Title: The Berkshires Vacation Packages & Trips 2025/2026 | 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 $128 CA $158 total Nov 2 - Nov 3 includes taxes & fees 8.6/10 Excellent! (2,028 reviews) "Great!" Reviewed on Sep 30, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=1066423&PinnedHotelID=1066423&HadPinnedHotel=true®ionId=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 $124 CA $169 total Oct 21 - Oct 22 includes taxes & fees 8.8/10 Excellent! (668 reviews) "Nice room, bathroom could use some repair, crumbling sheetrock surrounding tub enclosure, priced well" Reviewed on Sep 30, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F10%2F2025&endDate=22%2F10%2F2025&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=6047665) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 190 Meadow Street, South Lee, MA Fully refundableReserve now, pay when you stay CA $162 CA $200 total Nov 2 - Nov 3 includes taxes & fees 9/10 Wonderful! (741 reviews) "Clean property with plenty to do!" Reviewed on Sep 28, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=20875006&PinnedHotelID=20875006&HadPinnedHotel=true®ionId=6047665) [See all 1,118 properties in The Berkshires](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F10%2F2025&endDate=09%2F10%2F2025®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? > If you've yet to book your tickets, read the terms and conditions of the airline you're considering. If you've already secured your flight to The Berkshires, make use of our [Customer Service Portal](https://www.expedia.ca/service/?langId=1033). It has information that will help you determine which COVID-19 policies are applicable to your reservation and provide you with the next steps. ### What's the best way to find cheap flights to The Berkshires that have flexible change policies? > At Expedia, we've been channeling our inner yogi to give you the most flexible airfares in town. Simply tick the "No change fee" box directly below the "Flexible change policies" heading to find your dream flight to The Berkshires. ### What are some of the general tips for travelers to The Berkshires during the COVID-19 outbreak? > The COVID-19 outbreak has brought about substantial changes to the way we travel. If you plan to visit The Berkshires, the following tips will help you navigate these new challenges and rules: > > - 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? > Arrange your airfare with American Airlines and then start planning your The Berkshires to-do list. This popular carrier runs 607 flights each month to Bradley Intl. Airport (BDL), a main gateway. ### How can I find cheap tickets to The Berkshires? > One of the best ways to nab cheap tickets to The Berkshires is to be flexible with your travel dates. Search for your flights, then click "flexible dates" above the results. You'll see the cheapest prices for nearby days. The lowest price for a flight to The Berkshires in the last seven days was . Booking ahead will usually help you get an even better deal. ### How much is a flight to The Berkshires? > You could have nabbed a return flight to The Berkshires from anywhere between and in the last seven days. For one-way trips departing from (), the lowest price during this time was . ### What are the most popular airports to fly into in The Berkshires? > The Berkshires's main entryway is Bradley Intl. Airport (BDL). Get your next thrilling journey underway by booking a ticket on one of the 2149 flights a month to this destination. ### When is the cheapest time to fly to The Berkshires? > If you'd rather spend your vacation money enjoying the delights of The Berkshires rather than on getting there, leave early in the week. The cheapest day to fly is generally Tuesday, with Monday a close second. With many folks traveling over the weekend, Saturday often has the highest airfares. ### How much is a plane ticket to The Berkshires? > In the last seven days, airfares varied between and . Swipe through our terrific deals to The Berkshires, make a booking and then start packing your suitcase. ### Which airlines with flights to The Berkshires employ COVID-19 cleanliness policies? > In response to the COVID-19 pandemic, the majority of airlines have adopted new rules and measures to help their passengers and staff fly with confidence. Here are just a few examples: > > - 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 ### Lodging - [3 Star Hotels in Otis](https://www.expedia.ca/3Star-Otis-Hotels.s30-0-d6005412.Travel-Guide-Filter-Hotels) - [Hotels near Jacob's Pillow](https://www.expedia.ca/Jacobs-Pillow-Hotels.0-l553248621532666599-0.Travel-Guide-Filter-Hotels) - [Hotels near Lee Premium Outlets](https://www.expedia.ca/Lee-Premium-Outlets-Hotels.0-l6127084-0.Travel-Guide-Filter-Hotels) - [Farmstay in Mill River](https://www.expedia.ca/Mill-River-Agritourism.d3000748895-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Mill River](https://www.expedia.ca/Mill-River-Apart-Hotels.d3000748895-aaApartHotels.Travel-Guide-Accommodation) - 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[Flights from Monterey](https://www.expedia.ca/lp/flights/6005411/flights-from-monterey) - [Flights from Otis](https://www.expedia.ca/lp/flights/6005412/flights-from-otis) ### Packages - [Adams Vacations](https://www.expedia.ca/Adams.d6005393.Destination-Travel-Guides) - [Auburn Mall](https://www.expedia.ca/Auburn-Mall-Auburn.d6208533.Vacation-Attraction) - [Becket Land Trust Historic Quarry](https://www.expedia.ca/Becket-Land-Trust-Historic-Quarry-Becket.d553248621532666600.Vacation-Attraction) - [Big E](https://www.expedia.ca/Big-E-West-Springfield.d553248621533116953.Vacation-Attraction) - [Calvin Theatre and Performing Arts Center](https://www.expedia.ca/Calvin-Theatre-And-Performing-Arts-Center-Northampton.d553248621532666663.Vacation-Attraction) - [Canoe Meadows Wildlife Sanctuary](https://www.expedia.ca/Canoe-Meadows-Wildlife-Sanctuary-Pittsfield.d553248621532665285.Vacation-Attraction) - [Chicopee Falls Dam](https://www.expedia.ca/Chicopee-Falls-Dam-Chicopee.d6070279.Vacation-Attraction) - [Eastern States Exposition](https://www.expedia.ca/Eastern-States-Exposition-West-Springfield.d6070273.Vacation-Attraction) - [Florida Vacations](https://www.expedia.ca/Florida.d553248634999031091.Destination-Travel-Guides) - [Great Barrington Vacations](https://www.expedia.ca/Great-Barrington.d110336.Destination-Travel-Guides) - [Hancock Shaker Village](https://www.expedia.ca/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction) - [Lake Buel](https://www.expedia.ca/Lake-Buel-Great-Barrington.d553248635976196476.Vacation-Attraction) - [Lake Mansfield Park](https://www.expedia.ca/Lake-Mansfield-Park-Great-Barrington.d553248621560926695.Vacation-Attraction) - [Lenox Library](https://www.expedia.ca/Lenox-Library-Lenox.d553248621532665268.Vacation-Attraction) - [Leverett Vacations](https://www.expedia.ca/Leverett.d125601.Destination-Travel-Guides) - [Naismith Memorial Basketball Hall of Fame](https://www.expedia.ca/Naismith-Memorial-Basketball-Hall-Of-Fame-South-End.d6070299.Vacation-Attraction) - [National Shrine of the Divine Mercy](https://www.expedia.ca/National-Shrine-Of-The-Divine-Mercy-Stockbridge.d553248621532665250.Vacation-Attraction) - [Naumkeag Museum](https://www.expedia.ca/Naumkeag-Museum-Stockbridge.d6091843.Vacation-Attraction) - [Norman Rockwell Museum](https://www.expedia.ca/Norman-Rockwell-Museum-Stockbridge.d6091839.Vacation-Attraction) - [Old Sturbridge Village](https://www.expedia.ca/Old-Sturbridge-Village-Sturbridge.d6232666.Vacation-Attraction) - [Otis Vacations](https://www.expedia.ca/Otis.d6005412.Destination-Travel-Guides) - [Richmond Vacations](https://www.expedia.ca/Richmond.d151138.Destination-Travel-Guides) - [South Egremont Vacations](https://www.expedia.ca/South-Egremont.d183341.Destination-Travel-Guides) - [Visit South Lee](https://www.expedia.ca/South-Lee.dx183343) - [Springfield Vacations](https://www.expedia.ca/Springfield.d6047669.Destination-Travel-Guides) - [Three Rivers Vacations](https://www.expedia.ca/Three-Rivers.d3000441550.Destination-Travel-Guides) - [Ventfort Hall Mansion and Gilded Age Museum](https://www.expedia.ca/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Lenox.d553248621532665270.Vacation-Attraction) - [West Springfield Vacations](https://www.expedia.ca/West-Springfield.d7738.Destination-Travel-Guides) - [Western Massachusetts Vacations](https://www.expedia.ca/Western-Massachusetts.d6234063.Destination-Travel-Guides) - [Williamsburg Vacations](https://www.expedia.ca/Williamsburg.d175048.Destination-Travel-Guides) - [Worcester Vacations](https://www.expedia.ca/Worcester.d6023336.Destination-Travel-Guides) ### Cars - [Enterprise Rental Cars in New Marlborough](https://www.expedia.ca/Enterprise-Car-Rentals-In-New-Marlborough.d137834-c15.Car-Rental-Guide-Suppliers) \* Savings based on package bookings compared to the price of the same components booked separately. 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