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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.

Nice place, large room
7.6
Scored 7.6
Good
Rated good
251 reviews
Price from£104.90per night
Check availability
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.

Nothing
5.8
Scored 5.8
Above average
Rated okay
91 reviews
Price from£55.03per night
Check availability
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.

The breakfast was nicely prepared and hosts were very solicitous, inquiring what I might like best.
9.3
Scored 9.3
Superb
Rated superb
78 reviews
Price from£150.54per night
Check availability
Haven Point Inn, hotel in Chestertown

Haven Point Inn in Rock Hall provides adults-only accommodation with a garden, water sports facilities and barbecue facilities. The inn also offers free WiFi as well as a paid airport shuttle service....

The room was very comfortable; breakfast was delicious(!) and included fresh herbs, tomatoes, etc., all from the proprietor's lovely garden that actually piped in soft music! The dining area was lovely and looked out through a wall of windows, into the garden. Every table had a lovely view. The cottage, where one finds the breakfast room had a very large collection of hand crafter jewelry, artwork and other lovely, local items for purchase. Finally, the Inn is an easy walk or bike ride (bikes provided at no charge) into town. Loved everything about this place. Highly recommend.
9.5
Scored 9.5
Exceptional
Rated exceptional
101 reviews
Price from£138.07per night
Check availability
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.

We thought we would have breakfast at the Inn but we were given vouchers to get our breakfast at Jazz Rock in Rock Hall, which was fine. We really enjoyed the company of the two dogs. They were so friendly. The golf cart was very helpful for my husband since he doesn't get around very well. He was able to go to the waterfront with the golf cart.
9.3
Scored 9.3
Superb
Rated superb
32 reviews
Price from£175.06per night
Check availability
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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
  • 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

  • Driftwood Inn

    Driftwood Inn

    Chestertown
    From £55.03 per night
    5.8
    Scored 5.8
    Above average
    Rated okay
     · 91 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
  • Driftwood Inn

    Driftwood Inn

    Chestertown
    From £55.03 per night
    5.8
    Scored 5.8
    Above average
    Rated okay
     · 91 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
  • Comfort Inn & Suites Chestertown

    Comfort Inn & Suites Chestertown

    Chestertown
    From £105.24 per night
    7.6
    Scored 7.6
    Good
    Rated good
     · 251 reviews
    Our room was spotlessly clean, the bed was very comfortable. The hotel was quiet and within 5 minutes driving time from historic Chestertown. The price was quite reasonable for a weekend with a big event in town. Would not hesitate to stay here again.
    Julie
    United States
  • Brampton Bed and Breakfast Inn

    Brampton Bed and Breakfast Inn

    Chestertown
    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
  • Secluded Cottage in Middle of Chestertown

    Secluded Cottage in Middle of Chestertown

    Chestertown
    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
  • Driftwood Inn

    Driftwood Inn

    Chestertown
    From £55.03 per night
    5.8
    Scored 5.8
    Above average
    Rated okay
     · 91 reviews
    I found the Driftwood Inn to be very pleasant and affordable for great little weekend getaway !
    Byrnes
    United States
  • Comfort Inn & Suites Chestertown

    Comfort Inn & Suites Chestertown

    Chestertown
    From £105.24 per night
    7.6
    Scored 7.6
    Good
    Rated good
     · 251 reviews
    Location was great, overall condition of the hotel was clean, attendant was friendly.
    Cheryl
    United States
  • Comfort Inn & Suites Chestertown

    Comfort Inn & Suites Chestertown

    Chestertown
    From £105.24 per night
    7.6
    Scored 7.6
    Good
    Rated good
     · 251 reviews
    Central location in Chestertown. Good variety of breakfast options.
    Cara-Marie
    United States
  • Comfort Inn & Suites Chestertown

    Comfort Inn & Suites Chestertown

    Chestertown
    From £105.24 per night
    7.6
    Scored 7.6
    Good
    Rated good
     · 251 reviews
    THE HOTEL WASNT BAD THE ROOMS ARE NICE
    Margaret
    United States
  • Driftwood Inn

    Driftwood Inn

    Chestertown
    From £55.03 per night
    5.8
    Scored 5.8
    Above average
    Rated okay
     · 91 reviews
    convenient to Chestertown
    E
    Ed
    United States

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