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Chestertown – 2 hotels and places to stay
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Comfort Inn & Suites Chestertown
Hotel in Chestertown
Comfort Inn & Suites Chestertown is less than 1 mile from Washington College. Free Wi-Fi is available throughout the hotel.
Cara-Marie
United States of America
The location was central in Chestertown, which made it easy to get to our work locations.
7.6
Scored 7.6
Good
Rated good
250 reviews
Price from$117.77per night
Driftwood Inn
Chestertown
This motel is located just a 6-minute walk from Washington College. It offers free Wi-Fi and a 24-hour front desk. Downtown Chestertown, Maryland is 2 miles from the motel.
MELINDA
United States of America
Very clean and quiet. Great mattress. Loved the chart of the Chester river on the wwall.
5.8
Scored 5.8
Above average
Rated okay
91 reviews
Price from$499per night
Haven Point Inn
Rock Hall (Near Chestertown)
Haven Point Inn in Rock Hall provides adults only accommodations with a garden, water sports facilities and barbecue facilities.
Shari
United States of America
My husband and I enjoyed meeting Paul, the host and how personable he was. He was also very attentive to our questions/needs. Our breakfast was divine, coffee was awesome! The location was perfect, we very much enjoyed the vibe on the Eastern Shore of Maryland. Would love to return to area again!
9.5
Scored 9.5
Exceptional
Rated exceptional
101 reviews
Price from$155per night
Inn at Huntingfield Creek
Rock Hall (Near Chestertown)
Inn at Huntingfield Creek features air-conditioned rooms in Rock Hall. Boasting a shared lounge, this property also provides guests with a seasonal outdoor pool. Free WiFi is at guests' disposal.
Barbara
United States of America
Lovely two bedroom apartment above a super coffee shop. Lots and lots of room with great light. Well equipped and lovely town to walk around in and explore neighboring areas.
9.2
Scored 9.2
Wonderful
Rated wonderful
33 reviews
Price from$201.25per night
Inn at Osprey Point
Rock Hall (Maryland) (Near Chestertown)
Offering an outdoor pool and a restaurant, Inn at Osprey Point is located in Rock Hall. Free WiFi access is available. Each room here will provide you with a TV, air conditioning and cable channels.
JUDITH
United States of America
The residence and grounds were "grand" and staff made if so comfortable when one may have expected a pretentious welcome. Though the property small, the view and grounds were spectacular.
9.3
Scored 9.3
Wonderful
Rated wonderful
78 reviews
Price from$169per night
What Guests Said About Chestertown:
- 4.0Scored 4.0
Mondays, Tuesdays and Wednesdays restaurants are not open...
Mondays, Tuesdays and Wednesdays restaurants are not open because of shortage of workforce. Owners are working long hours during this Covid 19 restart. River cruise was pleasant evening. Fresh crab is available near waterfront. The new Y is great for exercise, swimming and pickleball.
JeanneUnited States of America - 10Scored 10
Chestertown is a beautiful historic small town founded in...
Chestertown is a beautiful historic small town founded in 1706. It has an historic district of wonderful old houses, along the Chester River on the eastern shore of Maryland. This is a very walkable town with historic houses. Several small eateries on the main street for lunch and a few restaurants for dinner, but be warned: restaurants close at 8 or 9 pm, so plan to eat early. Take a short trip to Rock Hall and have a dozen blue crabs on the dock of the Waterman's Crab Shack at a very reasonable price.
MarilynPortugal - 10Scored 10
First time visit as our son moved there in the summer with...
First time visit as our son moved there in the summer with his family. Very interesting area. The town itself was lovely. Information centre very interesting. The river and surroundings lovely and interesting history.
DavidUnited Kingdom
Explore guest reviews of hotels in Chestertown
- From $68.58 per night5.8Scored 5.8Above averageRated okay· 91 reviewsThe girl who works the desk is the same girl that cleans i s awesome, friendly, cool personality. If it weren’t for her this would be a terrible rating . The owner walked in my room ( like he owns the place) come on dude knock! A little shady not the Marriott but for the money great and location is unbeatable. Beer across the lot.PPaulUnited States of America
- 9.5Scored 9.5ExceptionalRated exceptional· 33 reviewsBeen here Many times and was always great as far as relaxing the best New ownership and the place looks fabulous and the service is as good if not a touch better then before Breakfast was excellent and different day .We will be back againGGeorgeUnited States of America
- From $68.58 per night5.8Scored 5.8Above averageRated okay· 91 reviewsIt was the only offering in Chestertown that was on Booking.com on the day that I made my reservation. Next time I will check a bed and breakfast site. I believe that the sheets and pillowcases were clean.JuliaUnited States of America
- From $68.58 per night5.8Scored 5.8Above averageRated okay· 91 reviewsFor the price the hotel was fine. It's an older place, but inside was clean. My first impression of the look of it wasn't great, but the staff was helpful and we actually had a nice quiet sleep.JJeffreyUnited States of America
- 10Scored 10ExceptionalRated exceptional· 2 reviewsThis cottage was absolutely beautiful! It had all the amenities you could think of or want. It is a short walk from historic Chestertown. It was a relaxing and comfortable space.JenniferUnited States of America
- From $131.15 per night7.6Scored 7.6GoodRated good· 250 reviewsLocation was great, overall condition of the hotel was clean, attendant was friendly.CherylUnited States of America
- From $131.15 per night7.6Scored 7.6GoodRated good· 250 reviewsit’s a welfare hotel. and has an indifferent staffjoanneUnited States of America
- From $131.15 per night7.6Scored 7.6GoodRated good· 250 reviewsTHE HOTEL WASNT BAD THE ROOMS ARE NICEMargaretUnited States of America
- From $131.15 per night7.6Scored 7.6GoodRated good· 250 reviewsHappy that Chestertown has a hotel.
WilbertUnited States of America - From $68.58 per night5.8Scored 5.8Above averageRated okay· 91 reviewsconvenient to ChestertownEEdUnited States of America
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