Great Barrington Vacation Packages

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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.
Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
7.8/10 Good! (1,174 reviews)
The bathroom smells so bad, looks clean but smells like mold

Reviewed on Jul. 30, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
per person
Oct 9 - Oct 13
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
7.4/10 Good! (491 reviews)
Beautiful setting! Comfortable rooms

Reviewed on Jul. 25, 2025

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
per person
Oct 9 - Oct 13
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
8.2/10 Very Good! (1,005 reviews)
We chose this property because it had a pool. It was summer and the pool was full of dead leaves. We were told it was “seasonal”. Perhaps it opens in the winter?

Reviewed on Jul. 31, 2025

Valley Craft Ales

Valley Craft Ales

2 out of 5
per person
Oct 9 - Oct 13
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
8.8/10 Excellent! (126 reviews)
A place to rest your head, no handicapped accessibility, not fancy but clean.

Reviewed on Jul. 28, 2025

The White House Inn

The White House Inn

3.5 out of 5
per person
Oct 9 - Oct 13
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
9.2/10 Wonderful! (206 reviews)
The room we stayed in was comfortable and had a great view from the balcony. The bed was very comfortable. I would have liked more space in the bathroom to put a cup and other things. Also, an exhaust fan would be nice in the bathroom. But it was pretty. The staff were all very gracious. We had a good meal Sunday night in the restaurant and our waiter was very nice. I knew that the restaurant would not be open on Monday and Tuesday, but it would have been nice to have the bar open for drinks on the patio in the evening on those nights.

Reviewed on Jul. 24, 2025

Ready to book your vacation to Great Barrington?

 

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Great Barrington Hotel Deals

Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Aug 17 to Aug 18
CA $140
CA $157 total
Aug 17 - Aug 18
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
"Close to city center, safe and great costumer experience"

Reviewed on Jul. 30, 2025

Quality Inn
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
Fully refundable
The price is CA $241 per night from Aug 12 to Aug 13
CA $241
CA $270 total
Aug 12 - Aug 13
includes taxes & fees
8.8/10 Excellent! (641 reviews)
"Nice stay overall, but way overpriced for a Holiday Inn!! The breakfast was underwhelming."

Reviewed on Jul. 27, 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is CA $209 per night from Aug 27 to Aug 28
CA $209
CA $234 total
Aug 27 - Aug 28
includes taxes & fees
9.2/10 Wonderful! (722 reviews)
"Didn’t like that the air conditioning and fan turned off . We woke up several times during the night because of the lack of sound and the room got warmer until the thermostat started the AC up again."

Reviewed on Jul. 29, 2025

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
See all 1,542 properties in Great Barrington
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Discover the most popular places to visit in Great Barrington

Lake Buel

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.

Lake Buel

Lake Mansfield Park

Explore the great outdoors at Lake Mansfield Park, a lovely green space in Great Barrington. Experience the area's theater scene and live music.

Lake Mansfield Park

Frequently asked questions

How much does a Great Barrington vacation package cost?
Offering excellent value package deals from CA $936 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.