Title: The Berkshires Vacation Packages & Trips 2026  | Expedia.ca

[The Berkshires Travel Guide](https://expedia.ca/The-Berkshires.dx6047665)[Hotels in The Berkshires](https://expedia.ca/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)[Vacation Rentals in The Berkshires](https://expedia.ca/The-Berkshires-Vacation-Rentals.d6047665.Travel-Guide-VacationRentals)[Flights to The Berkshires](https://expedia.ca/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights)[The Berkshires Car Rentals](https://expedia.ca/Car-Rentals-In-The-Berkshires.d6047665.Car-Rental-Guide)

![](https://images.trvl-media.com/place/6047665/bda2c66e-c12e-41fa-bcf4-6a6872be8f56.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# The Berkshires Vacation Packages

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

Photo by Photo courtesy of Berkshire Visitors Bureau

- ##  
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 The Berkshires Vacation

Leave the travel planning to us with a The Berkshires vacation package. With everything organized before you head off, the only thing left for you to do is relax and enjoy this destination's countless delights. A trip to The Berkshires wouldn't be complete without exploring some of its most renowned cities, starting with [Lenox](https://www.expedia.ca/Lenox.d8587.Destination-Travel-Guides). A couple of the top attractions here include National Shrine of the Divine Mercy and Norman Rockwell Museum. [Williamstown](https://www.expedia.ca/Williamstown.d7859.Destination-Travel-Guides) should also be on the itineraries of all The Berkshires travellers. Visitors to this city enjoy Massachusetts Museum of Contemporary Art and Mount Greylock. Expedia has flights, hotels, car rentals and more to help you organize your own customized The Berkshires vacation today.

## Ready to book your vacation to The Berkshires?

Choose your dates

## The Berkshires Hotel Deals

![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Fully refundableReserve now, pay when you stay

CA $142

CA $174 total

Feb 11 - Feb 12

includes taxes & fees

8.6/10 Excellent! (2,221 reviews)

Everything was great, the staff, the room, and the amenities. We will be coming back.

Reviewed on Jan 25, 2026

[](https://expedia.ca/Hotel-Search?startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&selected=1066423&PinnedHotelID=1066423&HadPinnedHotel=true&regionId=6047665)

![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Fully refundableReserve now, pay when you stay

CA $135

CA $181 total

Feb 10 - Feb 11

includes taxes & fees

9/10 Wonderful! (825 reviews)

We had a lovely extended family weekend here. The staff was outstanding, every staff member was helpful, friendly and courteous. The large room in back of the lobby was especially helpful for our large group to hang out in and be comfortable. Everyone enjoyed the pool and hot tub despite it being ...

Reviewed on Feb 1, 2026

[](https://expedia.ca/Hotel-Search?startDate=10%2F02%2F2026&endDate=11%2F02%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true&regionId=6047665)

![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Williams Inn

101 Spring Street Williamstown MA

Fully refundableReserve now, pay when you stay

CA $278

CA $311 total

Mar 9 - Mar 10

includes taxes & fees

9.6/10 Exceptional! (572 reviews)

Clean

Reviewed on Jan 31, 2026

[](https://expedia.ca/Hotel-Search?startDate=09%2F03%2F2026&endDate=10%2F03%2F2026&selected=35658765&PinnedHotelID=35658765&HadPinnedHotel=true&regionId=6047665)

[See all 1,086 properties in The Berkshires](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=07%2F02%2F2026&endDate=08%2F02%2F2026&regionId=6047665)

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 The Berkshires

![Autumn reflection while walking in the vicinity of Norman Rockwell Museum, Stockbridge. #LivingtheDream #Stockbridge #NewEngland #Reflection #Autumn #Walking](https://images.trvl-media.com/place/162575/c9de4f96-7bf3-4163-b4b9-feb67c2d801a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Norman Rockwell Museum

You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area. 

[](https://expedia.ca/Norman-Rockwell-Museum-Stockbridge.d6091839.Vacation-Attraction)

![Hancock Shaker Village, Hancock Massachusetts beautiful place; description 
Shakers, all supported themselves by the proceeds of their farmland. The Hancock Shakers were primarily dairy farmers. The raising and sale of garden seeds was perhaps the most lucrative of their early businesses.Land acquisition and conversion continued for decades, with the area peaking at 3,000 acres](https://images.trvl-media.com/place/112303/51d1465f-7568-4ca1-ab97-760ab0d2a7f2.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Hancock Shaker Village

You can browse the exhibits at Hancock Shaker Village, a museum with a storied past, during your trip to Pittsfield. Wander the lakeside in this quaint area. 

[](https://expedia.ca/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction)

#### National Shrine of the Divine Mercy

Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside. 

[](https://expedia.ca/National-Shrine-Of-The-Divine-Mercy-Stockbridge.d553248621532665250.Vacation-Attraction)

## Frequently asked questions

### Can I cancel my flight booking to The Berkshires due to COVID-19?

### What's the best way to find cheap flights to The Berkshires that have flexible change policies?

### What are some of the general tips for travelers to The Berkshires during the COVID-19 outbreak?

> - Find out if any travel restrictions apply to your destination and origin before locking in your flight. Also check if there are any requirements you'll have to follow on arrival, such as testing and quarantining.
> - You're required to wear a face mask at the airport, including at security checkpoints. Be prepared to adjust your mask to verify your identity when asked.
> - Do not hand your boarding pass directly to a TSA officer. Rather, you should position the pass on the scanner and then hold it up for the agent to visually inspect it.
> - One container of liquid hand sanitizer is now permitted in your carry-on baggage. It must not be larger than 12 oz (350 ml), and you'll need to remove it from your bag for X-ray scanning.
> - Put any personal items (like your phone and wallet) in your carry-on rather than a bin to minimize handling during screening.
> - Transport any food items in a clear plastic bag and also place them in a screening bin. Keeping food separate from your carry-on means it's less likely a TSA officer will need to open your bag for inspection.

### Which airlines fly to The Berkshires?

### How can I find cheap tickets to The Berkshires?

### How much is a flight to The Berkshires?

### What are the most popular airports to fly into in The Berkshires?

### When is the cheapest time to fly to The Berkshires?

### How much is a plane ticket to The Berkshires?

### Which airlines with flights to The Berkshires employ COVID-19 cleanliness policies?

> - American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
> - Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
> - Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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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.

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