Title: Pittsfield Vacation Packages & Trips 2025/2026 from CA $878 | Expedia.ca

  

[Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d9478.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d9478.Travel-Guide-VacationRentals)[Flights to Pittsfield](https://expedia.ca/Cheap-Flights-To-Pittsfield.d9478.Travel-Guide-Flights)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d9478.Car-Rental-Guide)

![](https://images.trvl-media.com/place/9478/5d9f4527-2b11-4f19-a1cd-36a7128d1304.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Pittsfield 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\*

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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 Pittsfield Vacation

When you book a Pittsfield vacation package, you can kick back and enjoy your escape to the fullest. Delve into the highlights of this exciting city knowing that all your travel arrangements have been looked after before you go. A trip to Pittsfield is a wonderful opportunity to sightsee. Be sure to stop by big-name attractions such as [Bousquet Ski Area](https://www.expedia.ca/Bousquet-Ski-Area-Pittsfield.d553248621532665283.Vacation-Attraction), [Colonial Theater](https://www.expedia.ca/Colonial-Theater-Pittsfield.d553248621532665289.Vacation-Attraction) and [Hancock Shaker Village](https://www.expedia.ca/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction). Expedia will help you escape the everyday. Tailor your vacation to Pittsfield to suit your style of travel, whatever that may look like.

## Top Pittsfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.

![La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area](https://images.trvl-media.com/lodging/16000000/15910000/15903000/15902994/5610d306_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

CA $878

per person

Nov 21 - Nov 23

found 1 hour ago

Roundtrip non-stop flight included

Montreal (YUL) to Albany (ALB)

8.8/10 Excellent! (1,011 reviews)

Property not maintained but room was comfortable and large. Room was not cleaned thoroughly and smelled of previous occupants perfume

Reviewed on Oct 2, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-21/2025-11-23/?FromAirport=YUL&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=15902994&paandie=true&dealMarker=6CuNs0vxu2uILjtBFDt_O8GXdVnpj1yEyfXw5MGa9QuMtTbX4_YjPZLYnMotAvfH)

![Crowne Plaza Albany - The Desmond Hotel by IHG](https://images.trvl-media.com/lodging/1000000/40000/37100/37096/97171d33_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Crowne Plaza Albany - The Desmond Hotel by IHG

CA $895

per person

Nov 21 - Nov 23

found 1 hour ago

Roundtrip non-stop flight included

Montreal (YUL) to Albany (ALB)

9.2/10 Wonderful! (1,009 reviews)

I dont have much to stay,i arrived later in the night and left at check out.

Reviewed on Oct 9, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-21/2025-11-23/?FromAirport=YUL&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37096&paandie=true&dealMarker=6CuNs0vxu2uILjtBFDt_O8GXdVnpj1yEyfXw5MGa9QumbHV9BlxYR9FDqpQPxAGq)

![The Landing Hotel at Rivers Casino & Resort](https://images.trvl-media.com/lodging/20000000/19100000/19093300/19093277/146e5c0f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Landing Hotel at Rivers Casino & Resort

Stockade Historic District

CA $973

per person

Nov 21 - Nov 23

found 1 hour ago

Roundtrip non-stop flight included

Montreal (YUL) to Albany (ALB)

9.2/10 Wonderful! (1,006 reviews)

Clean room. Great service. We got an upgrade with a view over the river.

Reviewed on Oct 8, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-21/2025-11-23/?FromAirport=YUL&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19093277&paandie=true&dealMarker=6CuNs0vxu2uILjtBFDt_O8GXdVnpj1yEyfXw5MGa9QvYzFac6lIW8Q_tl9myjLKp)

![Hampton Inn Albany-Wolf Road (Airport)](https://images.trvl-media.com/lodging/1000000/10000/700/698/61f54404_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hampton Inn Albany-Wolf Road (Airport)

CA $915

per person

Nov 21 - Nov 23

found 1 hour ago

Roundtrip non-stop flight included

Montreal (YUL) to Albany (ALB)

8.6/10 Excellent! (1,026 reviews)

Staff was amazing! Close to the airport. Loved the free shuttle to the airport. Carpet in room could have been cleaner, it smelled like dog.

Reviewed on Oct 9, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-21/2025-11-23/?FromAirport=YUL&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=698&paandie=true&dealMarker=6CuNs0vxu2uILjtBFDt_O8GXdVnpj1yEyfXw5MGa9QuUsgFQKPc-ym0_k-ZbJ_YA)

![Marriott Albany](https://images.trvl-media.com/lodging/1000000/20000/11000/10979/1856b3b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Marriott Albany

CA $909

per person

Nov 21 - Nov 23

found 1 hour ago

Roundtrip non-stop flight included

Montreal (YUL) to Albany (ALB)

8.2/10 Very Good! (706 reviews)

Clean and spacious room..the sofa bed was a big plus...everything in the room was perfect..from the lights,bed,pillows,AC and lights..staff were so helpful and respectful from the front desk up to the shuttle drivers...i enjoyed my stay in this hotel...will come back again ..

Reviewed on Oct 6, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-21/2025-11-23/?FromAirport=YUL&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=10979&paandie=true&dealMarker=6CuNs0vxu2uILjtBFDt_O8GXdVnpj1yEyfXw5MGa9Qvoi3ehDgCIU6fAj5OTNFM1)

## Ready to book your vacation to Pittsfield?

Choose your dates

## Pittsfield Hotel Deals

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

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Berkshire Mountain Lodge

8 Dan Fox Dr, Pittsfield, MA

Fully refundableReserve now, pay when you stay

CA $130

CA $176 total

Nov 9 - Nov 10

includes taxes & fees

8.8/10 Excellent! (678 reviews)

"Great lodge with 1 bedroom suites and fully stocked kitchens"

Reviewed on Oct 7, 2025

[](https://expedia.ca/Hotel-Search?startDate=09%2F11%2F2025&endDate=10%2F11%2F2025&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true&regionId=9478)

![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street, Pittsfield, MA

Fully refundable

CA $144

CA $161 total

Nov 9 - Nov 10

includes taxes & fees

7.8/10 Good! (893 reviews)

"Room was clean & comfortable. Thank you! Parking was kind of far."

Reviewed on Oct 5, 2025

[](https://expedia.ca/Hotel-Search?startDate=09%2F11%2F2025&endDate=10%2F11%2F2025&selected=2067&PinnedHotelID=2067&HadPinnedHotel=true&regionId=9478)

![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield, MA

Fully refundableReserve now, pay when you stay

CA $143

CA $159 total

Nov 2 - Nov 3

includes taxes & fees

8.4/10 Very Good! (1,000 reviews)

"Clean place. Good breakfast and friendly staff"

Reviewed on Oct 2, 2025

[](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=789964&PinnedHotelID=789964&HadPinnedHotel=true&regionId=9478)

[See all 1,358 properties in Pittsfield](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F10%2F2025&endDate=12%2F10%2F2025&regionId=9478)

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 Pittsfield

#### 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)

#### Canoe Meadows Wildlife Sanctuary

You can take time to visit Canoe Meadows Wildlife Sanctuary during your travels to Pittsfield. Wander the lakeside in this family-friendly area.

[](https://expedia.ca/Canoe-Meadows-Wildlife-Sanctuary-Pittsfield.d553248621532665285.Vacation-Attraction)

## Explore a world of travel with Expedia

\* 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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## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,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)