Chestertown Vacations from $459

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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 Inn at Lewes

The Inn at Lewes

3 out of 5
Price was $621, price is now $459 per person
$459
per person
Jul 23 - Jul 26
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
6.2/10 (100 reviews)
Pet friendly and a nice place to stay for our weekend getaway

Reviewed on Jun 15, 2026

Lankford Hotel and Lodge

Lankford Hotel and Lodge

3.5 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $691, price is now $501 per person
$501
per person
Jul 23 - Jul 26
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
8.6/10 Excellent! (645 reviews)
Fabulous vintage hotel right on the beach and close to everything. It seemed like there were a lot of different room options - I stayed in the one bedroom apartment and it was a great stay! Very helpful and friendly staff! And it’s quiet! I would stay here again!

Reviewed on Jun 16, 2026

Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay

3 out of 5
Midtown Ocean City
Save 100% on your flight
Price was $2,946, price is now $2,158 per person
$2,158
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Salisbury (SBY)
8.4/10 Very Good! (40 reviews)
Perfect spot for a vacation

Reviewed on Jun 14, 2026

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Save 100% on your flight
Price was $1,295, price is now $972 per person
$972
per person
Jul 23 - Jul 26
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
9.4/10 Exceptional! (770 reviews)
Rooms were spacious and very clean. Staff was very courteous

Reviewed on Jun 11, 2026

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $1,045, price is now $793 per person
$793
per person
Jul 23 - Jul 26
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
9/10 Wonderful! (3,657 reviews)
The Lobby upholstered furniture was very shabby. Upholstered furniture in guest rooms also needs to be updated. The staff at the desk and in the restaurant were extremely professional and helpful. Sadly this beautiful hotel that we have stayed at over the last 10 years has become somewhat shabby. The view is exceptional !

Reviewed on Jun 16, 2026

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Stay near popular Chestertown attractions

Washington College

8.6/5 (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 Jul 12 to Jul 13
$115 total
Jul 12 - Jul 13
Total with taxes and fees
8.6/10 Excellent! (925 reviews)
"Comfortable beds. Breakfast was decent, with hot and cold options. Shower did not have pressure. Pool was small but nice. Unfortunately we were there Wednesday -Sunday and never were given new towels or a room cleaning. And the last morning we found ants in the room."

Reviewed on Jun 14, 2026

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
$71 nightly
The price is $78 total per night from Jun 29 to Jun 30
$78 total
Jun 29 - Jun 30
Total with taxes and fees
7.2/10 Good! (457 reviews)
"Just ok"

Reviewed on Jun 14, 2026

Red Roof 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
$136 nightly
The price is $151 total per night from Jul 6 to Jul 7
$151 total
Jul 6 - Jul 7
Total with taxes and fees
7.8/10 Good! (88 reviews)
"Old facility but everywhere clean. There have a private beach. It was so nice. So cute place but restaurants are closed weekday. Microwave and coffee are not in room.AC was noisy."

Reviewed on Jun 16, 2026

The Lodge at Great Oak Landing
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 $459 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.