Great Barrington Vacation Rentals from ￥21,483: Search Short-Term Rentals

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

Spacious 5-bedroom house in charming Lee with WiFi : Located near Great Barrington, this vacation home rental offers a fireplace, a barbecue grill, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities like a dishwasher and a microwave can make your vacation run smoothly.

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Vacation Rentals in Great Barrington

"Spacious, welcoming, so well stocked, we felt lucky to find the property."

Indoor pool, outdoor pool, pool umbrellas, sun loungers

"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"

"Great stay!"

￥21,483 total

includes taxes & fees

Sep 25 - Sep 26

"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."

5 bedrooms, iron/ironing board, WiFi, bed sheets

￥90,602 total

includes taxes & fees

Oct 1 - Oct 2

"Beautiful, spacious house in a great location!"

"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "

￥101,731 total

includes taxes & fees

Sep 28 - Sep 29

"Comfortable home with amazing view. Enjoyed taking a walk around the lake (1 hour approx). Had an amazing dinner at Dream Away lodge which is 15 minutes away. "

"Everything was great...and beautiful!"

￥59,688 total

includes taxes & fees

Sep 30 - Oct 1

"The house has rustic charm and sits right on the lake. It is a beautiful peaceful spot. "

"Loved the property. Perfect for our gathering."

"Excellent stay!"

￥118,372 total

includes taxes & fees

Sep 26 - Sep 27

"Beautiful property and great location. A true retreat. "

￥172,778 total

includes taxes & fees

Sep 25 - Sep 26

"Great location for access to both Tanglewood and Lenox center. "

"Oriana was awesome and I look forward to staying there again."

"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "

"Hindsale-perfect little hideaway, minutes from where we needed to be. Harrison’s little home was equipped with amenities/tasteful luxuries, and cozy nooks. We all loved the loft-could not believe how large the space was! Hot tub nights-perfect ending:) Thank you, Harrison."

"We had a wonderful time, the property is lovely and the house is delightful."

"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "

"Home our mother's 83rd birthday party cookout at the lake house with a few family members and it was a great day. Everyone loved the house. We enjoyed the stay"

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Top Great Barrington Hotel Reviews

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent

"good"

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"Valerie at the front desk and who checked me in was above and beyond in customer service. She checked to see if I had a IGH account—which I did but had forgotten, and reminded me about the points and promotions. This Holiday Inn is a well managed property. Thank you"

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent

"We stayed for 5 nights and really enjoyed the surroundings and the drive to the property. The area is peaceful and quiet, with plenty to do for kids, including a mountain hike that even our 2- and 6-year-olds managed well. The grounds are beautiful for photos, very well maintained, and we often saw the crew cleaning and painting the sidewalks. I booked 2 suites, which were a good size for a family of four and offered plenty of space. The only downsides were that check-in felt a bit tedious it took several tries to swipe my card and there was no housekeeping service or follow-up to check on amenities during our stay. A self check-in option would make things smoother. Overall, we loved the quietness, the family-friendly activities, and the clean, well-kept property. With a few improvements in guest service, this could easily be a 5-star experience."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"I had a great stay at this comfortable, homey, family owned inn. The beds were vrry comfortable and the rooms had everything I needed including a fridge, lots of towels, a hair dryer etc. The property is clean, safe and very quiet. There’s an Indian restaurant on site with delicious food and a bar. The lake is lovely; I enjoyed a relaxing time sitting by the lake with my dog. The breakfast was good and the breakfast room has a gorgeous view of the lake. I will definitely be back for another stay."

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:

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Frequently asked questions

Can I find a vacation rental in Great Barrington?

Yes, there are vacation rentals close to the most popular points of interest in Great Barrington, or you can select a secluded option if you're looking for relaxation. 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?

Spacious 5-bedroom house in charming Lee with WiFi: Located near Great Barrington, this vacation home rental offers a fireplace, a barbecue grill, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities like a dishwasher and a microwave can make your vacation run smoothly.

How many vacation rentals are there in Great Barrington?

With 98 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?

Cultural attractions include Mahaiwe Performing Arts Center and Art et Industrie, whereas Housatonic River Walk and Housatonic River are a couple of picturesque spots to enjoy the outdoors. Lake Mansfield Park and Ski Butternut 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.

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Great Barrington Vacation Rentals

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Vacation Rentals in Great Barrington

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

The Ponds at Foxhollow

Micosta Leisure Inn

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Spacious 5-bedroom house in charming Lee with WiFi

Amore Estate - beautiful room with many places to explore and relax in.

Guesthouse Cabin vacation rentals in Berkshire County

Peace and quiet on the lake

The Blue Elm - A Historic Berkshire Cottage

Summer Lake Cottage, private beach, Berkshire Hills, small village

The Kemble- Built by a US Secretary of State in Lenox

The Lakeshore House

Whispering Estate Guest House - A Romantic Countryside Getaway

Enjoy comfortable elegance in this secluded grand home located in town

Charming cottage with lake access, wood burning fire place, and WiFi

BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Heaven Can't Wait, On Beautiful Kinderhook Lake!!

Top Great Barrington Hotel Reviews

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Monument Mountain Motel

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Berkshire Mountain Lodge

The Red Lion Inn

The Yankee, Trademark Collection by Wyndham

The Black Swan Lee - Lenox, an Ascend Collection Hotel

St. Charles Hotel

Find out more about Great Barrington

Frequently asked questions

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