An aerial view of a town with a river, buildings, and surrounding greenery.

Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Chestertown vacation rentals

House (3 Bedrooms) | Front of property

Family Fun Awaits! Waterfront Home on Marley Creek

Family Fun Awaits! Waterfront Home on Marley Creek
3.0 star property
Marley
The price is AED 1,168
AED 1,511 total
includes taxes & fees
6 Jul - 7 Jul
Family Fun Awaits! Waterfront Home on Marley Creek
House (4 Bedrooms) | Interior

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
3.0 star property
Glen Burnie
The price is AED 2,916
AED 4,991 total
includes taxes & fees
5 Jul - 6 Jul
Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
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.
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Top Chestertown Hotel Reviews

Hampton Inn Baltimore Bayview Campus

Hampton Inn Baltimore Bayview Campus

10/10 Excellent
"The hotel was very clean. The breakfast was ok. The items were not checked frequently for being hot and replenished. The staff was very helpful when asked for assistance even at breakfast. I would definitely stay again. We plan to come back in September. It was a convenient location to get to the Harbor area. The parking was convenient and free."
Florence 3-night trip
Posted 11 hours ago
Hampton Inn Baltimore Bayview Campus

Frequently asked questions

Are there vacation rentals in Chestertown?

Yes, we offer vacation rentals in Chestertown close to Garfield Center for the Arts at the Prince Theater, or you can go with a more secluded option if you're looking for extra privacy while you relax. Chestertown is known for its sporting events and university setting. Make sure you have time to check out the festivals and art during your trip.

What are some of the best vacation home rentals that Chestertown has to offer?

Circa 1700 Chesapeake Colonial home on the National Register.: This vacation home rental outside of Chestertown is located next to a golf course and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Chestertown?

Expedia has 28 vacation rentals for your stay in Chestertown.

What can I see and do in Chestertown?

Enjoy the outdoors at Northern Chesapeake Bay and Chesapeake Bay, or simply take in cultural attractions like Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. Chestertown Historic District and Rolphs Wharf Marina are other places to visit while you're in town.

What are vacation rentals like in Chestertown?

Vacation rentals are private properties you can stay in for a couple days or more in Chestertown. Vacation rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a family getaway.