Search hotels in Chestertown
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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.
Jennifer
Canada
It was okay. We stayed there because it was relatively close to the nascar race
7.6
Scored 7.6
Good
Rated good
252 reviews
Price from$117.68per night
Driftwood Inn
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.
Steven
United States of America
Location and price
5.8
Scored 5.8
Above average
Rated okay
92 reviews
Price from$63.50per night
Inn at Osprey Point
Rock Hall (Maryland) (Near 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.
Antonne
United States of America
Very Friendly
9.3
Scored 9.3
Wonderful
Rated wonderful
81 reviews
Price from$169per night
Haven Point Inn
Rock Hall (Near Chestertown)
Haven Point Inn in Rock Hall provides adults only accommodations with a garden, water sports facilities and barbecue facilities.
David
United States of America
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
Rock Hall (Near 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.
Barbara
United States of America
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 Bed and Breakfast Inn
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.
Sarah
United States of America
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
Rock Hall (Near Chestertown)
Inn at Haven Harbour has free bikes, seasonal outdoor swimming pool, a fitness center and garden in Rock Hall.
Shirley
United States of America
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
78 reviews
What Guests Said About Chestertown:
- 4.0Scored 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.JeanneUnited States of America - 10Scored 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.
MarilynPortugal - 10Scored 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.DavidUnited Kingdom
Explore guest reviews of hotels in Chestertown
- From $68.58 per night5.8Scored 5.8Above averageRated okay· 92 reviewsWe 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.
KimberlyUnited States of America - From $68.58 per night5.8Scored 5.8Above averageRated okay· 92 reviewsThe 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.PPaulUnited States of America
- 9.5Scored 9.5ExceptionalRated exceptional· 33 reviewsBeen 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 againGGeorgeUnited States of America
- From $68.58 per night5.8Scored 5.8Above averageRated okay· 92 reviewsFor 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.JJeffreyUnited States of America
- 10Scored 10ExceptionalRated exceptional· 2 reviewsThis 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.JenniferUnited States of America
- From $146.15 per night7.6Scored 7.6GoodRated good· 252 reviewsDidn't eat breakfast at the hotel. what was offered was typical fare for this type of accommodation.PatriciaUnited States of America
- From $146.15 per night7.6Scored 7.6GoodRated good· 252 reviewsGood big room. Looked renovated. Comfortable beds, good air conditioning, near Chestertown.Anne-MarieUnited States of America
- From $146.15 per night7.6Scored 7.6GoodRated good· 252 reviewsTHE HOTEL WASNT BAD THE ROOMS ARE NICE
MargaretUnited States of America - From $146.15 per night7.6Scored 7.6GoodRated good· 252 reviewsHappy that Chestertown has a hotel.
WilbertUnited States of America - From $68.58 per night5.8Scored 5.8Above averageRated okay· 92 reviewsconvenient to ChestertownEEdUnited States of America
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