Chesapeake Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Chesapeake

Kanawha River Mountain House

The price is AU$1,322
includes taxes & fees
14 July - 15 July
Kanawha River Mountain House

Spacious 4-bedroom house in Charlton Heights with hottub & game room

2.0 star property
10.0 out of 10, Exceptional, (6)
"We had a great time. Would highly recommend."
The price is AU$765
includes taxes & fees
13 July - 14 July
Spacious 4-bedroom house in Charlton Heights with hottub & game room

Budget Spacious townhome with Gigabit Internet

10.0 out of 10, Exceptional, (3)
"Very clean house, love the beautiful scenery. Perfect vaca house thank you 😊"
The price is AU$437
includes taxes & fees
12 July - 13 July
Budget Spacious townhome with Gigabit Internet

Large Updated 3 bedroom Townhome w/ mountain view nearby Kanawha river

The price is AU$492
includes taxes & fees
21 July - 22 July
Large Updated 3 bedroom Townhome w/ mountain view nearby Kanawha river

Kanawha River House Get Away with Hot Tub

8.8 out of 10, Excellent, (15)
"Nine family members had a ball playing pool, foosball with mountain and river views."
The price is AU$953
includes taxes & fees
13 July - 14 July
Kanawha River House Get Away with Hot Tub

Charming Riverfront Escape – Cozy Fire Pit, Stunning Gorge & Hidden Falls

10.0 out of 10, Exceptional, (2)
"We loved Deepwater. The house was very clean and fully updated. The host was terrific. She was very easy to work with and communicated with us throughout our stay. "
The price is AU$900
includes taxes & fees
6 Aug - 7 Aug
Charming Riverfront Escape – Cozy Fire Pit, Stunning Gorge & Hidden Falls

River View

8.0 out of 10, Very good, (19)
"Was very nice, "
The price is AU$310
includes taxes & fees
5 Aug - 6 Aug
River View

Cozy & Convenient - 20 Minutes to Charleston WV

9.0 out of 10, Wonderful, (4)
"Really enjoyed our stay! We were impressed with how clean the dwelling was. Host was super friendly and helpful. Looking forward to staying here again in the future!"
The price is AU$228
includes taxes & fees
14 July - 15 July
Cozy & Convenient - 20 Minutes to Charleston WV

Royal Retreat Downtown-Convention Center

8.8 out of 10, Excellent, (21)
"Good location "
The price is AU$345
includes taxes & fees
11 July - 12 July
Royal Retreat Downtown-Convention Center

Charming 2-bedroom Bungalow - Close to Everything!

9.6 out of 10, Exceptional, (18)
"It’s was so cozy and alll amenities that are needed were available I really enjoyed my stay I’m trying to book again week later "
The price is AU$286
includes taxes & fees
20 July - 21 July
Charming 2-bedroom Bungalow - Close to Everything!

Cozy River Cottage

2.0 star property
10.0 out of 10, Exceptional, (8)
"Great stay and good proximity"
The price is AU$317
includes taxes & fees
15 July - 16 July
Cozy River Cottage

Home in South Charleston, WV

10.0 out of 10, Exceptional, (3)
"You will love it here!! Property, property owners, communication, just the entire energy of this home is 5 STARS!!! Thanks for having us, we WILL be back in the future! Do yourself a favor if you're considering staying here.. press that book now button!!!"
The price is AU$312
includes taxes & fees
11 July - 12 July
Home in South Charleston, WV

Walking Distance to Shawnee Soccer Complex

9.6 out of 10, Exceptional, (9)
"Very close to resturants and easy walk into the fields."
The price is AU$449
includes taxes & fees
20 July - 21 July
Walking Distance to Shawnee Soccer Complex

Charming Apartment in CrossLanes

10.0 out of 10, Exceptional, (3)
"Came into town for a volleyball tournament. This was a perfect spot! The bed was so comfortable, a teammate stayed on the sofa bed and said it was very comfortable also. The place was clean and so cutely decorated. Communication with the host was great! Quiet area. I’m hoping to stay here again! "
The price is AU$241
includes taxes & fees
12 July - 13 July
Charming Apartment in CrossLanes

Charming 3-bedroom apartment with WiFi, AC in marvelous Charleston

10.0 out of 10, Exceptional, (4)
"This place was spacious, clean, and fantastic. Enjoyed our stay. "
The price is AU$275
includes taxes & fees
23 July - 24 July
Charming 3-bedroom apartment with WiFi, AC in marvelous Charleston

Cute 2 bed 1 bath with off street parking

8.0 out of 10, Very good, (8)
"We enjoyed our few days stay here. it had everything we needed and the neighborhood is quiet."
The price is AU$351
includes taxes & fees
31 July - 1 Aug
Cute 2 bed 1 bath with off street parking

Royal Retreat for corporate & family stay in Saint Albans area

7.8 out of 10, Good, (62)
"It was Good, only notes: no dust pan and upstairs got cold at night 2 thermosats up and down "
The price is AU$328
includes taxes & fees
20 July - 21 July
Royal Retreat for corporate & family stay in Saint Albans area

Spacious 5-bedroom house with AC, WiFi in brilliant Saint Albans

10.0 out of 10, Exceptional, (1)
"We needed a house that could put our family under one roof while we said goodbye to our Matriarch. This house provided 5 spacious bedrooms and 3 well equipped bathrooms, as well as a large living area and kitchen and a table that could seat all 10 of us. There was an issue with the AC but we had a repairman there soon after we reported the issue. Our host was quick to respond and provide answers and help when needed. Location is great; neighbors were friendly and we were conveniently...
The price is AU$1,180
includes taxes & fees
14 July - 15 July
Spacious 5-bedroom house with AC, WiFi in brilliant Saint Albans
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.
Save an average of 15% on thousands of hotels when you're signed in

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 Cabin Creek Quilts, or get out into nature at a spot like Kanawha State Forest. University of Charleston and West Virginia State Museum 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.