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Chestertown Vacation Rentals

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Vacation Rentals in Chestertown

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Other types of properties in Chestertown you may be interested in

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (727)
"Was there just one night and didn't eat breakfast, but staff were wonderful and the room seemed newly renovated. Room was large and clean with coffee maker and mini-fridge. "
The price is NT$3,476
NT$3,859 total
includes taxes & fees
Dec 22 - Dec 23
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (320)
"Comfortable room and fair price for the room size. Very clean. Bathroom was nice but had a broken wall mounted hair dryer and the bathroom door did not latch closed so it stayed open about an inch. Front desk was businesslike but not the least bit friendly. There is no breakfast or even coffee offered. You have to go out for breakfast. Excuse was not since Covid. That adds another $20 per couple for breakfast to the room price."
The price is NT$2,432
NT$2,699 total
includes taxes & fees
Dec 3 - Dec 4
Red Roof Inn & Suites Chestertown
Historic Inns of Annapolis
Exterior

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1707)
"I love staying at this property. It is within walking distance of everything, especially Main Street and the Naval Academy. The valet service is excellent, and the staff is always friendly and helpful. The rooms are always clean and comfortable."
The price is NT$3,623
NT$5,206 total
includes taxes & fees
Nov 27 - Nov 28
Historic Inns of Annapolis
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.

Frequently asked questions

Are there vacation rentals in Chestertown?

Yes, we offer vacation rentals in Chestertown close to Crumpton Auction, 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 30 vacation rentals for your stay in Chestertown.

What can I see and do in Chestertown?

Cultural attractions include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater, whereas Wilmer Park is one spot to enjoy nature. Rolphs Wharf Marina and Crumpton Auction 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.