Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Chestertown vacation 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 NT$12,934
NT$15,376 total
includes taxes & fees
Jun 9 - Jun 10
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
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 NT$4,588
NT$14,950 total
includes taxes & fees
Jun 25 - Jun 26
2 Mi to Apg: Edgewood Family Home w/ Fenced Yard
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 NT$24,954
NT$42,706 total
includes taxes & fees
Jun 8 - Jun 9
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 NT$13,929
NT$18,762 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

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2/10 Terrible
"Staff was pleasant and room was clean… but the shower/bathroom was awkward… shower curtain hung to allow no room to move around. Common areas were very dusty and vending machines not operable. Outside was very full of weeds. We booked online and didn’t expect these conditions."
Linda 1-night trip
Posted 10 hours ago
Red Roof Inn & Suites Chestertown

Find out more about Chestertown

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

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