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

Great Barrington Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Great Barrington vacation 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 ￥16,377
￥24,478 total
includes taxes & fees
Aug 31 - Sep 1
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 ￥32,042
￥49,754 total
includes taxes & fees
Sep 1 - Sep 2
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 ￥42,722
￥64,687 total
includes taxes & fees
Aug 24 - Aug 25
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 ￥34,192
￥53,285 total
includes taxes & fees
Sep 20 - Sep 21
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 ￥50,436
￥88,152 total
includes taxes & fees
Sep 1 - Sep 2
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)
"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 ￥89,574
￥207,691 total
includes taxes & fees
Aug 23 - Aug 24
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 traveler
The price is ￥145,385
￥243,584 total
includes taxes & fees
Aug 23 - Aug 24
Renovated Downtown Great Barrington House
Lobby

8. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,084 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
The price is ￥16,915
￥22,430 total
includes taxes & fees
Aug 30 - Aug 31
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 ￥27,690
￥50,548 total
includes taxes & fees
Sep 2 - Sep 3
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 ￥23,735
￥30,305 total
includes taxes & fees
Aug 23 - Aug 24
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 ￥20,472
￥22,931 total
includes taxes & fees
Aug 27 - Aug 28
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 ￥39,083
￥82,186 total
includes taxes & fees
Sep 7 - Sep 8
Cheerful 3-bedroom cottage with woodstove
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 ￥27,500
￥63,566 total
includes taxes & fees
Sep 14 - Sep 15
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 ￥15,522
￥20,927 total
includes taxes & fees
Aug 24 - Aug 25
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 ￥11,076
￥32,026 total
includes taxes & fees
Aug 23 - Aug 24
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 ￥44,827
￥92,579 total
includes taxes & fees
Sep 21 - Sep 22
Treetop Hideaway in Tyringham
Outdoor dining

17. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
The price is ￥63,688
￥100,545 total
includes taxes & fees
Aug 30 - Aug 31
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 ￥16,804
￥22,366 total
includes taxes & fees
Aug 24 - Aug 25
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 ￥9,697
￥47,763 total
includes taxes & fees
Sep 13 - Sep 14
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 ￥25,465
￥63,069 total
includes taxes & fees
Aug 25 - Aug 26
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Great Barrington Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

8/10 Good
"Excellent staff interaction. Great price and excellent location."
Irene 2-night trip
Posted 9 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Great Barrington

Search for holiday rentals in Great Barrington on Expedia! You can easily find your home rentals, villas, holiday apartments in Great Barrington using one of the methods below:

  • View our selection of featured holiday rentals in Great Barrington
  • Use the map to find apartments and other holiday homes in the Great Barrington neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Great Barrington while they last

Look no further and take a look at our great range of rental properties in Great Barrington!

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: This highly rated vacation 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 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. Our travelers also rate Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB! as a favorite home for rent in Great Barrington.

How many vacation rentals are there in Great Barrington?

With 95 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.