Title: Chester Vacation Packages & Trips 2026 from CA $1,338 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d3000446848.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d3000446848.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d3000446848.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Chester 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 Chester Vacation With plenty of highlights as well as some hidden gems, this city is best explored with a Chester vacation package. Find a place to stay in Downtown Manchester, which is great for cafes, history and bars and pubs. There's plenty to see and do during your trip to Chester, including [Zorvino Vineyards](https://www.expedia.ca/Zorvino-Vineyards-Sandown.d553248621532667359.Vacation-Attraction) and [Robert Frost Farm State Historic Site](https://www.expedia.ca/Robert-Frost-Farm-State-Historic-Site-Derry.d553248621532667105.Vacation-Attraction). No matter your travel plans or the size of your budget, organizing your ultimate tailored Chester vacation is a cinch with Expedia. ## Top Chester Vacation Deals Price found within the past 48 hours. Click for updated prices. ![The Langham, Boston](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/54f3deb7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Boston Downtown Boston CA $1,338 per person Apr 24 - Apr 27 found 24 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Boston (BOS) 9.6/10 Exceptional! (1,004 reviews) Room was spacious, clean & well set up. Nice that they use Dyptique hand soap shampoo & shower gel. That is a 5 star touch. Bed was nice and very quiet location. Reviewed on Mar 22, 2026 ![Boston Harbor Hotel](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boston Harbor Hotel North End CA $1,697 per person Apr 24 - Apr 27 found 24 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Boston (BOS) 9.8/10 Exceptional! (1,001 reviews) Everything was great, however the pool itself was not heated, it was cold and no one really stayed in it for that reason. Thankfully there was a hot tub. Reviewed on Mar 23, 2026 ![The Inn at Hastings Park, Relais & Chateaux - Boston](https://images.trvl-media.com/lodging/8000000/7990000/7980700/7980601/8dcd0e80_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn at Hastings Park, Relais & Chateaux - Boston CA $1,722 per person Jun 16 - Jun 20 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Boston (BOS) 9.6/10 Exceptional! (252 reviews) Excellent experience- clean and very helpful staff Reviewed on Mar 9, 2026 ![Fairmont Copley Plaza, Boston](https://images.trvl-media.com/lodging/1000000/30000/26000/25981/9ccd9e02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Copley Plaza, Boston Back Bay CA $2,277 per person Jun 2 - Jun 7 found 9 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Boston (BOS) 9/10 Wonderful! (1,196 reviews) Great experience here, staff was fantastic, rooms were clean and comfortable. Reviewed on Mar 23, 2026 ![The Colonnade Hotel Back Bay](https://images.trvl-media.com/lodging/1000000/20000/12700/12660/54848539_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Colonnade Hotel Back Bay Back Bay CA $2,007 per person Jun 2 - Jun 7 found 9 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Boston (BOS) 9.2/10 Wonderful! (2,282 reviews) Very good location, desk staff pleasant would definitely recommend Reviewed on Mar 22, 2026 ## Ready to book your vacation to Chester? Choose your dates ## Chester Hotel Deals ![DoubleTree by Hilton Manchester Downtown](https://images.trvl-media.com/lodging/1000000/20000/19900/19860/77ad6618_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Manchester Downtown 700 Elm St. Manchester NH Fully refundableReserve now, pay when you stay CA $164 CA $177 total Apr 5 - Apr 6 includes taxes & fees 9.2/10 Wonderful! (1,147 reviews) Mold on the wall Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=19860&PinnedHotelID=19860&HadPinnedHotel=true®ionId=3000446848) ![DoubleTree by Hilton Boston - Andover](https://images.trvl-media.com/lodging/1000000/30000/21600/21505/w5760h3835x0y5-76e7ea05_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Boston - Andover 123 Old River Rd Andover MA Fully refundableReserve now, pay when you stay CA $145 CA $162 total Apr 4 - Apr 5 includes taxes & fees 8.2/10 Very Good! (1,000 reviews) I was under the impression that the continental breakfast came with the room price, I was unpleasantly surprised when I had to pay $50 extra dollars for a breakfast I had already expected to have available to me with the price of the room. That really bothered me. Reviewed on Mar 22, 2026 [](https://expedia.ca/Hotel-Search?startDate=04%2F04%2F2026&endDate=05%2F04%2F2026&selected=21505&PinnedHotelID=21505&HadPinnedHotel=true®ionId=3000446848) ![Park View Inn - Salem](https://images.trvl-media.com/lodging/3000000/2520000/2515800/2515725/1f7211b5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Park View Inn - Salem 109 S Broadway Salem NH Fully refundableReserve now, pay when you stay CA $98 CA $106 total Mar 26 - Mar 27 includes taxes & fees 8.8/10 Excellent! (1,719 reviews) Very clean rooms, friendly staff Reviewed on Mar 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F03%2F2026&endDate=27%2F03%2F2026&selected=2515725&PinnedHotelID=2515725&HadPinnedHotel=true®ionId=3000446848) [See all 479 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F03%2F2026&endDate=27%2F03%2F2026®ionId=3000446848) 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