Skip to main content

Search hotels in Chestertown, MD

Enter your dates to see the latest prices and deals for Chestertown hotels

Chestertown – 5 hotels and places to stay

Filter by:

Star rating
Review score

Comfort Inn & Suites Chestertown

Hotel in Chestertown

Comfort Inn & Suites Chestertown in Chestertown has 2-star accommodation with a seasonal outdoor swimming pool, a fitness centre and a shared lounge.

W
Wilson
From
United States
For the most part, all was good, with the exception of the fact that my room did not have cream and sugar.
Scored out of 10, guest rating 7.9
Good - What previous guests thought, 241 reviews
Price from
US$109.65
1 night, 2 adults

Brampton 1860

Chestertown

Brampton 1860 in Chestertown provides adults-only accommodation with a garden and a shared lounge. Featuring a concierge service, this property also provides guests with DVD player.

C
CATHLEEN
From
United States
We chose the Emory suite for our wedding anniversary, to enjoy additional comfort and it’s peaceful surroundings. The rooms were delightful and we enjoyed the convenience of the location in main building. We thoroughly loved the manor, sitting on the porch outside, listening to the rain while sampling the fine selection of teas and baked goods available to guests round the clock. The breakfast options were amazing, the charcuterie tray and Cheese boards (available for order) were delicious and satisfying, and the wine and chocolate pairing was an informative and memorable experience. We loved our mid week, anniversary getaway and we plan to return!
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 14 reviews
Price from
US$262.90
1 night, 2 adults

Captain’s Quarters - unique home on Corsica River!

Centreville (Near Chestertown)

Boasting air-conditioned accommodation with a balcony, Captain’s Quarters - unique home on Corsica River! is situated in Centreville. Guests can benefit from a patio and an outdoor fireplace.

G
Gwen
From
United Kingdom
Beautiful house in perfect location for us. Would definitely recommend
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 10 reviews
Price from
US$215
1 night, 2 adults

Inn at Huntingfield Creek

Rock Hall (Near Chestertown)

Set in Rock Hall, Inn at Huntingfield Creek offers accommodation with seating area. With a seasonal outdoor swimming pool, the 4-star bed and breakfast has air-conditioned rooms with free WiFi.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 30 reviews
Price from
US$155.68
1 night, 2 adults

Haven Point Inn

Rock Hall (Near Chestertown)

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

P
Patricia
From
United Kingdom
The room was beautifully furnished with a lovely view of the garden. It is a quiet area and very friendly. The owners are very friendly and helpful. Breakfast was good too!
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 70 reviews
Price from
US$155
1 night, 2 adults

Inn at Osprey Point

Rock Hall (Near Chestertown)

Inn at Osprey Point features free bikes, seasonal outdoor swimming pool, a garden and restaurant in Rock Hall. With a bar, the property also has barbecue facilities.

B
BernardWelt
From
United States
The breakfast was nicely prepared and hosts were very solicitous, inquiring what I might like best.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 76 reviews
Price from
US$170
1 night, 2 adults

Inn at Haven Harbour

Rock Hall (Near Chestertown)

Inn at Haven Harbour has free bikes, seasonal outdoor swimming pool, a garden and private beach area in Rock Hall.

Scored out of 10, guest rating 6.4
Pleasant - What previous guests thought, 27 reviews
Price from
US$208.60
1 night, 2 adults

Carriage House Hideaway In Center of Chestertown

Chestertown

Set in Chestertown in the Maryland region, Carriage House Hideaway In Center of Chestertown features a garden. The accommodation is non-smoking. New Castle Airport is 77 km away.

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 6 reviews
See all hotels in and around Chestertown

Budget hotels in Chestertown and nearby

  • 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
    Jeanne
    United States
  • 10.0

    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
    Marilyn
    Portugal

See reviews by guests who stayed at hotels in Chestertown

See all
  • Scored out of 10, guest rating 4.4
    Disappointing - What previous guests thought, 80 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
    Margaret
    United States
  • From US$133.51 per night
    Scored out of 10, guest rating 7.9
    Good - What previous guests thought, 241 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.
    Guest review by
    Julie
    United States
  • Scored out of 10, guest rating 4.4
    Disappointing - What previous guests thought, 80 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.
    Guest review by
    Jeffrey
    United States
  • Scored out of 10, guest rating 10.0
    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
    Jennifer
    United States
  • From US$133.51 per night
    Scored out of 10, guest rating 7.9
    Good - What previous guests thought, 241 reviews
    Did not participate in breakfast, had coffee only. Great location in the city of Chestertown huge parking lot and a friendly staff.
    Guest review by
    Tom
    United States