Great Barrington Holiday Rentals: Short-Term Accommodations for Rent

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Holiday Rentals in Great Barrington

"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"

"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!"

HK$10,959 total

includes taxes & fees

25 Oct - 26 Oct

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

Indoor pool, outdoor pool, pool umbrellas, pool 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!"

HK$1,132 total

includes taxes & fees

22 Oct - 23 Oct

"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."

HK$6,150 total

includes taxes & fees

20 Oct - 21 Oct

"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. "

"We came out to see James Taylor on the 4th. Kathy and Kit were terrific hosts. Friendly, accommodating and their home was very comfortable and clean. We would definitely rent from them again. Thank you! "

"Loved the property. Perfect for our gathering."

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

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

"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."

"perfect location to go everywhere in the Berkshires"

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

HK$5,561 total

includes taxes & fees

29 Oct - 30 Oct

"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...

HK$2,278 total

includes taxes & fees

15 Oct - 16 Oct

"We had a great time. The owner Bill was a great host."

"Had a wonder fun stay! The place had everything you would need and the hosts were very helpful. We would definitely stay again!"

"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."

"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"

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Great Barrington Hotel Reviews

Berkshires Untold

10/10 Excellent

"We had a nice room and the food was delicious. Great place to stay. "

The Red Lion Inn

10/10 Excellent

"Room was comfortable and clean. The Inn is beautiful. We went to the Lions Den both evenings and had a drink and listened to live music. We couldn’t get a table at the restaurant but there are other good options in walking distance. The only disappointment was that the fireplace in our room was not working. "

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!

Explore a world of travel with Expedia

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?

Lakefront Fall Foliage in New England Just 2 Hours From NYC: This holiday home rental outside of 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. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a private garden and a selection of games.

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.

Unlock instant savings with Member Prices

Great Barrington Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Holiday Rentals in Great Barrington

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

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

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

The Ponds at Foxhollow

Micosta Leisure Inn

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

Spacious 5-bedroom house in charming Lee with WiFi

Peace and quiet on the lake

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

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

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

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

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Tranquil Lakeside Escape in the Berkshires

Guesthouse Cabin vacation rentals in Berkshire County

Charming 3-bedroom Cabin for nature lovers

Private Island - Largest Fresh Water Reservoir in Mass

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

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

Berkshires Untold

Find out more about Great Barrington

Explore a world of travel with Expedia

Frequently asked questions

Go further with the Expedia app