Title: Great Barrington Vacation Packages & Trips 2026 from CA $1,276 | Expedia.ca

[Great Barrington Travel Guide](https://expedia.ca/Great-Barrington.dx110336)[Hotels in Great Barrington](https://expedia.ca/Great-Barrington-Hotels.d110336.Travel-Guide-Hotels)[Vacation Rentals in Great Barrington](https://expedia.ca/Great-Barrington-Vacation-Rentals.d110336.Travel-Guide-VacationRentals)[Flights to Great Barrington](https://expedia.ca/Cheap-Flights-To-Great-Barrington.d110336.Travel-Guide-Flights)[Great Barrington Car Rentals](https://expedia.ca/Car-Rentals-In-Great-Barrington.d110336.Car-Rental-Guide)

![](https://images.trvl-media.com/place/110336/8bc0aa8d-68ce-4fbf-a4c5-ac032f9ce9c2.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Great Barrington Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, 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](https://www.expedia.ca/Ski-Butternut-Great-Barrington.d6182072.Vacation-Attraction), [Housatonic River Walk](https://www.expedia.ca/Housatonic-River-Walk-Great-Barrington.d553248621532665241.Vacation-Attraction) and [Lake Buel](https://www.expedia.ca/Lake-Buel-Great-Barrington.d553248635976196476.Vacation-Attraction), 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.

![The Cornell Inn, Lenox & The Berkshires](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/63812de9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Cornell Inn, Lenox & The Berkshires

CA $1,276

per person

Jun 7 - Jun 12

found 8 hours ago

Roundtrip flight included

Calgary (YYC) to Albany (ALB)

9/10 Wonderful! (1,001 reviews)

Always a pleasant experience. We stay once a year

Reviewed on Apr 6, 2026

![Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay](https://images.trvl-media.com/lodging/126000000/125310000/125305600/125305546/53d4f091_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay

CA $7,317

per person

Jun 7 - Jun 12

found 8 hours ago

Roundtrip flight included

Calgary (YYC) to Albany (ALB)

No reviews

![Prospect Berkshires](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/9aaa75ce_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Prospect Berkshires

CA $1,852

per person

Jun 7 - Jun 12

found 8 hours ago

Roundtrip flight included

Calgary (YYC) to Albany (ALB)

9.8/10 Exceptional! (23 reviews)

The cabins are brand new, the property is gorgeous, restaurant features local and quality product and the staff is very responsive via text message. The lakeside sauna is private and easy to reserve. Great place!

Reviewed on Feb 20, 2026

![Secluded Estate Optional Guest House, Pond, Playroom, Gym & Theater Sunny Pond by Avantstay](https://images.trvl-media.com/lodging/105000000/104350000/104348700/104348623/e8b5f5fc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Secluded Estate Optional Guest House, Pond, Playroom, Gym & Theater Sunny Pond by Avantstay

CA $7,294

per person

Jun 7 - Jun 12

found 8 hours ago

Roundtrip flight included

Calgary (YYC) to Albany (ALB)

No reviews

![Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!](https://images.trvl-media.com/lodging/91000000/90940000/90931100/90931052/5aa942e0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

CA $3,338

per person

Jun 7 - Jun 12

found 8 hours ago

Roundtrip flight included

Calgary (YYC) to Albany (ALB)

No reviews

## Ready to book your vacation to Great Barrington?

Choose your dates

## Great Barrington Hotel Deals

![Quality Inn Great Barrington](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/ed6ed4e8_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Fully refundableReserve now, pay when you stay

CA $93

CA $104 total

Apr 21 - Apr 22

includes taxes & fees

8.4/10 Very Good! (1,002 reviews)

Room and bed were clean as I would expect bath and toilet were clean, shower pressure was mediocre as I usually expect. Location was excellent as my ski resorts were within close proximity as well as restaurants (think Bogies, awesome food and reasonable prices). Check in was a breeze and Brian the ...

Reviewed on Apr 5, 2026

[](https://expedia.ca/Hotel-Search?startDate=21%2F04%2F2026&endDate=22%2F04%2F2026&selected=128208&PinnedHotelID=128208&HadPinnedHotel=true&regionId=110336)

![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Holiday Inn Express Hotel & Suites Great Barrington by IHG

415 Stockbridge Rd Great Barrington MA

Fully refundable

CA $160

CA $179 total

Apr 20 - Apr 21

includes taxes & fees

8.8/10 Excellent! (754 reviews)

This was a very nice stay. The gentleman that checked us in was friendly, funny, knowledgeable and very welcoming.

Reviewed on Apr 1, 2026

[](https://expedia.ca/Hotel-Search?startDate=20%2F04%2F2026&endDate=21%2F04%2F2026&selected=892229&PinnedHotelID=892229&HadPinnedHotel=true&regionId=110336)

![Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/9d0420c7_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

249 Stockbridge Rd Great Barrington MA

Fully refundableReserve now, pay when you stay

CA $211

CA $236 total

Apr 21 - Apr 22

includes taxes & fees

9.4/10 Exceptional! (776 reviews)

Front desk staff rocked. One younger girl even helped to shovel out our car for us!

Reviewed on Mar 9, 2026

[](https://expedia.ca/Hotel-Search?startDate=21%2F04%2F2026&endDate=22%2F04%2F2026&selected=913175&PinnedHotelID=913175&HadPinnedHotel=true&regionId=110336)

[See all 1,597 properties in Great Barrington](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F04%2F2026&endDate=09%2F04%2F2026&regionId=110336)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### Discover the most popular places to visit in Great Barrington

![new england foliage overlooking pond with beautiful reflection](https://images.trvl-media.com/place/553248621560926695/7f9cc7a3-0724-4ed8-8050-41ee54686943.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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. 

[](https://expedia.ca/Lake-Mansfield-Park-Great-Barrington.d553248621560926695.Vacation-Attraction)

#### 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. 

[](https://expedia.ca/Lake-Buel-Great-Barrington.d553248635976196476.Vacation-Attraction)

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- [Car rental Sheffield ](https://www.expedia.ca/Car-Rentals-In-Sheffield.d157238.Car-Rental-Guide)
- [Car rental Stockbridge ](https://www.expedia.ca/Car-Rentals-In-Stockbridge.d162575.Car-Rental-Guide)

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

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