Title: Chestertown Vacation Packages & Trips 2025/2026 | 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. ### Things to do in and around Chestertown Chestertown, Maryland, is perfect for an outdoor getaway, offering beautiful scenery and a range of activities. Visitors can enjoy house tours, explore recreational areas, stroll along the boardwalk, and participate in festival events. The downtown area hosts festive holiday activities, making it an ideal spot for a weekend escape or day trip, ensuring a delightful experience for all who visit. **Shopping** In Chestertown, you can enjoy local shops and boutiques for unique gifts. If you're up for a drive, visit the [Queenstown Premium Outlets](https://www.expedia.ca/Queenstown-Premium-Outlets-Hotels.0-l553248621532662352-0.Travel-Guide-Filter-Hotels), located 27.4km away, for brand-name bargains. [Paul Reed Smith Guitars](https://www.expedia.ca/Paul-Reed-Smith-Guitars-Hotels.0-l747757786500468736-0.Travel-Guide-Filter-Hotels), 33.8km away, offers a unique shopping experience for music enthusiasts. **Recreation** At [Ripken Stadium](https://www.expedia.ca/Ripken-Stadium-Hotels.0-l6145161-0.Travel-Guide-Filter-Hotels), you can immerse yourself in the vibrant sports atmosphere while enjoying various recreational events. Meanwhile, the [Queenstown Harbor Golf Club](https://www.expedia.ca/Queenstown-Harbor-Golf-Club-Hotels.0-l6091731-0.Travel-Guide-Filter-Hotels) and [Queenstown Harbor Golf Links](https://www.expedia.ca/Queenstown-Harbor-Golf-Links-Hotels.0-l553248621532662350-0.Travel-Guide-Filter-Hotels) offer beautiful outdoor settings for a relaxing yet active day on the greens, surrounded by nature's beauty. **Adventure** At the [Annapolis Sailing School](https://www.expedia.ca/Annapolis-Sailing-School-Hotels.0-l553248621532662324-0.Travel-Guide-Filter-Hotels), located 45.1km from Chestertown, you can immerse yourself in thrilling sailing experiences on the beautiful Chesapeake Bay. Alternatively, the Emmorton Recreation & Tennis Center, 38.6km away, offers various engaging recreational activities, while the Tose Family Tennis Center, also 45.1km away, boasts fantastic tennis facilities. **Nightlife** In Chestertown, the [Garfield Center for the Arts at the Prince Theater](https://www.expedia.ca/Garfield-Center-For-The-Arts-At-The-Prince-Theater-Hotels.0-l553248621561000401-0.Travel-Guide-Filter-Hotels) offers vibrant performances in a charming atmosphere. Just a short drive away, [Church Hill Theatre](https://www.expedia.ca/Church-Hill-Theatre-Hotels.0-l844528418122231808-0.Travel-Guide-Filter-Hotels) and [Avalon Theatre](https://www.expedia.ca/Avalon-Theatre-Hotels.0-l6286426-0.Travel-Guide-Filter-Hotels) also provide engaging shows, each with a touch of culture and romance, perfect for a delightful evening out. *\*Distances are measured in a straight line; actual driving distances may vary depending on the route.* ### Find the best attractions in Chestertown Chestertown, Maryland, offers a delightful mix of outdoor adventures and scenic beauty, perfect for a family beach vacation. Visitors can explore urban parks, marinas, and the picturesque Chester River. A stroll down Main Street Chestertown reveals charming shops and local attractions, making it an ideal destination for those seeking a relaxing getaway in nature. - **[Washington College:](https://www.expedia.ca/Washington-College-Hotels.0-l553248621561000403-0.Travel-Guide-Filter-Hotels)** Experience the charm of this historic institution, renowned for its picturesque campus and rich cultural heritage. Engage in various events, art exhibitions, and lectures that showcase the vibrant academic community. - **[Rolphs Wharf Marina:](https://www.expedia.ca/Rolphs-Wharf-Marina-Hotels.0-l553248621561879605-0.Travel-Guide-Filter-Hotels)** Dive into outdoor adventures at this scenic marina. Enjoy kayaking, paddleboarding, or simply relaxing by the water's edge, surrounded by beautiful beach vibes and stunning views of the Chester River. - **[Historical Society of Kent County Maryland:](https://www.expedia.ca/Historical-Society-Of-Kent-County-Maryland-Hotels.0-l553248621561000400-0.Travel-Guide-Filter-Hotels)** Discover the local history at this engaging museum. Explore fascinating exhibits that highlight the region's past, offering insight into the culture and traditions of Kent County. ### Best time to go to Chestertown The best time to visit Chestertown is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | --- | --- | --- | --- | --- | --- | | January | 34.2°F (1.2°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | February | 36.9°F (2.7°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | March | 43.7°F (6.5°C) | Light Rain | Mostly Sunny | Average | Average | | April | 54.3°F (12.4°C) | Light Rain | Mostly Sunny | Slightly High | Average | | May | 63.7°F (17.6°C) | Light Rain | Mostly Sunny | Average | Average | | June | 72.1°F (22.3°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | July | 77.4°F (25.2°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | August | 75.6°F (24.2°C) | Light Rain | Mostly Sunny | Average | Average | | September | 69.4°F (20.8°C) | Light Rain | Mostly Sunny | Average | Average | | October | 59.2°F (15.1°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 47.3°F (8.5°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | December | 40.1°F (4.5°C) | Light Rain | Mostly Sunny | Slightly Low | Average | ### Booking tips and Expedia advantages for Chestertown For a budget-friendly trip to Chestertown, consider visiting between January to February or November for lower accommodation rates. Tuesdays are the cheapest days to stay, while Saturdays tend to be pricier. Use Expedia’s search tool to find budget options, including eco-friendly hotels, and filter by price to uncover the best deals. Additionally, you can save money by bundling your hotel, flights, and activities into an Expedia package. Don’t forget to explore free local attractions to enhance your experience while keeping costs down. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Chestertown are January to February and November, where the prices are slightly lower. This is in comparison to June to July and October, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Chestertown is Tuesday. The most expensive day to stay in Chestertown is Saturday. - **Find cheap hotels on Expedia:** Utilize Expedia’s search tool to customize your travel preferences, such as your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified option will showcase sustainable and environmentally-friendly hotels that are currently available. To find the best prices and deals, simply sort the price filter from lowest to highest. - **Consider bundling your trip:** You can save some money by combining your Chestertown hotel reservation with your flights and activities through an Expedia package. ## Ready to book your vacation to Chestertown? Choose your dates ## Chestertown Hotel Deals ![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 $159 total Nov 4 - Nov 5 includes taxes & fees 8.4/10 Very Good! (835 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=04%2F11%2F2025&endDate=05%2F11%2F2025&selected=1700736&PinnedHotelID=1700736&HadPinnedHotel=true®ionId=7215) ![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 $101 CA $112 total Nov 30 - Dec 1 includes taxes & fees 7.2/10 Good! (407 reviews) Well received by front desk attendant. Clean room! Reviewed on Oct 10, 2025 [](https://expedia.ca/Hotel-Search?startDate=30%2F11%2F2025&endDate=01%2F12%2F2025&selected=40352&PinnedHotelID=40352&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 Fully refundable CA $139 CA $159 total Nov 3 - Nov 4 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=03%2F11%2F2025&endDate=04%2F11%2F2025&selected=96826266&PinnedHotelID=96826266&HadPinnedHotel=true®ionId=7215) [See all 1,072 properties in Chestertown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=03%2F11%2F2025&endDate=04%2F11%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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)