Chestertown Vacations from $649

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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.
The Surf Shanty Motel

The Surf Shanty Motel

2.5 out of 5
Price was $819, price is now $649 per person
$649
per person
Oct 14 - Oct 21
found 1 hour ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
9.8/10 Exceptional! (354 reviews)
Great little spot. Clean and comfortable. Only issue was dampness in room

Reviewed on Jul 29, 2026

Sea Breeze Inn

Sea Breeze Inn

2 out of 5
Downtown Ocean City
Price was $1,692, price is now $1,227 per person
$1,227
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Salisbury (SBY)
6.8/10 (31 reviews)

Americana Condos 10th street

Americana Condos 10th street

3.5 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $1,399, price is now $1,063 per person
$1,063
per person
Oct 14 - Oct 21
found 1 hour ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
8.4/10 Very Good! (21 reviews)

Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
Price was $1,257, price is now $972 per person
$972
per person
Aug 28 - Sep 2
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
8.2/10 Very Good! (754 reviews)
Room was a bit outdated. Everything worked fine. Staff was friendly for the most part. Largest flat screen TV I’ve ever had in a hotel before! Jacuzzi tub was much used and worked well. Parking is one of the main downfalls. Lack of close parking spaces made you not want to ever leave to go anywhere for fear of losing your spot! Overall good/great though. Absolutely perfect location!

Reviewed on Jul 29, 2026

Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
Price was $838, price is now $659 per person
$659
per person
Oct 14 - Oct 21
found 1 hour ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
8.8/10 Excellent! (1,016 reviews)
Friendly staff, fantastic location! Hotel was clean and room was spacious.

Reviewed on Jul 29, 2026

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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 refundableReserve now, pay when you stay
$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
$121 nightly
The price is $134 total per night from Aug 9 to Aug 10
$134 total
Aug 9 - Aug 10
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 9 to Aug 10
$68 total
Aug 9 - Aug 10
Total with taxes and fees
Red Roof Inn & Suites Chestertown
See all 1,083 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 $649 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.