Great Barrington Vacation Packages 2025/2026 from $737

Great Barrington flight + hotel vacation packages

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

Club Wyndham Bentley Brook

Save 100% on your flight

$737

per person

Oct 12 - Oct 18

found 14 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Albany (ALB)

Ski-in/ski-out access and an outdoor pool are featured at this smoke-free hotel. Take advantage of ski storage on site, and enjoy snowboarding. Enjoy the indoor pool and perks like free self parking and free WiFi.

The Equinox Golf Resort & Spa

Save 100% on your flight

$1,186

per person

Oct 12 - Oct 18

found 14 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Albany (ALB)

This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.

Lodges At Cresthaven

Save 100% on your flight

$1,101

per person

Oct 7 - Oct 14

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

A private beach, a 24-hour gym, and a restaurant are all featured at this smoke-free lodge. Enjoy the indoor pool and perks like free self parking and free WiFi. You'll appreciate the seasonal outdoor pool, bar/lounge, and laundry facilities.

Hotel Brookmere & Arbor Spa

Save 100% on your flight

$835

per person

Oct 15 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Orlando (ORL) to Albany (ALB)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. You'll appreciate the steam room, bar/lounge, and concierge services.

Brook Bound Inn

Save 100% on your flight

$910

per person

Oct 12 - Oct 18

found 14 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Albany (ALB)

A seasonal outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A garden, a lobby fireplace, and a communal living room are also on offer.

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

$93 nightly

$104 total

Sep 15 - Sep 16

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

415 Stockbridge Rd, Great Barrington, MA

Free Cancellation

$124 nightly

$139 total

Sep 8 - Sep 9

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

249 Stockbridge Rd, Great Barrington, MA

Free Cancellation

Reserve now, pay when you stay

$151 nightly

$169 total

Sep 7 - Sep 8

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

Prospect Berkshires

50 Prospect Lake Rd, Egremont, MA

$366 nightly

$409 total

Sep 15 - Sep 16

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

Monument Mountain Motel

247 Stockbridge Rd, Great Barrington, MA

Free Cancellation

Reserve now, pay when you stay

$86 nightly

$96 total

Sep 2 - Sep 3

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

Travelodge by Wyndham Great Barrington Berkshires

400 Stockbridge Rd, Great Barrington, MA

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$84 total

Sep 2 - Sep 3

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 dry cleaning are also on offer.

Pet friendly

Parking included

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.

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.

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.

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.

Frequently asked questions

How much are vacation packages to Great Barrington?

Your vacation daydreams can become a reality in Great Barrington from an impressive $737. 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.