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Compare 6 Guest Houses in Chester with updated reviews, rates, and availability.

Island Life! Kent Island Waterfront with Pool-Bring your boat!
Island Life! Kent Island Waterfront with Pool-Bring your boat!
10.0 out of 10, Exceptional, (184)

Newly Renovated Guest House located in Oxford MD
Newly Renovated Guest House located in Oxford MD
9.8 out of 10, Exceptional, (19)

Sandaway Suites & Beach
Sandaway Suites & Beach
9.2 out of 10, Wonderful, (133)
The price is AED 1,063
AED 1,170 total
includes taxes & fees
15 May - 16 May

Riverview Retreat on Warehouse Creek
Riverview Retreat on Warehouse Creek
10.0 out of 10, Exceptional, (22)
The price is AED 511
AED 1,325 total
includes taxes & fees
5 May - 6 May

West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
10.0 out of 10, Exceptional, (15)

Calico Cottage Guest House
Calico Cottage Guest House
10.0 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.
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Other property types in Chester

Waterfront Sunset Bayview: sleeps 6
Waterfront Sunset Bayview: sleeps 6
10.0 out of 10, Exceptional, (14)

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (214)

The Blue Crab Beach House - Free beach passes
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (54)
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.
Recent reviews of Chester hotels
Recent reviews of Chester hotels

Country Inn & Suites by Radisson, Annapolis, MD
5/5 Excellent
"Wonderful staff!"
A verified traveler stayed at Country Inn & Suites by Radisson, Annapolis, MD
Posted 1 day ago