Chestertown Vacations from $1,149
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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.
Sea Bay Hotel
Midtown Ocean City
$1,842
per person
Nov 26 - Nov 29
found 17 hours ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
8.2/10 Very Good! (673 reviews)
This was a nice motel in a very good location. Looked clean and well kept. The only complaints my husband and I had were that there were several gnats in the room, probably let in from the balcony door. Also the bed seemed to be old and we even felt the springs from the mattress. It definitely was not comfortable. The bedding wasn’t comfortable either. They were efficient in bringing us an additional blanket when we requested one and some more towels also. All in all it was just OK.
Reviewed on Sep 22, 2026
Inn at Perry Cabin
Downtown St. Michaels
$1,839
per person
Nov 26 - Nov 29
found 14 hours ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
9.6/10 Exceptional! (399 reviews)
Fantastic place; one of those that you don’t want to leave the property until the very sad time to go. Lovely staff, all of them, amazing food.
Reviewed on Sep 20, 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.
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.
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.
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.
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.
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.
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.
Chestertown Hotel Deals
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
$72 nightly
$80 total
Sep 29 - Sep 30
Total with taxes and 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
$124 nightly
$137 total
Sep 23 - Sep 24
Total with taxes and 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
$107 nightly
$119 total
Oct 13 - Oct 14
Total with taxes and 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.
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 $1,149 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.