Great Barrington Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Great Barrington Vacation
Say goodbye to the worries of planning and hello to a Great Barrington vacation package. With the finer details organized before you take off, you can focus on discovering the best of this city, starting with Canann Village Historic District, which is good for dining, culture and shopping. Fill your spare time with visits to Ski Butternut, Housatonic River Walk and Lake Buel, some of the things you simply have to see during a trip to Great Barrington. Expedia is here to help you escape the everyday. Tailor your vacation to Great Barrington to suit your travel style, whatever that may be!
Top Great Barrington Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Valley Craft Ales
CA $1,203
per person
Oct 10 - Oct 12
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
8.4/10 Very good! (233 reviews)
Good location, everything in walking distance. Traveled alone and felt very comfortable hanging out at the bar downstairs for dinner. The staff was super friendly and the food was excellent. The band stopped playing around 10:30 and the place was quiet enough to sleep after that time. My room was simple but comfortable.
Reviewed on Aug 10, 2026
Knotty Pine
CA $1,271
per person
Oct 10 - Oct 12
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
8.4/10 Very good! (127 reviews)
The room was clean. The property could use a little updating. The bathtub was nice and shower nice and no standing water in tub. Towels could be updated and matching. I was only there for one night, so I didn’t use the amenities. The beds were very comfortable.
Reviewed on Aug 14, 2026
Hotel Vervana, Trademark Collection by Wyndham
CA $1,265
per person
Oct 10 - Oct 12
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
8.2/10 Very good! (1,004 reviews)
The staff was great and welcoming. The room was comfortable and clean. The shower was strong and wonderful. The hotel was walking distance to pubs and restaurants. Overall a great night.
Reviewed on Aug 14, 2026
Ready to book your vacation to Great Barrington?
Great Barrington Hotel Deals
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
CA $129
CA $144 total
Sep 14 - Sep 15
includes taxes & fees
The Little Lion
506 Stockbridge Road Great Barrington MA
Fully refundableReserve now, pay when you stay
CA $152
CA $170 total
Sep 8 - Sep 9
includes taxes & fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
415 Stockbridge Rd Great Barrington MA
Fully refundable
CA $166
CA $185 total
Sep 13 - Sep 14
includes taxes & fees
8.8/10 Excellent! (800 reviews)
"Very nice facilities. My wife especially enjoyed the warm indoor pool."
Reviewed on Aug 11, 2026
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.
Ski Butternut
9.0/10 (134 reviews)
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
9.0/10 (22 reviews)
Enjoy a stop at Mahaiwe Performing Arts Center, an entertaining place to visit in Great Barrington. While you're here, you can savor the top-notch restaurants.
Lake Buel
8.8/10 (23 reviews)
Commune with nature and explore the great outdoors at Lake Buel during your travels in Great Barrington. While you're here, you can savor the top-notch restaurants.
Housatonic River Walk
9.2/10 (76 reviews)
You can take time to visit Housatonic River Walk during your travels to Great Barrington. Experience the area's theater scene and live music.
Great Barrington Historical Society & Museum
You can spend time studying the exhibits at Great Barrington Historical Society & Museum during your trip to Great Barrington. While you're here, you can savor the top-notch restaurants.
Monument Mountain
Learn about the local history of Great Barrington with a stop at Monument Mountain. While you're here, you can savor the top-notch restaurants.
Three Mile Pond Wildlife Management Area
You can take time to visit Three Mile Pond Wildlife Management Area during your travels to Great Barrington. While you're here, you can savor the top-notch restaurants.
Frequently asked questions
How much does a Great Barrington vacation package cost?
Offering excellent value package deals from CA $1,203 on Expedia, you'll be pleasantly surprised at how much a vacation to Great Barrington costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Great Barrington?
You can typically find lower rates and greater availability in March, April and November. Explore our cheap Great Barrington vacation packages and you could land some great off-season discounts.
How many days is enough for Great Barrington?
With a well-planned itinerary, you can easily tick off the most popular Great Barrington sights in a few days. But if you want to venture off the beaten track or go on day tours, consider booking your Great Barrington vacation for longer.
Is it worth booking a vacation package to Great Barrington?
Great Barrington offers everything you need for an amazing trip. Begin your Great Barrington vacation on a high note by exploring popular attractions like Housatonic River Walk.
How to find the best Great Barrington package deals?
Start your search for a Great Barrington package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Great Barrington package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Great Barrington escape underway.
Is it cheaper to book a Great Barrington vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customized Great Barrington vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Great Barrington?
If you've got your Great Barrington travel dates locked in, book early to bag some incredible deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Great Barrington?
- Pick the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Great Barrington.
- Plan your budget wisely: Besides the price of your hotel, you'll need to factor in other expenses. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that may arise during your trip to Great Barrington.
- Work out your trip length: Think about how long you want to spend exploring Great Barrington. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
- Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a customized Great Barrington vacation package.
Explore a world of travel with Expedia
- Luxury Hotels in Berkshire County
- Hotels near Lee Premium Outlets
- Stockbridge Hotels
- Hancock Hotels
- The Whitlock
- Becket Hotels
- Historic Rectory Retreat in Stockbridge – Getaway for 8
- Hupi House
- Lanesborough Hotels
- B&B in Russell
- Luxury Hotels in The Berkshires
- Springfield Hotels
- West Stockbridge Hotels
- Chalets in Becket
- 3 Star Hotels in Pittsfield
- Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak
- B&B in Lee
- Resorts in Lenox
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- Country Houses in Alford
- Motels in Granville
- Motels in Egremont
- Resorts in The Berkshires
- Washington Hotels
- Hotels near Frelinghuysen Morris House and Studio
- Apartments in Huntington
- Private Island
- Historic 1804 house in N Becket Village in the Berkshires
- Holiday Inn Express & Suites Pittsfield
- Sheffield Hotels
- The Egremont Village Inn
- Lee Hotels
- Cheap Hotels in The Berkshires
- Pet-Friendly Hotels in The Berkshires
- Pet-Friendly Hotels in Sheffield
- Pittsfield Hotels
- Condo Rentals in Otis
- Pet-Friendly Hotels in Pittsfield
- Cottages in Mill River
- Family Hotels in The Berkshires
- Villas in Beartown State Forest
- Great Barrington Hotels
- Chalets in Mount Washington
- Hotels near National Shrine of the Divine Mercy
- Cheap Hotels in Sandisfield
- Cottages in The Berkshires
- Relais & Chateaux Hotels in The Berkshires
- One Bedroom Luxury Cottage at Blantyre
- Cheap Hotels in Lee
- Lenox Hotels
- Pet-Friendly Hotels in Stockbridge
- The Red Door B&B
- Hotels near Maple Corner Farm Cross Country Ski Area
- Quality Inn Great Barrington
- Resorts in Mount Washington
- Chestnut Lodge
- Hotels near Tanglewood Music Center
- Cheap Hotels in Lenox
- Flights to Stockbridge
- Flights from Windsor
- Flights to Lenox
- Flights from Phoenix (PHX) to Pittsfield (PSF)
- Flights from Toronto (YYZ) to Pittsfield (PSF)
- Flights from Becket
- Flights from Lenox
- Flights to West Stockbridge
- Flights to Sheffield
- Flights to Pittsfield
- Flights from Ithaca (ITH) to Pittsfield (PSF)
- Flights from Plattsburgh (PBG) to Pittsfield (PSF)
- Flights to The Berkshires
- Flights from Boston (BOS) to Pittsfield (PSF)
- Flights from Dalton
- Flights from Seattle (SEA) to Pittsfield (PSF)
- Flights to Great Barrington
- Visit October Mountain State Forest
- Florida Vacations
- Adams Vacations
- Lenox Library
- Visit South Egremont
- Visit Stockbridge
- Naismith Memorial Basketball Hall of Fame
- Norman Rockwell Museum
- Visit Great Barrington
- National Shrine of the Divine Mercy
- Ventfort Hall Mansion and Gilded Age Museum
- Springfield Vacations
- Visit South Lee
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
