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.
Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

2.5 out of 5
Downtown Albany
Price was CA $961, price is now CA $909 per person
CA $909
per person
Dec 27 - Dec 31
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
8.2/10 Very good! (1,181 reviews)
Vieja y sucia

Reviewed on Oct 27, 2026

Marriott Albany

Marriott Albany

3.5 out of 5
Price was CA $1,147, price is now CA $1,017 per person
CA $1,017
per person
Dec 27 - Dec 31
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
8.4/10 Very good! (1,001 reviews)
This is a pretty tired hotel. They have tried to put lipstick on a pic, but needs a lot of work. They have done the rooms a little, but everything else looks tired and run down.

Reviewed on Oct 26, 2026

Albany Airport Inn

Albany Airport Inn

2.5 out of 5
Price was CA $994, price is now CA $910 per person
CA $910
per person
Dec 27 - Dec 31
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
6.6/10 (1,006 reviews)
needs up grade TV barely see the screen NO HOT WATER FOR SHOWERS I WOULD NEVER STAY THERE AGAIN

Reviewed on Oct 27, 2026

Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

3 out of 5
Downtown Albany
Price was CA $1,067, price is now CA $1,004 per person
CA $1,004
per person
Dec 27 - Dec 31
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
9.2/10 Wonderful! (1,901 reviews)

South Shire

South Shire

4 out of 5
Price was CA $1,575, price is now CA $1,492 per person
CA $1,492
per person
Jan 2 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Albany (ALB)
9/10 Wonderful! (137 reviews)
Bad bad bad bad bad bad bad

Reviewed on Oct 26, 2026

Ready to book your vacation to Great Barrington?

 

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Great Barrington Hotel Deals

Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundable
The price is CA $105 per night from Nov 22 to Nov 23
CA $105
CA $118 total
Nov 22 - Nov 23
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
"Room was clean and comfortably appointed. Parking was not an issue even though the hotel was full. Easy walking to restaurants and shops. Staff were very pleasant and welcoming."

Reviewed on Oct 27, 2026

Quality Inn Great Barrington
Prospect Berkshires

Prospect Berkshires

3 out of 5
50 Prospect Lake Rd Egremont MA
The price is CA $385 per night from Nov 23 to Nov 24
CA $385
CA $477 total
Nov 23 - Nov 24
includes taxes & fees
Prospect Berkshires
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
Fully refundableReserve now, pay when you stay
The price is CA $201 per night from Nov 2 to Nov 3
CA $201
CA $225 total
Nov 2 - Nov 3
includes taxes & fees
9.4/10 Exceptional! (818 reviews)
"We were very pleased with our experience here. Room was super clean and included a mini fridge and microwave. The mini fridge was much needed for storing milk as we were traveling with an 8 month old. We forgot the sheet for our pack and play and the staff was helpful in providing us with one. The ..."

Reviewed on Oct 25, 2026

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
See all 1,598 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
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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 does a Great Barrington vacation package cost?
Offering excellent value package deals from CA $909 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.

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