Search Resorts in Great Barrington

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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Compare 6 Resorts in Great Barrington with updated reviews, rates, and availability.

Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Property grounds

Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!

10.0 out of 10, Exceptional, (1)
"We loved everything about this place! It was quiet, centrally located, and everyone was friendly and helpful. We will stay here again for sure!"
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Holiday Inn Club Vacations Oak 'n Spruce Resort
View from property

Holiday Inn Club Vacations Oak 'n Spruce Resort

2.0 star property
Holiday Inn Club Vacations Oak 'n Spruce Resort
Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC
Pool

Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC

2.0 star property
Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
Property grounds

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
Mountain Lodge Apt!
Private kitchen

Mountain Lodge Apt!

Mountain Lodge Apt!
Canyon Ranch Lenox
Exterior

Canyon Ranch Lenox

3.0 star property
Canyon Ranch Lenox
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 property types in Great Barrington

Private Estate, Heated Yearround Outdoor Pool
Fridge, microwave, oven, stovetop

Private Estate, Heated Yearround Outdoor Pool

9.8 out of 10, Exceptional, (17)
"The home was beautiful and it was a gorgeous property too. It had all the right amenities in the kitchen. "
Private Estate, Heated Yearround Outdoor Pool
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Interior

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (45)
"We had an amazing long ski weekend at the Great Escape Ski Cottage. The listing is very accurate. Great communication with Shay. The house was immaculate upon arrival. The layout of the house was perfect for our family (6 adults and 4 children aged 4-9). One beautiful Master Bedroom on the first floor. Two of the other equally beautiful bedrooms are on the second floor. The linens were hotel quality! The "Kid's Quarters" was located off of the kitchen/laundry room. A playroom with multiple games...
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books

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!
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's a favorite resort in Great Barrington?
Here’s our top-rated resort near Great Barrington: Holiday Inn Club Vacations Oak ‘n Spruce Resort - Ski resort. 7.1 mi (11.5 km) from Great Barrington. Enjoy the sauna, fitness center, and terrace.
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 Housatonic River 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.