$10,980
Available: Right Now
Listed: 04/05/2024
Great Barrington, MA
This preserved 18th century farmhouse is situated on a picturesque 24 acre estate boasting southerly views of rolling hills down to northern Connecticut including the majestic Mount Everett, the highest peak in the south Taconic mountains and adj...
$17,880
Available: Right Now
Listed: 04/05/2024
Great Barrington, MA
Summary:Newly renovated three bedroom “on the hill” in Great Barrington awaits your next family stay. Short walk to downtown Great Barrington for dining, easy stroll to Lake Mansfield for swimming or fishing, and walking trails. Quick 20 minute d...
$12,000
Available: Right Now
Listed: 30/04/2024
Great Barrington, MA
Welcome to our cozy Berkshires retreat, located just a stone's throw away from downtown Great Barrington and minutes to ski slopes at Butternut! With three wood-burning fireplaces, this three-bedroom spacious and charming house is the perfect place t...
$64,830
Available: Right Now
Listed: 04/05/2024
Great Barrington, MA
Rosecliff Amenities: Main House, Heated Pool with Pool house, Sleeps 13 in beds or 15 max. high speed WIFI internet and good cell service, Smart TVs with Streaming TV channels, central AC throughout, several areas for outdoor seating, sun umbrellas, ...
$15,060
Available: Right Now
Listed: 04/05/2024
Great Barrington, MA
*20% discount for month stays/ 10% discount for week stays automatically applied* A recently renovated historic home with amazing nature views (perfect for fall leaf peeping!) and an even better location in The Berkshires hippest and charming tow...
$28,050
Available: Right Now
Listed: 04/05/2024
Great Barrington, MA
Welcome to Moose Lodge! This expansive home has everything your group needs to enjoy quality time together among the beauty of the Berkshires! Surrounded by trees, the large patio features a spacious outdoor dining table, comfortable lounge, and bars...
$6,330
Available: Right Now
Listed: 30/04/2024
Great Barrington, MA
Summary:Captivating home overlooking Stevens Lake within minutes from Butternut! Private and only a short distance from the many things Great Barrington has to offer.We have a 30 day Min.The Space:Impeccable home and location. Recen...
$92,490
Available: Right Now
Listed: 04/05/2024
Great Barrington, MA
A breathtaking estate nestled on a mountain slope of granite in the Berkshires. Immerse yourself in 120 acres of natural wonders & wildlife. A private oasis that delivers inner peace & rejuvenation. Main house: 9 bedrooms and 8 bathsGuest hou...
$7,500
Available: Right Now
Listed: 30/04/2024
Great Barrington, MA
Charming home steps away from downtown Great Barrington. Lots of modern amenities, close to all the fantastic cultural attractions of the Berkshires like Tanglewood, Jacobs Pillow as wells all the theater throughout the Berkshires. Huge backyard righ...
$12,630
Available: Right Now
Listed: 04/05/2024
Great Barrington, MA
NOTE: Our street name has changed to Woodland Hill (from Squaw Peak). Same house, same house number - different street name.) Booking for the rest of 2023 and through 2024 ! After a fully booked summer 2023, and bookings into September...
$10,290
Available: Right Now
Listed: 04/05/2024
Great Barrington, MA
Spacious house in excellent condition on 3 secluded acres in Great Barrington, the heart of the Southern Berkshires, available for periods from 1 to 3 weeks (1 week minimum, 3 week maximum). Rural feel, yet only 5 min from the center of town and even...
$34,290
Available: Right Now
Listed: 04/05/2024
Great Barrington, MA
Bright, comfortable house with pool and comfortable outdoor seating and eating areas, endless mountain views in front and acres of open pasture in back. Four bedrooms and 3.5 baths. Two bedrooms with king sized beds, large closets and en suite newly ...
$32,760
Available: Right Now
Listed: 01/05/2024
Great Barrington, MA
New Modern Farmhouse green home available for full month July rental. 4 minutes to Great Barrington, close to countless restaurants, has shared pool about 100 yards from house, grand yard with volleyball/badminton net, croquet set, blueberry plants, ...
$25,470
Available: Right Now
Listed: 02/05/2024
Great Barrington, MA
Won't last long! A recently renovated home on 10 acres less than 10 minutes from downtown Great Barrington. With two primary suites with balconies, a heated pool, and a screen-in porch, you'll get ultimate privacy while also having accessibility to a...
$12,720
Available: Right Now
Listed: 01/05/2024
Great Barrington, MA
Lovely 4 bedroom, sleeps 10. 3-story classic Victorian home in family-friendly neighborhood. Clean modern interiors and nature-enjoying exteriors including gardens, covered porch, screened deck and fenced yard. Easy walk to Main Street and Lake. Owne...
$9,780
Available: Right Now
Listed: 04/05/2024
Great Barrington, MA
Leave your busy schedule behind for a life of leisure at this vacation rental hideaway. This rustic 4-bed, 2-bath home is complete with woodsy-style decor, contemporary furnishings, and space for 10. It's truly a sportsman's paradise - tucked away in...
$4,950
Available: Right Now
Listed: 02/05/2024
Housatonic, MA, 01236
Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitc...
$12,000
Available: Right Now
Listed: 04/05/2024
Great Barrington, MA
Spread out in this spacious family home. The first floor has an easy flow from room to room and includes a sunny eat-in-kitchen with sit-down table and breakfast bar where family and friends have plenty of room to gather while meals are being prepare...
$26,010
Available: Right Now
Listed: 04/05/2024
Great Barrington, MA
This is a unique property located on more than 1000 feet of the Green River. Over a hundred and sixty acres of beautiful woods and fields. Large indoor gymnasium with full basketball court, also good for indoor skating and roller blading. Babbling st...
$16,770
Available: Right Now
Listed: 04/05/2024
Great Barrington, MA
We are thrilled to share our country escape with you and hope you enjoy it as much as we do. Set on 5 acres of land, with an open backyard with a trampoline and trees surrounding you, our fully stocked home is true escape from the busy, over schedule...
$6,750
Available: Right Now
Listed: 04/05/2024
Great Barrington, MA
This charming and appropriately named "Little Cottage" was newly renovated in2017.Enjoy a short walk (300 feet) down a dirt road to a small beach and private dock on Lake Buel, beautifully situated in the heart of the Berkshires. Experience new a...
$5,340
Available: Right Now
Listed: 04/05/2024
Housatonic, MA, 01236
Three second-floor bedrooms, two baths (one up, one down), in my sweet, cozy village home in a quiet, safe, and walkable neighborhood. Your dog is welcome (although I can't seem to update this in the settings)! This home is family-friendly, with a fi...