Cheriton Holiday Rentals

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Holiday Rentals in Cheriton

Modern Suite in Historic Building Two Blocks to Beach
9.8 out of 10, Exceptional, (51)
"Loved the details in this smaller but totally functional property. Host was attentive and helpful and the the room was just off the Main Street in Cape Charles. We lived it. The heated bathroom floor was a sweet bonus!"
Modern Suite in Historic Building Two Blocks to Beach
Private, 7-acre waterfront retreat on Winter Harbor Haven
10.0 out of 10, Exceptional, (113)
"This is a great place to kayak and get away from city noise! You hear only the wildlife, hunting dogs raised by the neighbor, and a few fishing boats. The house is well stocked, a back up of paper supplies such as toilet paper and paper towels would be helpful. We spent the majority of our time on the screened-in porch in the rocking chairs and at the picnic table - amazing! The afternoon sun hits the other side of the house, so you can enjoy the porch all day long! I would agree with a...
Private, 7-acre waterfront retreat on Winter Harbor Haven
Modern Suite in Historic Building Two Blocks to Beach
9.6 out of 10, Exceptional, (38)
"Property was great. Loved the heated floor. There is a coffee maker not a keurig— would bring items for coffee if it’s a must. Could hear some noise from the pub next door but it did not last past 9pm. Clean and located such that you could walk right to the Main Street."
Modern Suite in Historic Building Two Blocks to Beach
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Bay cottage, Beach 100 yards away! RESERVE NOW!!!
9.6 out of 10, Exceptional, (123)
"We enjoyed our first time in Cape Charles and hope to go back to spend more time. This rental is a very charming older home in a neighborhood filled with the same! The home had everything we needed inside and landscaping and w wonderful front porch to enjoy outside. Loved that we could park the car and walk to shops, restaurants and to the beach. Looking forward to another visit."
Bay cottage, Beach 100 yards away! RESERVE NOW!!!
Nassawadox Creek Waterfront Home with Private Pool
10.0 out of 10, Exceptional, (31)
"All girls weekend was a great success. The house was clean and comfortable. Very vintage style. The view was great."
Nassawadox Creek Waterfront Home with Private Pool
The Crows Nest. <br>Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!
9.8 out of 10, Exceptional, (126)
"Nice property. Great location."
The Crows Nest. <br>Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!
Sisters 3 by the Sea, 400 Feet To The Beach
9.4 out of 10, Exceptional, (134)
"Great location- had 3 days of awesome fishing"
The price is NZ$1,129
includes taxes & fees
29 Jun - 30 Jun
Sisters 3 by the Sea, 400 Feet To The Beach
Cute and Cozy Vacation Stay on the Eastern Shore!
8.8 out of 10, Excellent, (52)
"Tv only had one channel and floors were very dirty but I bought mop and cleaned them up not a problem everyone there I spoke to was very nice"
Cute and Cozy Vacation Stay on the Eastern Shore!
The most affordable BEACHFRONT vacation rental in Cape Charles!
9.4 out of 10, Exceptional, (32)
"My sisters, mom and I decided that cape Charles was a half way point to meet for a long weekend. The house was more affordable than others, it had a nice layout with a few places to sit and hang out. Our favorite was the sun room. Furniture is outdated but the space was perfect and we enjoyed our coffee there. The outdoor seating was great as well and we spent a few evenings out there as well . A short walk to town and a short walk to The beach. Parking was fine on the street for all 3 cars....
The most affordable BEACHFRONT vacation rental in Cape Charles!
Welcome to our charming vacation home in the historic district of Cape Charles!
10.0 out of 10, Exceptional, (1)
"We enjoyed our weekend stay in Cape Charles in this charming, quaint, and historic home. It felt like a step back in time, while enjoying modern efficiencies. The grill was convenient and we enjoyed the pool table in the game room. The linens and living areas were clean and the kitchen was well stocked with dishes, utensils, pots, pans, etc. The property manager was pleasant, communicative, and responsive. The only minor suggestions I have would be to have the cleaning crew set a reasonable...
Welcome to our charming vacation home in the historic district of Cape Charles!
Room for the Whole Family or Several Families and Just a Walk to the Beach
9.0 out of 10, Wonderful, (45)
"Great place to stay. Not too far from the beach and very close to a great little town with great shops."
Room for the Whole Family or Several Families and Just a Walk to the Beach
Cape Utopia - sister to existing ID# 7559899
9.6 out of 10, Exceptional, (23)
"We surprised my mom with a trip to Cape Charles. She had never been. so she was delighted. We have stayed at this location before. It is perfect for us. 😊 the house has so much charm and they have thought of everything you could possible need and more. This is our first choice when coming to Cape Charles. See you next trip. 😊"
Cape Utopia - sister to existing ID# 7559899
New Home On Rural Eastern Shore Farm
9.8 out of 10, Exceptional, (73)
"We have a group of senior men here to play golf. Exactly what we need and a great location."
New Home On Rural Eastern Shore Farm
Sea Salt Cottage: Your Tranquil Getaway 3 min to beach
9.8 out of 10, Exceptional, (21)
"My father and I attended my niece's wedding in Cape Charles. We enjoyed our stay and everything was as advertised. Very clean and tidy. I would recommend this house to anyone looking for a nice, clean and quiet place to stay. It is about a mile or so outside of town."
Sea Salt Cottage: Your Tranquil Getaway 3 min to beach
Cozy Cottage - quaint and comfy - 5 blocks to the beach, 1 block to Mason Ave.
10.0 out of 10, Exceptional, (54)
"This was our second time staying at the Cozy Cottage. We enjoyed it just as much as the first time. This house has everything you need. Will look to stay here again in the future!"
Cozy Cottage - quaint and comfy - 5 blocks to the beach, 1 block to Mason Ave.
Cape Haven -Condo 1.5 Blocks from Beach, New Roof Top Deck!
9.8 out of 10, Exceptional, (31)
"Very convenient location and quite close to the beach."
Cape Haven -Condo 1.5 Blocks from Beach, New Roof Top Deck!
Cute bungalow two blocks from the beach.
9.4 out of 10, Exceptional, (79)
"House was very clean on inside but outside needs to be cleaned better. There were spider webs in all the bushes, edges of windows, & mailbox, which is right at front door. TV is not a smart TV & Chrome Cast is not available; it's only a regular TV so was a little disappointed (& the remote had been lost when we arrived. Rental agency wasn't aware of this or only regular TV was available.) Very quiet & nice walk to beach."
Cute bungalow two blocks from the beach.
Game Barn! Next to Central Park! 2 Blocks 2 Beach/Resturants/Shops
10.0 out of 10, Exceptional, (39)
"The houses location to the downtown area and beach were incredible! We rented a golf cart and didn’t have to get back in our car after parking it! The house had everything we could think of and is such a charming place! The fenced yard could not have been better for our doggo and the game barn was perfect for one of the colder days! We will definitely be back!"
Game Barn! Next to Central Park! 2 Blocks 2 Beach/Resturants/Shops
Mid-century modern meets classic cape on the coast.
10.0 out of 10, Exceptional, (2)
"We took a trip to Moon/Mathews County for a short weekend getaway and were not disappointed. Our communication with Rebecca was smooth and she was quick to answer any questions. The home was beyond cozy and charming and we had everything we needed to fully enjoy the property and the weekend. Overall, a perfect experience!"
Mid-century modern meets classic cape on the coast.
Family Rental, Best location to Central Park and beach!
10.0 out of 10, Exceptional, (11)
"This was a great property in a safe neighborhood, just a 5 minute walk to the shops and restaurants in the historic downtown district. House was very clean and inviting, will definitely stay again!"
Family Rental, Best location to Central Park and beach!
Don't see what you're looking for?
See all available properties in Cheriton
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 Cheriton you may be interested in

Shore Stay Suites
2.0 star property
8.4 out of 10, Very good, (468)
"Spacious rooms, full kitchen and clean!"
The price is NZ$205
includes taxes & fees
4 Jun - 5 Jun
Shore Stay Suites
Holiday Inn Express and Suites Exmore, Eastern Shore, an IHG Hotel
2.5 star property
8.4 out of 10, Very good, (627)
"Great experience!"
The price is NZ$225
includes taxes & fees
2 Jun - 3 Jun
Holiday Inn Express and Suites Exmore, Eastern Shore, an IHG Hotel
Hampton Inn & Suites Exmore - Eastern Shore
2.5 star property
8.4 out of 10, Very good, (849)
"Consistent with the other Hampton inns"
The price is NZ$227
includes taxes & fees
31 May - 1 Jun
Hampton Inn & Suites Exmore - Eastern Shore
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cheriton holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cheriton. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Cheriton. Seeing all the best attractions is bound to make you fall in love with Cheriton. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Cheriton short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Cheriton?

Yes, there are holiday rentals close to the most popular sights in Cheriton, 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 Cheriton has to offer?

Private, 7-acre waterfront retreat on Winter Harbor Haven: This holiday home rental outside of Cheriton is located on the waterfront, and has a fireplace, a balcony 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 can I see and do in Cheriton?

While you're exploring the area, Cape Charles Beach and Kiptopeke State Park are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Bay Creek Golf Club and Chesapeake Bay Bridge-Tunnel.

What are holiday rentals like in Cheriton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cheriton. Holiday rentals offer amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for families.

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