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Compare 3 Villas in Chester with updated reviews, rates, and availability.

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

10.0 out of 10, Exceptional, (34)
"Wonderful stay for 75th and 50th birthday celebrations.Everyone from age 4 to 75 had a terrific time. So much to do we did not leave the property. View of the Chesapeake Bay is amazing - from sunrise to gorgeous sunsets. Plenty of room for everyone. Great communication from host with instructions and area suggestions. 5 Star"
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Breathtaking Waterfront Estate

10.0 out of 10, Exceptional, (70)
"We had a wonderful stay here. The house has a really functional kitchen so we were able to cook a lot of meals here. The pool was perfect for young swimmers (decent sized shallow end) and we loved hanging out on the dock, crabbing and kayaking. With plenty of adult bikes, we took a trip each morning to the playground too. We hope to be back!"
Breathtaking Waterfront Estate

Blake House Historic Estate with Private Inn

10.0 out of 10, Exceptional, (19)
"My family stayed at The Beach Club for our yearly vacation. In 6th"
Blake House Historic Estate with Private Inn
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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Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (14)
"Really great spot, the house was very clean and new. We had nice weather and spent a lot of time outside and in the enclosed sun room."
Waterfront Sunset Bayview: sleeps 6

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (213)
"Great location near the Naval Academy, Main Street, Paca House, St. John's...loved walking the streets every evening with our dog. Helpful restaurant trips from John, convenient parking spot, everything was just right! Thank you!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (54)
"Cute as a button. Very, very clean, kitchen has everything, living room very comfortable for us 4 adults. Fenced yard was perfect for our furry companion. Excellent location-quiet neighborhood, easy walk to beach and restaurants.Host is very prompt responding to any inquiry. You won’t regret this rental!!"
The Blue Crab Beach House - Free beach passes
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.