Title: Cheshire Vacation Packages & Trips 2026 from CA $1,003 | 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. ![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 $1,003 per person Apr 17 - Apr 20 found 4 hours ago Roundtrip flight included Halifax (YHZ) to Albany (ALB) 9.2/10 Wonderful! (218 reviews) Everything was fine. The only exception we had to leave because of the weather . When we asked f we can get a refund , the manager declined. I guess he or she was worried about there numbers . Reviewed on Feb 24, 2026 ![Lodges At Cresthaven](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320727/4993b753_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lodges At Cresthaven CA $1,164 per person Apr 17 - Apr 20 found 4 hours ago Roundtrip flight included Halifax (YHZ) to Albany (ALB) 9.4/10 Exceptional! (531 reviews) Wonderful stay as usual!! Our lodge was clean, comfortable and toasty warm with the gas fireplace. The view from every room of our lodge was beautiful. The Lodges never disappoint us. Can’t wait until next time!! Reviewed on Feb 15, 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 $1,067 per person Apr 17 - Apr 20 found 4 hours ago Roundtrip flight included Halifax (YHZ) to Albany (ALB) 7.4/10 Good! (567 reviews) We have been staying at the Equinox for over 35 yrs. Love the whole scene and vibe. Love the pool and hot tub. Love the big real wood fireplace. Reviewed on Jan 24, 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 $1,105 per person Apr 17 - Apr 20 found 4 hours ago Roundtrip flight included Halifax (YHZ) to Albany (ALB) 8.2/10 Very Good! (751 reviews) Clean room, friendly staff. Would stay again Reviewed on Feb 20, 2026 ![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 $1,030 per person Apr 17 - Apr 20 found 4 hours ago Roundtrip flight included Halifax (YHZ) to Albany (ALB) 8.8/10 Excellent! (1,001 reviews) Awesome Staff. Great Hotel! Reviewed on Feb 25, 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 $174 total Mar 31 - Apr 1 includes taxes & fees 8.8/10 Excellent! (2,269 reviews) Great and helpful stuff, clean room. Reviewed on Feb 27, 2026 [](https://expedia.ca/Hotel-Search?startDate=31%2F03%2F2026&endDate=01%2F04%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 $155 CA $204 total Mar 2 - Mar 3 includes taxes & fees 9/10 Wonderful! (864 reviews) Overcharged and lied to said security deposit was released back but never was Reviewed on Feb 26, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F03%2F2026&endDate=03%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 $269 CA $300 total Mar 3 - Mar 4 includes taxes & fees 9.6/10 Exceptional! (582 reviews) nice aesthetics Reviewed on Feb 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=03%2F03%2F2026&endDate=04%2F03%2F2026&selected=35658765&PinnedHotelID=35658765&HadPinnedHotel=true®ionId=6005398) [See all 1,003 properties in Cheshire](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=01%2F03%2F2026&endDate=02%2F03%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