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Clayton Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Clayton holiday rentals

A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

1. Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is HK$533
HK$981 total
includes taxes & fees
28 Oct - 29 Oct
Guest Suite for up to 2 in a Victorian on the Chester River
A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

2. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Dover
10.0 out of 10, Exceptional, (12 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is HK$941
HK$1,462 total
includes taxes & fees
2 Nov - 3 Nov
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A riverside dock with boats, a covered seating area, and a bridge in the background.

3. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (31 reviews)
"Cute place. Clean, comfortable, and convenient to the soccer complex. I wasn’t familiar with Chesapeake City but we had a great time at the waterfront restaurants."
United States
John P.
The price is HK$1,059
HK$2,444 total
includes taxes & fees
27 Oct - 28 Oct
Historic Chesapeake City Stay
A wooden cabin with a porch, surrounded by dense forest.

4. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (52 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is HK$549
HK$873 total
includes taxes & fees
2 Nov - 3 Nov
Country Get Away Studio Apartment
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

5. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (130 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is HK$776
HK$1,246 total
includes taxes & fees
2 Nov - 3 Nov
First Floor Studio Apartment in Historic Chestertown
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

6. 5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover

5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Host was great"
United States
mark o.
The price is HK$1,874
HK$4,853 total
includes taxes & fees
2 Nov - 3 Nov
5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
A bedroom with a bunk bed, a single bed, a desk, and a chair.

7. Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Frederica
9.6 out of 10, Exceptional, (25 reviews)
"We enjoy this place!!!"
United States
nahum f.
The price is HK$549
HK$1,483 total
includes taxes & fees
27 Oct - 28 Oct
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

8. Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Bear
9.8 out of 10, Exceptional, (7 reviews)
"The host was great and easy to communicate with. It was a first time experience staying on a boat for my family and I and we really enjoyed it. Perfect for a few nights to visit family nearby."
United States
Jessica
The price is HK$1,961
HK$2,331 total
includes taxes & fees
29 Oct - 30 Oct
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
A garden with a wooden bridge, lush greenery, and a variety of plants.

9. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is HK$1,440
HK$2,149 total
includes taxes & fees
27 Oct - 28 Oct
Secluded Cottage in Middle of Chestertown
A wooden deck with outdoor furniture, a small shed, and a view of a body of water.

10. Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
Chesapeake City
9.4 out of 10, Exceptional, (6 reviews)
"Everything was as advertised. Property is not new, but everything was clean and well cared for. Evenings on the water were peaceful and relaxing. We enjoyed our stay and definitely intend to return."
United States
John
The price is HK$1,129
HK$2,286 total
includes taxes & fees
5 Nov - 6 Nov
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
A covered deck area with a grill and outdoor seating.

11. Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
The price is HK$1,482
HK$1,831 total
includes taxes & fees
27 Oct - 28 Oct
Nature's Haven Tiny Home
A two-story residential building with a stone facade, a large front lawn, and a driveway.

12. Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful well kept property with lots of room to relax."
United States
Daniel J.
The price is HK$1,976
HK$2,763 total
includes taxes & fees
27 Oct - 28 Oct
Elegant Family Stay • Quiet Neighborhood • Comfort
A modern kitchen with a large island, bar stools, and pendant lighting.

13. Spacious 5 Bedroom w/Pool, Patio and Theater

Spacious 5 Bedroom w/Pool, Patio and Theater
Magnolia
9.2 out of 10, Wonderful, (12 reviews)
"The host was very accommodating and the house was excellent and served our needs perfectly."
United States
John K.
The price is HK$1,885
HK$5,106 total
includes taxes & fees
27 Oct - 28 Oct
Spacious 5 Bedroom w/Pool, Patio and Theater
Terrace/patio

14. Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (2 reviews)
"This was a stop over on our way to the beach- it was a convenient comfy space for our family."
United States
Erin C.
The price is HK$1,482
HK$2,081 total
includes taxes & fees
27 Oct - 28 Oct
Tiny Home Tranquil Oasis
A round window with a view of a garden, a tree, and a building in the background.

15. Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5

Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
Kitts Hummock
10.0 out of 10, Exceptional, (1 review)
"Our time here was an attraction in itself. There were so many small details. I won't mention all of them as I don't want to spoil the surprise but one of our favorites was a telescope pointed towards an ocean piling where birds frequently perch. The house felt interactive and playful. There were snacks and beverage options (including tea, coffee, water, and even other surprises) available. Very clean. One consideration is the stairscase. I would advise caution for those with mobility issues (bad...
United States
Alex L.
The price is HK$1,708
HK$3,016 total
includes taxes & fees
27 Oct - 28 Oct
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
Beach/ocean view

16. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is HK$2,852
HK$3,023 total
includes taxes & fees
27 Oct - 28 Oct
Bohemia Manor Farm
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

17. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
The price is HK$1,365
HK$1,679 total
includes taxes & fees
9 Nov - 10 Nov
Beachcomber Suite
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

18. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is HK$1,553
HK$2,236 total
includes taxes & fees
1 Nov - 2 Nov
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A spacious living area with a dining table, sofa, and a kitchen in the background.

19. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is HK$1,765
HK$2,770 total
includes taxes & fees
27 Oct - 28 Oct
Newly restored apartment in the heart of Chestertown
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

20. Turtle Cove Room

Turtle Cove Room
Kent County
The price is HK$1,270
HK$1,576 total
includes taxes & fees
2 Nov - 3 Nov
Turtle Cove Room
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

Sleep Inn & Suites Dover University Area

Sleep Inn & Suites Dover University Area

8/10 Good
"Staff was very friendly. Comfortable beds! Loved the grab-and-go breakfast bags! They didn’t skip on the offerings and my kids liked taking them back to the room for breakfast in bed!"
Amy 1-night trip
Posted 4 hours ago
Sleep Inn & Suites Dover University Area

Find out more about Clayton

Search for holiday rentals in Clayton on Expedia! You can easily find your home rentals, villas, holiday apartments in Clayton using one of the methods below:

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Look no further and take a look at our great range of rental properties in Clayton!

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?

Captain's Quarters: This holiday home rental outside of Clayton is located near the beach, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 Woodland Beach. 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.