Chestertown Vacations from $984
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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.
The Latest Chestertown vacation packages
Price found within the past 48 hours. Click for updated prices.
Boardwalk One
Downtown Ocean City
$984
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
7.4/10 Good! (174 reviews)
Room was as expected, worked well for our family. The women in the office were very kind and the check-in process was very smooth. We would stay here again.
Reviewed on Aug 3, 2026
Ocean 1 Hotel and Suites
Downtown Ocean City
$1,753
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
8.2/10 Very Good! (766 reviews)
The room was clean and spacious. The location is perfect for beach access and restaurants. Room is decor is outdated a d has basic amenities. I would return.
Reviewed on Aug 15, 2026
Sea Bay Hotel
Midtown Ocean City
$1,835
per person
Nov 6 - Nov 9
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
8.2/10 Very Good! (632 reviews)
Had to ask to have my room cleaned and bed made. Was done one time during my 4 night stay. Did not know if that is the norm, but would have been helpful to have known in advance.
Reviewed on Aug 14, 2026
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View all tripsStay 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 sidewalks 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 theater offers an intimate setting for plays, music, and lectures in downtown 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.
Chestertown Hotel Deals
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundable
$104 nightly
$115 total
Sep 13 - Sep 14
Total with taxes and fees
8.6/10 Excellent! (950 reviews)
"The door into the building from the parking lot is always locked, which is great, because it cannot be seen from the front desk, but it is difficult to enter with the room key. The key is a typical credit card-like key, but the electronic reader was wonky. Sometimes it worked and sometimes it didn’t. ..."
Reviewed on Aug 14, 2026
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
$121 nightly
$134 total
Sep 13 - Sep 14
Total with taxes and fees
8/10 Very Good! (98 reviews)
"The room was clean. Beds are very comfy. It would have been nice if there was a full length mirror on the wall somewhere and at least one chair."
Reviewed on Aug 14, 2026
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
$62 nightly
$68 total
Aug 25 - Aug 26
Total with taxes and 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 Aug 10, 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.
Find the Best Chestertown Vacation Packages
Chestertown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 5,100 |
Max Temp Winter | 45ºF |
Max Temp Summer | 80ºF |
Top Sights | Waterman’s Museum, Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater |
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Frequently asked questions
How much does a Chestertown vacation package cost?
Offering excellent value package deals from $984 on Expedia, you'll be thrilled with how little a vacation to Chestertown costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Chestertown?
May, November and December are great times to search for cheap Chestertown vacation packages. Choosing to travel in less busy months means you can generally find better prices on flights and hotels.
How many days is enough for Chestertown?
Generally, a few days is ideal for a Chestertown vacation. With a well-organized schedule, you can check out all the main attractions like Washington College, as well as discover some hidden gems along the way.
Is it worth booking a vacation package to Chestertown?
Chestertown has everything you need for a memorable trip — festivals, history and culture are just the start. Whether you'd like to visit sights such as River Arts Chestertown and Historical Society of Kent County Maryland, or take the path less traveled, you'll have plenty to explore on your Chestertown vacation.
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," "Traveler 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 traveling on a weekday, when prices are often lower.
Is it cheaper to book a Chestertown vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations individually. Better still, you can personalize 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 vacation 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.
Does Expedia offer Book Now, Pay Later Chestertown vacation packages?
Jet off on your dream escape to Chestertown with Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait until payday — we've joined forces with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to budget for your trip and snap up bargains before they disappear.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
