Clayton Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Clayton

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, 36 reviews
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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, 20 reviews
"Thoroughly enjoyed our stay! Betty is such a great host. Beautiful area...GREAT sunsets and close to the beach! Very comfortable weekend stay! Also close to some great wineries and Alpaca farms!"
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Wind Song Getaway on the Beach
Property grounds
Wind Song Getaway on the Beach
10.0 out of 10, Exceptional, 14 reviews
"Was the most relaxing vacation ever. The best front porch and great bay views. Loved all the spawning horseshoe crabs! Will definitely come again."
Wind Song Getaway on the Beach
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
Smart TV, fireplace, stereo, computer monitors
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
The price is AU$1,557
includes taxes & fees
6 July - 7 July
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
Rambling Victorian Beach House on Maryland's Eastern Shore
Beach nearby, sun-loungers, beach towels
Rambling Victorian Beach House on Maryland's Eastern Shore
10.0 out of 10, Exceptional, 13 reviews
"Our group of couples + kids enjoyed our getaway to the Eastern Shore. Betterton was a great home base to visit our alma mater, Washington College, in Chestertown. There, we visited the farmers market and waterfront park & playground with the kids. Back in Betterton, the house fit our group well. Plenty of bedrooms, bathrooms and space for each family. The kids & adults enjoyed spending time lounging in the third floor living room. We were pleased that the house had plenty of games, kids toys,...
Rambling Victorian Beach House on Maryland's Eastern Shore
Family-Friendly Cottage, Walk to the Beach!
Property grounds
Family-Friendly Cottage, Walk to the Beach!
10.0 out of 10, Exceptional, 14 reviews
"Great location "
Family-Friendly Cottage, Walk to the Beach!
First Floor Studio Apartment in Historic Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, 60 reviews
"It was a nice room in a nice neighborhood. Only complaint would be the coffee maker was awful."
The price is AU$249
includes taxes & fees
1 July - 2 July
First Floor Studio Apartment in Historic Chestertown
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Fridge, microwave, oven, stovetop
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
9.6 out of 10, Exceptional, 4 reviews
"Tv channels were sparse"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Captain's Quarters
Fridge, microwave, oven, stovetop
Captain's Quarters
9.8 out of 10, Exceptional, 67 reviews
"We had a wonderful time at Sean's house - it was clean, spacious and well equipped. And an easy walk to the beach! Sean was super responsive and helpful."
Captain's Quarters
Chesapeake City Overlook: Breathtaking View!
Property grounds
Chesapeake City Overlook: Breathtaking View!
10.0 out of 10, Exceptional, 5 reviews
"Lovely home and hostess! Very clean and responsive. Beautiful water views. Excellent vacation home"
Chesapeake City Overlook: Breathtaking View!
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
Fridge, microwave, oven, stovetop
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
10.0 out of 10, Exceptional, 3 reviews
"Couldn’t have asked for a better place for us. Lots of room and quiet neighborhood."
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
Beachfront Sunsets on the Water at Oakwood Beach
Property grounds
Beachfront Sunsets on the Water at Oakwood Beach
10.0 out of 10, Exceptional, 19 reviews
"The location was great for us because it was relatively close to Newark, DE and Philadelphia. Water views were great from so much of the house and owners had thought of every possible touch to make people feel at home. There were plenty of outlets, chargers, TVs, tables & chairs, hooks in bathrooms, nightlights, etc. The fridge was free of all sorts of open condiments that are probably supposed to be helpful for guests but that drive my husband crazy as they've taken up half the fridge in the...
Beachfront Sunsets on the Water at Oakwood Beach
Bowers Beach Vacation Rental: 2 Blocks Away!
Beach nearby
Bowers Beach Vacation Rental: 2 Blocks Away!
10.0 out of 10, Exceptional, 1 review
"Great place for us. Appreciate the bottled water dispenser and extra water bottle. Only thing I could say that was negative was the master bed mattress was way too soft and gave my wife and I some neck soreness. All in all we really enjoyed our stay."
Bowers Beach Vacation Rental: 2 Blocks Away!
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
Property grounds
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
9.8 out of 10, Exceptional, 80 reviews
"House was fine. Odd they did not provide sheets. Was difficult for folks who came from far away. But the house was lovely and we enjoyed our time there!!"
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
Pool
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
9.6 out of 10, Exceptional, 155 reviews
"This River property is a little bit of Paradise away from home! It is everything and more as advertised! My husband and I leased the property for 5 nights for a family reunion, ages 1 to 89 years old! My family of 5, my Mom, Dad and Grandmother, my brothers family of 4 and my nieces family of 3. The house was big enough for all of us to be together or everyone could have their own space. We enjoyed the pool, the hot tub, the playground and the sunsets across the river were amazing. My...
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
Private pier and pool at this waterfront Chestertown home
Aerial view
Private pier and pool at this waterfront Chestertown home
9.8 out of 10, Exceptional, 22 reviews
"We stayed at Peir Pleaseure for Washington college homecoming weekend. We had a BBQ by the pool for our son and his friends. We enjoyed the views of the Chester Riiver from the pier. The house was clean and easiliy accomodates 2 families ."
Private pier and pool at this waterfront Chestertown home
Home away from home
Interior
Home away from home
7.6 out of 10, Good, 5 reviews
"Nice place to stay for quick weekend. Close to everything."
Home away from home
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, 53 reviews
"Good location. House well stocked. Great pool. Short hike to river. Lots of kayaks ,a canoe and paddle boards"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
BEACH WITHOUT THE BUSTLE
Beach nearby, sun-loungers, beach towels
BEACH WITHOUT THE BUSTLE
10.0 out of 10, Exceptional, 22 reviews
"The condo was nicely decorated and comfortable, Except for the bunkbeds. The bunkbeds are probably great for kids, but we had an adult sleeping in one of them and, Despite the wider width, The mattress was not comfortable for a heavier body. A massive amount of little bugs made sitting outside in the dark Difficult. Kitchen was very well equipped and bathrooms Were lovely. There is not much around Betterton Beach, except the beach, which is on the river. The compound had a pool, but it was not...
BEACH WITHOUT THE BUSTLE
Blue Room in Delaware
1 bedroom, iron/ironing board, Internet
Blue Room in Delaware
8.0 out of 10, Very good, 1 review
"If you are looking for just a room at a reasonable price, this is for you. The bathroom is very tiny and in need of a remodel. The bedroom and bath were both very clean. The bed was comfortable, but the pullout single bed is not at all. Most pullouts aren’t, but this goes to a new level. This unit was fine for myself for a couple of nites because I was looking for an inexpensive option. But when my 15 yr old son spent the last nite there with me, I got the pullout which was not good at all. I...
Blue Room in Delaware
Don't see what you're looking for?
See all available properties in Clayton
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.

Other types of properties in Clayton you may be interested in

Bally's Dover Casino Resort
Front of property
Bally's Dover Casino Resort
4.0 star property
8.6 out of 10, Excellent, 1,400 reviews
"Great stay!"
The price is AU$134
includes taxes & fees
2 July - 3 July
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, 1,002 reviews
"Excellent staff and clean room, wish it had ice machine but everything was great!"
The price is AU$146
includes taxes & fees
23 June - 24 June
Microtel Inn & Suites by Wyndham Dover
Red Roof Inn & Suites Dover Downtown
Exterior
Red Roof Inn & Suites Dover Downtown
2.5 star property
7.4 out of 10, Good, 1,002 reviews
"This was a very clean and comfortable place to stay. Extra bonus that they do not charge for pets. Staff was friendly and helpful. I would definitely recommend this place "
The price is AU$133
includes taxes & fees
23 June - 24 June
Red Roof Inn & Suites Dover Downtown
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?

Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf: This holiday home rental outside of Clayton is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

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.

Recent reviews of Clayton properties
Expedia verified reviews

Wyndham Garden Dover

Wyndham Garden Dover

5/5 Excellent
"I stay at this place every time. Love it."
A verified traveller stayed at Wyndham Garden Dover
Posted 1 day ago
Wyndham Garden Dover