Top hotels in Chestertown
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
2.815.992 ₫
3.219.524 ₫ total
10 Sept - 11 Sept
includes taxes & fees
8/10 Very good! (105 reviews)
"Gem of a local place on the water. The rooms are big and the beds are soooo comfy. The pool is cute and the beach has bands on weekends. There are gas grills and a decent restaurant. It's not fancy (for fancy stay at the manor next door). But it's not corporate either. It's authentic, peaceful and ..."
Reviewed on 30 Aug 2026
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundableReserve now, pay when you stay
2.703.352 ₫
3.000.720 ₫ total
27 Sept - 28 Sept
includes taxes & fees
8.6/10 Excellent! (968 reviews)
"good stay"
Reviewed on 1 Sept 2026
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
1.877.021 ₫
2.083.495 ₫ total
14 Sept - 15 Sept
includes taxes & fees
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)
Founded in 1782, Washington College is the first college chartered in the sovereign United States. Explore its picturesque campus with historic architecture and Chester River waterfront views.
Chestertown Historic District
This preserved colonial port town showcases America's maritime heritage through 18th-century architecture. Stroll brick pavements along the Chester River or visit during the annual Tea Party Festival reenactments.
River Arts Chestertown
7.4/10 (6 reviews)
Chestertown RiverArts celebrates creativity with monthly themed exhibits and workshops. Explore rotating galleries, meet local artists, and time your visit for the spring "Paint the Town" event or October's Studio Tour.
Historical Society of Kent County Maryland
7.4/10 (6 reviews)
Step inside the Geddes-Piper House, home to Kent County's historical treasures and curated exhibits. Explore Maryland's rich past through intimate galleries and knowledgeable guides who bring local stories to life.
Wilmer Park
8.2/10 (13 reviews)
Nestled along the Chester River, Wilmer Park offers serene waterfront views and a modern playground for families. Bring a picnic to enjoy in the green spaces or time your visit for one of the community concerts.
Kings Town Park
Kings Town Park offers serene pathways winding through lush greenery in Chestertown, Maryland. Enjoy morning strolls or invigorating runs along the scenic trails away from urban bustle.
Sumner Hall
You can spend time exploring the galleries in Sumner Hall during your travels in Chestertown. Experience the area's festivals and art scene.
Rolling Road Park
Rolling Road Park offers scenic trails and a dedicated dog park for outdoor enthusiasts in Chestertown. Enjoy peaceful green spaces perfect for family picnics or afternoon strolls away from the bustle of town.
Frequently asked questions
How much does a Chestertown holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Chestertown costs! Expedia's packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Chestertown?
December, January and February are great times to search for cheap Chestertown holiday packages. Opting to travel in quieter periods means you can usually find better prices on flights and hotels.
How many days is enough for Chestertown?
Generally, a handful of days is great for a Chestertown holiday. With a well-planned itinerary, you can see all the popular attractions including Rolphs Wharf Marina, as well as discover some hidden gems along the way.
Is it worth booking a holiday package to Chestertown?
Chestertown has everything you need for an awesome getaway — festivals, history and culture are just the start. Whether you want to visit sights like River Arts Chestertown and Historical Society of Kent County Maryland, or venture off the beaten track, you'll find plenty to see and do on your Chestertown holiday.
How to find the best Chestertown package deals?
Finding a cheap Chestertown package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply some filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most economical Chestertown package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Chestertown holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging flights and accommodation individually. Better still, you can personalise your Chestertown escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Chestertown?
Score incredible bargains by reserving your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Chestertown break.
How to plan a trip to Chestertown?
- Choose when to travel: Check your diary and pack your bags. Your favourite time of year and the available activities will also help you decide when to visit Chestertown.
- Plan your budget wisely: On top of the price of your accommodation, you'll need to factor in other expenses too. These include transportation, flights and food. Also, set aside a little extra for unexpected expenses that may arise during your trip to Chestertown.
- Work out your trip length: Consider how long you'd like to spend exploring Chestertown. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
- Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customised Chestertown holiday package.
