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Browse Select Clayton Vacation Homes

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (166)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (13)
"This was a wonderful house for our family gathering. We enjoyed watching the birds, fish, and wildlife from the glassed-in porch. We cooked in the well appointed kitchen and we kayaked too. Evolve staff was top notch all around."
Pet-Friendly Home on Chester River w/ Dock!

Captain's Quarters

9.8 out of 10, Exceptional, (97)
"We had a great weekend stay for a tournament. Thank you!"
Captain's Quarters

Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

9.4 out of 10, Exceptional, (3)
"Adorable cottage. Excellent location. We will definitely rent again. "
Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.6 out of 10, Exceptional, (19)
"a great place to unwind. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

10.0 out of 10, Exceptional, (1)
"Property is beautiful, host answered our questions in a timely manner. Would stay again "
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (42)
"This is a jewel as it is private, peaceful with lovely setting."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

10.0 out of 10, Exceptional, (23)
"The house was amazing, and close to Killens Pond State Park where we had additional family camping."
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

9.8 out of 10, Exceptional, (6)
"Exactly as advertised and Brad was very helpful/responsive!"
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

Wind Song Getaway on the Beach

9.8 out of 10, Exceptional, (28)
"We enjoyed the home and the quiet town. The screened porch was a great place to relax and watch the tide come in and go out. "
Wind Song Getaway on the Beach

Waterfront Lodge packed with Amenities

Waterfront Lodge packed with Amenities

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

10.0 out of 10, Exceptional, (56)
"The house is roomy and was clean and well stocked."
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

9.8 out of 10, Exceptional, (83)
"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

8.4 out of 10, Very good, (6)
"Nice and quiet place to stay"
The price is CA $211
CA $420 total
includes taxes & fees
Aug 25 - Aug 26
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (20)
"We attended a wedding across the canal from this house at the Chesapeake Inn. It was very cool to see these really large ships go by as we sat on the deck. Very nice accommodations here! Jane was a great host!"
Chesapeake City Quiet Overlook

Luxurious and spacious townhome with all necessary amenities awaits your stay.

9.4 out of 10, Exceptional, (9)
"Great experience all around! "
Luxurious and spacious townhome with all necessary amenities awaits your stay.

Spacious 5 Bedroom w/Pool, Patio and Theater

9.8 out of 10, Exceptional, (7)
"Great house for a large family "
The price is CA $599
CA $1,226 total
includes taxes & fees
Sep 4 - Sep 5
Spacious 5 Bedroom w/Pool, Patio and Theater

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

10.0 out of 10, Exceptional, (15)
"Very friendly and helpful host and a great property. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

Bungalow by the Bay. Minutes to DE Turf Fields. 30 minutes to resort beaches.

10.0 out of 10, Exceptional, (5)
"We stayed at the property while all our children were at a tournament at the DE turf fields. It was convenient and very comfortable. The house was well supplied and maintained."
Bungalow by the Bay. Minutes to DE Turf Fields. 30 minutes to resort beaches.

Waterfront House on the Upper Chesapeake Bay

9.6 out of 10, Exceptional, (7)
"My boyfriend and i had a great 2 days! So peaceful bing on the water. Cottage was equipped with everything you would need!"
Waterfront House on the Upper Chesapeake Bay
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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Top Clayton Hotel Reviews