Title: Cheshire Vacation Packages & Trips 2026 from CA $1,348 | Expedia.ca [Hotels in Cheshire](https://expedia.ca/Cheshire-Hotels.d6005398.Travel-Guide-Hotels)[Vacation Rentals in Cheshire](https://expedia.ca/Cheshire-Vacation-Rentals.d6005398.Travel-Guide-VacationRentals)[Cheshire Car Rentals](https://expedia.ca/Car-Rentals-In-Cheshire.d6005398.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6005398/af3c140d-6448-4a00-9ca4-43cb22b4b44b.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Cheshire 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 Cheshire Vacation When an adventure in the city is calling your name, answer it with a Cheshire vacation package. With all your travel needs taken care of before you go, all you have to do here is focus on enjoying yourself. Like to explore your new surroundings? [Mount Greylock](https://www.expedia.ca/Mount-Greylock-Adams.d6091829.Vacation-Attraction), [Mount Greylock State Reservation](https://www.expedia.ca/Mount-Greylock-State-Reservation-Massachusetts.d637217485842313216.Vacation-Attraction) and [East Hoosac Quaker Meetinghouse](https://www.expedia.ca/East-Hoosac-Quaker-Meetinghouse-Adams.d553248621561173644.Vacation-Attraction) are just a few of the best places to visit during a trip to Cheshire. Don't delay visiting this destination any longer. The ultimate Cheshire vacation is a few quick clicks away with Expedia. ## Top Cheshire Vacation Deals Price found within the past 48 hours. Click for updated prices. ![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 $1,348 per person May 9 - May 16 found 1 day ago Roundtrip flight included Saskatoon (YXE) to Albany (ALB) 8.8/10 Excellent! (1,001 reviews) Room was clean. Only issue was when taking a shower the water didn’t drain. Reviewed on Feb 14, 2026 ![Hotel Brookmere & Arbor Spa](https://images.trvl-media.com/lodging/107000000/106890000/106887400/106887312/fd2345ba_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Brookmere & Arbor Spa CA $1,398 per person May 9 - May 16 found 1 day ago Roundtrip flight included Saskatoon (YXE) to Albany (ALB) 9.2/10 Wonderful! (218 reviews) The room was large, clean and beautiful. Will definitely come again! Reviewed on Feb 15, 2026 ![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 $1,574 per person May 9 - May 16 found 1 day ago Roundtrip flight included Saskatoon (YXE) to Albany (ALB) 8.2/10 Very Good! (751 reviews) Room was clean Someone was smoking marijuana and the smell was a little bothering check-in. Staff was very friendly. The staff member today when I checked out, put me on hold when I called down and never answered the phone back and then when I did call back, put me on hold again, but all in all must stay was OK. Reviewed on Feb 15, 2026 ![Holiday Inn Express Hotel & Suites West Coxsackie by IHG](https://images.trvl-media.com/lodging/3000000/2600000/2591600/2591583/2081618e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express Hotel & Suites West Coxsackie by IHG CA $1,422 per person May 9 - May 16 found 1 day ago Roundtrip flight included Saskatoon (YXE) to Albany (ALB) 8.4/10 Very Good! (971 reviews) This place would be 5 stars if someone hadn't smoked enough marijuana in the elevator and on our floor to stink up the entire floor. It was 1 day out of 4 that happened. Breakfast and room were great. Reviewed on Feb 13, 2026 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_6005398) ## Ready to book your vacation to Cheshire? Choose your dates ## Cheshire 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 $173 total Feb 22 - Feb 23 includes taxes & fees 8.6/10 Excellent! (2,235 reviews) Fairly clean and staff were friendly Reviewed on Feb 13, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=1066423&PinnedHotelID=1066423&HadPinnedHotel=true®ionId=6005398) ![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 $136 CA $183 total Mar 17 - Mar 18 includes taxes & fees 9/10 Wonderful! (840 reviews) Perfect location, big rooms, nice staff. Reviewed on Feb 10, 2026 [](https://expedia.ca/Hotel-Search?startDate=17%2F03%2F2026&endDate=18%2F03%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=6005398) ![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 $257 CA $288 total Mar 11 - Mar 12 includes taxes & fees 9.6/10 Exceptional! (573 reviews) A beautiful hotel to stay at while visiting the Williams campus. Our room had a nice view of the woods. Rooms were clean and with comfortable beds. The common areas of the hotel were beautiful and cozy with the fireplaces going. Easy check in and out with friendly staff. Reviewed on Feb 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=11%2F03%2F2026&endDate=12%2F03%2F2026&selected=35658765&PinnedHotelID=35658765&HadPinnedHotel=true®ionId=6005398) [See all 1,007 properties in Cheshire](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F02%2F2026&endDate=18%2F02%2F2026®ionId=6005398) 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) ## 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. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## 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