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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

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
8.8 out of 10, Excellent, (3 reviews)
"Very nice cabin. By the town and easy drive to everything. "
United States
Mark
The price is ₹38,164
₹45,369 total
includes taxes & fees
16 Apr - 17 Apr
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 ₹18,176
₹43,028 total
includes taxes & fees
6 May - 7 May
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 ₹41,099
₹55,361 total
includes taxes & fees
16 Apr - 17 Apr
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

Hampton Inn Baltimore Bayview Campus

Hampton Inn Baltimore Bayview Campus

10/10 Excellent
"Hotel lobby and room were clean, well-decorated. I enjoyed the heated pool and the breakfast was delicious with several options: eggs, waffles, sausage, hash browns, grits, cereal and breads. Great location, easy to get to Inner Harbor. Nearby Wawa is great for drinks, snacks and gas. Front desk staff were friendly and helpful. "
John 1-night trip
Posted 4 hours ago
Hampton Inn Baltimore Bayview Campus

Find out more about Chestertown

Holiday Rentals in Chestertown

Search for holiday rentals in Chestertown on Expedia.co.uk! 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 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 26 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 Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland. 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.