Clayton Holiday Rentals

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Holiday Rentals in Clayton

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
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
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
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, (28)
"This house exceeded our expectations! From the pictures, we knew it would be beautiful, but once we got there it seemed so much bigger and brighter than what the pictures show. Its so light and airy and was perfect for what we came for. It was VERY clean, each bedroom came with towels and makeup wipes. You can tell the hosts put a lot of thought into this home. We went in the fall, but was still such a wonderful time walking along the quiet beach and having drinks on the patio. Would highly...
Beachfront Sunsets on the Water at Oakwood Beach
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"
The price is HK$2,331
HK$3,945 total
includes taxes & fees
28 Dec - 29 Dec
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
BEACH WITHOUT THE BUSTLE
Beach nearby, sun-loungers, beach towels

BEACH WITHOUT THE BUSTLE

10.0 out of 10, Exceptional, (26)
"We enjoyed our stay. Condo was comfortable and very clean. It provided convenient access for our weekend plans in Kennedyville and Chestertown."
BEACH WITHOUT THE BUSTLE
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
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
Aerial view

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

10.0 out of 10, Exceptional, (15)
"We had an awesome wknd at this property. Everything was great. There were a few minor things but they did not impact our stay at all. Would stay again when in the area visiting family. "
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
Country Get Away 1 Bedroom Apartment
Property grounds

Country Get Away 1 Bedroom Apartment

9.8 out of 10, Exceptional, (29)
"We were attending my niece's wedding. Our stay was located in the beautiful countryside yet quick access to places to eat. Our apartment was decorated so cute and for the season. Very, Very clean and I would stay again!"
The price is HK$544
HK$864 total
includes taxes & fees
15 Jan - 16 Jan 2025
Country Get Away 1 Bedroom Apartment
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
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
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!
Waterfront Home & Dock, sleeps 8 Max. Eastern shore, Betterton Chestertown MD.
Miscellaneous

Waterfront Home & Dock, sleeps 8 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 8 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, (32)
"We had a great time in the pool, fishing off dock, paddle boarding, kayaking and swimming. The kids (5 under 8) loved playing in the bAsement."
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!
House casino
Exterior

House casino

House casino
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, (2051)
"Lovely king room. I appreciated the large desk as it provided a great work space and the room itself was large and comfortable."
The price is HK$482
HK$652 total
includes taxes & fees
20 Jan - 21 Jan 2025
Bally's Dover Casino Resort
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 HK$555
HK$611 total
includes taxes & fees
1 Jan - 2 Jan 2025
Microtel Inn & Suites by Wyndham Dover
Comfort Inn & Suites
Lobby

Comfort Inn & Suites

2.5 star property
8.8 out of 10, Excellent, (1000)
"The front desk employee was very welcoming, and provided excellent customer service"
The price is HK$631
HK$701 total
includes taxes & fees
5 Jan - 6 Jan 2025
Comfort Inn & Suites
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 holiday rentals in Clayton?

Yes, there are holiday rentals close to the most popular sights in Clayton, or you can select a more secluded option if you're looking for a relaxing stay.

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

Beachfront Sunsets on the Water at Oakwood Beach: This holiday home rental outside of Clayton is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Clayton?

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

What’s a holiday rental in Clayton like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Clayton. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a family trip or a small group gathering.