Search Resorts in Great Barrington

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Compare 2 Resorts in Great Barrington with updated reviews, rates, and availability.

Luxury one bedroom and one bathroom unit with full amenities
Exterior
Luxury one bedroom and one bathroom unit with full amenities
Luxury one bedroom and one bathroom unit with full amenities
Mountain Lodge Apt!
Dining
Mountain Lodge Apt!
Mountain Lodge Apt!
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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 property types in Great Barrington

The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Welcome to The Freeman Berkshires
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
Private Estate, Heated YEARROUND Outdoor Pool
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
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Great Barrington Vacation Rental | 4BR | 2BA | 2,000 Sq Ft | Stairs Required
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!
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

What is Great Barrington like for a resort vacation?
You deserve a break, and a resort is just the place to indulge in all the amenities and services you need for a relaxing stay in Great Barrington. One of the comfortable resorts in the area could be just what you’re looking for, whether you want great restaurants on site, shopping possibilities, or nightly entertainment options.
What can I do in Great Barrington?
Travelers enjoy the cultural offerings in Great Barrington, and have good things to say about its live music venues and theaters. Head for the ski slopes at Ski Butternut, or discover the theater scene at Mahaiwe Performing Arts Center. Housatonic River Walk and Lake Buel are a few additional attractions in the area that you might like.
What's the seasonal weather like in Great Barrington?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Great Barrington are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to and around Great Barrington?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 16.2 mi (26.1 km) from the heart of the city. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 19.2 mi (30.9 km) away. If you’d like to venture out around the area, consider renting a car to take in more sights.

Recent reviews of Great Barrington hotels
Expedia verified reviews

The Red Lion Inn

The Red Lion Inn

5/5 Excellent
"Historical. Beautiful night to sit outside. Friendly staff. "
A verified traveler stayed at The Red Lion Inn
Posted 3 days ago
The Red Lion Inn