Deals on vacations and trips to Great Barrington

Save when you book Great Barrington package deals

Choose two or more items and save on your trip:

Great Barrington flight + hotel vacation packages

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

Ambler Hotel

2 out of 5
Price was $727, price is now $568 per person
$568
per person
Oct 24 - Oct 30
found 1 day ago
Roundtrip flight included
New York (LGA) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-out is also provided.
South Shire

South Shire

4 out of 5
Save 100% on your flight
Price was $1,190, price is now $756 per person
$756
per person
Oct 24 - Oct 30
found 1 day ago
Roundtrip flight included
New York (LGA) to Albany (ALB)
A restaurant and a bar/lounge are featured at this bed & breakfast. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, express check-in, and express check-out are also on offer.
Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Save 100% on your flight
Price was $1,166, price is now $810 per person
$810
per person
Oct 24 - Oct 30
found 1 day ago
Roundtrip flight included
New York (LGA) to Albany (ALB)
A restaurant and a 24-hour gym are featured at this lodge. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A business center, a terrace, and a picnic area are also on offer.
Amsterdam Castle

Amsterdam Castle

3.5 out of 5
Price was $861, price is now $647 per person
$647
per person
Oct 24 - Oct 30
found 1 day ago
Roundtrip flight included
New York (LGA) to Albany (ALB)
Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. A terrace and express check-out are also provided.
Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was $867, price is now $652 per person
$652
per person
Oct 24 - Oct 30
found 1 day ago
Roundtrip flight included
New York (LGA) to Albany (ALB)
This smoke-free hotel features a casino, a nightclub, and a restaurant. Enjoy the indoor pool and perks like free self parking and a free area shuttle. You'll appreciate the 24-hour gym, bar/lounge, and snack bar/deli.

Top Great Barrington hotels deals

Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
$104 nightly
The price is $116 total per night
$116 total
Sep 17 - Sep 18
Total with taxes and fees
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A picnic area and barbecue grills are also provided.
Breakfast included
Parking included
Prospect Berkshires

Prospect Berkshires

3 out of 5
50 Prospect Lake Rd Egremont MA
$395 nightly
The price is $441 total per night
$441 total
Sep 17 - Sep 18
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the sauna and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a picnic area are also on offer.
Pool
Spa
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
$129 nightly
The price is $144 total per night
$144 total
Sep 20 - Sep 21
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
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
$125 nightly
The price is $140 total per night
$140 total
Sep 16 - Sep 17
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a picnic area, and express check-in are also on offer.
Pet friendly
Parking included
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
Free Cancellation
Reserve now, pay when you stay
$195 nightly
The price is $217 total per night
$217 total
Sep 20 - Sep 21
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd Great Barrington MA
$86 nightly
The price is $96 total per night
$96 total
Sep 22 - Sep 23
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area and barbecue grills are also provided.
Parking included
Free WiFi
Don't see what you're looking for?
See all available properties in Great Barrington
View all properties
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

Frequently asked questions

How much are vacation packages to Great Barrington?
Your vacation daydreams can become a reality in Great Barrington from an impressive $568. 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 100 mi 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 40 mi southeast of the city center. Your other choices are Albany Intl. Airport (ALB) (45 mi away from central Great Barrington) and Stewart Intl. Airport (SWF) (60 mi 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.

Explore More Ways to Travel with Travelocity