Chestertown Vacations from $1,146

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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
Save 100% on your flight
Price was $1,475, price is now $1,146 per person
$1,146
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Salisbury (SBY)
9.6/10 Exceptional! (765 reviews)
Rooms were spacious and very clean. Staff was very courteous

Reviewed on Jun 11, 2026

Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
Price was $2,336, price is now $1,782 per person
$1,782
per person
Jul 20 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
8.2/10 Very Good! (723 reviews)
WE DIDN'T REALIZE THAT THERE WOULD BE A VOLLEYBALL TOURNAMENT DIRECTLY IN FRONT OF OUR ROOM!! THE VIEW WAS BREATHTAKING, BEING SO CLOSE TO THE LIT UP FERRIS WHEEL AT NIGHT. WE WERE IN WALKING DISTANCE TO OUR FAVORITE RESTAURANTS. THERE WERE MORE TV STATIONS THAN MOST HOTELS HAVE. WE WILL STAY THERE AGAIN!

Reviewed on Jun 12, 2026

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
Price was $2,785, price is now $2,131 per person
$2,131
per person
Jul 20 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
8.8/10 Excellent! (2,439 reviews)
We did experience one disappointment during our stay — finding mouse droppings in the bathroom. Once we brought it to the hotel’s attention, the staff addressed the issue promptly and ensured the area was cleaned thoroughly.Aside from that, the ocean view, the spacious condo layout, and the in‑room amenities were all excellent. We genuinely enjoyed our time and appreciated the comfort and atmosphere the property provided.

Reviewed on Jun 13, 2026

Sahara Motel

Sahara Motel

2.5 out of 5
Downtown Ocean City
Price was $1,897, price is now $1,467 per person
$1,467
per person
Jul 20 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
7.6/10 Good! (560 reviews)
It is a older property but has been partially upgraded. Bathroom to small. Aircondition/heater was in the wrong place. It did not work very well and very noisy. Advertised as two queen beds but the beds were only full size and extremely hard to sleep on.

Reviewed on Jun 12, 2026

Monte Carlo Boardwalk Oceanfront Ocean City

Monte Carlo Boardwalk Oceanfront Ocean City

3 out of 5
Downtown Ocean City
Price was $2,551, price is now $1,983 per person
$1,983
per person
Jul 20 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
8/10 Very Good! (1,000 reviews)
Room was great- plenty of space and the mini kitchen was a plus. The location was perfect. We had a view of the beach. Parking was about a block away but there was an area to load and unload the car. Staff was friendly and the restaurant downstairs was fantastic. You can hear everything in the halls outside your room and in the rooms next to you, but overall it was great and would stay there again.

Reviewed on Jun 8, 2026

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Discover the most popular places to visit in Chestertown

Washington College

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

River Arts Chestertown

Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.

River Arts Chestertown

Chestertown Hotel Deals

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Fully refundable
$106 nightly
The price is $118 total per night from Jul 5 to Jul 6
$118 total
Jul 5 - Jul 6
Total with taxes and fees
8.6/10 Excellent! (922 reviews)
"There are no other options in the area. We traveled a few hours for a 4 pm wedding. Arrived at 2:15. Empty parking overall and room was ready. They would not release early unless we paid $50. We had no choice as we had to get ready and could not wait until 3:00. Our son and his wife arrived at 2:30. ..."

Reviewed on Jun 13, 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 22 to Jun 23
$78 total
Jun 22 - Jun 23
Total with taxes and fees
7.2/10 Good! (455 reviews)
"The staff,( if you want to call them that)don't greet you when you walk in to register, I had to initiate the conversation. The elevator floor was filthy nasty and it creaked and groaned. We got off of the elevator on our floor and was greeted by Marijuana smoke and smell. I went back down to inform ..."

Reviewed on Jun 7, 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
$148 nightly
The price is $164 total per night from Jul 9 to Jul 10
$164 total
Jul 9 - Jul 10
Total with taxes and fees
7.8/10 Good! (87 reviews)
"We left 1 hour after arrival... Enough said! This is very much a buyer beware situation. It's no resort. There was absolutely no food available. Tiki bar is permanently closed. Small restaurant was also closed and our only option was food from the front desk. It's about a 30 minute drive to the closest ..."

Reviewed on Jun 10, 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 $1,146 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.