Chestertown Vacation Packages
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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, Rolphs Wharf Marina and Garfield Center for the Arts at the Prince Theater, 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.
Ready to book your vacation to Chestertown?
Chestertown Hotel Deals
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
CA $101
CA $112 total
Sep 29 - Sep 30
includes taxes & fees
7.2/10 Good! (496 reviews)
"Property inside and out needs attention. Abandoned car with garbage around it, towels outdated, rugs worn. Staff was unwilling to see if a room was available for us before 3pm. We had to get ready for a wedding in a random bathroom, as we walked out she was checking others in."
Reviewed on Sep 21, 2026
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
CA $152
CA $173 total
Sep 24 - Sep 25
includes taxes & fees
8/10 Very good! (112 reviews)
"Unique location with a beachy feel. Comfortable with basic amenities. Communication with the lodge staff was very good as I checked in late and they sent me my room entry information. I would stay there again."
Reviewed on Sep 21, 2026
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundableReserve now, pay when you stay
CA $150
CA $167 total
Oct 13 - Oct 14
includes taxes & fees
8.6/10 Excellent! (983 reviews)
"Too many fly on the first floor, also the sheet is not clean, please make sure check sheet while you clean room"
Reviewed on Sep 20, 2026
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.
Stay near popular Chestertown attractions
Washington College
8.6/10 (87 reviews)
Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
River Arts Chestertown
7.4/10 (6 reviews)
Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.
Chestertown Historic District
Find out about the history of Chestertown with a stop at Chestertown Historic District. Experience the area's festivals and art scene.
Historical Society of Kent County Maryland
7.4/10 (6 reviews)
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.
Rolphs Wharf Marina
8.2/10 (15 reviews)
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
Wilmer Park
8.2/10 (13 reviews)
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.
Rolling Road Park
Rolling Road Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene.
Kings Town Park
Kings Town Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene.
Frequently asked questions
How much does a Chestertown vacation package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a vacation to Chestertown costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chestertown?
If you're hoping to snag a cheap Chestertown vacation package, consider travelling in December, January and February. You'll typically find lower rates on hotels and flights during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Chestertown?
You can explore all the main sights in Chestertown within a few days, including the must-see Historical Society of Kent County Maryland. If you're after a longer Chestertown vacation, look at what kind of activities and day trips are available in the area.
Is it worth booking a vacation package to Chestertown?
Well known for its festivals, history and culture, a Chestertown vacation is a hit with all kinds of travellers. Be sure to visit leading sights like River Arts Chestertown and Historical Society of Kent County Maryland, and consider renting some wheels for day trips to discover even more.
How to find the best Chestertown package deals?
Begin your search for a Chestertown package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Chestertown package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chestertown getaway off to a flying start.
Is it cheaper to book a Chestertown vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging stays and flights separately. Better still, you can tailor your Chestertown escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Chestertown?
Land amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Chestertown getaway.
How to plan a trip to Chestertown?
- Choose when to go: Check your calendar and get your bags packed. Your preferred time of year and the activities on offer will also help you decide when to vacation in Chestertown.
- Calculate your budget: Ensure you have enough money to cover everything from food and transportation to experiences and flights. Your accommodations will probably be the largest expense during your trip to Chestertown.
- Set the duration of your trip: Start by compiling a list of the activities and sights you want to get to in Chestertown. Then, estimate how long you'll need at each, as well as any travel time.
- Bundle your airfare and accommodations: After you've settled on your trip dates and duration, book the perfect Chestertown vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
