Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Chestertown vacation rentals

House (3 Bedrooms) | Interior

2 Mi to Apg: Edgewood Family Home w/ Fenced Yard

2 Mi to Apg: Edgewood Family Home w/ Fenced Yard
3.0 star property
Edgewood
The price is ₩218,048
₩710,418 total
includes taxes & fees
Jun 25 - Jun 26
2 Mi to Apg: Edgewood Family Home w/ Fenced Yard
Room, Multiple Beds, Hot Tub (LC) | Interior

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
2.0 star property
North East
9.0 out of 10, Wonderful, (4 reviews)
"Very nice cabin. By the town and easy drive to everything. "
United States
Mark
The price is ₩614,642
₩730,674 total
includes taxes & fees
Jun 4 - Jun 5
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
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 ₩1,144,006
₩1,981,755 total
includes taxes & fees
Jun 1 - Jun 2
Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
Interior

Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
The price is ₩292,722
₩692,975 total
includes taxes & fees
Jun 4 - Jun 5
Idyllic Pasadena Retreat With Garden + Hot Tub!
Outdoor pool

Top Floor Master Suite Bay View

Top Floor Master Suite Bay View
3.0 star property
North East
The price is ₩661,910
₩891,595 total
includes taxes & fees
Jun 26 - Jun 27
Top Floor Master Suite Bay View
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Great hotel..will definitely be back"
Randy 1-night trip
Posted 1 hour ago
Historic Inns of Annapolis

Find out more about Chestertown

Search for Vacation rentals in Chestertown on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Chestertown using one of the methods below:

  • View our selection of featured Vacation rentals in Chestertown
  • Use the map to find apartments and other Vacation homes in the Chestertown neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Chestertown while they last

Look no further and take a look at our great range of rental properties in Chestertown!

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.

How many vacation rentals are there in Chestertown?

Expedia has 27 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. Rolphs Wharf Marina and Chestertown Historic District 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.