Chesapeake Holiday Rentals

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Our top choices for Chesapeake holiday rentals

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 NZ$204
includes taxes & fees
25 Feb - 26 Feb
RealTree Camo Cabin 2
9.8 out of 10, Exceptional, (18 reviews)
"Cleanliness and location"
United States
Charles
The price is NZ$503
includes taxes & fees
25 Feb - 26 Feb
Rosie's Cabin is an authentic log cabin located just 10 minutes from Charleston.
9.6 out of 10, Exceptional, (28 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 NZ$294
includes taxes & fees
25 Feb - 26 Feb
Charming 2-bedroom Bungalow - Close to Everything!

Holiday Home in Boomer

River View
8.2 out of 10, Very good, (22 reviews)
"The house was very clean. Had all the amenities that we needed to cook. Very quiet neighborhood and pretty view of the river in the morning."
United States
Lorie H.
The price is NZ$326
includes taxes & fees
25 Feb - 26 Feb
River View
9.6 out of 10, Exceptional, (7 reviews)
"Everything about this property was amazing"
United States
Corey
The price is NZ$270
includes taxes & fees
25 Feb - 26 Feb
Cozy & Convenient - 20 Minutes to Charleston WV

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 NZ$350
includes taxes & fees
25 Feb - 26 Feb
Royal Retreat Downtown-Convention Center
10.0 out of 10, Exceptional, (38 reviews)
"Great location and had everything we needed. "
United States
Noah B.
The price is NZ$373
includes taxes & fees
25 Feb - 26 Feb
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 NZ$243
includes taxes & fees
1 Mar - 2 Mar
Historical land mark Gauley Bridge 1893 train station
8.8 out of 10, Excellent, (10 reviews)
"We loved this place!"
United States
Megan
The price is NZ$329
includes taxes & fees
25 Feb - 26 Feb
Hiding Place is near Montgomery colleges, hospital, NRG, & trails

Holiday Home in Dunbar

Cozy River Cottage
9.8 out of 10, Exceptional, (17 reviews)
"It was great for a quiet get away"
United States
sallie c.
The price is NZ$339
includes taxes & fees
26 Feb - 27 Feb
Cozy River Cottage
7.8 out of 10, Good, (13 reviews)
"Jim is an awesome host! The house is clean, comfortable and well equipped. We LOVE sitting around the firepit just taking in the gorgeous view!"
United States
Suzette B.
The price is NZ$273
includes taxes & fees
25 Feb - 26 Feb
The Boomer: sky, river, and mtn your postage stamp for a week of relaxation!
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 NZ$497
includes taxes & fees
25 Feb - 26 Feb
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 NZ$238
includes taxes & fees
26 Feb - 27 Feb
Off grid Couples Cabin in Southern West Virginia
9.0 out of 10, Wonderful, (20 reviews)
"Nice people great stay"
United States
John B.
The price is NZ$330
includes taxes & fees
25 Feb - 26 Feb
Cozy loft in private country setting 5 mins from downtown, Pet Friendly
7.8 out of 10, Good, (10 reviews)
"Easy check-in. Hosts are very accommodating to needs. Kitchen was adequate. "
United States
Alicia G.
The price is NZ$335
includes taxes & fees
25 Feb - 26 Feb
Travelers Rest slps 5 Riverview, near NRG, trails, fishing. NRG, Falls, & more.

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 NZ$533
includes taxes & fees
26 Mar - 27 Mar
Budget Spacious townhome with Gigabit Internet

Mobile Home in Charleston

Prayer Mountain-Off Grid Farm spot#2
The price is NZ$255
includes taxes & fees
2 Mar - 3 Mar
Prayer Mountain-Off Grid Farm spot#2
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 NZ$518
includes taxes & fees
8 Mar - 9 Mar
Walking Distance to Shawnee Soccer Complex
The price is NZ$488
includes taxes & fees
25 Mar - 26 Mar
Cozy 4 Bedroom house in the historic Glen Ferris, WV
8.0 out of 10, Very good, (63 reviews)
"Nice property and after some communication issues all was well for the time we were there. "
United States
Kay G.
The price is NZ$355
includes taxes & fees
8 Mar - 9 Mar
Royal Retreat for corporate & family stay in Saint Albans area
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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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, 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 NZ$243 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?

South Hills Charmer: This holiday home rental outside of Chesapeake is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

What’s there to see and do in Chesapeake?

Explore the area and family-friendly sights such as Memorial Ice Arena, 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.