Great Barrington Vacation Rentals

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Vacation Rentals in Great Barrington

7 bedrooms, iron/ironing board, cribs/infant beds, travel crib
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Fridge, microwave, oven, stovetop
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (8)
"The pictures simply do not do this place justice, it’s an incredible home. Our friend group was cozy all weekend! We loved the hot tub/pool, the really interesting artwork, the driving range mat and basketball hoop. Plenty of towels and kitchen supplies. The in law apartment (which we didn’t use as sadly part of our group was unable to join us) is attached to the main home and is so cute. We had a small issue upon arrival and the hosts were immediately responsive with us troubleshooting and...
Private Estate, Heated YEARROUND Outdoor Pool
TV, fireplace, DVD player, books
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
"This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home."
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
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Outdoor dining
Moose Lodge by AvantStay | Luxe Berkshires Escape
10.0 out of 10, Exceptional, (11)
"We had a wonderful time at the Moose Lodge. It was perfect for our family. Very clean, everything we needed and the property managers were extremely communicative. Thank you!"
Moose Lodge by AvantStay | Luxe Berkshires Escape
TV, DVD player
Peaceful, Post and Beam Loft, Sleeps 9
10.0 out of 10, Exceptional, (8)
"beautifully stay for couples."
Peaceful, Post and Beam Loft, Sleeps 9
Property grounds
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, (49)
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is ￥23,466
per night
May 16 - May 17
Perfect Vacation Get Away - Historical New Marlborough
7 bedrooms, free WiFi, bed sheets
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington
10.0 out of 10, Exceptional, (23)
"Interesting and lovely! We had a great time and the hosts were very welcoming and responsive"
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (183)
"We rented the house to celebrate mom’s 70th birthday. We wanted a quiet, simple place where we could spend time together, visit, and spend time outdoors. That’s exactly what we got. We all fished and kayaked and enjoyed the peaceful scenery. Thank you."
Peace and quiet on the lake
Balcony
Micosta Leisure Inn
3.0 star property
8.8 out of 10, Excellent, (71)
"super nice and clean I think I will return the only thing is that it is under construction."
The price is ￥19,618
per night
May 16 - May 17
Micosta Leisure Inn
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (195)
"We’ve stayed at the cabin with our dog four times and always enjoy our peaceful stay. It’s cozy, clean and private. Also, the Sherwood Shoppe - just down the road - is a wonderful place for breakfast, homemade chili and much more."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Interior
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Fridge, microwave, oven, stovetop
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (7)
"My wife and young daughters live in central CT, and the drive to Becket was both scenic and relatively short at around an hour and a half. The property offers great privacy in a remote wooded setting in the heart of the always beautiful Berkshires. We brought our dog along, and we all were able to relax by the fire, read our favorite books, as well as peruse interesting titles on the impressive bookshelf built into the living room wall—a book lover’s delight. We admired the openness and light...
Pristine Home In Becket Woods
Fridge, microwave, oven, stovetop
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
Exterior
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, (4)
"We had a great time. Place is amazing. Highly recommend. We had four different families and we never felt cramped. Lovely open main room allowed us to stay connected. Bedrooms were nice and spacious, good bed options. Nice decor."
Quintessential 6-BR Berkshires Lodge
Fridge, microwave, oven, stovetop
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, (2)
"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Interior
Rockspring by AvantStay | Huge Berkshires Estate
8.8 out of 10, Excellent, (10)
"We stayed with friends and family and had plenty of room. The separate game room is great! The house was as pictured and described. It is close to a few ski mountains and Great Barrington. We would happily stay at RockSpring or a different AvantStay again!"
Rockspring by AvantStay | Huge Berkshires Estate
Property grounds
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (4)
"Perfect place to relax and have dogs as part of a mini vacation. Very clean, organized, and provided helpful local information. Will definitely stay there again."
Serene Acreage - Pond - Hiking Trails Nearby
Property grounds
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (119)
"My wife and I and our daughter and dog spent the week. Everything we needed was provided. Nice quiet and relaxing time. Great location down the street from the AMC Noble View trails. We all had a wonderful hike and a wonderful week."
The price is ￥31,288
per night
May 16 - May 17
Big farmhouse in the foothills of the Berkshires
Property grounds
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, (3)
"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"
Private Island - Largest Fresh Water Reservoir in Mass....
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (203)
"Very clean, tastefully decorated place perfect for our weekend getaway for two. Enjoyed the reading nooks and kitchen amenities, comfortable bed and peacefulness of this carriage house!"
Berkshire Village Carriage House - Super Private!!
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See all available properties in Great Barrington
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.

Other types of properties in Great Barrington you may be interested in

Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel
2.5 star property
9.0 out of 10, Wonderful, (593)
"Great stay for one night. "
The price is ￥10,403
per night
May 16 - May 17
Monument Mountain Motel
Standard Room, 2 Queen Beds, Non Smoking | 1 bedroom, premium bedding, pillowtop beds, desk
Quality Inn
2.5 star property
8.0 out of 10, Very Good, (1000)
"Whenever we are in the area we have stayed and been pleased. "
The price is ￥12,531
per night
May 16 - May 17
Quality Inn
Standard Room | Premium bedding, pillowtop beds, in-room safe, desk
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (497)
"Really enjoyed the seating outside and pool side was very relaxing. The staff was very helpful and informative. Great experience!!!"
The price is ￥21,889
per night
Jun 4 - Jun 5
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
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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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?

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!: Visitors give good reviews to this Great Barrington vacation home rental, which is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the books in this rental home to help you unwind.

How many vacation rentals are there in Great Barrington?

With 103 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 Lake Buel are a couple of picturesque spots to enjoy the outdoors. Ski Butternut and Catamount Ski Area 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.

Recent reviews of Great Barrington properties
Expedia verified reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

5/5 Excellent
"Just like home"
A verified traveler stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Posted 1 day ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel