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Chesapeake Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Chesapeake holiday rentals

A basketball court surrounded by trees with autumn foliage, a stone staircase, and a metal railing.

1. Completely renovated for you Mountain View Cottage

Completely renovated for you Mountain View Cottage
Charleston
10.0 out of 10, Exceptional, (9 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 AU$313
includes taxes & fees
15 Nov - 16 Nov
Completely renovated for you Mountain View Cottage
A living room with a sofa, coffee table, and chairs. There is a TV on the wall and a plant on the table.

2. Royal Retreat Downtown-Convention Center

Royal Retreat Downtown-Convention Center
Downtown Charleston
8.4 out of 10, Very good, (39 reviews)
"Great spot for needs near the convention center."
United States
randall h.
The price is AU$298
includes taxes & fees
20 Nov - 21 Nov
Royal Retreat Downtown-Convention Center
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a dishwasher.

3. Charming 2-bedroom Bungalow - Close to Everything!

Charming 2-bedroom Bungalow - Close to Everything!
Charleston
9.6 out of 10, Exceptional, (58 reviews)
"Great and easy stay"
United States
Carly R.
The price is AU$264
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom Bungalow - Close to Everything!
A rustic cabin surrounded by dense forest, with a gravel driveway leading to a wooden deck.

4. 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, (44 reviews)
"Amazing place! Great for adults and kids!"
United States
Daniel E.
The price is AU$424
includes taxes & fees
17 Nov - 18 Nov
Rosie's Cabin is an authentic log cabin located just 10 minutes from Charleston.
A cabin interior with a wooden floor, a sofa, a TV, a kitchen area, and a bed with a patterned blanket.

5. RealTree Camo Cabin 2

RealTree Camo Cabin 2
Clendenin
9.2 out of 10, Wonderful, (13 reviews)
"Stayed in cabin #2 for the weekend and it was fantastic. Has all the amenities you need for a relaxing and quiet getaway. Our small dog also had a great time. Great communication from host, very accommodating. You will certainly need 4wd to get up to the site, full size truck or SUV with a little ground clearance."
United States
Gerald M.
The price is AU$169
includes taxes & fees
15 Nov - 16 Nov
RealTree Camo Cabin 2
A rustic cabin with a fire pit and a small wooden structure.

6. Get A Clear Signal Here To Up Above - 100% Secluded Wilderness Cabin Creekside

Get A Clear Signal Here To Up Above - 100% Secluded Wilderness Cabin Creekside
Clendenin
The price is AU$70
includes taxes & fees
12 Dec - 13 Dec
Get A Clear Signal Here To Up Above - 100% Secluded Wilderness Cabin Creekside
A wooden deck with a view of a stream and blooming trees.

7. 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
9.2 out of 10, Wonderful, (24 reviews)
"Great location close to downtown Charleston, big yard, very pet friendly, plenty of parking and the hosts are some of the nicest people you will meet."
United States
Alex C.
The price is AU$338
includes taxes & fees
16 Nov - 17 Nov
Cozy loft in private country setting 5 mins from downtown, Pet Friendly
A wooden deck with a metal table and chairs, overlooking a residential area with trees and houses.

8. Hillview - 3-bedroom house in peaceful Dunbar

Hillview - 3-bedroom house in peaceful Dunbar
Dunbar
10.0 out of 10, Exceptional, (9 reviews)
"Great stay! Definitely will be back"
United States
Todd A.
The price is AU$393
includes taxes & fees
17 Nov - 18 Nov
Hillview - 3-bedroom house in peaceful Dunbar
A house with a dock extending into a lake, a bridge in the background, and a picnic table in the foreground.

9. Cozy River Cottage

Cozy River Cottage
Dunbar
9.6 out of 10, Exceptional, (29 reviews)
"Quaint little cottage. It had everything we needed for our two night stay."
United States
Patricia T.
The price is AU$308
includes taxes & fees
18 Nov - 19 Nov
Cozy River Cottage
On a good night here is where you can enjoy your company and dream big!

10. 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
8.2 out of 10, Very good, (22 reviews)
"I'd definitely stay here again. Price was perfect and awesome for what my needs were. Host was very helpful with great communication."
United States
Anthony
The price is AU$271
includes taxes & fees
15 Nov - 16 Nov
The Boomer: sky, river, and mtn your postage stamp for a week of relaxation!
A hallway with wooden floors and doors, a doormat, and a metal vent.

11. Cozy & Convenient - 20 Minutes to Charleston WV

Cozy & Convenient - 20 Minutes to Charleston WV
Quick
9.2 out of 10, Wonderful, (11 reviews)
"Such a nice place to stay yo get away from it all!!!"
United States
Courtney R.
The price is AU$183
includes taxes & fees
18 Nov - 19 Nov
Cozy & Convenient - 20 Minutes to Charleston WV
A picnic setup with a table and chairs by a lake, surrounded by lush greenery and hills.

12. “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
9.4 out of 10, Exceptional, (8 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 AU$268
includes taxes & fees
15 Nov - 16 Nov
“The Mountain View” is a welcoming apartment with AC in charming Boomer by river
A room with a wooden cabinet, a black-framed door, and a tiled floor.

13. Fun Pit Stop- Rustic Camper- Beautiful View- Easy Access- All The Necessities

Fun Pit Stop- Rustic Camper- Beautiful View- Easy Access- All The Necessities
Clendenin
The price is AU$119
includes taxes & fees
22 Nov - 23 Nov
Fun Pit Stop- Rustic Camper- Beautiful View- Easy Access- All The Necessities
A compact RV interior with a kitchenette, a dining area, and a seating space.

14. Looks Small But It's Big - Convenient Location - 20 Minutes From Interstates

Looks Small But It's Big - Convenient Location - 20 Minutes From Interstates
Clendenin
The price is AU$136
includes taxes & fees
15 Nov - 16 Nov
Looks Small But It's Big - Convenient Location - 20 Minutes From Interstates
A wooden deck with a view of the surrounding landscape.

15. 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, (58 reviews)
"This was a great cabin! Exactly what we needed, was comfortable and relaxing. Bed was comfortable and the location was perfect."
United States
Claire S.
The price is AU$324
includes taxes & fees
17 Nov - 18 Nov
Luxurious cabin, 6 mi HM trails, 12 mi Charleston
A sign for Dutch Ridge Estates LLC Fishing Pond with admission fees and rules.

16. The Best of West Virginia - Beautiful New Camper - Easy Access -Mountain View

The Best of West Virginia - Beautiful New Camper - Easy Access -Mountain View
Clendenin
The price is AU$159
includes taxes & fees
15 Nov - 16 Nov
The Best of West Virginia - Beautiful New Camper - Easy Access -Mountain View
A kitchen with white cabinets, a stainless steel stove, a microwave, and a dishwasher.

17. Walking Distance to Shawnee Soccer Complex

Walking Distance to Shawnee Soccer Complex
Dunbar
9.6 out of 10, Exceptional, (22 reviews)
"Definitely would stay again."
United States
Lisa M.
The price is AU$409
includes taxes & fees
21 Nov - 22 Nov
Walking Distance to Shawnee Soccer Complex
A room with a poster, a television, a sofa with themed cushions, and a decorative rug.

18. Fun Starts Here - Rustic Camper - Hideaway

Fun Starts Here - Rustic Camper - Hideaway
Clendenin
The price is AU$86
includes taxes & fees
18 Nov - 19 Nov
Fun Starts Here - Rustic Camper - Hideaway
A compact room with a bed, wooden cabinets, and a window with blinds.

19. Beautiful, Spacious, Nice & New Camper 16 Miles To WV State Capitol

Beautiful, Spacious, Nice & New Camper 16 Miles To WV State Capitol
Quick
The price is AU$152
includes taxes & fees
1 Dec - 2 Dec
Beautiful, Spacious, Nice & New Camper 16 Miles To WV State Capitol
A lakeside seating area with Adirondack chairs, a table, and a fire pit.

20. River View

River View
Boomer
8.2 out of 10, Very good, (30 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 AU$289
includes taxes & fees
26 Nov - 27 Nov
River View
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

Sleep Inn Charleston North

Sleep Inn Charleston North

10/10 Excellent
"Everything was good. I would stay here again."
mary 1-night trip
Posted less than an hour ago
Sleep Inn Charleston North

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 favourite 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 depend 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 AU$264 per night. Entering your travel dates in the search wizard might find you 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 Memorial Ice Arena, 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.