Title: Cheshire County Vacations & Trips 2026 | Expedia.ca [Cheshire County Travel Guide](https://expedia.ca/Cheshire-County.dx553248635976430851)[Cheshire County Hotels](https://expedia.ca/Destinations-In-Cheshire-County.d553248635976430851.Hotel-Destinations)[Vacation Rentals in Cheshire County](https://expedia.ca/Destinations-In-Cheshire-County.d553248635976430851.Vacation-Rental-Destinations)[Cheshire County Car Rentals](https://expedia.ca/Destinations-In-Cheshire-County.d553248635976430851.Car-Rental-Destinations) ![](https://images.trvl-media.com/place/6123341/a0d75d64-c95b-4611-b551-1f08145f2c0c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Cheshire County Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by mike dobias - ## 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 County Vacation Book a vacation package to Cheshire County and make travel planning easy. With all the logistics arranged before you leave, you can focus on enjoying every minute in this destination. With so much to see on a trip to Cheshire County, it can be tricky to know where to begin. Kick off your journey in [Jaffrey](https://www.expedia.ca/Jaffrey.d183569.Destination-Travel-Guides) at Laurel Lake and Friendly Farm — two popular attractions here. Another top city worth adding to your itinerary is [Walpole](https://www.expedia.ca/Walpole.d6123341.Destination-Travel-Guides). Be sure not to miss Vermont Country Store and Bellows Falls Opera House. Expedia is your one-stop shop when it comes to planning your Cheshire County vacation. From flights and hotels, to activities and more, we know how to curate a travel experience like no other. ## Top vacation destinations in Cheshire County ![](https://mediaim.expedia.com/destination/2/9b320961fd585a1c4407ed1c1d8d7b7c.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Jaffrey [](https://expedia.ca/Jaffrey.d183569.Destination-Travel-Guides) ![Dublin which includes a small town or village](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105788-Dublin.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Dublin [](https://expedia.ca/Dublin.d98112.Destination-Travel-Guides) ![](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_553248635976430851) ## Cheshire County Hotel Deals ![Best Western Plus Keene Hotel](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Plus Keene Hotel 401 Winchester St Keene NH Fully refundableReserve now, pay when you stay CA $152 CA $165 total Feb 24 - Feb 25 includes taxes & fees 8.4/10 Very Good! (1,001 reviews) Great Reviewed on Feb 18, 2026 [](https://expedia.ca/Hotel-Search?startDate=24%2F02%2F2026&endDate=25%2F02%2F2026&selected=15916&PinnedHotelID=15916&HadPinnedHotel=true®ionId=553248635976430851) ![Keene Elm City Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Keene Elm City Hotel, an Ascend Collection Hotel 175 Key Rd Keene NH Fully refundableReserve now, pay when you stay CA $142 CA $154 total Feb 22 - Feb 23 includes taxes & fees 8.4/10 Very Good! (985 reviews) Great welcoming agent, spotless room and a very quiet floor. Reviewed on Feb 16, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=14439&PinnedHotelID=14439&HadPinnedHotel=true®ionId=553248635976430851) ![Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.](https://images.trvl-media.com/lodging/119000000/118340000/118332100/118332023/266d4a20_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond. Fitzwilliam NH 10/10 Exceptional! (10 reviews) It was a lovely stay! Lake is beautiful and the house is cozy. Reviewed on Oct 16, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=07%2F03%2F2026&endDate=08%2F03%2F2026&selected=118332023&PinnedHotelID=118332023&HadPinnedHotel=true®ionId=553248635976430851) [](https://expedia.ca/Hotel-Search?startDate=07%2F03%2F2026&endDate=08%2F03%2F2026&selected=118332023&PinnedHotelID=118332023&HadPinnedHotel=true®ionId=553248635976430851) [See all 2,064 properties in Cheshire County](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=22%2F02%2F2026&endDate=23%2F02%2F2026®ionId=553248635976430851) 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) ## Frequently asked questions ### How much does a Cheshire County vacation package cost? ### How do I get a cheap travel package to Cheshire County? ### What are the top hotels in Cheshire County? ### How far in advance should I book my Cheshire County vacation? ### What does an Expedia Cheshire County travel package include? ### What should I know before booking a Cheshire County travel package? ### Can I choose my airline with a Cheshire County Expedia vacation package? ### If I'm not able to travel, can I cancel my Cheshire County vacation package? \* 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