Great Barrington holiday homes
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
15% off
Price is NZ$12,277
NZ$12,277
NZ$1,754 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 NZ$5,132
NZ$5,132
NZ$733 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 NZ$3,839
NZ$3,839
NZ$548 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 NZ$4,384
NZ$4,384
NZ$626 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 NZ$16,057
NZ$16,057
NZ$2,294 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 NZ$4,190
NZ$4,190
NZ$599 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 NZ$4,166
NZ$4,166
NZ$595 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 NZ$16,535
NZ$16,535
NZ$2,362 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 NZ$3,966
NZ$3,966
NZ$567 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 NZ$4,126
NZ$4,126
NZ$589 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 NZ$2,412
NZ$2,412
NZ$345 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 NZ$15,856
NZ$15,856
NZ$2,265 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 NZ$21,905
NZ$21,905
NZ$3,129 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 NZ$6,173
NZ$6,173
NZ$882 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 NZ$9,404
NZ$9,404
NZ$1,343 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 NZ$4,870
NZ$4,870
NZ$696 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 NZ$7,349
NZ$7,349
NZ$1,050 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 NZ$7,449
NZ$7,449
NZ$1,064 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 NZ$13,599
NZ$13,599
NZ$1,943 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 NZ$8,403
NZ$8,403
NZ$1,200 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 NZ$5,867
NZ$5,867
NZ$838 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
14% off
Price is NZ$6,093
NZ$6,093
NZ$870 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 NZ$6,391
NZ$6,391
NZ$913 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 NZ$3,108
NZ$3,108
NZ$444 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Great Barrington
Showing deals for: 4 Oct - 7 Oct
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)
The current price is NZ$7,906
NZ$7,906
for 3 nights, 1 home
NZ$2,635 per night
includes taxes & fees
10 Acre Country Estate with Pool, Hot Tub & Views!
Sleeps 14 · 5 bedrooms · 4 bathrooms
9.89.8 out of 10
Exceptionalexceptional
The current price is NZ$4,317
NZ$4,317
for 3 nights, 1 home
NZ$1,439 per night
includes taxes & fees
Private Berkshires Getaway Minutes to Ski Butternut
Sleeps 6 · 4 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
The current price is NZ$2,939
NZ$2,939
for 3 nights, 1 home
NZ$980 per night
includes taxes & fees
NEW RENO - Chalet-style farm loft near Tanglewood
Sleeps 5 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
The current price is NZ$933
NZ$933
for 3 nights, 1 room
NZ$311 per night
includes taxes & fees
Resort Stay with Arcade, Heated Pool, Sports Courts & Family Perks
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
8 reviews(8 reviews)
The current price is NZ$993
NZ$993
for 3 nights, 1 home
NZ$331 per night
includes taxes & fees
Hudson Valley private 70's-style cabin on five acres, five minutes to town!
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
The current price is NZ$890
NZ$890
for 3 nights, 1 cabin
NZ$297 per night
includes taxes & fees
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