Customized for your search:

Chestertown Hotels

Chestertown Hotels

Hotel + Flight Deals in Chestertown

See all Chestertown Package Deals

Top Trending Hotels in Chestertown

Holiday Inn Express Hotel & Suites Chestertown - Chestertown Hotels
Rating: 2.5 Stars

Holiday Inn Express Hotel & Suites Chestertown

150 Scheeler Road, Chestertown - Map
"Best hotel in Chesterown"
The rooms have two double beds, good television, good climate control. The hotel has a fitness center, swimming pool, and good breakfast. People are friendly, as ever in Chesterton.
Traveller from Bethesda, MD
Located 1 mile from Washington College, this Holiday Inn hotel is also 2 miles from the Candlelight Walking Tour.Guestrooms …More
Quality Suites - Chestertown Hotels
Rating: 2.5 Stars

Quality Suites

160 Scheeler Rd, Chestertown - Map
"no surprises - comfortable"
no surprises - comfortable stay at the hotel. Clean and good location.....
A Traveller
Great Oak Manor - Chestertown Hotels
Rating: 4.0 Stars

Great Oak Manor

10568 Cliff Rd, Chestertown - Map
Driftwood Inn - Chestertown Hotels
Rating: 2.0 Stars

Driftwood Inn

609 Washington Avenue, Chestertown - Map
"Ok "
My stay was okay. Room was clean and check in was easy
A Traveller
Escape from the busy hustles and stress of life and let us pamper you at Driftwood Inn. Combining traditional hospitality and …More
Simply Bed & Bread - Chestertown Hotels

Simply Bed & Bread

208 Mt Vernon Ave, Chestertown - Map
John L Stam House - Chestertown Hotels
Rating: 3.0 Stars

John L Stam House

114 Washington Ave, Chestertown - Map
Awesome hotel, remarkable atmosphere, welcoming staff
A Traveller

Search from 6 Chestertown Hotels


    Why book with Expedia ?

    • Best Price Guarantee
    • Over 271,000 hotels worldwide
    • No Expedia cancellation fee
    • 91% customer satisfaction

    Chestertown Hotel Guide offers a selection of 6 hotels in Chestertown. You are sure to find cheap deals and discount rates among them with our Best Price Guarantee. No matter what type of hotel strikes your fancy, we will let you search for your preferred one to accommodate your travel needs. will not only save you time, but also money when booking your stay at a hotel in Chestertown. Making reservations so you can stay within your budget is easy with us. even provides you with a map so you may find hotels in the Chestertown neighborhood you prefer.

    Go ahead. Enter your travel dates to view the best offers on hotel rooms in Chestertown, Maryland now!

    Customers Rate Expedia
    Powered by feefo
    91% recommended
    From 29,939 Reviews
    *For these packages, package savings is at least equal to the cost of the flight or hotel if booked separately. Note: For packages including flights, you will be charged by the airline for the flight, but your savings on the package will equal the cost of the flight.