Title: The Berkshires Vacation Packages & Trips 2026 from CA $1,114 | 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. ## Top The Berkshires Vacation Deals Price found within the past 48 hours. Click for updated prices. ![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/b534a8c8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Manchester View CA $1,114 per person Feb 13 - Feb 16 found 4 hours ago Roundtrip flight included Toronto (YYZ) to Albany (ALB) 9.4/10 Exceptional! (772 reviews) The place is great. Especially the wood burning stove in the room. Reviewed on Jan 7, 2026 ![The Equinox Golf Resort & Spa](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Equinox Golf Resort & Spa Manchester Village Historic District CA $2,209 per person Feb 13 - Feb 16 found 4 hours ago Roundtrip flight included Toronto (YYZ) to Albany (ALB) 7.4/10 Good! (567 reviews) Was surprised at the dirty floors in common area and in my room one of the curtain sheers was ripped, other curtains were hanging off hokks, caulking at sink looked old, cracked, carpets in staircase dirty. I fear this beautiful hotel is in a downward spiral. One front desk person directed me to closed restaurants... Reviewed on Jan 9, 2026 ![Aspen At Manchester](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/6f88107a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aspen At Manchester CA $1,223 per person Feb 13 - Feb 16 found 4 hours ago Roundtrip flight included Toronto (YYZ) to Albany (ALB) 8.8/10 Excellent! (600 reviews) Everything was good, The refrigerator was barely working, so we had to take the food outside. Reviewed on Jan 7, 2026 ![Wilburton Inn](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634223/8673c9ed_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wilburton Inn CA $1,580 per person Feb 13 - Feb 16 found 4 hours ago Roundtrip flight included Toronto (YYZ) to Albany (ALB) 9/10 Wonderful! (128 reviews) Beautiful property and the staff is wonderful and super helpful. We went skiing in Stratton and stayed at the Wilburton Inn for a couple of nights. We will be back! Reviewed on Jan 6, 2026 ![Hill Farm Inn](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502179/2544c235_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hill Farm Inn CA $1,376 per person Feb 13 - Feb 16 found 4 hours ago Roundtrip flight included Toronto (YYZ) to Albany (ALB) 9.6/10 Exceptional! (171 reviews) Never expected to stay in a 4 bedroom house with 6 bathroom, 5 showers, steam room and sauna. The place was fully and beautifully funished. I would definitely book the same place for this spring or summer. Reviewed on Jan 7, 2026 ## 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 $144 CA $176 total Jan 13 - Jan 14 includes taxes & fees 8.6/10 Excellent! (2,202 reviews) Clean rooms, chimney did not work Reviewed on Jan 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=13%2F01%2F2026&endDate=14%2F01%2F2026&selected=1066423&PinnedHotelID=1066423&HadPinnedHotel=true®ionId=6047665) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Downstreet, an Ascend Collection Hotel 40 Main St North Adams MA Fully refundable CA $173 CA $194 total Feb 2 - Feb 3 includes taxes & fees 8.6/10 Excellent! (1,002 reviews) friendly accommodating staff Reviewed on Jan 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F02%2F2026&endDate=03%2F02%2F2026&selected=2943&PinnedHotelID=2943&HadPinnedHotel=true®ionId=6047665) ![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 $136 CA $152 total Jan 30 - Jan 31 includes taxes & fees 8/10 Very Good! (1,007 reviews) Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN Reviewed on Jan 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=30%2F01%2F2026&endDate=31%2F01%2F2026&selected=2067&PinnedHotelID=2067&HadPinnedHotel=true®ionId=6047665) [See all 1,079 properties in The Berkshires](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F01%2F2026&endDate=12%2F01%2F2026®ionId=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 ![Norman Rockwell Museum](https://mediaim.expedia.com/destination/2/8f946ea40f181d64f9531da690351b5f.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) #### 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) #### Naumkeag Museum You can spend time browsing the exhibits at Naumkeag Museum during your travels in Stockbridge. While you're in the area, stroll along the lakeside. [](https://expedia.ca/Naumkeag-Museum-Stockbridge.d6091843.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. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [3 Star Hotels in Otis ](https://www.expedia.ca/3Star-Otis-Hotels.s30-0-d6005412.Travel-Guide-Filter-Hotels) - 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