Title: Chester Vacation Packages & Trips 2026 from CA $1,289 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d553248635975871760.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d553248635975871760.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d553248635975871760.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 Art, food, entertainment and more … There's so much to discover with a Chester vacation package. And with the ability to easily customize your city break, it's guaranteed to be one that's tough to forget. In the mood for a bit of sightseeing? A trip to Chester isn't complete without exploring [Lincoln Memorial Library](https://www.expedia.ca/Lincoln-Memorial-Library-Lincoln.d6332700.Vacation-Attraction), [Jato Highlands Golf Course](https://www.expedia.ca/Jato-Highlands-Golf-Course-Lincoln.d6332688.Vacation-Attraction) and other popular attractions. Don't delay visiting this destination any longer. Your dream Chester vacation is a couple of clicks away with Expedia. ## Top Chester Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Terrapin Hostel](https://images.trvl-media.com/lodging/95000000/94860000/94858800/94858719/f77562fe_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Terrapin Hostel CA $1,289 per person Mar 16 - Mar 19 found 7 hours ago Roundtrip non-stop flight included Halifax (YHZ) to Bangor (BGR) 9.8/10 Exceptional! (96 reviews) Nice and cozy hostel. Very clean. No hairdryer, so it’s a bit inconvenient if you have long hair. The breakfast is self-served (you can cook/prepare it on your own. Ingredients provided) Reviewed on Dec 29, 2025 ![Sugarloaf Mountain Hotel](https://images.trvl-media.com/lodging/1000000/610000/604200/604151/f526efea_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sugarloaf Mountain Hotel CA $1,646 per person Mar 16 - Mar 19 found 7 hours ago Roundtrip non-stop flight included Halifax (YHZ) to Bangor (BGR) 9.2/10 Wonderful! (536 reviews) Amazing stuff, clean room Reviewed on Feb 11, 2026 ![Hostel Of Maine](https://images.trvl-media.com/lodging/24000000/23130000/23125000/23124947/d3cf6093_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hostel Of Maine CA $1,547 per person Mar 16 - Mar 19 found 7 hours ago Roundtrip non-stop flight included Halifax (YHZ) to Bangor (BGR) 9.8/10 Exceptional! (86 reviews) This place is a gem! Despite Expedia making things complicated to upgrade a reservation, the management helped make it happen. Beautiful building, clean, quiet, comfy. Highly recommend. Reviewed on Jan 26, 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_553248635975871760) ## Ready to book your vacation to Chester? Choose your dates ## Chester Hotel Deals ![Gateway Inn](https://images.trvl-media.com/lodging/18000000/17300000/17290900/17290844/4c572285_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Gateway Inn 1963 Medway Road Medway ME Fully refundableReserve now, pay when you stay CA $136 CA $148 total Mar 1 - Mar 2 includes taxes & fees 8.4/10 Very Good! (433 reviews) Very nice place. Nice clean rooms with small fridge and microwave. Several nearby options for dining. Close to I-95\. Very nice!/professional staff. Reviewed on Jan 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=17290844&PinnedHotelID=17290844&HadPinnedHotel=true®ionId=553248635975871760) ![Katahdin Inn & Suites](https://images.trvl-media.com/lodging/1000000/910000/904000/903905/35db4cf3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Katahdin Inn & Suites 740 Central St Millinocket ME CA $201 CA $219 total Feb 28 - Mar 1 includes taxes & fees 7.4/10 Good! (260 reviews) Friendly staff, large clean rooms, good location for snowmobiling trails & gas, ample parking. Reviewed on Feb 8, 2026 [](https://expedia.ca/Hotel-Search?startDate=28%2F02%2F2026&endDate=01%2F03%2F2026&selected=903905&PinnedHotelID=903905&HadPinnedHotel=true®ionId=553248635975871760) ![Baxter Park Inn](https://images.trvl-media.com/lodging/1000000/20000/15900/15829/9cbb469f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Baxter Park Inn 935 Central St Millinocket ME Fully refundableReserve now, pay when you stay CA $196 CA $214 total Feb 28 - Mar 1 includes taxes & fees 8.4/10 Very Good! (534 reviews) Very clean rooms, staff was great. But if you book this on Expedia they charge you an extra $150.00 when you get there. Reviewed on Jan 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=28%2F02%2F2026&endDate=01%2F03%2F2026&selected=15829&PinnedHotelID=15829&HadPinnedHotel=true®ionId=553248635975871760) [See all 111 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=15%2F02%2F2026&endDate=16%2F02%2F2026®ionId=553248635975871760) 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