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Chesapeake Holiday Rentals

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Our top choices for Chesapeake holiday rentals

RealTree Camo Cabin 2

RealTree Camo Cabin 2
Clendenin
9.0 out of 10, Wonderful, (9 reviews)
"Our host , Liz was very welcoming, Nice clean cabin. Cute little camp ground. Wood for firepit, was provided also free wifi and fully set up kitchen , full bath with water on the mand water heater, multiple space heaters, extra pillows and blankets. Loved our stay. "
United States
Bela M.
The price is NZ$210
includes taxes & fees
19 July - 20 July
RealTree Camo Cabin 2

The Boomer: sky, river, and mtn your postage stamp for a week of relaxation!

The Boomer: sky, river, and mtn your postage stamp for a week of relaxation!
Boomer
8.0 out of 10, Very good, (16 reviews)
"A dated traditional property but clean and tidy."
United Kingdom
Paul
The price is NZ$287
includes taxes & fees
20 July - 21 July
The Boomer: sky, river, and mtn your postage stamp for a week of relaxation!

Ivy Branch Cottage - Danville

Ivy Branch Cottage - Danville
Danville
9.8 out of 10, Exceptional, (14 reviews)
"Nice, small very livable home. Close to everything shopping , dining etc"
Singapore
Shirley F.
The price is NZ$542
includes taxes & fees
16 July - 17 July
Ivy Branch Cottage - Danville

Rosie's Cabin is an authentic log cabin located just 10 minutes from Charleston.

Rosie's Cabin is an authentic log cabin located just 10 minutes from Charleston.
South Charleston
10.0 out of 10, Exceptional, (35 reviews)
"We had a great time, definitely will be staying again"
United States
Tara M.
The price is NZ$521
includes taxes & fees
16 July - 17 July
Rosie's Cabin is an authentic log cabin located just 10 minutes from Charleston.

Luxurious cabin, 6 mi HM trails, 12 mi Charleston

Luxurious cabin, 6 mi HM trails, 12 mi Charleston
Alum Creek
10.0 out of 10, Exceptional, (48 reviews)
"Great location and had everything we needed. "
United States
Noah B.
The price is NZ$395
includes taxes & fees
20 July - 21 July
Luxurious cabin, 6 mi HM trails, 12 mi Charleston

Completely renovated for you Mountain View Cottage

Completely renovated for you Mountain View Cottage
Charleston
10.0 out of 10, Exceptional, (4 reviews)
"It was a great stay, host even stocked the fridge with fresh fruit and water. House was very clean and had a great location. Secluded yet close to downtown."
United States
Bryan S.
The price is NZ$360
includes taxes & fees
19 July - 20 July
Completely renovated for you Mountain View Cottage

Charming 2-bedroom Bungalow - Close to Everything!

Charming 2-bedroom Bungalow - Close to Everything!
Charleston
9.6 out of 10, Exceptional, (44 reviews)
"Very clean, quiet and comfortable.I would definitely stay there again. It's close to shopping, gas, food and easily accessible from the highway. "
United States
Elvira
The price is NZ$332
includes taxes & fees
19 July - 20 July
Charming 2-bedroom Bungalow - Close to Everything!

Cozy River Cottage

Cozy River Cottage
Dunbar
9.8 out of 10, Exceptional, (22 reviews)
"Very clean, comfortable cottage on the river. Small, but fine for 1-2 people. Convenient to shopping. Would stay here again."
United States
Liz J.
The price is NZ$352
includes taxes & fees
19 July - 20 July
Cozy River Cottage

Charming Apartment in CrossLanes

Charming Apartment in CrossLanes
Charleston
9.8 out of 10, Exceptional, (14 reviews)
"The cleanliness of this apartment was top-notch! It was well equipped with everything to make our stay comfortable and convenient. It is in a very quiet area, yet conveniently located to stores and restaurants. "
United States
Stacey B.
The price is NZ$283
includes taxes & fees
20 July - 21 July
Charming Apartment in CrossLanes

Remote Mountain A-Frame with BBQ Perfect for Nature Lovers in West Virginia

Remote Mountain A-Frame with BBQ Perfect for Nature Lovers in West Virginia
Charleston
The price is NZ$235
includes taxes & fees
16 July - 17 July
Remote Mountain A-Frame with BBQ Perfect for Nature Lovers in West Virginia

Hiding Place is near Montgomery colleges, hospital, NRG, & trails

Hiding Place is near Montgomery colleges, hospital, NRG, & trails
Montgomery
8.8 out of 10, Excellent, (10 reviews)
"We loved this place!"
United States
Megan
The price is NZ$307
includes taxes & fees
29 July - 30 July
Hiding Place is near Montgomery colleges, hospital, NRG, & trails

Walking Distance to Shawnee Soccer Complex

Walking Distance to Shawnee Soccer Complex
Dunbar
9.8 out of 10, Exceptional, (18 reviews)
"Very clean and comfortable "
United States
Kyle D.
The price is NZ$498
includes taxes & fees
16 July - 17 July
Walking Distance to Shawnee Soccer Complex

River View

River View
Boomer
8.4 out of 10, Very good, (26 reviews)
"It was a great stay! Thank you so much! It was a great spot to rest our heads!!"
United States
Stephanie F.
The price is NZ$335
includes taxes & fees
16 July - 17 July
River View

Cozy & Convenient - 20 Minutes to Charleston WV

Cozy & Convenient - 20 Minutes to Charleston WV
Quick
9.2 out of 10, Wonderful, (9 reviews)
"Great stay. Just remember to get the WiFi name and password. You will need it, phone service is a bit sketchy."
United States
Meredith H.
The price is NZ$277
includes taxes & fees
19 July - 20 July
Cozy & Convenient - 20 Minutes to Charleston WV

Royal Retreat Downtown-Convention Center

Royal Retreat Downtown-Convention Center
Downtown Charleston
8.4 out of 10, Very good, (37 reviews)
"Check in was easy. The townhouse was perfect for our stay. It is in a great location, close to everything downtown. "
United States
Kelly M.
The price is NZ$358
includes taxes & fees
26 July - 27 July
Royal Retreat Downtown-Convention Center

“The Mountain View” is a welcoming apartment with AC in charming Boomer by river

“The Mountain View” is a welcoming apartment with AC in charming Boomer by river
Boomer
9.6 out of 10, Exceptional, (5 reviews)
"This was a perfect spot 30 min from the NRG. The hosts were very active in responding. The spot was easy to find and close to some WV must stops like Tudors! We had our pup with us and she had the best time!"
United States
Nicole P.
The price is NZ$322
includes taxes & fees
16 July - 17 July
“The Mountain View” is a welcoming apartment with AC in charming Boomer by river

Cozy loft in private country setting 5 mins from downtown, Pet Friendly

Cozy loft in private country setting 5 mins from downtown, Pet Friendly
Charleston
9.0 out of 10, Wonderful, (22 reviews)
"A welcoming and comfortable place after a long drive!"
United States
Juliet K.
The price is NZ$339
includes taxes & fees
20 July - 21 July
Cozy loft in private country setting 5 mins from downtown, Pet Friendly

Royal Retreat Townhouse 2

Royal Retreat Townhouse 2
St Albans
6.4 out of 10, (31 reviews)
"Very nice place. Very spacious."
United States
Tara S.
The price is NZ$307
includes taxes & fees
20 July - 21 July
Royal Retreat Townhouse 2
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, 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 NZ$210 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?

Luxurious getaway Home: This holiday home rental outside of Chesapeake offers a balcony, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What’s there to see and do in Chesapeake?

Explore the area and family-friendly sights such as Jefferson Park, or get out into nature at a spot like Kanawha State Forest. University of Charleston and West Virginia State Capitol Building are a couple of places you'll find in the wider area.

What’s a holiday rental in Chesapeake like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesapeake. Holiday rentals provide amenities like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for families.