Chesapeake Vacation Rentals

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Tonight
Nov 18 - Nov 19
Tomorrow
Nov 19 - Nov 20
This weekend
Nov 21 - Nov 23
Next weekend
Nov 28 - Nov 30

Vacation Rentals in Chesapeake

Fridge, microwave, oven, stovetop
Cozy River Cottage

Cozy River Cottage

2.0 star property
Dunbar
9.8 out of 10, Exceptional, (16)
"Very cute little cottage on the river. "
United States
Kristie
The price is ￥13,214
￥31,338 total
includes taxes & fees
Nov 19 - Nov 20
Cozy River Cottage
Microwave, oven, stovetop, dishwasher
Relaxing 3-bedroom apartment with WiFi, AC in Crosslanes.

Relaxing 3-bedroom apartment with WiFi, AC in Crosslanes.

Charleston
9.6 out of 10, Exceptional, (8)
"This place was spacious, clean, and fantastic. Enjoyed our stay. "
United States
Lindsay U.
The price is ￥12,364
￥27,510 total
includes taxes & fees
Dec 1 - Dec 2
Relaxing 3-bedroom apartment with WiFi, AC in Crosslanes.
Private kitchen
Charming 2-bedroom Bungalow - Close to Everything!

Charming 2-bedroom Bungalow - Close to Everything!

Charleston
9.6 out of 10, Exceptional, (21)
"Me and 2 friends stayed here for a weekend of dirtbike riding on July 4th and it was exactly what we needed "
United States
Quinn P.
The price is ￥11,823
￥27,147 total
includes taxes & fees
Nov 20 - Nov 21
Charming 2-bedroom Bungalow - Close to Everything!
Exterior
Budget Spacious townhome with Gigabit Internet

Budget Spacious townhome with Gigabit Internet

Charlton Heights
10.0 out of 10, Exceptional, (3)
"Very clean house, love the beautiful scenery. Perfect vaca house thank you 😊"
United States
Mia K.
The price is ￥16,691
￥41,620 total
includes taxes & fees
Nov 19 - Nov 20
Budget Spacious townhome with Gigabit Internet
Private kitchen
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
9.4 out of 10, Exceptional, (19)
"Had a great stay here. Clean, convenient pet friendly place. "
United States
James M.
The price is ￥17,943
￥30,298 total
includes taxes & fees
Dec 1 - Dec 2
Cozy loft in private country setting 5 mins from downtown, Pet Friendly
Exterior
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, (35)
"Great location nice clean cabin great host "
United States
Bernie G.
The price is ￥16,552
￥33,109 total
includes taxes & fees
Nov 19 - Nov 20
Luxurious cabin, 6 mi HM trails, 12 mi Charleston
Exterior
“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
10.0 out of 10, Exceptional, (1)
"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 ￥18,546
￥31,299 total
includes taxes & fees
Dec 4 - Dec 5
“The Mountain View” is a welcoming apartment with AC in charming Boomer by river
Fridge, microwave, oven, stovetop
Royal Retreat Downtown-Convention Center

Royal Retreat Downtown-Convention Center

Downtown Charleston
8.8 out of 10, Excellent, (29)
"The condo was centrally located for our visit to Charleston. The home was neat, clean, quiet, welcoming and comfortable. We felt right at home!"
United States
Pat M.
The price is ￥17,001
￥32,289 total
includes taxes & fees
Nov 20 - Nov 21
Royal Retreat Downtown-Convention Center
Terrace/patio
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, (12)
"This is a wonderful little cabin that is perfect for a small family. We enjoyed the back and front porch decks, the hot tub and the beautiful shower. It was so nice to come back to the cabin each day to unwind."
United States
Emily H.
The price is ￥23,183
￥50,903 total
includes taxes & fees
Nov 23 - Nov 24
Rosie's Cabin is an authentic log cabin located just 10 minutes from Charleston.
Outdoor dining
River View

River View

Boomer
8.2 out of 10, Very Good, (22)
"It was a good stay. "
United States
Bradley B.
The price is ￥17,773
￥30,598 total
includes taxes & fees
Dec 4 - Dec 5
River View
Fridge, microwave, oven, stovetop
RealTree Camo Cabin 2

RealTree Camo Cabin 2

Clendenin
8.4 out of 10, Very Good, (6)
"The place is just beautiful and the owner is great she made sure we had everything we needed and took very good care of our needs"
United States
Robin S.
The price is ￥12,519
￥17,298 total
includes taxes & fees
Nov 19 - Nov 20
RealTree Camo Cabin 2
Fridge, microwave, oven, stovetop
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)
"We loved this place!"
United States
Megan
The price is ￥19,319
￥32,620 total
includes taxes & fees
Nov 20 - Nov 21
Hiding Place is near Montgomery colleges, hospital, NRG, & trails
Terrace/patio
Home in South Charleston, WV

Home in South Charleston, WV

South Charleston
9.6 out of 10, Exceptional, (5)
"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!!!"
United States
Nester D.
The price is ￥17,001
￥31,581 total
includes taxes & fees
Dec 1 - Dec 2
Home in South Charleston, WV
Property grounds
Historical land mark Gauley Bridge 1893 train station

Historical land mark Gauley Bridge 1893 train station

Gauley Bridge
8.4 out of 10, Very Good, (6)
The price is ￥18,082
￥22,443 total
includes taxes & fees
Nov 30 - Dec 1
Historical land mark Gauley Bridge 1893 train station
Smart TV, books, stereo
Cozy & Convenient - 20 Minutes to Charleston WV

Cozy & Convenient - 20 Minutes to Charleston WV

Quick
9.6 out of 10, Exceptional, (7)
"Everything about this property was amazing"
United States
Corey
The price is ￥17,387
￥22,750 total
includes taxes & fees
Nov 20 - Nov 21
Cozy & Convenient - 20 Minutes to Charleston WV
Fridge, microwave, oven, stovetop
Walking Distance to Shawnee Soccer Complex

Walking Distance to Shawnee Soccer Complex

Dunbar
9.6 out of 10, Exceptional, (10)
"Lots of room for 6 adults to stay for a long weekend. This property was as stated, clean and nice and roomy. A few properties around it were run down."
United States
Tylee F.
The price is ￥20,961
￥44,935 total
includes taxes & fees
Nov 19 - Nov 20
Walking Distance to Shawnee Soccer Complex
Smart TV, books
Ivy Branch Cottage - Danville

Ivy Branch Cottage - Danville

2.0 star property
Danville
The price is ￥16,073
￥38,171 total
includes taxes & fees
Dec 1 - Dec 2
Ivy Branch Cottage - Danville
Property grounds
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
7.6 out of 10, Good, (11)
"We enjoyed our stay while exploring the area. Will recommend most definitely."
United States
Lee Ann J.
The price is ￥17,001
￥29,241 total
includes taxes & fees
Nov 22 - Nov 23
The Boomer: sky, river, and mtn your postage stamp for a week of relaxation!
Property grounds
Off grid Couples Cabin in Southern West Virginia

Off grid Couples Cabin in Southern West Virginia

Charleston
8.0 out of 10, Very Good, (3)
"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 "
United States
Hayden M.
The price is ￥16,691
￥21,970 total
includes taxes & fees
Nov 20 - Nov 21
Off grid Couples Cabin in Southern West Virginia
Fridge, microwave, oven, stovetop
Charming Apartment in CrossLanes

Charming Apartment in CrossLanes

Charleston
10.0 out of 10, Exceptional, (6)
"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! "
United States
Michele E.
The price is ￥10,819
￥24,048 total
includes taxes & fees
Nov 19 - Nov 20
Charming Apartment in CrossLanes
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

Embassy Suites Charleston

Embassy Suites Charleston

10/10 Excellent
"The breakfast was fresh and free. Staff was friendly and helpful. Rooms were quiet and clean. The hotel it’s self was clean. The only part I did not like was the parking."
Sandra 2-night trip
Posted 2 days ago
Embassy Suites Charleston

Find out more about Chesapeake

Search for holiday rentals in Chesapeake on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesapeake using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chesapeake!

Frequently asked questions

Can I find a vacation rental in Chesapeake?

Yes, you can find vacation rentals close to the most popular attractions in Chesapeake, or you can select a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Chesapeake?

Historical land mark Gauley Bridge 1893 train station: This vacation home rental near Chesapeake has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a microwave to make your meal-planning easier.

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 larger area.

What’s a vacation rental in Chesapeake like?

A vacation rental is a private property you can stay in for several days or longer in Chesapeake. Vacation rentals offer amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a family getaway.