Holiday Rentals in Chesapeake

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Our top choices for Chesapeake holiday rentals

8.8 out of 10, Excellent, (10 reviews)
"We loved this place!"
United States
Megan
The price is €183
includes taxes & fees
19 Jan - 20 Jan
Hiding Place is near Montgomery colleges, hospital, NRG, & trails

Cabin in Clendenin

RealTree Camo Cabin 2
8.6 out of 10, Excellent, (7 reviews)
"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 €109
includes taxes & fees
18 Feb - 19 Feb
RealTree Camo Cabin 2

Holiday Home in Boomer

River View
8.2 out of 10, Very good, (22 reviews)
"Cute little apartment. Has everything we needed. The host is a joy to work with!"
United States
Suzette B.
The price is €172
includes taxes & fees
19 Jan - 20 Jan
River View

Holiday Home in Dunbar

Cozy River Cottage
2.0 star property
9.8 out of 10, Exceptional, (17 reviews)
"Great stay and good proximity"
United States
skyphygames
The price is €179
includes taxes & fees
19 Jan - 20 Jan
Cozy River Cottage

Holiday Home in Downtown Charleston

Royal Retreat Downtown-Convention Center
8.4 out of 10, Very good, (34 reviews)
"Shops and convention center within walking distance "
United States
Smokey 2.
The price is €183
includes taxes & fees
19 Jan - 20 Jan
Royal Retreat Downtown-Convention Center
7.8 out of 10, Good, (12 reviews)
"It was very pleasant , comfortable and convenient."
United States
Courtney Paige M.
The price is €178
includes taxes & fees
19 Jan - 20 Jan
Remodeled townhouse - 5 mins from Shawnee Sports Complex!
7.8 out of 10, Good, (13 reviews)
"Nice view."
United States
Michael W.
The Boomer: sky, river, and mtn your postage stamp for a week of relaxation!
9.6 out of 10, Exceptional, (26 reviews)
"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 €164
includes taxes & fees
15 Feb - 16 Feb
Charming 2-bedroom Bungalow - Close to Everything!
10.0 out of 10, Exceptional, (1 review)
"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 €178
includes taxes & fees
19 Jan - 20 Jan
“The Mountain View” is a welcoming apartment with AC in charming Boomer by river
9.6 out of 10, Exceptional, (8 reviews)
"Cute little space, served us perfect for a good resting spot for a couple of days. "
United States
kelly v.
Relaxing 3-bedroom apartment with WiFi, AC in Crosslanes.
7.8 out of 10, Good, (10 reviews)
"Easy check-in. Hosts are very accommodating to needs. Kitchen was adequate. "
United States
Alicia G.
Travelers Rest slps 5 Riverview, near NRG, trails, fishing. NRG, Falls, & more.
2.0 star property
9.8 out of 10, Exceptional, (14 reviews)
"Nice, small very livable home. Close to everything shopping , dining etc"
Singapore
Shirley F.
The price is €266
includes taxes & fees
19 Jan - 20 Jan
Ivy Branch Cottage - Danville
8.0 out of 10, Very good, (3 reviews)
"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 €127
includes taxes & fees
19 Jan - 20 Jan
Off grid Couples Cabin in Southern West Virginia
10.0 out of 10, Exceptional, (38 reviews)
"Great place to stay! Everything was clean "
United States
Roy K.
The price is €173
includes taxes & fees
19 Jan - 20 Jan
Luxurious cabin, 6 mi HM trails, 12 mi Charleston
9.0 out of 10, Wonderful, (9 reviews)
"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
21 Jan - 22 Jan
Historical land mark Gauley Bridge 1893 train station
9.6 out of 10, Exceptional, (7 reviews)
"Everything about this property was amazing"
United States
Corey
The price is €131
includes taxes & fees
19 Jan - 20 Jan
Cozy & Convenient - 20 Minutes to Charleston WV
10.0 out of 10, Exceptional, (16 reviews)
"Everything there was nice and beautiful."
United States
Kevin H.
The price is €258
includes taxes & fees
19 Jan - 20 Jan
Rosie's Cabin is an authentic log cabin located just 10 minutes from Charleston.

Holiday Home in Charlton Heights

Budget Spacious townhome with Gigabit Internet
10.0 out of 10, Exceptional, (3 reviews)
"Very clean house, love the beautiful scenery. Perfect vaca house thank you 😊"
United States
Mia K.
The price is €299
includes taxes & fees
1 Feb - 2 Feb
Budget Spacious townhome with Gigabit Internet
9.0 out of 10, Wonderful, (20 reviews)
"Nice people great stay"
United States
John B.
The price is €174
includes taxes & fees
19 Jan - 20 Jan
Cozy loft in private country setting 5 mins from downtown, Pet Friendly
9.6 out of 10, Exceptional, (12 reviews)
"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 €272
includes taxes & fees
5 Feb - 6 Feb
Walking Distance to Shawnee Soccer Complex
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 €129 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?

2-bedroom- hot tub-pool-NRG-Hawks Nest State Park: This holiday home rental outside of Chesapeake is located on a river, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

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.