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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 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 SAR 1,014
SAR 1,527 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 SAR 797
SAR 1,235 total
includes taxes & fees
19 Aug - 20 Aug
Cozy Riverside Berkshires Retreat
Beach nearby, sun loungers, beach towels

3. 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 SAR 773
SAR 1,103 total
includes taxes & fees
13 Sep - 14 Sep
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
3 bedrooms, iron/ironing board, WiFi, bed sheets

4. 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 SAR 1,554
SAR 2,558 total
includes taxes & fees
8 Sep - 9 Sep
Cozy. Clean. Free bagel shop. 3 Fireplaces.
TV, fireplace, printers

5. 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 SAR 2,125
SAR 4,928 total
includes taxes & fees
19 Aug - 20 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Coffee/tea maker, fridge, microwave, oven

6. 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 SAR 4,755
SAR 7,493 total
includes taxes & fees
23 Aug - 24 Aug
Renovated Downtown Great Barrington House
Lobby

7. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,070 reviews)
"A beautiful, spacious and conveniently located suite just a few minutes away that everything the Berkshires have to offer. I really love this place!"
United States
Karilyn
The price is SAR 355
SAR 481 total
includes taxes & fees
31 Aug - 1 Sep
Berkshire Mountain Lodge
Desk, iron/ironing board, WiFi, bed sheets

8. 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 SAR 563
SAR 723 total
includes taxes & fees
16 Aug - 17 Aug
The Brooks Motel: Exceptional Suite
Interior

9. 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 SAR 657
SAR 1,199 total
includes taxes & fees
1 Sep - 2 Sep
Sweet Cozy Victorian in Housatonic. Close to everything.
Exterior

10. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (165 reviews)
"This inn with cabins is a gorgeous setting with a nice vegetable garden, the setting is a bit remote and we like it, very quiet, unfortunately the restaurant was close."
United States
philippe
The price is SAR 501
SAR 561 total
includes taxes & fees
16 Aug - 17 Aug
Micosta Leisure Inn
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 SAR 927
SAR 1,950 total
includes taxes & fees
7 Sep - 8 Sep
Cheerful 3-bedroom cottage with woodstove
Property grounds

12. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (56 reviews)
"👍"
United States
Mike
The price is SAR 368
SAR 497 total
includes taxes & fees
16 Aug - 17 Aug
All comforts of home
Smart TV

13. 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 SAR 760
SAR 1,642 total
includes taxes & fees
24 Aug - 25 Aug
stylish Berkshires Retreat
Outdoor dining

14. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
The price is SAR 1,511
SAR 2,386 total
includes taxes & fees
30 Aug - 31 Aug
Stockbridge In-town Escape
TV

15. 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 SAR 1,239
SAR 2,405 total
includes taxes & fees
2 Sep - 3 Sep
Treetop Hideaway in Tyringham
Coffee/tea maker, fridge, microwave, oven

16. 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.
The price is SAR 2,118
SAR 4,089 total
includes taxes & fees
17 Aug - 18 Aug
Historic Stockbridge Villa on 25 acres
Coffee/tea maker, fridge, microwave, oven

17. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is SAR 285
SAR 812 total
includes taxes & fees
16 Aug - 17 Aug
NEW RENO - Chalet-style farm loft near Tanglewood
Property grounds

18. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (35 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is SAR 399
SAR 531 total
includes taxes & fees
20 Aug - 21 Aug
All the comforts of home
Coffee/tea maker, fridge, microwave, oven

19. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (31 reviews)
"This was a wonderful place to stay. We especially loved the easy access to the toys so the kids could start playing while we unloaded the car. It was perfect and just what we needed."
United States
Megan A.
The price is SAR 544
SAR 1,296 total
includes taxes & fees
31 Aug - 1 Sep
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
4 bedrooms, travel crib, WiFi, bed sheets

20. 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 SAR 1,909
SAR 3,278 total
includes taxes & fees
2 Sep - 3 Sep
Stylish Mid-century Modern Berkshires Cape
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

The Red Lion Inn

The Red Lion Inn

8/10 Good
"Historic Inn with lots of nostalgia, character, esteemed guest list and many museum-worthy artifacts and memorabilia items! Rooms are quaint, and though expected to be somewhat rustic, are a bit run down - stained carpeting, leaky tub, lukewarm shower in the evening, etc. Great mattress on the bed, and nice clean linens, robe, etc! Great location! Friendly staff!"
Michael 2-night trip
Posted 2 hours ago
The Red Lion Inn

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.