A large stone church with a tall bell tower and arched windows.

Great Barrington Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Great Barrington vacation rentals

Coffee/tea maker, fridge, microwave, oven

1. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is AED 992
AED 1,502 total
includes taxes & fees
24 Aug - 25 Aug
Home in Great Barrington
Interior

2. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is AED 702
AED 1,105 total
includes taxes & fees
16 Sep - 17 Sep
Cozy Riverside Berkshires Retreat
TV, fireplace, printers

3. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is AED 2,079
AED 4,874 total
includes taxes & fees
19 Aug - 20 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Beach nearby, sun loungers, beach towels

4. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is AED 737
AED 1,053 total
includes taxes & fees
16 Sep - 17 Sep
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
3 bedrooms, iron/ironing board, WiFi, bed sheets

5. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is AED 1,198
AED 2,093 total
includes taxes & fees
31 Aug - 1 Sep
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Coffee/tea maker, fridge, microwave, oven

6. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (2 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is AED 380
AED 568 total
includes taxes & fees
24 Aug - 25 Aug
Cozy 1-bedroom studio in serene Great Barrington with AC
Coffee/tea maker, fridge, microwave, oven

7. Renovated Downtown Great Barrington House

Renovated Downtown Great Barrington House
Great Barrington
8.0 out of 10, Very Good, (2 reviews)
"This is a very nice place to stay. My wife and I both remarked on how comfortable we felt there. A proper home away from home. It was well stocked on all fronts, including the kitchen. And I think what put the finishing touch on was the attention to detail... The towels were large, the bathroom rolls were Charmin Ultrasoft, and there were tissue boxes everywhere you're likely to need them. The hosts seem to work with a service, so you can reach someone with questions immediately, and the hosts...
United States
Anonymous traveler
The price is AED 3,721
AED 6,074 total
includes taxes & fees
23 Aug - 24 Aug
Renovated Downtown Great Barrington House
Interior

8. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (9 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is AED 643
AED 1,169 total
includes taxes & fees
1 Sep - 2 Sep
Sweet Cozy Victorian in Housatonic. Close to everything.
Exterior

9. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (168 reviews)
"Clean, quiet and relaxing stay."
United States
Andrea
The price is AED 509
AED 570 total
includes taxes & fees
24 Aug - 25 Aug
Micosta Leisure Inn
Lobby

10. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,077 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
The price is AED 347
AED 470 total
includes taxes & fees
31 Aug - 1 Sep
Berkshire Mountain Lodge
Property grounds

11. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 907
AED 1,908 total
includes taxes & fees
7 Sep - 8 Sep
Cheerful 3-bedroom cottage with woodstove
Coffee/tea maker, fridge, microwave, oven

12. Historic Stockbridge Villa on 25 acres

Historic Stockbridge Villa on 25 acres
Stockbridge
10.0 out of 10, Exceptional, (20 reviews)
"Great home, warm and welcoming!! Hosts were great! Very attentive, enjoyed meeting Lisa. Plenty of room for our gathering, accommodations were excellent! "
United States
Amy M.
Historic Stockbridge Villa on 25 acres
Smart TV, books

13. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is AED 2,094
AED 3,266 total
includes taxes & fees
19 Aug - 20 Aug
Fantastic 2-bedroom house with AC in quaint Hillsdale.
4 bedrooms, travel crib, WiFi, bed sheets

14. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is AED 1,868
AED 3,206 total
includes taxes & fees
2 Sep - 3 Sep
Stylish Mid-century Modern Berkshires Cape
Desk, iron/ironing board, WiFi, bed sheets

15. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is AED 551
AED 699 total
includes taxes & fees
19 Aug - 20 Aug
The Brooks Motel: Exceptional Suite
TV

16. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is AED 1,043
AED 2,131 total
includes taxes & fees
16 Sep - 17 Sep
Treetop Hideaway in Tyringham
Smart TV

17. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (4 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is AED 654
AED 1,493 total
includes taxes & fees
14 Sep - 15 Sep
stylish Berkshires Retreat
Property grounds

18. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (10 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is AED 918
AED 1,506 total
includes taxes & fees
23 Aug - 24 Aug
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
House (4 Bedrooms) | Interior

19. Mtn-view Retreat in Huson Valley: Great for Groups

Mtn-view Retreat in Huson Valley: Great for Groups
3.0 star property
Hudson
The price is AED 948
AED 2,797 total
includes taxes & fees
21 Aug - 22 Aug
Mtn-view Retreat in Huson Valley: Great for Groups
Dining

20. Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is AED 955
AED 1,230 total
includes taxes & fees
17 Sep - 18 Sep
Sugar Shack - 300 square feet of pure sweetness.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Great Barrington Hotel Reviews

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"Having the pool and hot tub was great. Very clean. Breakfast was complete with oatmeal and hot breakfast choices. Location was Central to all sites like Tanglewood. Highly recommended."
Joseph 1-night trip
Posted 5 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Frequently asked questions

Can I find a vacation rental in Great Barrington?

Yes, there are vacation rentals in Great Barrington close to Mahaiwe Performing Arts Center, or you can select a more secluded option if you'd like a relaxing place to stay. Visitors like the top-notch restaurants and live music in Great Barrington. Leave some time to check out the ski slopes and theater scene during your trip.

What are some of the best vacation rentals in Great Barrington?

Cozy Riverside Berkshires Retreat: Visitors give good reviews to this Great Barrington vacation home rental, which is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Great Barrington?

With 96 Expedia vacation rentals, you're sure to find just the right place for your Great Barrington stay.

What can I see and do in Great Barrington?

Housatonic River Walk and Housatonic River are a couple of scenic spots to enjoy the outdoors, whereas Art et Industrie is one of the cultural attractions. Mahaiwe Performing Arts Center and Lake Mansfield Park are other places to visit while you're in town.

What are vacation rentals like in Great Barrington?

Vacation rentals are privately owned properties you can reserve for several days or more in Great Barrington. Vacation rentals offer extras such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for a family getaway.