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Compare 4 Villas in Chester with updated reviews, rates, and availability.

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, (33)

Breathtaking Waterfront Estate
Breathtaking Waterfront Estate
10.0 out of 10, Exceptional, (70)

Blake House Historic Estate with Private Inn
Blake House Historic Estate with Private Inn
10.0 out of 10, Exceptional, (19)
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, (12)

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
10.0 out of 10, Exceptional, (118)

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, (209)
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

Annapolis Waterfront Hotel, Autograph Collection
5/5 Excellent
"Good "
A verified traveler stayed at Annapolis Waterfront Hotel, Autograph Collection
Posted 16 hours ago