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Find Resorts & Hotels with Spas in Chestertown, MD
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Compare Chestertown Resorts & Hotels with Spas room rates, reviews, and availability. Most hotels are fully refundable.

Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
8.6 out of 10, Excellent, (758)
The price is AED 418
AED 464 total
includes taxes & fees
8 May - 9 May

Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
7.4 out of 10, Good, (346)
The price is AED 251
AED 279 total
includes taxes & fees
8 May - 9 May

Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
9.8 out of 10, Exceptional, (22)

First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (82)
The price is AED 360
AED 579 total
includes taxes & fees
6 May - 7 May

Harbor View Haven | Waterfront w/ Hot Tub + Dock!
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
10.0 out of 10, Exceptional, (17)

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
9.8 out of 10, Exceptional, (80)

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
10.0 out of 10, Exceptional, (76)

Circa 1900 Home in the Heart of Historic Downtown Chestertown
Circa 1900 Home in the Heart of Historic Downtown Chestertown
10.0 out of 10, Exceptional, (68)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find out more about Chestertown
Find out more about Chestertown
Recent reviews of Chestertown hotels
Recent reviews of Chestertown hotels

Sagamore Pendry Baltimore
5/5 Excellent
"Absolutely stunning property. Rooms are beautiful and CLEAN. The hotel itself is gorgeous and so well designed. This is our third stay and we will continue to treat ourselves to this wonderful luxurious hotel. The staff is extremely friendly and helpful. Can’t wait for our next stay! "
A verified traveler stayed at Sagamore Pendry Baltimore
Posted 2 days ago
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Hotels near popular Chestertown Attractions
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Chestertown Hotels by Star Rating
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