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Clayton Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Clayton vacation rentals

A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

1. 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 CA $170
CA $266 total
includes taxes & fees
Oct 27 - Oct 28
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

2. 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, (29 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is CA $96
CA $177 total
includes taxes & fees
Oct 28 - Oct 29
Guest Suite for up to 2 in a Victorian on the Chester River
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, (30 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."
United States
Martha J.
The price is CA $153
CA $400 total
includes taxes & fees
Oct 28 - Oct 29
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, (50 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is CA $99
CA $157 total
includes taxes & fees
Oct 26 - Oct 27
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 CA $140
CA $225 total
includes taxes & fees
Oct 20 - Oct 21
First Floor Studio Apartment in Historic Chestertown
A bedroom with a bunk bed, a single bed, a desk, and a chair.

6. 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 CA $113
CA $282 total
includes taxes & fees
Nov 17 - Nov 18
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

7. 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 CA $338
CA $763 total
includes taxes & fees
Oct 30 - Oct 31
5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
A bedroom with a single bed, a wooden wardrobe, and a ceiling light.

8. 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 CA $217
CA $435 total
includes taxes & fees
Nov 5 - Nov 6
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
A round window with a view of a garden, a tree, and a building in the background.

9. 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 CA $308
CA $544 total
includes taxes & fees
Oct 25 - Oct 26
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
A covered deck area with a grill and outdoor seating.

10. 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 CA $267
CA $329 total
includes taxes & fees
Oct 19 - Oct 20
Nature's Haven Tiny Home
A modern kitchen with a large island, bar stools, and pendant lighting.

11. 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 CA $364
CA $962 total
includes taxes & fees
Oct 18 - Oct 19
Spacious 5 Bedroom w/Pool, Patio and Theater
A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

12. 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, (6 reviews)
"My boyfriend and I had a fantastic night on the yacht. We arrived right on time and found the AC and the lights on and ready for our arrival. I sunbathed on the front of the yacht and danced on the back after dinner at Grain H2O. The restaurant is located at the top of the hill on the marina . There was a band and we could hear the music from the boat. The marina was clean and everyone is friendly. At night it was very peaceful and easy to fall asleep. The morning we enjoyed our last couple of...
United States
Karen
The price is CA $354
CA $420 total
includes taxes & fees
Oct 23 - Oct 24
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

13. 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 CA $247
CA $302 total
includes taxes & fees
Oct 19 - Oct 20
Beachcomber Suite
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

14. 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 CA $260
CA $392 total
includes taxes & fees
Oct 28 - Oct 29
Secluded Cottage in Middle of Chestertown
A two-story residential building with a stone facade, a large front lawn, and a driveway.

15. 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 CA $356
CA $504 total
includes taxes & fees
Oct 26 - Oct 27
Elegant Family Stay • Quiet Neighborhood • Comfort
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

16. Turtle Cove Room

Turtle Cove Room
Kent County
The price is CA $230
CA $282 total
includes taxes & fees
Oct 19 - Oct 20
Turtle Cove Room
Terrace/patio

17. 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 CA $267
CA $375 total
includes taxes & fees
Oct 26 - Oct 27
Tiny Home Tranquil Oasis
A bunk bed room with white bedding and blue throw blankets.

18. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is CA $444
CA $471 total
includes taxes & fees
Oct 20 - Oct 21
Bohemia Manor Farm
A deck with outdoor furniture, a potted plant, and a house in the background.

19. 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 CA $311
CA $442 total
includes taxes & fees
Oct 28 - Oct 29
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.

20. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (33 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 CA $318
CA $495 total
includes taxes & fees
Oct 18 - Oct 19
Newly restored apartment in the heart of Chestertown
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

Hampton Inn Middletown

Hampton Inn Middletown

10/10 Excellent
"The room was clean and comfortable, and the staff was friendly. Breakfast was great"
Vincent 2-night trip
Posted 10 hours ago
Hampton Inn Middletown

Find out more about Clayton

Everything you need to know about Clayton vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Clayton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Clayton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Clayton vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Clayton. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Clayton vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Clayton vacation rentals we have selected for you start as low as CA $157 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Clayton rentals

At Expedia, we put the best Clayton vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Clayton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Clayton vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Clayton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 Woodland Beach. 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.