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Chestertown – 5 hotels and places to stay

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Comfort Inn & Suites Chestertown

Hotel in Chestertown

Located in Chestertown, Comfort Inn & Suites Chestertown offers 2-star accommodations with a seasonal outdoor swimming pool, a fitness center and a shared lounge.

Z
Zoraida
From
Puerto Rico
The breakfast was excellent! All the staff was very friendly and able to answer any questions. They always had a smile!
Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 236 reviews
Price from
$109.65
1 night, 2 adults
Check availability

Carriage House Hideaway In Center of Chestertown

Chestertown

Offering a garden, Carriage House Hideaway In Center of Chestertown offers accommodations in Chestertown. The accommodation is non-smoking. New Castle Airport is 48 miles away.

A
Antonella
From
United States
Everything was good, bed was comfortable, kitchen well stocked, quiet, very clean
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 6 reviews
Price from
$270
1 night, 2 adults
Check availability

Brampton 1860

Chestertown

Brampton 1860 in Chestertown provides adults-only accommodations with a garden and a shared lounge.

S
Sarah
From
United States
Beautiful grounds, lovely helpful staff, with far as the eye can see farmland and great seafood nearby. What more can you ask for?
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 15 reviews
Price from
$262.90
1 night, 2 adults
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Captain’s Quarters - unique home on Corsica River!

Centreville (Near Chestertown)

Featuring a garden, Captain’s Quarters - unique home on Corsica River! provides accommodations in Centreville. This property offers access to a balcony and free private parking.

J
Jessica
From
United States
There was thoughtfulness put into every inch of every room in this amazing home! It is absolutely adorable and honors the history of the home!
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 9 reviews
Price from
$215
1 night, 2 adults
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Inn at Huntingfield Creek

Rock Hall (Near Chestertown)

Inn at Huntingfield Creek provides air-conditioned accommodations in Rock Hall.

J
John
From
United States
Everything was great. Grounds well kept. Room was clean. Breakfast was great.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 29 reviews
Price from
$155.68
1 night, 2 adults
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Haven Point Inn

Rock Hall (Near Chestertown)

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

R
Robin Gordon Bunting
From
United States
Loved the quiet and easy location.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 70 reviews
Price from
$155
1 night, 2 adults
Check availability

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.

J
Judith
From
United States
Osprey Point Inn is located right on the water in a peaceful setting. There is so much wildlife around-my husband went birdwatching every morning, finding birds and seeing deer. The breakfast choices were amazing-frittatas, quiche, casseroles, fresh fruit, freshly baked pastries and so much more! While in an isolated quiet area, easy to get to restaurants in Rock Hall as well as a quick trip to get to Chestertown. Everyone was beyond wonderful!
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 79 reviews
Price from
$170
1 night, 2 adults
Check availability

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. The property has water sports facilities, as well as a shared lounge and a bar.

p
pat
From
United States
Breakfast was great. Sat on deck. Beautiful view. Enjoyed pool. Added a day to our stay and was given great service
Scored out of 10, guest rating 5.9
Fair - What previous guests thought, 29 reviews
Price from
$193.70
1 night, 2 adults
Check availability
See all hotels in and around Chestertown

Best hotels with breakfast in Chestertown and nearby

  • Thornton offers accommodations in Kennedyville, 26 miles from Bohemia Vista Marina. This property offers a private pool, free Wifi, and free private parking.

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

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  • Secluded Cottage in Middle of Chestertown

    Chestertown
    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

  • Comfort Inn & Suites Chestertown

    Chestertown
    From $132.76 per night
    Scored out of 10, guest rating 8.1
    Very Good - What previous guests thought, 236 reviews
    Bathroom was impressively clean as this is how I judge the hotel we usually stay at. The entire hotel was clean, breakfast was really 👍 great
    Guest review by
    GLORY
    United States

  • Comfort Inn & Suites Chestertown

    Chestertown
    From $132.76 per night
    Scored out of 10, guest rating 8.1
    Very Good - What previous guests thought, 236 reviews
    The breakfast was fine, about average for these types of motels.
    Guest review by
    msocean
    United States

  • Driftwood Inn

    Chestertown
    Scored out of 10, guest rating 4.5
    Disappointing - What previous guests thought, 84 reviews
    Clean, nice firm mattresses. The best value for the price.
    Guest review by
    Dmitriy
    United States

  • Driftwood Inn

    Chestertown
    Scored out of 10, guest rating 4.5
    Disappointing - What previous guests thought, 84 reviews
    convenient to Chestertown
    Guest review by
    Ed
    United States
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