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Find Adventure Hotels in Chestertown, MD
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Top Chestertown Adventure Hotels
Our top choices for Chestertown adventure hotels

Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-South
9.4 out of 10, Exceptional, (1011)
The price is AED 325
AED 364 total
includes taxes & fees
9 Sep - 10 Sep

Hampton Inn Baltimore/White Marsh
Hampton Inn Baltimore/White Marsh
7.8 out of 10, Good, (1011)
The price is AED 356
AED 411 total
includes taxes & fees
8 Sep - 9 Sep

First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (99)
The price is AED 364
AED 583 total
includes taxes & fees
8 Sep - 9 Sep

Hilton Garden Inn Baltimore/White Marsh
Hilton Garden Inn Baltimore/White Marsh
7.8 out of 10, Good, (1018)
The price is AED 373
AED 431 total
includes taxes & fees
7 Sep - 8 Sep

Charming Pet-Friendly Stay - Near Bay & Beaches.
Charming Pet-Friendly Stay - Near Bay & Beaches.
10.0 out of 10, Exceptional, (3)

Waterfront Retreat with Private Dock and Beach
Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (24)
The price is AED 643
AED 1,120 total
includes taxes & fees
1 Oct - 2 Oct

Cozy Fells Point Gem / In The Heart of Fells Point
Cozy Fells Point Gem / In The Heart of Fells Point
9.8 out of 10, Exceptional, (194)
The price is AED 228
AED 759 total
includes taxes & fees
8 Sep - 9 Sep

Secluded Tiny Pool House -Private Pool -Self Check in
Secluded Tiny Pool House -Private Pool -Self Check in
9.6 out of 10, Exceptional, (8)
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.
Top Chestertown Hotel Reviews

Historic Inns of Annapolis
10/10 Excellent
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Hotels near popular Chestertown Attractions
Chestertown Hotels by Star Rating
Explore more hotels
- Courtyard by Marriott Baltimore Downtown/McHenry Row
- Hampton Inn & Suites Edgewood/Aberdeen-South
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- The Inn at Henderson's Wharf, Ascend Hotel Collection
- Hyatt Place Kent Narrows & Marina
- Annapolis Waterfront Hotel, Autograph Collection
- Best Western Kent Narrows Inn
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- Americas Best Value Inn Edgewood
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