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Hotels and More in Chestertown

Lodging at The Imperial

Hotel in Chestertown

Located in Chestertown, Lodging at The Imperial features Restaurant, garden, bar, and free WiFi. Featuring a concierge service, this property also provides guests with a terrace.

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Avg. price/night:
$204.93
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Holiday Inn Express Hotel & Suites Chestertown

Hotel in Chestertown

This Maryland hotel is less than 1 mile from Washington College. Free Wi-Fi is available throughout the hotel. Only problem I had was signing in....they had no record, or could find no record of my oredering a reservation with an out side company. However, the girl took care of it all to our satisfaction in a short time.

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8.5
Very Good
114 reviews
Avg. price/night:
$91.99
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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. the fritata was excellent. I appreciated that the staff was able to take out the green onions so I could have this excellent dish. the tea on Saturday afternoon was fun, relaxing and extremely enjoyable.

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8.8
Excellent
11 reviews
Avg. price/night:
$219
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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.

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5.5
Review score
72 reviews
Avg. price/night:
$69.49
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Great Oak Manor

Great Oak Landing (Near Chestertown)

Featuring free WiFi throughout the property, Great Oak Manor offers accommodations in Chestertown. Free private parking is available on site. Every room comes with a flat-screen TV. Beautiful, comfortable, romantic

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9.3
Awesome
14 reviews
Avg. price/night:
$199
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The Blissful Retreat

Rock Hall (Near Chestertown)

The Blissful Retreat is located in Rock Hall. The nearest airport is New Castle [Greater Wilmington] Airport, 65 miles from the vacation home.

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Avg. price/night:
$304.71
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Inn at Osprey Point

Rock Hall (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. Our needs were consistently met. I have Celiac Disease, of which I informed them by phone and upon arrival. For breakfast, I had my own gluten free French toast casserole. They also had gluten free frittatas, hard boiled eggs, yogurt, fresh fruit, and would have made me fresh eggs if I had chosen. The staff were consistently professional and courteous. As we checked out, they asked for suggestions for improvement. We met the owner, who was warm and quick with suggestions for sightseeing and travel suggestions. The stay was 10 out of 10, and we will be back.

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9.7
Exceptional
23 reviews
Avg. price/night:
$180
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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. The hosts and staff were excellent and friendly and really made us comfortable

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9.9
Exceptional
26 reviews
Avg. price/night:
$192.50
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Haven Point Inn

Rock Hall (Near Chestertown)

Located in Rock Hall, Haven Point Inn features free bikes, garden, water sports facilities, and free WiFi. The location is centrally located. The rooms are beautifully designed and up to date. The owners take great pains to make you feel welcomed and respond to your requests. The breakfast is delicious and tasty. We spend a few enjoyable days . I highly recommend it.

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9.6
Exceptional
37 reviews
Avg. price/night:
$145
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104 Chesapeake House Condo

Centreville (Near Chestertown)

104 Chesapeake House Condo is located in Centreville. Guests staying at this apartment can use the free WiFi and a fully equipped kitchen.

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Avg. price/night:
$372.87
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