Great Barrington Holiday Rentals

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Check prices for these dates

Tonight
16 Apr - 17 Apr
Tomorrow
17 Apr - 18 Apr
This weekend
18 Apr - 20 Apr
Next weekend
25 Apr - 27 Apr

Holiday Rentals in Great Barrington

Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Fridge, microwave, oven, stovetop

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (19)
"We loved the location of the rental and how we could just walk to town, walk to church, walk the River walk. It was a perfect spot! Quiet neighborhood. We liked that! Lots of terrific little shops. We will definitely be back! "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Property grounds

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (43)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Lakeside Retreat Just You, The Lake & The View!
Exterior

Lakeside Retreat Just You, The Lake & The View!

9.8 out of 10, Exceptional, (70)
"It's a really lovely home on a beautiful property, with all the amenities we could have possibly needed, and also perfectly peaceful. The host was so welcoming and responsive, which made it that much nicer, too. My only regret is that we couldn't stay longer, and I would definitely want to stay there again. "
Lakeside Retreat Just You, The Lake & The View!
Private Estate, Heated Yearround Outdoor Pool
Fridge, microwave, oven, stovetop

Private Estate, Heated Yearround Outdoor Pool

9.6 out of 10, Exceptional, (19)
"Lovely horse farm in the woods but not too far from useful shops. We had a great experience."
Private Estate, Heated Yearround Outdoor Pool
Quiet rustic cottage with shared lake access
Fridge, microwave, oven, stovetop

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (104)
"I am originally from Western Mass, and was looking for a quiet get away for my fiancé and I for my birthday weekend. This more than fit the bill, we had many romantic nights in front of the fire (big y or tractor supply good for indoor wood). The cabin was delightful, quaint. And it was so quiet this time of year with no one else around us, which was just what I was looking for. Our hosts were great, made everything very easy for check in and check out and were easily valve through the App....
Quiet rustic cottage with shared lake access
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (96)
"Lovely, and quiet, with water nearby. Everything was nice and worked, and owner responded to communication quickly. Will visit again! "
The price is HK$1,008
HK$1,089 total
includes taxes & fees
30 Apr - 1 May
Micosta Leisure Inn
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Terrace/patio

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (61)
"3 day holiday getaway, my husband and our 2 pups. A hike in nearby trails in the woods, enjoyed Lee downtown eateries and shops. Beautiful winter wonderland in the Berkshires. The guest rental was perfect!!! Warm, spacious, comfortable, perfect location. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Terrace/patio

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (8)
"The location was great and just a short walk to downtown. We thought the pictures on the site were a bit misleading. The house looked a little more open than it actually was, especially in the kitchen. The outside fire pit area was a little run down. A chair was broken and the string lights were down on the ground, water filled and no outlet to plug into. Plenty of bed space for everyone to sleep and beds were comfortable. Plenty of extra sheets and towels and the kitchen was well equipped. We...
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
The Meadows House @ Otis Ridge w/ 7-person hot tub
Outdoor spa tub

The Meadows House @ Otis Ridge w/ 7-person hot tub

9.8 out of 10, Exceptional, (28)
"perfect size for group of 7 adults...Good location especially for snow shoeing....cross country sking...enjoyed being in berkshires..."
The Meadows House @ Otis Ridge w/ 7-person hot tub
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Exterior

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (25)
"Our family of 4 stayed here while skiing at Catamount - great proximity, exactly as pictured, clean, and perfect size. Host was responsive - would stay here again!"
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Dining

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (121)
"Would definetely stay again.IF....LOL minor but not so minor.Need t.v. in master bedroom.Would not be a huge iinvestment.Cc"
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Private Access To Laurel Lake, Enjoy Lake Life
TV, fireplace, DVD player, offices

Private Access To Laurel Lake, Enjoy Lake Life

10.0 out of 10, Exceptional, (14)
"The property was better than advertised. Everything anyone could need was provided and we could not have hoped for a better experience. Very large home and could easily accomodate 8 people or more. The Berkshires are magical and this home was great for out time there."
Private Access To Laurel Lake, Enjoy Lake Life
Big farmhouse in the foothills of the Berkshires
Property grounds

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (131)
"The house is so charming. Beautifully decorated and very clean, with everything you could need easy to find. Plenty of space for 8 people. The hosts are very helpful and communicative. Would definitely stay here again."
The price is HK$1,551
HK$2,820 total
includes taxes & fees
24 Apr - 25 Apr
Big farmhouse in the foothills of the Berkshires
Deluxe Queen Room with 2 Queen Beds
1 bedroom, WiFi, bed sheets

Deluxe Queen Room with 2 Queen Beds

2.0 star property
The price is HK$846
HK$1,118 total
includes taxes & fees
17 Apr - 18 Apr
Deluxe Queen Room with 2 Queen Beds
Large Barn styled vacation home that fits groups with space to spare.
Property grounds

Large Barn styled vacation home that fits groups with space to spare.

9.8 out of 10, Exceptional, (57)
"Everything was ideal for our Thanksgiving get together. Setting and views were perfect, made even more so with a timely blanket of fresh snow. An amazing amount of cooking provisions allowed us to cook as if we were in our own kitchen. Lots of options for keeping a large group entertained, and sleeping accomodations that pleased everyone. Host was very helpful with check-in communications and gracious with check in and out times without other bookings adjacent to ours. All in all a very special...
Large Barn styled vacation home that fits groups with space to spare.
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Terrace/patio

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (40)
"We had a great time here and the hosts were friendly and accommodating of our request for a later checkout. Our only complaint is the 325 cleaning fee, which is excessive given how much cleaning guests are asked to do (and given that one of the bathrooms was not even perfectly clean upon arrival). We would otherwise happily consider a future stay."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop

Near Tanglewood: Historic Summer Retreat

9.4 out of 10, Exceptional, (20)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
Near Tanglewood: Historic Summer Retreat
Peace and quiet on the lake
Fridge, microwave, oven, stovetop

Peace and quiet on the lake

9.6 out of 10, Exceptional, (213)
"Beautiful house in idyllic setting. Great host- we’ll be back!"
Peace and quiet on the lake
Heart of Lenox Walk to Town Cozy Cottage!
Exterior

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (70)
"Was as nice as the pictures. A plus for a very comfortable king sized bed! Right in town for walking to shops and restaurants. Thank you!"
Heart of Lenox Walk to Town Cozy Cottage!
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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Other types of properties in Great Barrington you may be interested in

Quality Inn
1 bedroom, premium bedding, pillow-top beds, desk

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1000)
"We like Great Barrington. This is a great location. This is a great value.. We will be back. "
The price is HK$521
HK$582 total
includes taxes & fees
1 May - 2 May
Quality Inn
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Premium bedding, pillow-top beds, in-room safe, desk

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (610)
"Staff was very nice and the room was clean and quiet. "
The price is HK$962
HK$1,074 total
includes taxes & fees
24 Apr - 25 Apr
Holiday Inn Express Hotel & Suites Great Barrington by IHG
The Little Lion
Pet-friendly

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (480)
"A cozy little inn! I recommend it! "
The price is HK$593
HK$663 total
includes taxes & fees
29 Apr - 30 Apr
The Little Lion
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.

Frequently asked questions

Can I find a holiday rental in Great Barrington?

Yes, there are holiday rentals close to the most popular sights in Great Barrington, 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?

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!: This highly rated holiday home rental in Great Barrington is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Make the most of books in this rental home to help you unwind. Some other top choices in Great Barrington are Lakeside Retreat Just You, The Lake & The View! and Private Estate, Heated Yearround Outdoor Pool.

How many holiday rentals are there in Great Barrington?

With 96 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?

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 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.