Search hotels in Chestertown, MD
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Chestertown – 8 hotels and places to stay
- Scored out of 10, guest rating 8.0Very good - What previous guests thought, 238 reviewsFromUS$1101 night, 2 adults
- Scored out of 10, guest rating 9.7Exceptional - What previous guests thought, 14 reviewsFromUS$2411 night, 2 adults
- Scored out of 10, guest rating 9.2Superb - What previous guests thought, 10 reviewsFromUS$2151 night, 2 adults
- Scored out of 10, guest rating 9.6Exceptional - What previous guests thought, 28 reviewsFromUS$1561 night, 2 adults
- Scored out of 10, guest rating 9.6Exceptional - What previous guests thought, 67 reviewsFromUS$1551 night, 2 adults
- Scored out of 10, guest rating 9.4Superb - What previous guests thought, 78 reviewsFromUS$1701 night, 2 adults
- Scored out of 10, guest rating 7.3Good - What previous guests thought, 27 reviewsFromUS$2091 night, 2 adults
- Scored out of 10, guest rating 9.8Exceptional - What previous guests thought, 6 reviews
Best hotels with breakfast in Chestertown and nearby
Thornton
Hotel in Kennedyville
Breakfast options
Situated in Kennedyville, Thornton features accommodation with private pool, free WiFi and free private parking for guests who drive.
What guests said about Chestertown:
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.
Guest review by
JeanneUnited States
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.
Guest review by
MarilynPortugal
See reviews by guests who stayed at hotels in Chestertown
From US$127.75 per night
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 238 reviews
The breakfast is in a large room right off the lobby. I was there early, about 6:45. the offering is very mediocre at best. Preformed crescents of "scrambled egg" , bread, sausages, juice and a bowl of apples.
The only thing that appealed to me was the apple. Small, but delicious.
Guest review by
EDPUnited States
Scored out of 10, guest rating 4.4
Disappointing - What previous guests thought, 76 reviews
We needed a place in Chestertown just for a quick overnight stay -- it met all our needs. We did not need anything luxurious, just serviceable. The front desk clerk (I assumed owner) was very accommodating and helpful. We will stay there again next month for the same reasons.
Guest review by
MargaretUnited States
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 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.
Guest review by
JenniferUnited States
Scored out of 10, guest rating 4.4
Disappointing - What previous guests thought, 76 reviews
I found the Driftwood Inn to be very pleasant and affordable for great little weekend getaway !
Guest review by
ByrnesUnited States
From US$127.75 per night
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 238 reviews
Nice hotel
Guest review by
ParisellaUnited States
