Title: Chestertown Vacation Packages & Trips 2025/2026 from CA $1,203 | Expedia.ca [Hotels in Chestertown](https://expedia.ca/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.ca/Chestertown-Vacation-Rentals.d7215.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.ca/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Chestertown Car Rentals](https://expedia.ca/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide) ![](https://images.trvl-media.com/place/7215/6507b0e9-7981-44e0-9a0d-e95b6eb38908.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chestertown 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 Chestertown Vacation There's no better way to embark on an adventure than with one of our vacation packages to Chestertown. The colonial history and cultural experiences are just two of the countless reasons to spend some time in this captivating city. Fill your free time with visits to [Washington College](https://www.expedia.ca/Washington-College-Chestertown.d553248621561000403.Vacation-Attraction), [Rolphs Wharf Marina](https://www.expedia.ca/Rolphs-Wharf-Marina-Chestertown.d553248621561879605.Vacation-Attraction) and [Garfield Center for the Arts at the Prince Theater](https://www.expedia.ca/Garfield-Center-For-The-Arts-At-The-Prince-Theater-Chestertown.d553248621561000401.Vacation-Attraction), some of the things you simply have to see during a trip to Chestertown. A couple of quick clicks is all it takes to put together a tailor-made Chestertown vacation on Expedia. ## Top Chestertown Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Grand Hotel Ocean City Oceanfront](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/35e46ff3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Grand Hotel Ocean City Oceanfront Downtown Ocean City CA $1,203 per person Dec 26 - Dec 29 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Salisbury (SBY) 9/10 Wonderful! (3,258 reviews) Free parking. Great view. Friendly staff. Reviewed on Oct 24, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2025-12-29/?FromAirport=YUL&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=800771&paandie=true&dealMarker=8hXe3TWR6KnKbyZw6VvS4dCYVyUpzIDVt0JKu_DNw1d5KwoN8KDscFe_cm-l0fRT) ![Club Ocean Villas II](https://images.trvl-media.com/lodging/63000000/62980000/62974900/62974891/fdc6bf96_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Club Ocean Villas II North Ocean City CA $1,398 per person Dec 26 - Dec 29 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Salisbury (SBY) 8.6/10 Excellent! (58 reviews) Did not like the outdated furniture, small televisions and the hot tub wasn’t sanitized until the next day. Notified office told them hot tub cover was not on and they said they were waiting for a new cover to come in. Pools don’t open until 10 There were ants on the counter tops and the first night we were locked out . Staff said they had us listed as checked out . We did get new cards immediately. We have stayed in the condos for over 30 years Disappointed especially for paying g what we paid Reviewed on Jul 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2025-12-29/?FromAirport=YUL&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=62974891&paandie=true&dealMarker=8hXe3TWR6KnKbyZw6VvS4dCYVyUpzIDVt0JKu_DNw1fpH5KvZhXH6QR_P5gZt4I7) ![Americana Condos 10th street](https://images.trvl-media.com/lodging/65000000/64560000/64555700/64555604/105643e1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Americana Condos 10th street Downtown Ocean City CA $1,643 per person Dec 26 - Dec 29 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Salisbury (SBY) 8.4/10 Very Good! (19 reviews) straight fire, definitely going back Reviewed on Jun 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2025-12-29/?FromAirport=YUL&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=64555604&paandie=true&dealMarker=8hXe3TWR6KnKbyZw6VvS4dCYVyUpzIDVt0JKu_DNw1fenMUkRHCW9_CRIzJRb5Td) ![OCHG Ocean Block 7-11](https://images.trvl-media.com/lodging/105000000/104270000/104261200/104261188/62657a02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### OCHG Ocean Block 7-11 Downtown Ocean City CA $1,567 per person Dec 26 - Dec 29 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Salisbury (SBY) 8/10 Very Good! (5 reviews) The house was clean and spacious. The kitchen was well stocked with plates, cups, mugs, and silverware but other than that it was pretty bare bones throughout. From reading reviews beforehand, we brought a lot of items with us which helped a lot- towels, hand soap, oven mitts, cooking supplies, laundry detergent, dishwasher detergent, etc. Some of the furniture is falling apart but the house was very clean and the beds were comfortable and it was great having 2 bathrooms and the layout is spacious and we were able to walk to the festival grounds at the end of the boardwalk. If you bring the extra items you need and aren’t looking for luxury, then it’s a great place to stay and it’s right off the boardwalk and with free parking. Reviewed on Sep 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2025-12-29/?FromAirport=YUL&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=104261188&paandie=true&dealMarker=8hXe3TWR6KnKbyZw6VvS4dCYVyUpzIDVt0JKu_DNw1e5MrHq78GASM1rSlDujtCW) ![OCHG Townhouse 102 10](https://images.trvl-media.com/lodging/105000000/104540000/104533500/104533421/3a1227a2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### OCHG Townhouse 102 10 Downtown Ocean City CA $1,306 per person Dec 26 - Dec 29 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Salisbury (SBY) 8.4/10 Very Good! (5 reviews) Parking was a little tight but to be expected! Couches smelt bad and not the cleanest! But other then that not bad for a long weekend getaway! Reviewed on Sep 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2025-12-29/?FromAirport=YUL&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=104533421&paandie=true&dealMarker=8hXe3TWR6KnKbyZw6VvS4dCYVyUpzIDVt0JKu_DNw1cOJ9vfXTTY4XCkjVKGwC3C) ## Ready to book your vacation to Chestertown? Choose your dates ## Chestertown Hotel Deals ![Red Roof Inn & Suites Chestertown](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Red Roof Inn & Suites Chestertown 160 Scheeler Rd, Chestertown, MD Fully refundableReserve now, pay when you stay CA $113 CA $126 total Nov 2 - Nov 3 includes taxes & fees 7.2/10 Good! (406 reviews) Well received by front desk attendant. Clean room! Reviewed on Oct 10, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=40352&PinnedHotelID=40352&HadPinnedHotel=true®ionId=7215) ![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites Chestertown 150 Scheeler Road, Chestertown, MD Fully refundableReserve now, pay when you stay CA $143 CA $158 total Oct 27 - Oct 28 includes taxes & fees 8.4/10 Very Good! (834 reviews) Everything was great - the beds and pillows are very comfortable, room very clean and breakfast was decent and staff very friendly. Reviewed on Oct 20, 2025 [](https://expedia.ca/Hotel-Search?startDate=27%2F10%2F2025&endDate=28%2F10%2F2025&selected=1700736&PinnedHotelID=1700736&HadPinnedHotel=true®ionId=7215) ![The Lodge at Great Oak Landing](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/b3c72334_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Lodge at Great Oak Landing 22170 Great Oak Landing Rd, Chestertown, MD CA $185 CA $212 total Oct 26 - Oct 27 includes taxes & fees 7.8/10 Good! (72 reviews) Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!! Reviewed on Sep 5, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%2F2025&selected=96826266&PinnedHotelID=96826266&HadPinnedHotel=true®ionId=7215) [See all 1,073 properties in Chestertown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F10%2F2025&endDate=27%2F10%2F2025®ionId=7215) 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 Chestertown #### Historical Society of Kent County Maryland You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals. [](https://expedia.ca/Historical-Society-Of-Kent-County-Maryland-Chestertown.d553248621561000400.Vacation-Attraction) #### Wilmer Park Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals. [](https://expedia.ca/Wilmer-Park-Chestertown.d553248621561000402.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 ![QR code to download the app](data:image/png;base64,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)