Chesapeake Holiday Rentals

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Holiday Rentals in Chesapeake

Royal Retreat Downtown-Convention Center

8.8 out of 10, Excellent, (21)
"Good location "
The price is NZ$373
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 NZ$309
includes taxes & fees
20 July - 21 July
Charming 2-bedroom Bungalow - Close to Everything!

ADULT ONLY Naughty Pines log cabin located in South Charleston, WV

10.0 out of 10, Exceptional, (10)
"Great communication with the host, very clean, enjoyed a couple nice fires and the hot tub. Was a great relaxing getaway. "
The price is NZ$842
includes taxes & fees
14 July - 15 July
ADULT ONLY Naughty Pines log cabin located in South Charleston, WV

Travelers Rest slps 5 Riverview, near NRG, trails, fishing. NRG, Falls, & more.

8.0 out of 10, Very good, (7)
"Location beside the river is very nice and the place was clean and quiet."
The price is NZ$338
includes taxes & fees
10 July - 11 July
Travelers Rest slps 5 Riverview, near NRG, trails, fishing. NRG, Falls, & more.

Luxurious getaway Home

10.0 out of 10, Exceptional, (57)
"Very clean, great hospitality. Thank you for letting us stay! We had a great time and appreciate everything! "
Luxurious getaway Home

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

The price is NZ$339
includes taxes & fees
10 July - 11 July
“The Mountain View” is a welcoming apartment with AC in charming Boomer by river

Cozy River Cottage

2.0 star property
10.0 out of 10, Exceptional, (8)
"Great stay and good proximity"
The price is NZ$363
includes taxes & fees
15 July - 16 July
Cozy River Cottage

2-bedroom- hot tub-pool-NRG-Hawks Nest State Park-NO CLEANING FEE!

10.0 out of 10, Exceptional, (25)
"We had a wonderful stay! It was very clean and cozy. We really enjoyed the hot tub and pac man machine. Communication with the host was easy. Would definitely recommend to anyone staying in the area! "
2-bedroom- hot tub-pool-NRG-Hawks Nest State Park-NO CLEANING FEE!

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

9.8 out of 10, Exceptional, (7)
"The cabin was very well made with so many amenities. "
The price is NZ$549
includes taxes & fees
13 July - 14 July
Rosie's Cabin is an authentic log cabin located just 10 minutes from Charleston.

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 NZ$337
includes taxes & fees
10 July - 11 July
Home in South Charleston, WV

River View

8.0 out of 10, Very good, (19)
"Was very nice, "
The price is NZ$336
includes taxes & fees
26 July - 27 July
River View

Riverfront Bungalow on the New River Dries

10.0 out of 10, Exceptional, (6)
"We had an amazing stay. The house was adorable with an old school charm and modern amenities. The drives to everything was beautiful winding roads. The river was perfect for kayaking/paddle boarding and lots of fishing. It was absolutely perfect for my husband and I and our 2 teen boys. Highly recommend River Expedition for white water rafting and New River ATV. Also, had a blast at Pirates Cove cliff jumping."
Riverfront Bungalow on the New River Dries

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 NZ$352
includes taxes & fees
15 July - 16 July
Charming 3-bedroom apartment with WiFi, AC in marvelous Charleston

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

8.4 out of 10, Very good, (6)
"Myself, my mother and brother were passing through on our way to Virginia Beach. The hiding place was clean and just enough for us for our one night stay. Communication was good and price was fair."
The price is NZ$346
includes taxes & fees
10 July - 11 July
Hiding Place is near Montgomery colleges, hospital, NRG, & trails

Off grid Couples Cabin in Southern West Virginia

10.0 out of 10, Exceptional, (1)
"We had a little weekend getaway planned, and Brandon was the perfect host! It was a bit rainy and muddy when we came but Brandon was more than accommodating to make sure everything went smoothly. Would definitely recommend and stay again "
The price is NZ$237
includes taxes & fees
10 July - 11 July
Off grid Couples Cabin in Southern West Virginia

Comfortable Cozy Walk to Camc Hospital

2.0 star property
10.0 out of 10, Exceptional, (2)
"Love this place!!!"
Comfortable Cozy Walk to Camc Hospital

Luxurious cabin, 6 mi HM trails, 12 mi Charleston

10.0 out of 10, Exceptional, (27)
"Such a cute place. Close by to anything you might need but nestled away for a peaceful place to relax and enjoy. "
The price is NZ$375
includes taxes & fees
14 July - 15 July
Luxurious cabin, 6 mi HM trails, 12 mi Charleston

Riverfront-NO CLEANING FEE -3BR-NRG-Deck-Dock-Hike-Firepit-Pets-OK-Boat-Kayak

10.0 out of 10, Exceptional, (45)
"We loved the place. Right on the river it was very nice. She provided treats like small bags of chips, Popsicles, etc.. "
Riverfront-NO CLEANING FEE -3BR-NRG-Deck-Dock-Hike-Firepit-Pets-OK-Boat-Kayak

King and 2 Queens 55 Smart tv

2.0 star property
8.6 out of 10, Excellent, (4)
"This property was very clean and close to just about everything. I would highly recommend staying at the property versus a hotel in the area. "
King and 2 Queens 55 Smart tv

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

7.6 out of 10, Good, (9)
"We enjoyed our stay while exploring the area. Will recommend most definitely."
The price is NZ$328
includes taxes & fees
10 July - 11 July
The Boomer: sky, river, and mtn your postage stamp for a week of relaxation!
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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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.