from NYC and found this place in search of a July 4th weekend getaway. The house itself is gorgeous and very spacious (at least compared...
    See all reviews
    From
    $375
    / Night
    Payment Protection
    View Details
    1 / 10
    5 of 5 stars (2) Excellent
    Sheffield, MA
    3 Bedrooms, 6 Bathrooms, Sleeps 8
    Overview Reviews (2) Make Inquiry
    Overview Reviews (2)
    Amenities & Details
    • Air Conditioning
    • Watersports Nearby
    • Housekeeping...
    • Hot Tub
    • TV
    • There Are Tennis...
    • Mountain Views
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Charmingly restored 1840 cottage in the apple orchard of a working organic farm. Completely renovated in 2015 with thoughtful amenities, fresh eggs and produce and acres of trails and views. Close to waterfalls and lakes. Nearby ski hills, Tanglewood concerts, theatre, film festival, dance and... View all property information
    Make Inquiry
    Location Information
    Sheffield, Berkshires 01257
    5 of 5 stars Reviewed July 24, 2015
    New England working farm. Lovely setting Great hospitality. Easy access to Tanglewood and other Berkshire attractions.
    5 of 5 stars Reviewed July 22, 2015
    What a beautifully decorated and comfortable cottage! Incredible deck for long lazy summer afternoons. Property owners were wonderful ... friendly & helpful. Cannot wait to...
    See all reviews
    From
    $1,250
    / Week
    Payment Protection
    View Details
    1 / 15
    5 of 5 stars (1) Excellent
    Sandisfield, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6
    other traveler has booked this property
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Stereo System
    • Satellite TV
    • Horse Riding Nearby
    • Wi-Fi
    • DVD Player
    • Shared Tennis Court
    • Central Heating
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Sandisfield, Berkshires 01255
    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
    $465
    / Night
    Payment Protection
    View Details
    1 / 33
    5 of 5 stars (3) Excellent
    Great Barrington, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 12
    other traveler has booked this property
    Overview Reviews (3) Make Inquiry
    Overview Reviews (3)
    Amenities & Details
    • Game Room
    • Stereo System
    • Boat Available
    • DVD Player
    • Mountain Views
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    Location Information
    Great Barrington, Berkshires 01230
    From
    $1,700
    / Week
    Payment Protection
    View Details
    1 / 10
    4 of 5 stars (1) Very good
    Great Barrington, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Refrigerator
    • Porch
    • Deck
    • DVD Player
    • Washer
    • TV
    • Dryer
    • Internet Access
    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
    Make Inquiry
    Location Information
    Great Barrington, Berkshires 01230
    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
    $150
    / Night
    Payment Protection
    View Details
    1 / 37
    5 of 5 stars (1) Excellent
    Salisbury
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    other traveler has booked this property
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • DVD Player
    • Internet Access
    • TV
    • Waterfront
    • Mountain Views
    • Deck
    • Water Views
    • 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 17 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
    Make Inquiry
    Location Information
    Salisbury, Connecticut 06079
    5 of 5 stars Reviewed September 8, 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
    From
    $259
    / Night
    Payment Protection
    View Details
    Tyringham, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • DVD Player
    • Deck
    • Dryer
    • Washer
    • Mountain Views
    • Central Heating
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This turn of the century cottage is located on a 130 acre property, and is stocked with linens. Three and a half baths, three full bedrooms, kitchen, living room, dining room, screened porches, a deck, and washer dryer. The house is across the brook and up a stone staircase (30 steps) from the... View all property information
    Make Inquiry
    Location Information
    Tyringham, Berkshires 01264
    From
    $230
    / Night
    Payment Protection
    View Details
    Great Barrington, MA
    1 Bedroom, 1 Bathroom, Sleeps 2
    other traveler has booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Refrigerator
    • Linens Provided
    • Stove
    • Fireplace
    • Mountain Views
    • Wi-Fi
    • Deck
    • Parking
    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
    Make Inquiry
    Location Information
    Great Barrington, Berkshires 01230
    From
    $1,200
    / Week
    Payment Protection
    View Details
    Great Barrington, MA
    3 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Patio
    • Dryer
    • TV
    • Washer
    • Stereo System
    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
    Make Inquiry
    Location Information
    Great Barrington, Berkshires 01230
    From
    $500
    / Night
    Payment Protection
    View Details
    Great Barrington, MA
    3 Bedrooms, 8 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Ping Pong Table
    • Game Room
    • Satellite TV
    • Central Heating
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    SummerStone is an elegant country home beside a state forest the NYT once referred to as 'the best kept secret in the Berkshires'. Enjoy red oak floors, tumbled marble showers, cozy fireplaces and soaring ceilings. Go kayaking, biking, swimming or hiking then relax on the 600 sq. ft. porch. Ping... View all property information
    Make Inquiry
    Location Information
    Great Barrington, Berkshires 01258
    From
    $495
    / Night
    Payment Protection
    View Details
    New Hartford
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    other traveler has booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Shared Tennis Court
    • Water Views
    • DVD Player
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Come enjoy a stay in this newly remodeled waterfront property on West Hill Lake in Litchfield County. Located on 4+ acres, 3 wooded, this 4bed/3bath 2600+ square foot home can comfortably accommodate up to 8 guests. Beautifully appointed, the features include; wood burning fireplace, marble... View all property information
    Make Inquiry
    Location Information
    New Hartford, Connecticut 06057
    From
    $1,250
    / Week
    Payment Protection
    View Details
    Monterey, MA
    Studio, 2 Bathrooms, Sleeps 7
    Overview Make Inquiry
    Overview
    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
    Make Inquiry
    Location Information
    Monterey, Berkshires 01245
    From
    $1,600
    / Week
    Payment Protection
    View Details
    New Marlborough, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Grill
    • Dryer
    • Central Heating
    • Wi-Fi
    • Washer
    • DVD Player
    • Refrigerator
    • TV
    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
    Make Inquiry
    Location Information
    New Marlborough, Berkshires 01230
    From
    $200
    / Night
    View Details
    1 / 11
    5 of 5 stars (15) Excellent
    Falls Village
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Reviews (15) Make Inquiry
    Overview Reviews (15)
    Amenities & Details
    • Water Views
    • Deck
    • Stereo System
    • 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
    Make Inquiry
    Location Information
    Falls Village, Connecticut 06031
    5 of 5 stars Reviewed May 29, 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 April 9, 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
    From
    $525
    / Night
    View Details
    1 / 35
    5 of 5 stars (16) Excellent
    Sheffield, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Reviews (16) Make Inquiry
    Overview Reviews (16)
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Deck
    • DVD Player
    • Stereo System
    • Mountain Views
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Enjoy your vacation in a beautiful historic house located in the heart of the Berkshires. Located two and a quarter hours north of New York City, this circa-1770s center chimney colonial will charm and delight your family and guests. 88 acres of land with views of Mt. Washington and Mount Everett... View all property information
    Make Inquiry
    Location Information
    Sheffield, Berkshires 01257
    From
    $225
    / Night
    Payment Protection
    View Details
    Tyringham, MA
    1 Bedroom, 1 Bathroom, Sleeps 2
    other travelers have booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Refrigerator
    • Parking
    • Satellite TV
    • Linens Provided
    • Internet Access
    • DVD Player
    • Balcony
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Tyringham, Berkshires 01264
    From
    $188
    / Night
    View Details
    1 / 12
    Great Barrington, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 10
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Satellite TV
    • Private Fishing...
    • Watersports Nearby
    • Waterfront
    • Water Views
    • Mountain Views
    • Central Heating
    • Internet Access
    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
    Make Inquiry
    Location Information
    Great Barrington, Berkshires 01236
    From
    $150
    / Night
    View Details
    1 / 22
    4.5 of 5 stars (2) Very good
    West Cornwall
    2 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Reviews (2) Make Inquiry
    Overview Reviews (2)
    Amenities & Details
    • Dryer
    • Refrigerator
    • Satellite TV
    • Deck
    • Stereo System
    • Air Conditioning
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Furnished cottage, with large deck, on 4 acres of woods, with brook and 200 feet Housatonic River frontage. Use of Sharon beach, tennis courts, and children's play area. Located in the beautiful Litchfield Hills, the cottage is 2 minutes from West Cornwall and its covered bridge,10 minutes from... View all property information
    Make Inquiry
    Location Information
    West Cornwall, Connecticut 06796
    5 of 5 stars Reviewed August 18, 2015
    Really enjoyed staying here with y sister and partner and my family (three young kids), who played endlessly in the stream which was full of frogs and stones. We could relax from...
    4 of 5 stars Reviewed January 30, 2015
    This was a wonderful cabin, no bells or whistles, but all of the amenities. It was comfortable clean and very spacious. The floor plan lends itself to lots of nooks and crannies...
    See all reviews
    From
    $357
    / Night
    View Details
    1 / 23
    Great Barrington, MA
    6 Bedrooms, 5 Bathrooms, Sleeps 12
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Stereo System
    • Hot Tub
    • Satellite TV
    • Deck
    • Air Conditioning
    • Internet Access
    • Fireplace
    • 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
    Make Inquiry
    Location Information
    Great Barrington, Berkshires 01230