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

Great Barrington Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
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 holiday rentals

Coffee/tea maker, fridge, microwave, oven

1. 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 NZ$259
includes taxes & fees
31 Aug - 1 Sept
Cozy 1-bedroom studio in serene Great Barrington with AC
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 NZ$490
includes taxes & fees
21 Sept - 22 Sept
Cozy Riverside Berkshires Retreat
Coffee/tea maker, fridge, microwave, oven

3. 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 NZ$676
includes taxes & fees
24 Aug - 25 Aug
Home in Great Barrington
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 NZ$559
includes taxes & fees
21 Sept - 22 Sept
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 NZ$917
includes taxes & fees
1 Sept - 2 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
TV, fireplace, printers

6. 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)
"Beautiful house with great amenities in a convenient location. We loved the open concept that provided a great space for cooking, hanging out and playing games together while enjoying a beautiful view. The gameroom was so much fun, and we’d love to visit again when the sauna is finished. Our family of 6 and family dog loved it!"
United States
Rebecca K.
The price is NZ$2,123
includes taxes & fees
24 Aug - 25 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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 traveller
Renovated Downtown Great Barrington House
Lobby

8. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,086 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
The price is NZ$214
includes taxes & fees
31 Aug - 1 Sept
Berkshire Mountain Lodge
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, (10 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 NZ$523
includes taxes & fees
1 Sept - 2 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.
Desk, iron/ironing board, WiFi, bed sheets

10. 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 NZ$319
includes taxes & fees
9 Sept - 10 Sept
The Brooks Motel: Exceptional Suite
Exterior

11. 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 NZ$242
includes taxes & fees
27 Aug - 28 Aug
Micosta Leisure Inn
Property grounds

12. 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 NZ$832
includes taxes & fees
22 Sept - 23 Sept
Cheerful 3-bedroom cottage with woodstove
Smart TV

13. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.2 out of 10, Wonderful, (5 reviews)
The price is NZ$632
includes taxes & fees
21 Sept - 22 Sept
stylish Berkshires Retreat
Property grounds

14. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (56 reviews)
"👍"
United States
Mike
The price is NZ$221
includes taxes & fees
27 Aug - 28 Aug
All comforts of home
Coffee/tea maker, fridge, microwave, oven

15. 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 NZ$347
includes taxes & fees
24 Aug - 25 Aug
NEW RENO - Chalet-style farm loft near Tanglewood
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 NZ$932
includes taxes & fees
21 Sept - 22 Sept
Treetop Hideaway in Tyringham
Outdoor dining

17. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
The price is NZ$1,052
includes taxes & fees
30 Aug - 31 Aug
Stockbridge In-town Escape
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 NZ$236
includes taxes & fees
24 Aug - 25 Aug
All the comforts of home
Interior

19. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is NZ$476
includes taxes & fees
13 Sept - 14 Sept
Real Estate: Therapy - Lake, Laundry, Love it
Outdoor spa tub

20. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is NZ$654
includes taxes & fees
24 Aug - 25 Aug
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
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 Yankee Inn

The Yankee Inn

8/10 Good
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."
Luann 1-night trip
Posted 9 hours ago
The Yankee Inn

Find out more about Great Barrington

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Great Barrington holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Great Barrington. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Great Barrington. Seeing all the best attractions is bound to make you fall in love with Great Barrington. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Great Barrington short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Great Barrington?

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

What are some of the best holiday rentals that Great Barrington has to offer?

Cozy Riverside Berkshires Retreat: This highly rated holiday home rental in Great Barrington 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Our travellers also rate Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB! as a favourite home for rent in Great Barrington.

How many holiday rentals are there in Great Barrington?

With 95 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Great Barrington?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Great Barrington. Holiday rentals offer amenities like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for family trips.