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Chestertown – 6 hotels and places to stay

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Comfort Inn & Suites Chestertown

Hotel in Chestertown

Located in Chestertown, Comfort Inn & Suites Chestertown offers 4-star accommodations with a seasonal outdoor swimming pool, a fitness center and a shared lounge.

M
Maggie
From
United States
I was pleasantly surprised at the cleanliness and updated features of the double queen room. It has been awhile since I've stayed in a hotel, but was delighted to have a frig, microwave and a KEURIG coffee maker similar to my one at home!
Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 255 reviews
Price from
$104.84
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 9.0
Wonderful - What previous guests thought, 17 reviews
Price from
$284.90
1 night, 2 adults
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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.

H
Hague
From
United States
It was quiet and clean. For what it is you get what you pay for. Its not the Hilton but for $70 a night you get what you pay for. We were happy.
Scored out of 10, guest rating 5.5
Fair - What previous guests thought, 59 reviews
Price from
$63.50
1 night, 2 adults
Check availability

The Still Pond Inn

Still Pond (Near Chestertown)

The Still Pond Inn in Still Pond provides accommodations with a garden and barbecue facilities. This apartment provides free private parking and free Wifi.

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 5 reviews
Price from
$163.58
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.

Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 7 reviews
Price from
$265
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.

C
Christelia
From
United States
The most important thing that I enjoy was the welkin friendly, nice warm people Joanne and her husband was so welcoming, talking and eating breakfast with them was the most important thing that I really enjoyed. Also, my cottage was so beautiful and comfortable.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 38 reviews
Price from
$200.48
1 night, 2 adults
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Haven Point Inn and Gallery

Rock Hall (Near Chestertown)

Facing the beachfront in Rock Hall, Haven Point Inn and Gallery features a garden and a terrace. The property provides free WiFi throughout the property.

D
Denise
From
United States
We had a great stay. Paul was an excellent host, serving us the most delicious breakfasts, giving us helpful tourist tips and overall being warm and welcoming. The room was clean and comfortable and had everything we needed, the grounds were beautifully maintained and we appreciated the bikes and amenities. Would definitely recommend.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 63 reviews
Price from
$155
1 night, 2 adults
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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.

Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 60 reviews
Price from
$235
1 night, 2 adults
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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.

S
Shirley
From
United States
Breakfast was amazing. Other guests were very friendly. Owners/staff were the best. Facilities and amenities were exceptional.
Scored out of 10, guest rating 7.3
Good - What previous guests thought, 18 reviews
Price from
$194.60
1 night, 2 adults
Check availability
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Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 255 reviews

What Guests Said About Chestertown:

Scored out of 10, guest rating 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 byJeanne
United States
Scored out of 10, guest rating 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 byMarilyn
Portugal

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Comfort Inn & Suites Chestertown

Chestertown
From $126.43 per night
Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 255 reviews
This is certainly not a luxury hotel where you stay and enjoy the facilities, but it is clean, updated and budget friendly. Staff is nice. The breakfast is basic. I am happy with our stay! The one complaint that I have is the air conditioner unit is quite noisy. Hope the hotel can fix this issue.
Guest review byChristine
United States

Driftwood Inn

Chestertown
From $68.58 per night
Scored out of 10, guest rating 5.5
Fair - What previous guests thought, 59 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 byMargaret
United States

Secluded Cottage in Middle of Chestertown

Chestertown
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 byJennifer
United States

Comfort Inn & Suites Chestertown

Chestertown
From $126.43 per night
Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 255 reviews
Central location in Chestertown. Good variety of breakfast options.
Guest review byCara-Marie
United States

Driftwood Inn

Chestertown
From $68.58 per night
Scored out of 10, guest rating 5.5
Fair - What previous guests thought, 59 reviews
Clean, nice firm mattresses. The best value for the price.
Guest review byDmitriy
United States

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