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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.

7.5
Scored 7.5
Good
Rated good
252 reviews
Price from$109.65per night
Driftwood Inn, hotel in 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.

5.8
Scored 5.8
Above average
Rated okay
90 reviews
Price from$72.50per night
Inn at Huntingfield Creek, hotel in 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.

9.2
Scored 9.2
Wonderful
Rated wonderful
34 reviews
Price from$201.25per night
Inn at Osprey Point, hotel in 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.

9.3
Scored 9.3
Wonderful
Rated wonderful
79 reviews
Price from$169per night
Haven Point Inn, hotel in Chestertown

Haven Point Inn in Rock Hall provides adults only accommodations with a garden, water sports facilities and barbecue facilities.

9.5
Scored 9.5
Exceptional
Rated exceptional
101 reviews
Price from$155per night
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What Guests Said About Chestertown:

  • 4.0
    Scored 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.
    Jeanne
    United States of America
  • 10
    Scored 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.
    Marilyn
    Portugal
  • 10
    Scored 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.
    David
    United Kingdom

Explore guest reviews of hotels in Chestertown

  • From $126.43 per night
    7.5
    Scored 7.5
    Good
    Rated good
     · 252 reviews
    The place has mildew and heavy mold particles in the air in the rooms. We first had room 116 where the carpet was wet and mildew strong. The attendant put us in 108 which was slightly improved but still had mold smell and particulates in the air. The room door would not lock. and the outside card reader and door stuck and was intermittent, pool was closed, and overall, the accommodations were not as advertised. I immediately got sick with asthma and could not swallow or breathe. We left and had to book a new hotel room at another hotel.
    C
    Carri
    United States of America
  • From $78.30 per night
    5.8
    Scored 5.8
    Above average
    Rated okay
     · 90 reviews
    We came in late and left early, only looking for a bed for the night and a roof over our heads, which this satisfied. The location was in the center of the commercial area of Chestertown, easy to get to, and within walking distance of several breakfast options. Some reviewers said they felt the area unsafe; we didn't have that feeling but we were traveling as a family and not alone.
    Kimberly
    United States of America
  • From $78.30 per night
    5.8
    Scored 5.8
    Above average
    Rated okay
     · 90 reviews
    The 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.
    P
    Paul
    United States of America
  • 9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 33 reviews
    Been 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 again
    G
    George
    United States of America
  • From $78.30 per night
    5.8
    Scored 5.8
    Above average
    Rated okay
     · 90 reviews
    It 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.
    Julia
    United States of America
  • 10
    Scored 10
    Exceptional
    Rated exceptional
     · 2 reviews
    This 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.
    Jennifer
    United States of America
  • From $126.43 per night
    7.5
    Scored 7.5
    Good
    Rated good
     · 252 reviews
    The Hotel location was perfect for us. Really good Breakfast, despite COVID Restrictions and staff very helpful and nice. Highly recommended!!
    PABLO
    United States of America
  • From $126.43 per night
    7.5
    Scored 7.5
    Good
    Rated good
     · 252 reviews
    Good big room. Looked renovated. Comfortable beds, good air conditioning, near Chestertown.
    Anne-Marie
    United States of America
  • From $126.43 per night
    7.5
    Scored 7.5
    Good
    Rated good
     · 252 reviews
    The breakfast was fine, about average for these types of motels.
    msocean
    United States of America
  • From $126.43 per night
    7.5
    Scored 7.5
    Good
    Rated good
     · 252 reviews
    THE HOTEL WASNT BAD THE ROOMS ARE NICE
    Margaret
    United States of America
  • From $78.30 per night
    5.8
    Scored 5.8
    Above average
    Rated okay
     · 90 reviews
    convenient to Chestertown
    E
    Ed
    United States of America