Clayton Vacation Rentals

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Check prices for these dates

Tonight
Jan 14 - Jan 15
Tomorrow
Jan 15 - Jan 16
This weekend
Jan 17 - Jan 19
Next weekend
Jan 24 - Jan 26

Vacation Rentals in Clayton

Captain's Quarters
Fridge, microwave, oven, stovetop

Captain's Quarters

9.8 out of 10, Exceptional, (83)
"Great place to stay! The communication with the property manager was very good. The house was big enough for my husband and I, four of our adult children and some grandchildren. The bedrooms are spacious and we had enough beds and pillows for all. Our stay was in November, and we still enjoyed walking the beach, which was about a block away from the house, and watching the sunrise. The kitchen was very well equipped and everything was in working order. The only odd thing, that we got use to in...
Captain's Quarters
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach nearby, sun loungers

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (78)
"Very clean, excellent communications,"
The price is ￥15,415
￥24,811 total
includes taxes & fees
Jan 15 - Jan 16
First Floor Studio Apartment in Historic Chestertown
Beachfront Sunsets on the Water at Oakwood Beach
On the beach, sun loungers, beach towels

Beachfront Sunsets on the Water at Oakwood Beach

10.0 out of 10, Exceptional, (30)
"You're messaging ChatGPT, an AI We have no words to describe the perfect experience that John's cabin on the Delaware River provided us. John was a patient and generous host. From the beginning of the process, he was available for any questions, and even agreed to change our arrival date due to an unexpected issue with one of our friends. The house was very clean, delicately and beautifully decorated, and filled with everything one could possibly imagine needing on a vacation. When we arrived, a...
Beachfront Sunsets on the Water at Oakwood Beach
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
Aerial view

Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf

10.0 out of 10, Exceptional, (5)
"Perfect rental for our family of 6 adults! Great location on the water with a fun restaurant just steps away. Highly recommend!!"
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
Stunning waterfront villa with indoor pool and kids swing set and play area.
Spa

Stunning waterfront villa with indoor pool and kids swing set and play area.

10.0 out of 10, Exceptional, (11)
"Celebrated my wife’s special birthday and our family from NY, CT, TX, PA and MD all stayed for the weekend. 12 of us. Plenty of space to all gather together or gather in smaller groups. Game room, pool and hot tub were probably the two favorite places to hang out. Oh and you can’t forget the view overlooking the Bohemia River. Beautiful house. "
Stunning waterfront villa with indoor pool and kids swing set and play area.
Wind Song Getaway on the Beach
Interior

Wind Song Getaway on the Beach

9.8 out of 10, Exceptional, (25)
"This is a beautiful beach house, right on the water. Lots of amenities and upgrades. We loved the screened porch and upstairs deck. We were fine with the spiral stairs but they may be potentially challenging for some guests. The area is a little isolated and the beach was quiet in mid-October, which was perfect for us! I highly recommend this property."
Wind Song Getaway on the Beach
Bowers Beach Vacation Rental: 2 Blocks Away!
Beach nearby

Bowers Beach Vacation Rental: 2 Blocks Away!

9.6 out of 10, Exceptional, (5)
"The easy of check-in was the best I have had in all my VRBO rentals. The home was clean and well appointed. They provided all linens/towels and extra were available in a linen closet. The kitchen was well stocked. Great place. Can't wait to stay again. "
Bowers Beach Vacation Rental: 2 Blocks Away!
Historic Chesapeake City Stay
Pool

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (8)
"Property was clean and close to everything in Chesapeake City"
Historic Chesapeake City Stay
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Beach nearby, sun loungers, beach towels

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

9.6 out of 10, Exceptional, (36)
"We had a great time at the house with friends from our apartment building and neighborhood for the long Thanksgiving weekend. Debbie and Bob had everything we needed to cook with, the porch overlooking the Bay was amazing, and the living room, TV room and dining room were all used frequently. We also played games, and had a nice fire in the portable fire pit outside. Weather got coooold but the house was always warm and cozy. It was a really fun stay. The bedrooms were great, too. They've taken...
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Chesapeake City Quiet Overlook
Outdoor dining

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (13)
"This home was amazing. Nicely decorated for the holiday. Labels on kitchen cavinets. Host was easy to communicate with. Fast responses. doors made it easy to find things (huge kitchen). "
Chesapeake City Quiet Overlook
Quiet beach escape. Close to DE TURF fields.<br>TAX FREE SHOPPING!
Fridge, microwave, oven, stovetop

Quiet beach escape. Close to DE TURF fields.<br>TAX FREE SHOPPING!

9.6 out of 10, Exceptional, (26)
"Was perfect for our needs. "
Quiet beach escape. Close to DE TURF fields.<br>TAX FREE SHOPPING!
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Outdoor pool

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

10.0 out of 10, Exceptional, (61)
"Great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Fridge, microwave, oven, stovetop

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (65)
"Great space. Cozy fireplace. Well appointed house. Perfect location, we walked everywhere."
Circa 1900 Home in the Heart of Historic Downtown Chestertown
A cottage on the shore of the Delaware River
On the beach

A cottage on the shore of the Delaware River

9.8 out of 10, Exceptional, (59)
"The coziest house we have ever stayed at ! The host went above and beyond to have everything we could need! Would definitely recommend ! "
A cottage on the shore of the Delaware River
Waterfront Home & Dock, sleeps 10 Max. Eastern shore, Betterton Chestertown MD.
Miscellaneous

Waterfront Home & Dock, sleeps 10 Max. Eastern shore, Betterton Chestertown MD.

9.8 out of 10, Exceptional, (87)
"The house and location on Still Pond Maryland was great!! House was clean and tiddy. Caught perch, catfish and bass off their dock!! Area is beautiful and quiet! "
Waterfront Home & Dock, sleeps 10 Max. Eastern shore, Betterton Chestertown MD.
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Exterior

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

10.0 out of 10, Exceptional, (52)
"We had an unforgettable stay at this property! The house and two bungalows exceeded all expectations. The entertainment/living room is massive—one of the largest I’ve ever seen—and offers incredible views of the river from almost every angle. Watching the sunrise and sunset through the large windows was absolutely breathtaking. The kitchen was impressively well-stocked, making meal prep a breeze. There are two dining areas: one table that seats ten and another that seats six, offering...
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

10.0 out of 10, Exceptional, (34)
"Great location, wonderful place and fantastic owner. Recommendations on restaurants and things to do were perfect. We had a great time and Betty Ann was very kind and responsive in communications. Will definitely visit again!"
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
A heated pool

Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!

9.4 out of 10, Exceptional, (33)
"This was the best Christmas yet and on top of that, the home was amazing, great amenities, great view, great time. Thank you to the host! "
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
Family-Friendly Cottage, Walk to the Beach!
Interior

Family-Friendly Cottage, Walk to the Beach!

10.0 out of 10, Exceptional, (18)
"Another amazing stay at Robin’s Rest. Highly recommend for a quiet weekend getaway "
Family-Friendly Cottage, Walk to the Beach!
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 types of properties in Clayton you may be interested in

Bally's Dover Casino Resort
Interior detail

Bally's Dover Casino Resort

4.0 star property
8.8 out of 10, Excellent, (2131)
" Very clean and relaxing."
The price is ￥9,768
￥13,202 total
includes taxes & fees
Jan 19 - Jan 20
Bally's Dover Casino Resort
Comfort Inn & Suites
Lobby

Comfort Inn & Suites

2.5 star property
8.8 out of 10, Excellent, (1000)
"It was decent "
The price is ￥12,749
￥14,151 total
includes taxes & fees
Jan 26 - Jan 27
Comfort Inn & Suites
Microtel Inn & Suites by Wyndham Dover
Exterior

Microtel Inn & Suites by Wyndham Dover

2.0 star property
8.0 out of 10, Very Good, (1001)
"Clean and easy to access"
The price is ￥11,231
￥12,366 total
includes taxes & fees
Jan 26 - Jan 27
Microtel Inn & Suites by Wyndham Dover
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.

Frequently asked questions

Are there vacation rentals in Clayton?

Yes, we offer vacation rentals close to the most popular sights in Clayton, or you can go with a secluded option if you're looking for relaxation.

What are some of the best vacation rentals that Clayton has to offer?

Captain's Quarters: This vacation home rental near Clayton is located near the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Clayton?

While exploring the area, visit family-friendly sights like Frightland, or get outside and enjoy nature at Wheel of Fortune. In the larger area, you’ll find Dover Mall and Delaware State University.

What’s a vacation rental in Clayton like?

Vacation rentals are private properties you can stay in for several days or longer in Clayton. Vacation rentals feature extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for a small group gathering.