Plan your trip

A building with a marquee sign reading "MAHAIWE Performing Arts Center" and a smaller sign for "Black Violin" performances.

Great Barrington Vacation Rentals

Bundle & Save

Get more, spend less whenever you see Bundle & Save deals

OneKeyCash

Earn OneKeyCash on all your eligible bookings

Upfront pricing

We are not like the others - we include taxes and fees

Check prices for these dates

Check prices for these dates, December 13 – 14, 2026

View in a map

Our top choices for Great Barrington vacation rentals

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

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

Location: Great Barrington
Guest rating: 8.8/10 (Excellent, 10 reviews)
Price: $104 nightly, $116 total, Nov 20 - Nov 21, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals
Review: great location , berkshires are awesome . very clean , host is excellent ., by bob i.

2. Home in Great Barrington

A cabin with a wooden deck and a stone pathway leading to the entrance.

Location: Great Barrington
Guest rating: 9.8/10 (Exceptional, 42 reviews)
Price: $271 nightly, $303 total, Dec 13 - Dec 14, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals
Review: Wonderful property and host very responsive., by Janet G.

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

A sandy beach with a lake and forest in the background.

Location: Great Barrington
Guest rating: 10/10 (Exceptional, 7 reviews)
Price: $291 nightly, $325 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals
Review: We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!, by Kristin O.

4. A Cozy Berkshire Escape l Close to the Slopes

A picnic table in a grassy yard with trees and a fence in the background.

Location: Great Barrington
Guest rating: 9.6/10 (Exceptional, 29 reviews)
Price: $269 nightly, $300 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals
Review: If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step., by Kelly B.

5. Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

A sign for East Rock Inn with a gravel path leading to a building surrounded by lush greenery.

Location: Great Barrington
Price: $329 nightly, $368 total, Nov 20 - Nov 21, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals

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

A modern kitchen with a granite countertop, stainless steel appliances, and a large island with drawers.

Location: Great Barrington
Guest rating: 10/10 (Exceptional, 5 reviews)
Price: $597 nightly, $667 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals
Review: 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!, by Mary R.

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

A modern two-story house with a stone foundation, a covered porch, and a small shed.

Location: Great Barrington
Guest rating: 10/10 (Exceptional, 10 reviews)
Price: $1,065 nightly, $1,189 total, Nov 20 - Nov 21, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals
Review: 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!, by Roberta

8. Berkshire Mountain Lodge

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

Location: Pittsfield
Guest rating: 9/10 (Wonderful, 1270 reviews)
Price: $107 nightly, $119 total, Dec 14 - Dec 15, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals
Review: Excellent stay!!!!, by Susan J

9. Micosta Leisure Inn

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

Location: Hudson
Guest rating: 9.2/10 (Wonderful, 197 reviews)
Price: $82 nightly, $92 total, Nov 19 - Nov 20, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals
Review: Great stay, by George

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

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

Location: Housatonic
Guest rating: 9.8/10 (Exceptional, 12 reviews)
Price: $259 nightly, $289 total, Nov 14 - Nov 15, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals
Review: This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again., by Eric H.

11. The Brooks Motel: Exceptional Suite

A room with a bed, a small table, and a chair. There is a window with blinds and a door leading to another room.

Location: Hillsdale
Guest rating: 7.2/10 (Good, 5 reviews)
Price: $191 nightly, $214 total, Nov 14 - Nov 15, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals
Review: Close to the competition I was in, by Joan

12. Cheerful 3-bedroom cottage with woodstove

An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

Location: Sheffield
Guest rating: 10/10 (Exceptional, 46 reviews)
Price: $366 nightly, $409 total, Nov 18 - Nov 19, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals
Review: The property was centrally located for skiing, and was a comfortable stay., by Kelly R.

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

A spacious living room with a wooden staircase, a dining area, and a television.

Location: Sherwood Forest
Guest rating: 9.6/10 (Exceptional, 4 reviews)
Price: $253 nightly, $283 total, Nov 18 - Nov 19, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals
Review: Very good trip overall. Great location. Just a few things needed to make it over the top!, by William C B.

14. Ideal location for summer and winter activities with plenty of outdoor space.

A stone fire pit surrounded by grass and trees in a wooded area.

Location: Hillsdale
Guest rating: 9.8/10 (Exceptional, 80 reviews)
Price: $307 nightly, $344 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals
Review: We very much enjoyed our two week stay in July. The cabin suited our needs in every regard. Our lab was also able to fully relax, whether it was napping on the screen porch or sitting by the fire pit. For those looking to explore the region, the location could not be better situated. Hoping to return over Christmas., by Richard M.

15. All comforts of home

A wooden deck with a staircase leading to a covered porch area.

Location: Hudson
Guest rating: 9.6/10 (Exceptional, 65 reviews)
Price: $110 nightly, $123 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals
Review: The room was sufficient to our needs. Didn’t realize it was a multi-unit property or that it was on the second floor., by Douglas

16. Secluded Family Home in Serene Stockbridge Woods

A covered porch with string lights, a ceiling fan, and outdoor seating.

Location: Stockbridge
Guest rating: 10/10 (Exceptional, 30 reviews)
Price: $533 nightly, $595 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals
Review: We had a wonderful time, we’d be happy to come back again , by Ofer C.

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

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

Location: New Lebanon
Guest rating: 8.8/10 (Excellent, 8 reviews)
Price: $192 nightly, $193 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals
Review: We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. , by Joanna P.

18. Cozy Camper tucked into the woods

A rural property with a wooden barn, a white fence, and a mobile home.

Location: Sandisfield
Guest rating: 10/10 (Exceptional, 1 review)
Price: $156 nightly, $174 total, Nov 14 - Nov 15, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals
Review: "This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably..., by hannah w.

19. 1800s Carriage house in Berkshires / Hudson Valley

A gazebo with a stone floor and a grassy area with trees in the background.

Location: New Lebanon
Guest rating: 7/10 (Good, 2 reviews)
Price: $207 nightly, $208 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals
Review: Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan), by Leslie H.

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

A hot tub with a string of lights above it, set against a dark night sky.

Location: Sherwood Forest
Guest rating: 9.6/10 (Exceptional, 20 reviews)
Price: $337 nightly, $377 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Great Barrington vacation rentals
Review: Great place and welcoming stay!, by Frank M.

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

Find vacation rentals that suit your style

Top Great Barrington Hotel Reviews

Prospect Berkshires

A wooden house with a porch, surrounded by trees and a body of water.

Location: Egremont
Review: So fantastic!! The cabins are gorgeous and very well appointed. We are going back!, by Emily, July 7, 2025, rated 10/10 Excellent

Devonfield Inn B&B

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

Location: Lee
Review: The history behind the inn was great. Doug one of the owners could not have been any more hospitable. He made sure to go above and beyond throughout our entire stay. Our room was comfortably sized and the fireplace was a great perk to have at night. Breakfast and treats were delicious. We will be back!, by Anonymous traveler, January 20, 2019, rated 10/10 Excellent

Changing Times Boutique Country Lodging

A fire pit with two Adirondack chairs, a table with drinks, and a house in the background.

Location: Craryville
Review: Our second time staying here was even more lovely than the first! We brought more family members after our great experience last year. We love the easy check in, cozy comfortable rooms, lots of extras (books and DVDs in the hallway, sweet treats downstairs and in the rooms) and Loretta is the BEST host! She makes an exquisite breakfast and accommodates our early start time. Can’t wait to stay here again., by Kathleen, January 3, 2023, rated 10/10 Excellent

Wilder House Berkshires

A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.

Location: Sheffield
Review: Clean, cozy, and charming. The breakfast is delicious and all went smoothly., by Liliana, October 19, 2026, rated 10/10 Excellent

Inn at Silver Maple Farm

A spacious kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.

Location: East Chatham
Review: This is a super clean, comfortable, and relaxing Inn. The Inn-keepers, Chloe and Shawn are wonderful. I could not have been happier with the service, the level of cleanliness, and the comfort of my room and common areas. Breakfast was delicious!, by Michelle, March 7, 2022, rated 10/10 Excellent

The White Hart

A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

Location: Salisbury
Review: We enjoyed our stay at the White Hart. We got a room in the back of the building overlooking a garden. We loved sitting out there and relaxing. The room was a nice size and comfortable. The complementary breakfast provided a good selection and was tasty. The lobby is a nice place to have coffee or wine. The chairs are everywhere and make it a nice place to relax. Service was friendly and attentive and Provisions provides excellent sandwiches. We were also able to park right outside our..., by thomas, August 29, 2021, rated 10/10 Excellent

East Rock Inn

Location: Great Barrington
Review: Great room, recently renovated. Very close to Butternut and other areas of interest., by Heather, July 22, 2024, rated 10/10 Excellent

Howard Hotel

A hallway with a staircase, a framed painting, a mirror, and a potted plant.

Location: Hudson
Review: Wonderful hotel, by zehava, November 4, 2026, rated 10/10 Excellent

Little Cat Lodge

A wooden fire pit surrounded by six Adirondack chairs in a forested area.

Location: Copake Falls
Review: I didn't want to leave and wish I had time to stay longer. Room was exceptional. Staff was exceptional. A truly great stay., by Elisabeth, April 6, 2025, rated 10/10 Excellent

Inn at Pine Plains

A dining area with a table set for breakfast, a chalkboard menu, and various kitchen utensils hanging on the wall.

Location: Pine Plains
Review: Our second time visiting the Inn. Such a cute and cozy spot, real hidden gem if you're looking for a weekend escape from the city. The inn keeper Patti is super helpful and always makes sure we have the best plans while in town! Rooms are clean with a homey feel and the beds are dreamy. We'll def be back for our now annual visit to Pine Plains., by Kevin, November 27, 2023, rated 10/10 Excellent

Shaker Mill Inn

Location: West Stockbridge
Review: This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to..., by Joe, February 27, 2022, rated 10/10 Excellent

Element by Marriott Lenox Berkshires

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

Location: Lenox
Review: Clean and spacious room., by Richard, November 12, 2026, rated 10/10 Excellent

The Inn at Stockbridge

Location: Stockbridge
Review: Great B&B with everything you need especially for a quick getaway to vist Stockbridge & Great Barrington Massachusetts. The new owners have added new touches to this Inn and the pride of ownership shows. Highly recommended 👌, by Kevin, February 19, 2024, rated 10/10 Excellent

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

Location: Great Barrington
Review: We were greeted by extremely friendly staff. Check in and check out was seamless. Room was very nice and immaculate. We especially liked the bathroom design - didn't have to trip over the toilet to get in the shower as in most hotels! Free breakfast was the usual fare, but in a very pleasant and uncrowded room. Appreciated the free US News and NY Times Beautiful indoor pool - wish we'd brought our bathing suits!, by Anonymous traveler, June 30, 2017, rated 10/10 Excellent

Brook Farm Inn

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

Location: Lenox
Review: We were very happy with our stay… Maureen was so hospitality and made sure all our needs were taken care of, from lending us an Apple plug, making dinner reservations for us to making sure we had all enough breakfast food. We love Lennox and would definitely want to stay at her place again, when we come back. Thank Maureen for the special time!, by roberta, January 8, 2024, rated 10/10 Excellent

Hotel On North

A multi-story hotel with a classic facade, large windows, and a prominent entrance.

Location: Pittsfield
Review: The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and..., by Steve, February 28, 2016, rated 10/10 Excellent

Chambery Inn

A vintage turquoise Ford truck parked in front of a building labeled "CHAMBÉRY INN."

Location: Lee
Review: The building is like going back in time -- the separate boys and girls stairways, the chalkboards in the rooms and historical pictures on the walls. Breakfast was so well done, selections and presentation were wonderful. Room was extremely comfortable, especially the seating area for watching tv. Lots of nice restaurants and shops within walking distance., by Elaine, June 22, 2016, rated 10/10 Excellent

The Nest Hudson

A window with a gold-framed shelf containing a potted plant, a white bowl, and two gold pitchers.

Location: Hudson
Review: The Nest Hotel is a lovely place that is well situated within walking distance to shops, restaurants, and the river. The room was very comfortable and well appointed and they had a small, but well stocked kitchen with coffee, espresso, and small snacks. Hudson is a beautiful area and perfect for a fall weekend. My sister and I appreciated the hotel's recommendations and the self check-in/check-out instructions were easy to follow. The only downside was that the house next door was under..., by Felicia, October 28, 2026, rated 10/10 Excellent

Find out more about Great Barrington

Everything you need to know about Great Barrington vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Great Barrington vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Great Barrington vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Great Barrington vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Great Barrington. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Great Barrington in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $92 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Great Barrington rentals

At Expedia, we put the best Great Barrington vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Great Barrington rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Great Barrington vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Great Barrington. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Riverside Retreat in the Berkshires: This highly rated vacation home rental in Great Barrington is located on a river and has a fireplace, a selection of games, 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. Some other top choices in Great Barrington are Great Barrington, Cabin Sleeps 14, Walk To Town and Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!.

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.