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We offer 7 hotels in Chestertown
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Best Chestertown MD hotels, motels and accommodations of 2019

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Quality Suites Chestertown160 Scheeler Rd, Chestertown, United States, 21620View on map
1.3 mi from City Center1600 yd from Washington College
Located 3 km away from Chestertown city center, this hotel features 53 rooms and an outdoor swimming pool.
  • The hotel has
    • 24-hour reception
    +1
8.2
Great35 reviews
Price fromUS$ 178per nightSelect
Holiday Inn Express Hotel & Suites Chestertown150 Scheeler Road, Chestertown, United States, 21620View on map
1.3 mi from City Center1600 yd from Washington College
Set close to Washington College, the hotel boasts American meals served at the onsite outdoor restaurant.
  • The hotel has
    • On-site car park
    +1
  • The hotel has
    • Late check-in/ -out
    • 24-hour reception
    +2
8.4
Great14 reviews
Price fromUS$ 142per nightSelect
Driftwood Inn Chestertown609 Washington Avenue, Chestertown, United States, 21620View on map
1700 yd from City Center1000 yd from Washington College
Within easy reach of Poor Richards of Chestertown, this hotel comprises 28 rooms with private bathrooms.
  • The motel has
    • On-site car park
    +1
  • The motel has
    • 24-hour check-in
    • 24-hour reception
    +2
5.2
Guest rating18 reviews
Price fromUS$ 79per nightSelect
Brampton Bed And Breakfast Inn Chestertown25227 Chestertown Road, Chestertown, United States, 21620View on map
1.5 mi from City Center
Located next to Historical Society of Kent County, the venue comprises 13 rooms with garden views.
  • The bed & breakfast has
    • Free Wi-Fi in rooms
    +1
  • The bed & breakfast has
    • Off-site car park
    +1
  • The bed & breakfast has
    • Snack bar
    +1
Price fromUS$ 232per nightSelect
John L Stam House Apartment ChestertownApartment114 Washington Ave, Chestertown, United StatesView on map
400 yd from City Center200 yd from Kent County Arts Council Inc
Select
Great Oak Manor Bed & Breakfast Great Oak Landing10568 Cliff Road, Chestertown, United States, 21620View on map
8.4 mi from City Center
The hotel offers 12 rooms with the sea views, a first floor restaurant, and a music bar.
  • The bed & breakfast has
    • On-site car park
    +1
Price fromUS$ 343per nightSelect
Lodging At The Imperial Hotel ChestertownHotel208 High Street, Chestertown, United States, MD 21620View on map
200 yd from City Center400 yd from Kent County Arts Council Inc
There are rooms facing the sea and the hotel is set close to Wilmer Park.
  • The hotel has
    • Free Wi-Fi in rooms
    +1
  • The hotel has
    • Off-site car park
    +1
  • The hotel has
    • Bar/ Lounge area
    • Restaurant
    +2
Price fromUS$ 321per nightSelect
Similar properties near Chestertown
Hilton Garden Inn Kent Island Grasonville3206 Main Street, Grasonville, United States, 21638View on map
19.1 mi from Chestertown19.1 mi from City Center
This hotel, featuring 90 non-smoking rooms and an air-conditioned restaurant, is centrally based in the heart of the city.
  • The hotel has
    • On-site car park
    +1
  • The hotel has
    • 24-hour reception
    +1
8.8
Great14 reviews
Price fromUS$ 156per nightSelect
Country Inn & Suites By Radisson, Bel Air/Aberdeen, Md1435 Handlir Drive, Bel Air, United States, 21015View on map
21.3 mi from Chestertown21.3 mi from City Center
This eco-friendly hotel overlooks the river boasting its location in busy area.
  • The hotel has
    • Free Wi-Fi in rooms
    +1
  • The hotel has
    • On-site car park
    +1
8.8
Great32 reviews
Price fromUS$ 128per nightSelect
Homewood Suites By Hilton Bel Air Riverside4170 Philadelphia Road, Riverside, United States, 21015View on map
21.3 mi from Chestertown21.3 mi from City Center
This conveniently located hotel in Riverside boasts 92 beautiful rooms along with a spa area and a Jacuzzi.
  • The hotel has
    • On-site car park
    +1
  • The hotel has
    • Late check-in/ -out
    • 24-hour reception
    +2
8.4
Great14 reviews
Price fromUS$ 140per nightSelect
Home2 Suites By Hilton Baltimore/Aberdeen20 Newton Road, Aberdeen, United States, 21001View on map
20.6 mi from Chestertown20.6 mi from City Center
This historic-style hotel is set at a short distance to Ripken Museum.
  • The hotel has
    • On-site car park
    +1
Price fromUS$ 135per nightSelect
Holiday Inn Belcamp - Aberdeen Area1326 Policy Drive, Belcamp, United States, 21017View on map
21.0 mi from Chestertown21.0 mi from City Center
Boasting an infinity pool, the hotel is about 20 minutes' walk from the center of Belcamp.
  • The hotel has
    • On-site car park
    +1
8.8
Great9 reviews
Price fromUS$ 107per nightSelect
Springhill Suites By Marriott Edgewood/Aberdeen Bel Air1420 Handlir Drive, Bel Air, United States, 21015View on map
21.3 mi from Chestertown21.3 mi from City Center
This suburban hotel with 119 modern rooms is located in the heart of Bel Air.
  • The hotel has
    • Free Wi-Fi in rooms
    +1
  • The hotel has
    • On-site car park
    +1
  • The hotel has
    • 24-hour reception
    +1
8.4
Great17 reviews
Price fromUS$ 118per nightSelect
Quality Inn Grasonville101 Vfw Avenue, Grasonville, United States, 21638View on map
18.6 mi from Chestertown18.6 mi from City Center
Featuring 59 rooms, this hotel offers a scenic view of Chesapeake Bay and Sandy Point State Park and is located close to a motorway.
  • The hotel has
    • On-site car park
    +1
  • The hotel has
    • 24-hour reception
    +1
7.8
Very good13 reviews
Price fromUS$ 128per nightSelect
Best Western Kent Narrows Inn Grasonville3101 Main Street, Grasonville, United States, 21638-1029View on map
19.1 mi from Chestertown19.1 mi from City Center
Opened in 1989, this pleasant accommodation includes an indoor swimming pool, a shared lounge and a golf course, within 30 minutes' walk from the center of Grasonville.
  • The hotel has
    • On-site car park
    +1
8.4
Great38 reviews
Price fromUS$ 110per nightSelect
Extended Stay America - Baltimore - Bel Air - Aberdeen1361 James Way, Bel Air, United States, 21015View on map
21.3 mi from Chestertown21.3 mi from City Center
Situated in a business area of Bel Air, this hotel features an outdoor swimming pool and a golf course.
  • The hotel has
    • On-site car park
    +1
7.6
Very good1 review
Price fromUS$ 79per nightSelect
Holiday Inn Express Annapolis East-Kent Island Grasonville1020 Kent Narrows Road, Grasonville, United States, 21638View on map
19.0 mi from Chestertown19.0 mi from City Center
The hotel offers easy access to Chesapeake Exploration Center, boasting 76 rooms in the heart of Grasonville.
  • The hotel has
    • On-site car park
    +1
  • The hotel has
    • Late check-in/ -out
    • 24-hour reception
    +2
8.6
Great2 reviews
Price fromUS$ 179per nightSelect
Inn At Osprey Point Grasonville20786 Avenue, Rock Hall, United StatesView on map
10.9 mi from Chestertown10.9 mi from City Center
The hotel features a large pool and a spectacular view, boasting great setting.
Price fromUS$ 159per nightSelect
Candlewood Suites Aberdeen-Edgewood-Bel Air4216 Philadelphia Road, Bel Air, United States, 21015-6626View on map
21.3 mi from Chestertown21.3 mi from City Center
Featuring a casino, barbeque grills and a library, the property offers accommodation since 2009 in a busy area.
  • The hotel has
    • On-site car park
    +1
  • The hotel has
    • Late check-in/ -out
    • 24-hour reception
    +2
8.4
Great4 reviews
Price fromUS$ 104per nightSelect
Inn At Huntingfield Creek Rock Hall4928 Eastern Neck Rd, Rock Hall, United States, 21661View on map
11.0 mi from Chestertown11.0 mi from City Center
Located 30 minutes' drive from Rock Hall city center, this hotel offers a shared lounge, barbeque grills and a library.
  • The bed & breakfast has
    • On-site car park
    +1
  • The bed & breakfast has
    • Seasonal outdoor pool
    +1
Price fromUS$ 289per nightSelect

Your booking experience in Chestertown

If you are searching for comfortable accommodation for your next city escape in Chestertown, we are always ready to indulge you with good Maryland hotel deals. Booked.net features a handpicked selection of modern and historical hotels in Chestertown, searches for places to stay in the most popular corners of United States and offers the best rates from 94US$. Our website is equipped with search filters, filters that you may find pretty useful while looking for 5-star hotels and places to stay in Chestertown. We have cheap and luxury hotels with a huge list of services and amenities together with other amazing accommodation options which grant you an extensive base for exploring.

Convenience of staying in the city center

An option near the city centre is John L Stam House next to MassoniArt Gallery.

Check out Holiday Inn Express Hotel & Suites Chestertown to visit Upper Shore Comm Hlth Ctr, set 5 minutes' walk away and Luisa's Cucina Italiana, which is about 350 metres from the hotel.

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27 hotels found