Best Resorts in Great Barrington

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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

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
Mountain Lodge Apt!
Private kitchen

Mountain Lodge Apt!

Mountain Lodge Apt!
Oak n' Spruce Resort in the Berkshires. Charming 2-bedroom in quaint Lee
Exterior

Oak n' Spruce Resort in the Berkshires. Charming 2-bedroom in quaint Lee

Oak n' Spruce Resort in the Berkshires. Charming 2-bedroom in quaint Lee
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

Lakeside Oasis Just You, The Lake & The View!
Exterior

Lakeside Oasis Just You, The Lake & The View!

9.8 out of 10, Exceptional, (70)
"Perfect location for a peaceful, scenic vacation."
Lakeside Oasis Just You, The Lake & The View!
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!
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Food and drink

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.6 out of 10, Exceptional, (21)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet 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.

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.