Photo by Patricia Knorr

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Compare 5 Villas in Chester with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (32)
"Beautiful home, beautiful property! My family meets up annually and the house fit us perfectly. Plenty of room to spread out and congregate together. The home also provides so much to do with all the amenities! Thanks for the memories "
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Breathtaking Waterfront Estate

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
LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12
Pool

LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12

LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12
Blake House Historic Estate with Private Inn

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
Exquisite 14,000 sq ft Waterfront Mansion with Pool
Exterior

Exquisite 14,000 sq ft Waterfront Mansion with Pool

Exquisite 14,000 sq ft Waterfront Mansion with Pool
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

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Ready to Relax and Enjoy the Water and Sunset Views?

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!

10.0 out of 10, Exceptional, (8)
"Overall it was a wonderful stay for me and 4 of my friends. Plenty of space for everyone to spread out and enjoy the wonderful view of the water while we were between wedding events. The home was off the beaten path, which added to the relaxing feeling of the house. Also it was never more than a 20 min drive to get to our events accross the island. The host was very responsive and more than accommodating for my group. The only very minor suggestion I'd like to make is that the trash in the...
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Exterior

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (38)
"This home was perfect for our 12-person family. There was plenty of room to spread out, and the house was well stocked with everything we needed. It would be a great place to vacation in the summer as well. The owner was helpful, communicated well, and accommodating. We hope we can return sometime in the future."
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Terrace/patio

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
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.