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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.

It was okay. We stayed there because it was relatively close to the nascar race
7.6
Scored 7.6
Good
Rated good
251 reviews
Price from$113.22per 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.

Location to the workplace
5.8
Scored 5.8
Above average
Rated okay
92 reviews
Price from$63.50per 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.

Very Friendly
9.3
Scored 9.3
Wonderful
Rated wonderful
80 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.

The owner, Paul, was an absolute gentleman. The accommodations were very clean, stylish, and comfortable.
9.5
Scored 9.5
Exceptional
Rated exceptional
102 reviews
Price from$155per 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.

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.
9.3
Scored 9.3
Wonderful
Rated wonderful
32 reviews
Price from$196per night
Brampton 1860, hotel in Chestertown

This 19th century estate is located on Maryland’s Eastern Shore and features lush gardens, outdoor seating, and a large wrap-around terrace with ceiling fans. Chestertown center is 2 miles away.

Beautiful grounds, lovely helpful staff, with far as the eye can see farmland and great seafood nearby. What more can you ask for?
9.5
Scored 9.5
Exceptional
Rated exceptional
33 reviews
Inn at Haven Harbour, hotel in Chestertown

Inn at Haven Harbour has free bikes, seasonal outdoor swimming pool, a fitness center and garden in Rock Hall.

Breakfast was amazing. Other guests were very friendly. Owners/staff were the best. Facilities and amenities were exceptional.
8.6
Scored 8.6
Excellent
Rated excellent
77 reviews
See all hotels in and around Chestertown
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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 $148.98 per night
    7.6
    Scored 7.6
    Good
    Rated good
     · 251 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
  • 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 $68.58 per night
    5.8
    Scored 5.8
    Above average
    Rated okay
     · 92 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
  • From $68.58 per night
    5.8
    Scored 5.8
    Above average
    Rated okay
     · 92 reviews
    For 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.
    J
    Jeffrey
    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 $148.98 per night
    7.6
    Scored 7.6
    Good
    Rated good
     · 251 reviews
    Didn't eat breakfast at the hotel. what was offered was typical fare for this type of accommodation.
    Patricia
    United States of America
  • From $68.58 per night
    5.8
    Scored 5.8
    Above average
    Rated okay
     · 92 reviews
    I found the Driftwood Inn to be very pleasant and affordable for great little weekend getaway !
    Byrnes
    United States of America
  • From $148.98 per night
    7.6
    Scored 7.6
    Good
    Rated good
     · 251 reviews
    The location was central in Chestertown, which made it easy to get to our work locations.
    Cara-Marie
    United States of America
  • From $148.98 per night
    7.6
    Scored 7.6
    Good
    Rated good
     · 251 reviews
    Happy that Chestertown has a hotel.
    Wilbert
    United States of America
  • From $68.58 per night
    5.8
    Scored 5.8
    Above average
    Rated okay
     · 92 reviews
    convenient to Chestertown
    E
    Ed
    United States of America
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