Book Exclusive Great Barrington Vacation Packages

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Great Barrington flight + hotel packages

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

Saratoga Casino Hotel

4 out of 5
Price was CA $1,211, price is now CA $1,046 per person
CA $1,046
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Thunder Bay (YQT) to Albany (ALB)
Stay at this hotel in Saratoga Springs. Enjoy free WiFi, free parking, and a casino. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Saratoga Racetrack and Saratoga Performing Arts Center are located nearby.
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was CA $1,839, price is now CA $1,447 per person
CA $1,447
per person
Nov 6 - Nov 11
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this golf hotel in Wilmington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and North Branch Deerfield River are located nearby.
The White House Inn

The White House Inn

3.5 out of 5
Price was CA $1,610, price is now CA $1,374 per person
CA $1,374
per person
Nov 6 - Nov 11
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Stay at this hotel in Wilmington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions South Main Street and Pettee Memorial Library are located nearby.
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

4.5 out of 5
Manchester Village Historic District
Price was CA $1,592, price is now CA $1,407 per person
CA $1,407
per person
Nov 6 - Nov 11
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
The Manchester View

The Manchester View

2.5 out of 5
Price was CA $1,265, price is now CA $1,120 per person
CA $1,120
per person
Nov 6 - Nov 11
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this business-friendly hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bromley Mountain Ski Resort and Dana L. Thompson Memorial Park are located nearby.

Top Great Barrington hotels deals

Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Free cancellation
The price is CA $107 per night
CA $107
CA $120 total
Nov 1 - Nov 2
includes taxes & fees
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.
Breakfast included
Parking included
Prospect Berkshires

Prospect Berkshires

3 out of 5
50 Prospect Lake Rd Egremont MA
The price is CA $442 per night
CA $442
CA $542 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area are located nearby.
Pool
Spa
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

3 out of 5
249 Stockbridge Rd Great Barrington MA
The price is CA $205 per night
CA $205
CA $229 total
Nov 2 - Nov 3
includes taxes & fees
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 Housatonic River and Housatonic River Walk are located nearby.
Pool
Breakfast included
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd Great Barrington MA
Free cancellation
The price is CA $135 per night
CA $135
CA $151 total
Nov 2 - Nov 3
includes taxes & fees
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
The Little Lion

The Little Lion

3 out of 5
506 Stockbridge Road Great Barrington MA
Free cancellation
Reserve now, pay when you stay
The price is CA $148 per night
CA $148
CA $165 total
Oct 18 - Oct 19
includes taxes & fees
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Monument Mountain and Monument Mountain Reservation are located nearby.
Pet-friendly
Parking included
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd Great Barrington MA
Free cancellation
Reserve now, pay when you stay
The price is CA $85 per night
CA $85
CA $95 total
Nov 1 - Nov 2
includes taxes & fees
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.
Parking included
Free WiFi
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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.

Stay near popular Great Barrington attractions

Lake Mansfield Park

9.0/10 (22 reviews)
Explore the great outdoors at Lake Mansfield Park, a lovely green space in Great Barrington. Experience the area's theater scene and live music.
See properties

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 $1,046. 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.

Photos of local treasures

Browse Great Barrington vacation photos for more inspiration

A row of parked cars along a street lined with brick buildings, including a sign for 'Vault Studio' and 'Hotpoint'.
A street lined with parked cars, trees, and buildings including a church and a bank.
A street scene with a restaurant named 'Baba Louie's' and a car parked on the side of the road.
A large stone church with a tall bell tower and arched windows.
A brick building with a white door, arched windows, and a clock tower.