
Chestertown Vacations from $838
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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.

Princess Royale Oceanfront Resort
North Ocean City
Save 100% on your flight
Price was $1,093, price is now $838 per person
$838
per person
Sep 25 - Sep 28
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
8.8/10 Excellent! (2,551 reviews)
We were there for the beach and it had great access. The hotel room was in need of major repair. The hallways and elevators had no air conditioning. I bet your wondering why does that matter. We'll you spend a lot of time at the elevator because it takes forever. Staff was friendly and we had a good stay overall.
Reviewed on Aug 2, 2026

Sea Breeze Inn
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)
The staff never cleaned our room after we checked in the room needed a lot of attention fixed the water pressure was non existent had to wear socks or shoes because they was so much sand and we didn't go to the beach it wasn't from us too much money for this place
Reviewed on Aug 3, 2026


Ocean Terrace Family Apartments
Downtown Ocean City
Price was $1,653, price is now $1,364 per person
$1,364
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
7.8/10 Good! (40 reviews)
There is NO WAY this is a 3-star property, 1.5 at the MOST. The apt I was rented is nowhere near the condition of the photos provided. Complete bait and switch. The carpeting in the place had to be at least 30 years old and furniture from the 1950/60s. There was ONE light in the combo living room/dining room over the TV. Totally dark at the dining table. There were 2 spoons and 2 forks provided. ONE coffee mug. The coffee maker sprayed water all over. The double beds in each room were old and springy and wobble when you lay in them. The twin beds were OK. We tripped the breaker on our 2nd day. You are not given a phone number to call and there is no phone number provided at the office for emergencies. No one answers the call once you track down the correct #. I had to call all the properties managed by the company to track down someone to flip the switch. After a 2nd time I was told at 7:30 p.m. that if it happened after 8, no one would be available until 11 the next day. I came home from dinner to find the breaker tripped. We had ONE LIGHT in the LR/DR that night and the next morning....more than 14 hours, until someone flipped it. I was told they only have 1 maintenance person for the multiple properties. On the + side, the A/C worked and I had a view of the ocean. Not very secure...someone can get in by breaking the window in the door and reach in to unlock it. And there's no window treatment on the door for privacy. And no blackout shades, too bright for me to sleep.
Reviewed on Aug 2, 2026

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Chestertown Hotel Deals

Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundable
$107 nightly
The price is $119 total per night from Aug 24 to Aug 25
$119 total
Aug 24 - Aug 25
Total with taxes and fees
8.6/10 Excellent! (943 reviews)
"We got a free upgrade just by asking!"
Reviewed on Jul 31, 2026

The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
$111 nightly
The price is $123 total per night from Aug 6 to Aug 7
$123 total
Aug 6 - Aug 7
Total with taxes and fees

Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $68 total per night from Aug 31 to Sep 1
$68 total
Aug 31 - Sep 1
Total with taxes and fees
7.2/10 Good! (470 reviews)
"X"
Reviewed on Aug 1, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















