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Check prices for these dates

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

Our top choices for Chestertown holiday rentals

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 10.838.581 ₫
12.884.704 ₫ total
includes taxes & fees
11 Jun - 12 Jun
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
Interior

Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
The price is 5.163.620 ₫
12.224.080 ₫ total
includes taxes & fees
4 Jun - 5 Jun
Idyllic Pasadena Retreat With Garden + Hot Tub!
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 20.173.376 ₫
34.946.217 ₫ total
includes taxes & fees
10 Jun - 11 Jun
Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
Outdoor pool

Top Floor Master Suite Bay View

Top Floor Master Suite Bay View
3.0 star property
North East
The price is 11.672.115 ₫
15.722.381 ₫ total
includes taxes & fees
11 Jun - 12 Jun
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

Country Inn & Suites by Radisson, Baltimore North, MD

Country Inn & Suites by Radisson, Baltimore North, MD

6/10 Okay
"Air conditioning wasn't working properly. Carpet needed shampooing. Floor on entry not very clean. Seat on toilet had a broken hinge. Room setup adequate. Breakfast meager."
Christine 4-night trip
Posted less than an hour ago
Country Inn & Suites by Radisson, Baltimore North, MD

Frequently asked questions

Are there holiday rentals in Chestertown?

Yes, there are holiday rentals in Chestertown close to Garfield Center for the Arts at the Prince Theater, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals are there in Chestertown?

Expedia has 27 holiday 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 holiday rentals like in Chestertown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chestertown. Holiday rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.