Holiday Rentals in Chesapeake

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Holiday Rentals in Chesapeake

Holiday Home in Dunbar

2.0 star property
9.8 out of 10, Exceptional, (16)
"Great stay and good proximity"
United States
skyphygames
The price is €188
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy River Cottage

Holiday Home in Charleston

9.6 out of 10, Exceptional, (23)
"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 €155
includes taxes & fees
7 Dec - 8 Dec
Charming 2-bedroom Bungalow - Close to Everything!

Holiday Home in Boomer

8.2 out of 10, Very good, (22)
"It was a good stay. "
United States
Bradley B.
The price is €157
includes taxes & fees
5 Dec - 6 Dec
River View

Cottage in Danville

2.0 star property
9.8 out of 10, Exceptional, (13)
"Nice, small very livable home. Close to everything shopping , dining etc"
Singapore
Shirley F.
The price is €345
includes taxes & fees
3 Jan - 4 Jan 2026
Ivy Branch Cottage - Danville

Holiday Home in 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 €226
includes taxes & fees
8 Dec - 9 Dec
Budget Spacious townhome with Gigabit Internet

Cabin in Alum Creek

10.0 out of 10, Exceptional, (36)
"Great location nice clean cabin great host "
United States
Bernie G.
The price is €189
includes taxes & fees
5 Dec - 6 Dec
Luxurious cabin, 6 mi HM trails, 12 mi Charleston

Apartment in 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 €138
includes taxes & fees
6 Dec - 7 Dec
Charming Apartment in CrossLanes

Cabin in 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 €100
includes taxes & fees
5 Dec - 6 Dec
RealTree Camo Cabin 2

Apartment in 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 €204
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy loft in private country setting 5 mins from downtown, Pet Friendly

Apartment in 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 €177
includes taxes & fees
5 Dec - 6 Dec
“The Mountain View” is a welcoming apartment with AC in charming Boomer by river

Holiday Home in Gauley Bridge

8.6 out of 10, Excellent, (7)
"What’s great little find for a short stay. Such a cute place and plenty of room for more than just the 2 of us needed. "
United States
sara m.
The price is €129
includes taxes & fees
5 Dec - 6 Dec
Historical land mark Gauley Bridge 1893 train station

Apartment in Montgomery

8.8 out of 10, Excellent, (10)
"We loved this place!"
United States
Megan
The price is €185
includes taxes & fees
5 Dec - 6 Dec
Hiding Place is near Montgomery colleges, hospital, NRG, & trails

Holiday Home in 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 €178
includes taxes & fees
3 Jan - 4 Jan 2026
Home in South Charleston, WV

Apartment in Boomer

7.8 out of 10, Good, (12)
"We enjoyed our stay while exploring the area. Will recommend most definitely."
United States
Lee Ann J.
The price is €167
includes taxes & fees
3 Jan - 4 Jan 2026
The Boomer: sky, river, and mtn your postage stamp for a week of relaxation!

Holiday Home in Quick

9.6 out of 10, Exceptional, (7)
"Everything about this property was amazing"
United States
Corey
The price is €131
includes taxes & fees
5 Dec - 6 Dec
Cozy & Convenient - 20 Minutes to Charleston WV

Holiday Home in Dunbar

9.8 out of 10, Exceptional, (11)
"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.
Walking Distance to Shawnee Soccer Complex

Apartment in Boomer

7.8 out of 10, Good, (10)
"Easy check-in. Hosts are very accommodating to needs. Kitchen was adequate. "
United States
Alicia G.
The price is €176
includes taxes & fees
3 Jan - 4 Jan 2026
Travelers Rest slps 5 Riverview, near NRG, trails, fishing. NRG, Falls, & more.

Cabin in South Charleston

10.0 out of 10, Exceptional, (14)
"This cabin is everything a cabin should be and more!! From the high quality, rustic decor to the availability of wood for cozy fires and fun games available it is the perfect stay for our family!!"
United States
Monique H.
The price is €285
includes taxes & fees
30 Dec - 31 Dec
Rosie's Cabin is an authentic log cabin located just 10 minutes from Charleston.

Holiday Home in Downtown Charleston

8.4 out of 10, Very good, (33)
"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 €184
includes taxes & fees
6 Dec - 7 Dec
Royal Retreat Downtown-Convention Center

Mobile Home in Charleston

The price is €109
includes taxes & fees
3 Jan - 4 Jan 2026
Prayer Mountain-Off Grid Farm spot#2
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

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, apart-hotels, 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 favorite 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 depends 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 €109 per night. Entering your travel dates in the search wizard you might find 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?

Historical land mark Gauley Bridge 1893 train station: This holiday home rental outside of 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 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.