Chestertown Vacations from $998

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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.
Best Western Ocean City Hotel & Suites

Best Western Ocean City Hotel & Suites

2.5 out of 5
Midtown Ocean City
Price was $1,469, price is now $998 per person
$998
per person
Sep 18 - Sep 21
found 2 hours ago
Roundtrip flight included
New York (LGA) to Salisbury (SBY)
8.6/10 Excellent! (1,010 reviews)
the staff was very nice. the hotel can use upgrades, especially in the bathroom. otherwise the hotel was good overall. I would recommend it for a night stay for the price and location.

Reviewed on Jul 29, 2026

Microtel Inn & Suites by Wyndham Ocean City

Microtel Inn & Suites by Wyndham Ocean City

2.5 out of 5
West Ocean City
Price was $1,479, price is now $1,008 per person
$1,008
per person
Sep 18 - Sep 21
found 2 hours ago
Roundtrip flight included
New York (LGA) to Salisbury (SBY)
8.2/10 Very Good! (1,015 reviews)

Hampton Inn & Suites Ocean City/Bayfront-Convention Center

Hampton Inn & Suites Ocean City/Bayfront-Convention Center

2.5 out of 5
Midtown Ocean City
Price was $1,623, price is now $1,120 per person
$1,120
per person
Sep 18 - Sep 21
found 2 hours ago
Roundtrip flight included
New York (LGA) to Salisbury (SBY)
8.8/10 Excellent! (1,005 reviews)
The staff was very friendly and efficient.

Reviewed on Jul 30, 2026

Tru by Hilton Ocean City Bayside

Tru by Hilton Ocean City Bayside

2.5 out of 5
Midtown Ocean City
Price was $1,569, price is now $1,086 per person
$1,086
per person
Sep 18 - Sep 21
found 2 hours ago
Roundtrip flight included
New York (LGA) to Salisbury (SBY)
9/10 Wonderful! (1,008 reviews)

Comfort Inn Ocean City Boardwalk

Comfort Inn Ocean City Boardwalk

2.5 out of 5
Downtown Ocean City
Price was $1,595, price is now $1,115 per person
$1,115
per person
Sep 18 - Sep 21
found 2 hours ago
Roundtrip flight included
New York (LGA) to Salisbury (SBY)
9/10 Wonderful! (1,047 reviews)

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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.
See properties

Chestertown Hotel Deals

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Fully refundable
$103 nightly
The price is $115 total per night from Aug 23 to Aug 24
$115 total
Aug 23 - Aug 24
Total with taxes and fees
8.6/10 Excellent! (942 reviews)
"Clean and affordable amenities and a decent breakfast!"

Reviewed on Jul 29, 2026

Comfort Inn & Suites Chestertown
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3 out of 5
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
$111 nightly
The price is $123 total per night from Aug 6 to Aug 7
$123 total
Aug 6 - Aug 7
Total with taxes and fees
The Lodge at Great Oak Landing
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $68 total per night from Aug 19 to Aug 20
$68 total
Aug 19 - Aug 20
Total with taxes and fees
Red Roof Inn & Suites Chestertown
See all 1,091 properties in Chestertown
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 $998 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.