Deals on vacations and trips to Great Barrington

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Great Barrington flight + hotel vacation packages

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

The Wiltwyck

3.5 out of 5
Price was $941, price is now $743 per person
$743
per person
Nov 5 - Nov 10
found 3 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) to Albany (ALB)
Free WiFi in public areas is available at this guesthouse. Take advantage of the free self parking.
The Old Catskill Game Farm Inn

The Old Catskill Game Farm Inn

3.5 out of 5
Save 100% on your flight
Price was $5,305, price is now $3,825 per person
$3,825
per person
Nov 5 - Nov 10
found 3 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) to Albany (ALB)
A sauna, free self parking, and laundry facilities are featured at this guesthouse. WiFi in public areas is free. A communal living room, a picnic area, and free newspapers are also on offer.
The Perch Hotel

The Perch Hotel

2 out of 5
Save 100% on your flight
Price was $1,575, price is now $1,137 per person
$1,137
per person
Nov 5 - Nov 10
found 3 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
Hotel Kinsley

Hotel Kinsley

3.5 out of 5
Stockade District
Price was $1,209, price is now $948 per person
$948
per person
Nov 5 - Nov 10
found 3 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) to Albany (ALB)
This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the sauna and free perks like continental breakfast and free self parking.
Farmhouse at Leeds by Avantstay Catskills Farmhouse + Barn Suite + Firepit Mins to Hudson + Kaaterskill Falls

Farmhouse at Leeds by Avantstay Catskills Farmhouse + Barn Suite + Firepit Mins to Hudson + Kaaterskill Falls

3 out of 5
Save 100% on your flight
Price was $1,987, price is now $1,582 per person
$1,582
per person
Nov 5 - Nov 10
found 3 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) to Albany (ALB)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.

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
$93 nightly
The price is $103 total per night
$103 total
Sep 7 - Sep 8
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
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 1 - Sep 2
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
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
$119 nightly
The price is $133 total per night
$133 total
Sep 13 - Sep 14
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.
Prospect Berkshires

Prospect Berkshires

3 out of 5
50 Prospect Lake Rd Egremont MA
$445 nightly
The price is $497 total per night
$497 total
Aug 30 - Aug 31
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.
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
Aug 19 - Aug 20
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.
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
$95 nightly
The price is $106 total per night
$106 total
Sep 1 - Sep 2
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.
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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

Frequently asked questions

How much are vacation packages to Great Barrington?
Your vacation daydreams can become a reality in Great Barrington from an impressive $743. 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.

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