Great Barrington holiday rentals
We found 967 holiday rentals — enter your dates for availability
Select the perfect holiday rental within easy reach of Great Barrington, MA (GBR-Walter J. Koladza). Holiday rentals offer the best amenities for your family, friends or furry companion, such as parking and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Great Barrington, MA (GBR-Walter J. Koladza)
Showing deals for:10 Oct - 17 Oct
Image gallery for Berkshires Summer Chalet w/ Pool + Private Hiking Trails
1010 out of 10 rating
Exceptional
(6 reviews)
Berkshires Summer Chalet w/ Pool + Private Hiking Trails
Great Barrington, MA
16% off
Price is AU$10,808
AU$10,808
AU$1,544 per night
includes taxes & fees
Image gallery for Waterfront Cottage 10 Min From Great Barrington
1010 out of 10 rating
Exceptional
(97 reviews)
Waterfront Cottage 10 Min From Great Barrington
Great Barrington, MA
8% off
Price is AU$4,724
AU$4,724
AU$675 per night
includes taxes & fees
Image gallery for Peaceful, Post and Beam Loft, Sleeps 9
1010 out of 10 rating
Exceptional
(19 reviews)
Peaceful, Post and Beam Loft, Sleeps 9
Great Barrington, Massachusetts
14% off
Price is AU$3,535
AU$3,535
AU$505 per night
includes taxes & fees
Image gallery for Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
9.29.2 out of 10 rating
Wonderful
(11 reviews)
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Great Barrington, MA
8% off
Price is AU$4,036
AU$4,036
AU$577 per night
includes taxes & fees
Image gallery for Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10
1010 out of 10 rating
Exceptional
(6 reviews)
Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Stockbridge, MA
8% off
Price is AU$14,173
AU$14,173
AU$2,025 per night
includes taxes & fees
Image gallery for Lakefront Summer Spectacular in New England Just 2 Hours From NYC
1010 out of 10 rating
Exceptional
(73 reviews)
Lakefront Summer Spectacular in New England Just 2 Hours From NYC
Sharon, CT
8% off
Price is AU$3,858
AU$3,858
AU$551 per night
includes taxes & fees
Image gallery for Konkapot Cottage, Pastoral Bliss With Wide Views
1010 out of 10 rating
Exceptional
(20 reviews)
Konkapot Cottage, Pastoral Bliss With Wide Views
New Marlborough, MA
8% off
Price is AU$3,835
AU$3,835
AU$548 per night
includes taxes & fees
Image gallery for Charming Columbia County Farm House
9.69.6 out of 10 rating
Exceptional
(24 reviews)
Charming Columbia County Farm House
Hillsdale, NY
8% off
Price is AU$3,650
AU$3,650
AU$521 per night
includes taxes & fees
Image gallery for Modern home with Catskill views, guesthouse and heated pool near Chatham/Hudson
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Modern home with Catskill views, guesthouse and heated pool near Chatham/Hudson
Chatham, NY
8% off
Price is AU$14,581
AU$14,581
AU$2,083 per night
includes taxes & fees
Image gallery for 1500 sqft private entrance with beautiful views of the Berkshire Mountains
1010 out of 10 rating
Exceptional
(42 reviews)
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Lee, MA
8% off
Price is AU$3,793
AU$3,793
AU$542 per night
includes taxes & fees
Image gallery for Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
9.69.6 out of 10 rating
Exceptional
(17 reviews)
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
Sandisfield, MA
8% off
Price is AU$2,250
AU$2,250
AU$321 per night
includes taxes & fees
Image gallery for General Williams Estate House Lenox/Stockbridge
9.89.8 out of 10 rating
Exceptional
(110 reviews)
General Williams Estate House Lenox/Stockbridge
Stockbridge, MA
8% off
Price is AU$13,997
AU$13,997
AU$2,000 per night
includes taxes & fees
Image gallery for Beautiful anytime of the Year.. Sunny Pond will not disappoint.
1010 out of 10 rating
Exceptional
(8 reviews)
Beautiful anytime of the Year.. Sunny Pond will not disappoint.
Austerlitz, NY
8% off
Price is AU$18,741
AU$18,741
AU$2,677 per night
includes taxes & fees
Image gallery for Fun Getaway Lakehouse in the Hudson Valley
1010 out of 10 rating
Exceptional
(15 reviews)
Fun Getaway Lakehouse in the Hudson Valley
Craryville, NY
12% off
Price is AU$5,699
AU$5,699
AU$814 per night
includes taxes & fees
Image gallery for Luxurious Mountain Retreat - Private 40-Acre Family Haven
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Luxurious Mountain Retreat - Private 40-Acre Family Haven
New Marlborough, MA
16% off
Price is AU$8,736
AU$8,736
AU$1,248 per night
includes taxes & fees
Image gallery for Berkshire Lake at the Pillow, and EV!
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Berkshire Lake at the Pillow, and EV!
Lee, MA
8% off
Price is AU$4,484
AU$4,484
AU$641 per night
includes taxes & fees
Image gallery for Catamount, Zip Line, Private Setting, Book Now!
1010 out of 10 rating
Exceptional
(6 reviews)
Catamount, Zip Line, Private Setting, Book Now!
Great Barrington, Massachusetts
7% off
Price is AU$6,847
AU$6,847
AU$978 per night
includes taxes & fees
Image gallery for Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
1010 out of 10 rating
Exceptional
(10 reviews)
Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
Lee, MA
8% off
Price is AU$6,728
AU$6,728
AU$961 per night
includes taxes & fees
Image gallery for Imagine Being Lakeside This Summer! Book Now!
1010 out of 10 rating
Exceptional
(16 reviews)
Imagine Being Lakeside This Summer! Book Now!
Lenox, Massachusetts
15% off
Price is AU$7,591
AU$7,591
AU$1,084 per night
includes taxes & fees
Image gallery for Mountain Luxury Retreat-Amazing Views/Saltwater Pool/Family Friendly/Berkshires
1010 out of 10 rating
Exceptional
(45 reviews)
Mountain Luxury Retreat-Amazing Views/Saltwater Pool/Family Friendly/Berkshires
Copake Falls, NY
8% off
Price is AU$11,875
AU$11,875
AU$1,696 per night
includes taxes & fees
Image gallery for Berkshire Rural Retreat
1010 out of 10 rating
Exceptional
(21 reviews)
Berkshire Rural Retreat
Canaan, NY
8% off
Price is AU$5,408
AU$5,408
AU$773 per night
includes taxes & fees
Image gallery for Serene Berkshires Home On 5+ Acres, Rustic & Chic
8.88.8 out of 10 rating
Excellent
(6 reviews)
Serene Berkshires Home On 5+ Acres, Rustic & Chic
Otis, Massachusetts
15% off
Price is AU$5,616
AU$5,616
AU$802 per night
includes taxes & fees
Image gallery for Beautifully Restored, Secluded Farmhouse
1010 out of 10 rating
Exceptional
(23 reviews)
Beautifully Restored, Secluded Farmhouse
Hillsdale, NY
7% off
Price is AU$5,903
AU$5,903
AU$843 per night
includes taxes & fees
Image gallery for Cozy Cabin in the Berkshires
1010 out of 10 rating
Exceptional
(16 reviews)
Cozy Cabin in the Berkshires
Sandisfield, MA
12% off
Price is AU$2,861
AU$2,861
AU$409 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Great Barrington
Amazing 5 Star Estate! FREE Day Passes to Wellness Center included w/ your stay!
Sleeps 8 · 4 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Cozy retreat in beautiful country setting
Sleeps 2 · 1 bedroom
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
10 Acre Country Estate with Pool, Hot Tub & Views!
Sleeps 14 · 5 bedrooms · 4 bathrooms
9.89.8 out of 10
Exceptionalexceptional
Private Berkshires Getaway Minutes to Ski Butternut
Sleeps 6 · 4 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
Perfect Vacation Get Away - Historical New Marlborough
Sleeps 4 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
54 reviews(54 reviews)
NEW RENO - Chalet-style farm loft near Tanglewood
Sleeps 5 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value