Great Barrington Holiday Rentals: Short-Term Accommodations for Rent

Q: What are some of the best holiday rentals that Great Barrington has to offer?

Private Estate, Heated Yearround Outdoor Pool : This highly rated holiday home rental in Great Barrington offers a balcony, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 7 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. Our travellers also rate Lakefront Berkshires Retreat w/ Deck, Dock & Boat! as a favourite home for rent in Great Barrington.

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Holiday Rentals in Great Barrington

"We had a wonderful stay for our mother’s birthday with her 4 children and 10 of her 12 grandchildren. There was plenty to do for everyone especially with a 75 year difference in ages!!"

"We had a wonderful stay. Would most definitely book again! "

HK$25,749 total

includes taxes & fees

19 Feb - 20 Feb

"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"

1 bedroom, iron/ironing board, WiFi, bed sheets

"House and grounds are large! Firepit is great! Local hiking and restaurants were fantastic! Enjoyed the large rooms and decor and artworks and prints."

"Beautiful wrap-around porch. Views were wonderful. Had to use the pullout sofa, because the stairs to the loft was basically a stepladder and for us seniors, was a no go. It does need a microwave. We gave it a four star overall, but for a younger couple would be a five."

"It was a quirky and interesting house!"

"Well-located home, comfortable home with a well-stocked kitchen and plenty of space. We hope to return! "

HK$4,641 total

includes taxes & fees

26 Jan - 27 Jan

"Absolutely wonderful. Charming, pristine and cozy for an overnight stay. "

HK$1,764 total

includes taxes & fees

26 Jan - 27 Jan

"Second time I’ve stayed. Nice place. Owner very communicative. Good prices. "

HK$1,092 total

includes taxes & fees

4 Feb - 5 Feb

"The house was great with plenty to do in the area. It was warm, comfortable, and just what we were looking for a quick weekend away. Would definitely return.Thanks,-Mike"

"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."

"The Cabin Had All The Amenities You Would Need and With A Quiet and Serene Area. For Me It Was Relaxing Stay!"

"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...

"Wonderful accommodation."

"From beginning to end, could not have dreamed of a better island getaway, in the Berkshire’s none-the -less. Bill was a wonderful host. Very friendly, responsive and helpful. Super welcoming. The home was simple, quaint, and super cozy. Perfect for a nice long relaxing weekend for both the dogs and people. The views from the sun room were lovely. The deck/patio area had a beautiful view of the water. The fire pit was a nice perk in the evening. Surrounded by water, the place felt so private....

"Fantastic, large house with tons of places to explore in the house and on the property. We came for a long weekend with 3 families and both the adults and kids felt quickly at home and really enjoyed our stay. We cannot wait to some back!"

"The hosts were extremely responsive and helpful, providing us with hiking ideas, questions regarding the house and suggesting best shopping spots for incidentals. The living room was cozy, seating five comfortably. The kitchen was well stocked so cooking a Thanksgiving meal was a pleasure. We thoroughly enjoyed ourselves."

"Beautiful, well-stocked home with a lovely lake view. "

"Well located and comfortable "

HK$2,939 total

includes taxes & fees

26 Jan - 27 Jan

"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "

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

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

"Good area, close to the restaurant and shop"

HK$735 total

includes taxes & fees

2 Feb - 3 Feb

Premium bedding, pillow-top beds, in-room safe, desk

"It was nice and clean experience. Staff was very friendly."

HK$1,086 total

includes taxes & fees

26 Jan - 27 Jan

Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

"Rooms have been recently renovated and were clean and spotless. Great comfortable room with convenient gas station and sandwich shop across the street as well as several other eateries close by. Owner and staff were very friendly and made me feel welcome. I will definitely come back here in the future...... Good job 👍"

HK$578 total

includes taxes & fees

27 Jan - 28 Jan

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!

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All accommodation types in Great Barrington

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?

Private Estate, Heated Yearround Outdoor Pool: This highly rated holiday home rental in Great Barrington offers a balcony, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 7 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. Our travellers also rate Lakefront Berkshires Retreat w/ Deck, Dock & Boat! as a favourite home for rent in Great Barrington.

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.

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Great Barrington Holiday Rentals

Plan, book, stay with confidence

Check prices for these dates

Holiday Rentals in Great Barrington

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

Private Estate, Heated Yearround Outdoor Pool

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Peaceful, Post and Beam Loft, Sleeps 9

Perfect Vacation Get Away - Historical New Marlborough

Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington

Great Barrington Get Away

Berkshire Village Carriage House - Super Private!!

Micosta Leisure Inn

Peace and quiet on the lake

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

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Pristine Home In Becket Woods

Serene Acreage - Pond - Hiking Trails Nearby

Private Island - Largest Fresh Water Reservoir in Mass....

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

Berkshires Cabin 2 Mi to Appalachian Trail!

Quintessential 6-BR Berkshires Lodge

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

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

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

Quality Inn

Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

Monument Mountain Motel

Find out more about Great Barrington

Explore a world of travel with Expedia

Frequently asked questions