Great Barrington Vacations 2024/2025 from CA $2,134

Great Barrington flight + hotel packages

Price found within the past 48 hours. Click for updated prices.

Hampton Inn Bennington

per person

Dec. 29 - Jan. 5

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Albany (ALB)

Book a stay at this business-friendly hotel in Bennington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Bennington Battle Monument and Old First Congregational Church are located nearby.

The Equinox Golf Resort & Spa

per person

Dec. 29 - Jan. 5

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Albany (ALB)

Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, a full-service spa, and 4 restaurants. Our guests praise the property condition in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.

Lodges At Cresthaven

per person

Dec. 29 - Jan. 5

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Albany (ALB)

Stay at this 4-star beach lodge in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Hearthstone Point Campground and Dark Bay are located nearby.

South Shire

per person

Dec. 29 - Jan. 5

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Albany (ALB)

Stay at this 4-star inn in Bennington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Bennington Arts Guild Gallery and Fiddlehead at Four Corners are located nearby.

Wilburton Inn

per person

Dec. 29 - Jan. 5

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Albany (ALB)

Stay at this 3.5-star golf hotel in Manchester. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Museum of Creative Process and Hildene are located nearby.

Top Great Barrington hotels deals

Quality Inn

372 Main Street, Rte 7 and Main Street, Great Barrington, MA

Free cancellation

Reserve now, pay when you stay

CA $100

CA $112 total

includes taxes & fees

12 Dec - 13 Dec

Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mahaiwe Performing Arts Center and Housatonic River Walk are located nearby.

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

415 Stockbridge Rd, Great Barrington, MA

Free cancellation

CA $166

CA $185 total

includes taxes & fees

10 Dec - 11 Dec

Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lake Mansfield Park and Housatonic River are located nearby.

Pool

Breakfast included

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

249 Stockbridge Rd, Great Barrington, MA

Free cancellation

Reserve now, pay when you stay

CA $213

CA $238 total

includes taxes & fees

1 Dec - 2 Dec

Book a stay at this spa hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Housatonic River and Housatonic River Walk are located nearby.

Monument Mountain Motel

247 Stockbridge Rd, Great Barrington, MA

Free cancellation

Reserve now, pay when you stay

CA $93

CA $104 total

includes taxes & fees

1 Dec - 2 Dec

Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Housatonic River and Housatonic River Walk are located nearby.

The Little Lion

506 Stockbridge Road, Great Barrington, MA

Free cancellation

Reserve now, pay when you stay

CA $100

CA $112 total

includes taxes & fees

11 Dec - 12 Dec

Stay at this 3-star motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Art et Industrie and Lake Mansfield Park are located nearby.

Travelodge by Wyndham Great Barrington Berkshires

400 Stockbridge Rd, Great Barrington, MA

Free cancellation

Reserve now, pay when you stay

CA $97

CA $108 total

includes taxes & fees

1 Dec - 2 Dec

Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Art et Industrie and Lake Mansfield Park are located nearby.

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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.

Popular places to visit

Ski Butternut

Hit the slopes in Great Barrington with a visit to Ski Butternut. While you're in the area, stroll along the lakeside.

Housatonic River Walk

You can take time to visit Housatonic River Walk during your travels to Great Barrington. Experience the area's theater scene and live music.

Mahaiwe Performing Arts Center

You can enjoy a show at Mahaiwe Performing Arts Center on your trip to Great Barrington. While you're here, you can savor the top-notch restaurants.

Great Barrington Vacations

Whether you're going on a weekend break or an extended vacation, it's best to know a couple of things about Great Barrington before setting off.

Great Barrington lies 100 miles (161 kilometers) to the north of New York, a noteworthy city.

With so much to see and do in this corner of The Berkshires, it's easy to understand why 2,000 people choose to call it home.

Places to visit in Great Barrington

Whether you're an expert or total beginner, it's time pull out your skis and enjoy the slopes. Ski Butternut guarantees a world of fun for everybody! Need some more options? Theater can challenge our world views and asks us to aspire to be more. Attend a show at Mahaiwe Performing Arts Center and open your mind to some big ideas. But there's more. A bit of outdoor fun is good for our mental and physical health. Why not take the family and play some sports in the large open space at Lake Mansfield Park?

Where do you fly into for Great Barrington?

Say hello to amazing new experiences in Great Barrington. Once you've stepped out of Bradley International Airport (BDL), the main streets will be just 40 miles (64 kilometers) to the northwest.

Frequently asked questions

How much are vacation packages to Great Barrington?

Your vacation daydreams can become a reality in Great Barrington from an impressive CA $2,134. Vacation packages include flights and hotels, so they’re bound to make booking easy as pie. All you’ll have to worry about is getting out there and having a great time.

How long should my Great Barrington vacation be?

There aren’t any hard and fast rules when it comes to how long you should spend in Great Barrington, but the majority of people like to stay around 2 nights. Got some flexibility with your departure date? Extend your vacation by an extra night or two. That way, you’ll have sufficient time to check out the area’s hidden treasures as well.

Where can I get the best vacation package deals for Great Barrington?

Travelocity has everything you need to score a great Great Barrington package deal. Choose from as many as 400 partner airlines and 1,000,000 properties worldwide and put together a vacation package that suits your style. With so much choice, it’s easy to organize your next big getaway.

Why should I book my Great Barrington vacation package with Travelocity?

Because life is one amazing journey, and we have everything you need to help you on the way. With our exceptional service and Price Match Guarantee, you can book your trip with confidence. What’s more, you can sleep easy on the road knowing you can reach us with our 24/7 support.

Can I save on my Great Barrington car rental if I book it with hotels and flights?

With a Great Barrington vacation package, you can bundle your car, hotel and flight bookings and save a whole lot. If you can’t wait to explore the best of this impressive part of the world, why not make a beeline for Times Square? This top sight is 161 kilometers from Great Barrington. With your own wheels, you’ll be there before you know it.

Which airport is best for Great Barrington?

Bradley Intl. Airport (BDL) is one of the busiest airports in Great Barrington. It’s roughly 64 kilometers southeast of the city center. Your other choices are Albany Intl. Airport (ALB) (72 kilometers away from central Great Barrington) and Stewart Intl. Airport (SWF) (97 kilometers away from central Great Barrington).

What is there to do in Great Barrington?

You’ll feel a certain kind of magic as you stroll through the streets of Great Barrington. Housatonic River Walk and Mahaiwe Performing Arts Center are just two attractions that lure visitors to this fantastic city, so add them to your itinerary.

Where should I stay when visiting Great Barrington?

If you’re after someplace comfortable to lay your head, check out the Quality Inn. It’s the top pick for many travelers.