Chesapeake Holiday Rentals

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Check prices for these dates

Tonight
23 Sept - 24 Sept
Tomorrow
24 Sept - 25 Sept
This weekend
26 Sept - 28 Sept
Next weekend
3 Oct - 5 Oct

Holiday Rentals in Chesapeake

208 New Downtown Living Studio
Interior

208 New Downtown Living Studio

2.0 star property
10.0 out of 10, Exceptional, (3)
"Overall Amazing, Would stay again! "
208 New Downtown Living Studio
203 New Downtown Living
Interior

203 New Downtown Living

2.0 star property
10.0 out of 10, Exceptional, (3)
"I’ve stayed here a few times. This is a safe and quiet area. He is very responsive and address any issues that you may have. Definitely recommend this location. "
203 New Downtown Living
Country Comfy Right in Town
Exterior

Country Comfy Right in Town

2.0 star property
6.0 out of 10, (1)
"Mr. Husson allowed me to check in a couple hrs. early-which he did not have to. The interior was clean and reasonably furnished. Price was reasonable for area. However, advertisement was misleading. Rental is for a floor/flat of a house. Not the whole house. Finished basement was rented to another party (who had a puppy that cried throughout the nights). Also, yard was trashy with litter strewn about."
Country Comfy Right in Town
King and 2 Queens 55 Smart tv
Exterior

King and 2 Queens 55 Smart tv

2.0 star property
9.0 out of 10, Wonderful, (6)
"Property was nice clean and we felt safe I would recommend this property to anyone "
King and 2 Queens 55 Smart tv
Charming Charleston Home w/ Yard & Fire Pit!
Interior

Charming Charleston Home w/ Yard & Fire Pit!

3.0 star property
10.0 out of 10, Exceptional, (1)
"very clean and well kept."
Charming Charleston Home w/ Yard & Fire Pit!
Comfortable Cozy Walk to Camc Hospital
Miscellaneous

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
202 New Downtown Living
Miscellaneous

202 New Downtown Living

2.0 star property
8.0 out of 10, Very good, (2)
"Location "
202 New Downtown Living
Treetops in Town
Interior

Treetops in Town

3.0 star property
9.8 out of 10, Exceptional, (7)
"Three bedroom house with a great view. Full length windows that look out to several balconies surrounded by forest. Comfortable beds."
Treetops in Town
Country Living Patio Apartment in Town
Interior

Country Living Patio Apartment in Town

2.0 star property
6.0 out of 10, (2)
"It was a beautiful and quiet place. I loved it. The scenery was awesome with the snow we had."
Country Living Patio Apartment in Town
Quaint, Comfy, Close & Convenient
Interior

Quaint, Comfy, Close & Convenient

2.0 star property
9.2 out of 10, Wonderful, (22)
"Very cute house, quiet and cozy. "
Quaint, Comfy, Close & Convenient
Pet-friendly Charleston Home w/ Fenced Yard!
Front of property

Pet-friendly Charleston Home w/ Fenced Yard!

3.0 star property
10.0 out of 10, Exceptional, (1)
Pet-friendly Charleston Home w/ Fenced Yard!
201 New Downtown Living
Private kitchen

201 New Downtown Living

2.0 star property
9.0 out of 10, Wonderful, (6)
"Great location, very clean and comfortable. "
201 New Downtown Living
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
"Room was clean, comfortable and breakfast had many choices. Loved the complimentary cookies and coffee "
Kristi 1-night trip
Posted 1 day ago
Sleep Inn Charleston North

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’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.