Chestertown Vacations from $302

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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.
White Marlin Inn

White Marlin Inn

2.5 out of 5
Downtown Ocean City
per person
Sep 11 - Sep 14
found 7 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
4.8/10 (765 reviews)
The shower was clogged so it filled up quickly. I moved the bed and the floor was utterly disgusting. Bed was comfortable. The room was smaller than I expected. Overall for the cost, I couldn't complain.

Reviewed on Jul 6, 2025

Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay

3 out of 5
Midtown Ocean City
per person
Sep 13 - Sep 20
found 6 hours ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
8/10 Very Good! (27 reviews)
This property was excellent. The room was very clean and cozy. Hotel staff was very friendly abs helpful. Location was awesome. We could see the go karts from our balcony. The beach was a 5 min walk Minus the hotel not being on the beach it was awesome. There were 8 people in my party total ages everybody was comfortable.

Reviewed on Jul 2, 2025

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
per person
Aug 16 - Aug 19
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
9/10 Wonderful! (2,932 reviews)
Kyle at the desk was excellent

Reviewed on Jul 6, 2025

The Surf Shanty Motel

The Surf Shanty Motel

2.5 out of 5
Save 100% on your flight
per person
Aug 24 - Aug 27
found 10 hours ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
9.8/10 Exceptional! (251 reviews)
Very well kept clean property. Excellent location to the beach and dinning close by. A few minor inconvenience. A place to hang a wet bathing suit or towel. No place to unpack your clothes. No microwave but overall very nice for a short stay.

Reviewed on Jul 5, 2025

Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Downtown Ocean City
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Salisbury (SBY)
8.6/10 Excellent! (24 reviews)
The only thing we didnt like was the living room furniture was uncomfortable

Reviewed on Aug 21, 2024

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Discover the most popular places to visit in Chestertown

Washington College

4/5(13 reviews)

Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Washington College

Rolphs Wharf Marina

Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.

Rolphs Wharf Marina

Historical Society of Kent County Maryland

You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Historical Society of Kent County Maryland

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
$112 nightly
The price is $124 total per night from Aug 3 to Aug 4
$124 total
Aug 3 - Aug 4
Total includes taxes and fees
8.4/10 Very Good! (775 reviews)
"Smokers smoking at parking lot entry."

Reviewed on Jul 1, 2025

Comfort Inn & Suites Chestertown
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
$68 nightly
The price is $76 total per night from Jul 21 to Jul 22
$76 total
Jul 21 - Jul 22
Total includes taxes and fees
7.2/10 Good! (370 reviews)
"Had a good time and enjoyed the quietness at the hotel."

Reviewed on Jul 3, 2025

Red Roof Inn & Suites Chestertown
The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
3.5 out of 5
22170 Great Oak Landing Rd, Chestertown, MD
$147 nightly
The price is $163 total per night from Jul 8 to Jul 9
$163 total
Jul 8 - Jul 9
Total includes taxes and fees
7.8/10 Good! (53 reviews)
"not super fancy but really well done. comfy beds and a first rate chef. plus great for the boating crowd"

Reviewed on Jun 22, 2025

The Lodge at Great Oak Landing
See all 1,073 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 $302 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.