Title: Chester Vacation Packages & Trips 2026 from CA $1,040 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d3000440455.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d3000440455.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d3000440455.Car-Rental-Guide) ![](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chester Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Patricia Knorr - ## 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 Reserve a Chester vacation package and get set to experience the best of this city. Consider basing yourself in the neighborhood of Kent Narrows, which is good for cycling, views and nature. If your trip to Chester includes some sightseeing, check out renowned attractions like [Chesapeake Bay Environmental Center](https://www.expedia.ca/Chesapeake-Bay-Environmental-Center-Grasonville.d553248621561196328.Vacation-Attraction), [Eastern Neck National Wildlife Refuge](https://www.expedia.ca/Eastern-Neck-National-Wildlife-Refuge-Rock-Hall.d553248635974660968.Vacation-Attraction) and [Love Point State Park](https://www.expedia.ca/Love-Point-State-Park-Annapolis.d637198025113260032.Vacation-Attraction). Stop daydreaming and start doing. Browse the multitude of options on Expedia today and finally put your Chester vacation plans into gear! ## Top Chester Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Eurostars Saint Gregory Dupont Circle Georgetown](https://images.trvl-media.com/lodging/1000000/480000/470900/470863/acc99fd8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars Saint Gregory Dupont Circle Georgetown Downtown Washington D.C. CA $1,040 per person Apr 10 - Apr 13 found 6 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Washington (DCA) 8.6/10 Excellent! (1,008 reviews) Clean room, staff very polite and gentle Reviewed on Jan 19, 2026 ![Nice House](https://images.trvl-media.com/lodging/121000000/120070000/120069200/120069165/21a16006_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Nice House Groveton CA $2,322 per person Mar 16 - Mar 20 found 5 hours ago Roundtrip non-stop flight included Toronto (YTO) to Washington (DCA) No reviews ![Global Luxury Suites at The White House](https://images.trvl-media.com/lodging/10000000/9660000/9658600/9658584/b6a1170d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Global Luxury Suites at The White House Downtown Washington D.C. CA $1,576 per person Apr 10 - Apr 13 found 6 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Washington (DCA) 8/10 Very Good! (262 reviews) Staff was responsive once we let them know of minor issues. Great location for eating and walking to the White House and other sites. Apartment accommodated all five of us easily with comfort. Reviewed on Dec 31, 2025 ![Hotel Hive](https://images.trvl-media.com/lodging/17000000/16120000/16111700/16111647/b0ea67b2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Hive Northwest CA $1,173 per person Apr 1 - Apr 6 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Washington (DCA) 9.2/10 Wonderful! (1,331 reviews) I had a great stay at Hotel Hive. The room was clean, comfortable, and exactly what we needed for our trip to DC. Everything felt well-maintained, and housekeeping did a solid job keeping things fresh. The staff really stood out — everyone we interacted with was friendly, welcoming, and genuinely helpful. They made check-in and the overall stay feel easy and stress-free. We also tried the pizza and it was surprisingly good, and the bar had a nice vibe with solid drinks. It was convenient having food and drinks right in the hotel. Overall, great location, great service, and a really pleasant stay. I’d definitely come back Reviewed on Jan 25, 2026 ![Elegant 2BR Apartment - Minutes to D.C.](https://images.trvl-media.com/lodging/107000000/106790000/106781700/106781675/7dcd30c9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Elegant 2BR Apartment - Minutes to D.C. Crystal City CA $1,469 per person Mar 16 - Mar 20 found 5 hours ago Roundtrip non-stop flight included Toronto (YTO) to Washington (DCA) 9.8/10 Exceptional! (7 reviews) ## Ready to book your vacation to Chester? Choose your dates ## Chester Hotel Deals ![Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!](https://images.trvl-media.com/lodging/34000000/33560000/33554400/33554342/409af264_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets! Chester MD 9.8/10 Exceptional! (94 reviews) Perfect vacation home....large and comfortable.....relaxing, peaceful, close to bike trails, a great homebase for sightseeing many small towns...loved meeting the homeowner, very friendly.. Reviewed on Sep 14, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=33554342&PinnedHotelID=33554342&HadPinnedHotel=true®ionId=3000440455) [](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=33554342&PinnedHotelID=33554342&HadPinnedHotel=true®ionId=3000440455) ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Graduate by Hilton Annapolis 126 West St Annapolis MD Fully refundableReserve now, pay when you stay CA $214 CA $244 total Feb 22 - Feb 23 includes taxes & fees 9.2/10 Wonderful! (1,004 reviews) The room was very spacious. Staff were nice. Amenities were excellent. Good location for our stay. Reviewed on Feb 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=846&PinnedHotelID=846&HadPinnedHotel=true®ionId=3000440455) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Historic Inns of Annapolis 58 State Circle Annapolis MD Fully refundableReserve now, pay when you stay 9/10 Wonderful! (1,883 reviews) Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back! Reviewed on Jan 31, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=42068&PinnedHotelID=42068&HadPinnedHotel=true®ionId=3000440455) [](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=42068&PinnedHotelID=42068&HadPinnedHotel=true®ionId=3000440455) [See all 1,205 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026®ionId=3000440455) 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) ### Discover the most popular places to visit in Chester #### Chesapeake Exploration Center Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants. [](https://expedia.ca/Chesapeake-Exploration-Center-Chester.d553248621561879491.Vacation-Attraction) ## 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