Holiday Rentals in Chesapeake

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Holiday Rentals in Chesapeake

Secluded Ohio Forest Escape at Fuller's Fifty

Patriot
10.0 out of 10, Exceptional, (78)
"It was a perfect spot for a quick getaway! "
United States
Patricia
The price is €159
includes taxes & fees
8 Dec - 9 Dec
Secluded Ohio Forest Escape at Fuller's Fifty

The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.

Catlettsburg
10.0 out of 10, Exceptional, (119)
"It was jus what we needed for our fishing trip plenty of parking and peaceful close to everything as well will stay again next year "
United States
Josh P.
The price is €190
includes taxes & fees
1 Dec - 2 Dec
The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.

The Market Place by Nest and Bloom <br>Suite 4 (5045)

Ashland
10.0 out of 10, Exceptional, (2)
"Amazing place for a stay. The beds are comfortable, everything is fully stocked, and it all felt like home. Would recommend to anyone traveling through the area. Can't wait to return!"
United States
t g.
The price is €264
includes taxes & fees
1 Dec - 2 Dec
The Market Place by Nest and Bloom <br>Suite 4 (5045)

Historic & Chic apartment by Arena, University, Hospital - Dog Friendly

Huntington
9.6 out of 10, Exceptional, (4)
"Comfortable convenient to everything. It was a home away from home."
United States
Kimberly M.
The price is €274
includes taxes & fees
26 Dec - 27 Dec
Historic & Chic apartment by Arena, University, Hospital - Dog Friendly

Charming 2-bedroom house located in beautiful wooded setting!

Raceland
10.0 out of 10, Exceptional, (5)
"Throughly enjoyed our stay at the home! It was very accommodating and comfortable. And very convenient for our local family to visit."
United States
Doug & Sandra N.
The price is €176
includes taxes & fees
1 Dec - 2 Dec
Charming 2-bedroom house located in beautiful wooded setting!

Cozy 2-bedroom apartment located next to St. Mary's Hospital!

Huntington
10.0 out of 10, Exceptional, (11)
"Great place, clean cozy love the 2 bathrooms!!"
United States
Katherine D.
The price is €188
includes taxes & fees
1 Dec - 2 Dec
Cozy 2-bedroom apartment located next to St. Mary's Hospital!

Carroll Manor: RecentlyRenovated English Tutor. Sleeps 8

Ashland
9.8 out of 10, Exceptional, (11)
"Beautiful house with all of the accommodations to make us comfortable for our stay!"
United States
Darrin I.
The price is €323
includes taxes & fees
11 Dec - 12 Dec
Carroll Manor: RecentlyRenovated English Tutor. Sleeps 8

Pointer Palace

South Point
10.0 out of 10, Exceptional, (4)
"An excellent place to stay. Clean, comfortable, in a safe feeling neighborhood. Probably the most thoughtfully appointed VRBO I've ever stayed in. "
United States
Jon W.
The price is €159
includes taxes & fees
1 Dec - 2 Dec
Pointer Palace

The Eagle's Nest:5 bed 3BathBeautiful Craftsman Home

Ashland
9.8 out of 10, Exceptional, (22)
"A great property; warm, cozy and accommodating. "
United States
Kevin C.
The price is €323
includes taxes & fees
1 Dec - 2 Dec
The Eagle's Nest:5 bed 3BathBeautiful Craftsman Home

Relaxing 2 bdrm retreat. Mountain View w hottub & ATV option 5th night free

Crown City
9.8 out of 10, Exceptional, (26)
"This is the 2nd time we’ve stayed here and we love it! What a beautiful and peaceful place to stay. Feels like our own little world when we’re there. We definitely didn’t want to leave. We will be back! Everything was perfect.. Awesome place! "
United States
chris p.
The price is €330
includes taxes & fees
7 Dec - 8 Dec
Relaxing 2 bdrm retreat. Mountain View w hottub & ATV option 5th night free

Riverside Cabin with Homemade Breakfast

Gallipolis
9.8 out of 10, Exceptional, (41)
"The property was in excellent condition facilities and beds were absolutely perfect the view over the river was spectacular the breakfast was delicious "
United States
Samuel H.
The price is €158
includes taxes & fees
4 Dec - 5 Dec
Riverside Cabin with Homemade Breakfast

4-bedroom vacation home short drive to Huntington Mall, Marshall, & St. Mary’s

3.0 star property
Ona
8.4 out of 10, Very good, (7)
"Great place to stay!"
United States
Sharon B.
The price is €402
includes taxes & fees
18 Dec - 19 Dec
4-bedroom vacation home short drive to Huntington Mall, Marshall, & St. Mary’s

The Bunkhouse

Crown City
10.0 out of 10, Exceptional, (28)
"Great place! Quiet and peaceful lots of wildlife. Very relaxing weekend."
United States
Shelley R.
The price is €188
includes taxes & fees
7 Dec - 8 Dec
The Bunkhouse

Corner Cottage 2 bedroom pets welcome and close to downtown

Ashland
9.0 out of 10, Wonderful, (2)
"Very quiet, clean, nice house "
United States
Karen S.
The price is €233
includes taxes & fees
7 Dec - 8 Dec
Corner Cottage 2 bedroom pets welcome and close to downtown

Cozy Fonzie Flat

Ashland
10.0 out of 10, Exceptional, (1)
"It was a very pleasant stay, it was well maintained and clean. The property manager answered my questions quickly and efficiently,also was very professional. As a Veteran it was nice to have a place that accepts pets. "
United States
James F.
The price is €254
includes taxes & fees
2 Dec - 3 Dec
Cozy Fonzie Flat

2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.

Kenova
10.0 out of 10, Exceptional, (29)
"Love the property and the way it was made up nice and clean comfortable and just far enough away from everything to be peaceful"
United States
Wanda W.
The price is €166
includes taxes & fees
1 Dec - 2 Dec
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.

Huntington Modern History - 4BR MU, DT, St Marys

Huntington
10.0 out of 10, Exceptional, (5)
"Great house – everything is clean and new."
United States
JonathanK
The price is €416
includes taxes & fees
3 Dec - 4 Dec
Huntington Modern History - 4BR MU, DT, St Marys

Cozy With A Little Touch of Love

Huntington
7.8 out of 10, Good, (6)
"I liked the homely feeling even though i am front out of town. The street was a bit narrow with limited parking."
United States
Nate
The price is €414
includes taxes & fees
7 Dec - 8 Dec
Cozy With A Little Touch of Love

Rush Creek Camp, Lot # 03

Rush
The price is €72
includes taxes & fees
1 Dec - 2 Dec
Rush Creek Camp, Lot # 03

THE LUXURY CABIN IN THE WOODS

Catlettsburg
10.0 out of 10, Exceptional, (217)
"Great property with good catch and release fishing, would stay at again."
United States
Dave S.
The price is €300
includes taxes & fees
22 Dec - 23 Dec
THE LUXURY CABIN IN THE WOODS
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 Chesapeake Hotel Reviews

Find out more about Chesapeake

Everything you need to know about Chesapeake holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Chesapeake holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesapeake holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesapeake. 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 Chesapeake holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake holiday rentals we have selected for you start as low as €158 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesapeake rentals

At Expedia, we put the best Chesapeake holiday 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 Chesapeake 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 Chesapeake holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake. 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

Can I find a holiday rental in Chesapeake?

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

The Eagle's Nest:5 bed 3BathBeautiful Craftsman Home: This holiday home rental outside of Chesapeake offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You can relax into your holiday with a garden and a selection of books.

What can I see and do in Chesapeake?

Explore the area and family-friendly sights such as Camden Park Amusement Park, or get out into nature at a spot like Ohio River Valley. In the wider area, you’ll find Mountain Health Arena and Pullman Square.

What are holiday rentals like in Chesapeake?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesapeake. Holiday rentals offer amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family getaway.