Chestertown Holidays
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Your Chestertown Holiday
There's no better way to embark on an adventure than with one of our holiday 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 Centre for the Arts at the Prince Theatre, 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 holiday on Expedia.
Chestertown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 5,100 |
Max Temp Winter | 7ºC |
Max Temp Summer | 27ºC |
Top Sights | Historical Society of Kent County Maryland, Garfield Centre for the Arts at the Prince Theatre and Crow Farm and Vineyard |
Top hotels in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundable
£88
7 Sept - 8 Sept
includes taxes & fees
8.6/10 Excellent! (946 reviews)
"The entire hotel smelled so fresh and clean…beds very comfortable and our room was spotless. Would recommend and stay there again"
Reviewed on 11 Aug 2026
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
£91
24 Aug - 25 Aug
includes taxes & fees
8/10 Very good! (96 reviews)
"Great location. Clean rooms."
Reviewed on 10 Aug 2026
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
£52
20 Aug - 21 Aug
includes taxes & fees
7.2/10 Good! (478 reviews)
"Very nice hotel. Have stayed here every year for the Pirates and Wenches Festival in Rock Hall."
Reviewed on 10 Aug 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)
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.
Garfield Center for the Arts at the Prince Theater
6.8/10 (5 reviews)
This historic 1928 theatre offers an intimate setting for plays, music, and lectures in city centre Chestertown. Catch a performance during the Jazz Festival or Short Attention Span Theatre for a memorable evening.
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.
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.
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.
Crumpton Auction
8.8/10 (3 reviews)
Dixon's Auction at Crumpton showcases thousands of antiques, collectibles, and furniture in weekly discovery auctions. Arrive early to preview treasures and secure a bidder number before the fast-paced action begins.
Frequently asked questions
How much does a Chestertown travel package cost?
From as low as . Yes, you read that right. Our Chestertown travel packages are the quickest way to make your dollars go much further. Bundle your hotels, flights and rental car and get out and explore this fabulous destination.
If I'm not able to travel, can I cancel my Chestertown travel package?
You sure can, and we're here to help. You may be able to cancel or change your Chestertown travel package for free if you booked in the last 24 hours. However, you may be charged a fee by your airline, hotel or car rental company if your booking is older than that. If your circumstances unexpectedly change, take a look at our Customer Service Portal for more information.
How do I get a cheap travel package to Chestertown?
Simply by bundling. Flights, rental cars and hotels — combine whatever you need into a Chestertown travel package to save a pile of cash. Score even more deals when you add extras such as day tours to your booking. But that's not the only impressive part. You have the flexibility to customize your holiday your way. We offer over 550 partner airlines and 1,000,000 hotels throughout the world, so that everyone has an opportunity to travel and fulfil those holiday fantasies.
Does Expedia offer Book Now, Pay Later Chestertown holidays?
We do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in instalments. Simply pick the payment plan that works for you during the checkout process and take away the stress of budgeting for your next trip. Remember to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your holiday buck. Browse our flexible payment options below:
- Pay monthly holidays: Klarna offers easy monthly payment plans that suit all budgets, so you can have that well-deserved holiday sooner.
- Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay off your trip across multiple transactions.
- Low deposit holidays: If paying a small percentage of your trip (rather than all of it upfront) makes it easier to hit that "book now" button, choose a low deposit holiday payment plan from Klarna.
Where should I stay in Chestertown?
With loads to explore in Chestertown, it's a good idea to lock in a hotel near its attractions. Washington College, Historical Society of Kent County Maryland and Rolphs Wharf Marina are some good ones to add to your to-do list.
What are the top hotels in Chestertown?
If it's your first time in Chestertown, lock in a room at Comfort Inn & Suites Chestertown or Red Roof Inn & Suites Chestertown. Both hotels offer comfortable beds and are popular options with many travellers.
How far in advance should I book my Chestertown holiday?
Reserving your seat early with Expedia means one less thing to have to worry about. Most air carriers advertise tickets up to 12 months prior to departure dates. This is usually the cheapest time to book. If circumstances have left you booking late, last-minute deals to Chestertown are still known to appear just a few weeks before departure.
What does an Expedia Chestertown travel package include?
Select from any combination of rental cars, flights and hotels. Once you've made your booking, you can add the fun stuff like experiences and tours. Want to pick your airfare class? That's also easy to do. The choice is all yours when it comes to crafting your perfect Chestertown escape.
What should I know before booking a Chestertown travel package?
You'll pick up amazing savings when you combine your hotels, flights and rental cars into a travel package. Not just that, booking everything in one place simply makes planning easier. So why waste your time or money? Whether you're putting together a luxury romantic escape or a low-cost family break, have a look at our travel packages today.
Can I choose my airline with a Chestertown Expedia travel package?
Expedia has access to more than 550 partner airlines globally, so you sure can! Just select the airline you want and put together your ideal Chestertown getaway.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
