Chestertown Vacations from $817

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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.
Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was $985, price is now $817 per person
$817
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
9.4/10 Exceptional! (805 reviews)

Sea Breeze Inn

Sea Breeze Inn

2 out of 5
Downtown Ocean City
Price was $1,702, price is now $1,232 per person
$1,232
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Salisbury (SBY)
6.6/10 (39 reviews)

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
Price was $1,021, price is now $831 per person
$831
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
8.8/10 Excellent! (2,551 reviews)

Monte Carlo Boardwalk Oceanfront Ocean City

Monte Carlo Boardwalk Oceanfront Ocean City

3 out of 5
Downtown Ocean City
Price was $1,133, price is now $930 per person
$930
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
8.2/10 Very Good! (1,016 reviews)
Ac was hitting fr

Reviewed on Aug 4, 2026

Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $1,710, price is now $1,422 per person
$1,422
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
9.4/10 Exceptional! (24 reviews)
Excellent location. Spacious 2 bedroom condo. FYI.I brought a mattress pad for pull out couch otherwise would not recommend sleeping on it. Double beds were smaller. Hot tub was cold. Kitchen was not stocked with measuring cups or drink pitcher. Only big coffee pot(no keurig).

Reviewed on Jul 31, 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 refundable
$107 nightly
The price is $119 total per night from Aug 25 to Aug 26
$119 total
Aug 25 - Aug 26
Total with taxes and fees
8.6/10 Excellent! (943 reviews)
"We got a free upgrade just by asking!"

Reviewed on Jul 31, 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 Sep 2 to Sep 3
$123 total
Sep 2 - Sep 3
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
$63 nightly
The price is $70 total per night from Aug 11 to Aug 12
$70 total
Aug 11 - Aug 12
Total with taxes and fees
7.2/10 Good! (471 reviews)
"I will never stay here again . Only Customer service was great ,Mary was wonderful. And what i mean by that is she did what she could with what she had ., but my shower water didn't work.So I had to pack my things up and move to another room .Then my microwave in the second room didn't work..This ..."

Reviewed on Aug 4, 2026

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 $817 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.