Chesapeake Holiday Rentals

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Our top choices for Chesapeake holiday rentals

RealTree Camo Cabin 2

RealTree Camo Cabin 2
Clendenin
8.8 out of 10, Excellent, (8 reviews)
"Our host , Liz was very welcoming, Nice clean cabin. Cute little camp ground. Wood for firepit, was provided also free wifi and fully set up kitchen , full bath with water on the mand water heater, multiple space heaters, extra pillows and blankets. Loved our stay. "
United States
Bela M.
The price is NZ$208
includes taxes & fees
29 May - 30 May
RealTree Camo Cabin 2

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 reviews)
"We loved this place!"
United States
Megan
The price is NZ$321
includes taxes & fees
27 May - 28 May
Hiding Place is near Montgomery colleges, hospital, NRG, & trails

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, (44 reviews)
"Great location and had everything we needed. "
United States
Noah B.
The price is NZ$369
includes taxes & fees
31 May - 1 June
Luxurious cabin, 6 mi HM trails, 12 mi Charleston

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, (25 reviews)
"Relaxing and overall good experience. Enjoyed the amenities and decent location with close access to a few key locations in southern WV."
United States
Carson S.
The price is NZ$512
includes taxes & fees
7 June - 8 June
Rosie's Cabin is an authentic log cabin located just 10 minutes from Charleston.

Ivy Branch Cottage - Danville

Ivy Branch Cottage - Danville
Danville
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$561
includes taxes & fees
27 May - 28 May
Ivy Branch Cottage - Danville

Cozy & Convenient - 20 Minutes to Charleston WV

Cozy & Convenient - 20 Minutes to Charleston WV
Quick
9.2 out of 10, Wonderful, (9 reviews)
"Everything about this property was amazing"
United States
Corey
The price is NZ$275
includes taxes & fees
2 June - 3 June
Cozy & Convenient - 20 Minutes to Charleston WV

River View

River View
Boomer
8.4 out of 10, Very good, (24 reviews)
"It was a good stay. "
United States
Bradley B.
The price is NZ$281
includes taxes & fees
27 May - 28 May
River View

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
7.8 out of 10, Good, (14 reviews)
"A dated traditional property but clean and tidy."
United Kingdom
Paul
The price is NZ$285
includes taxes & fees
27 May - 28 May
The Boomer: sky, river, and mtn your postage stamp for a week of relaxation!

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

Relaxing 3-bedroom apartment with WiFi, AC in Crosslanes.
Charleston
9.8 out of 10, Exceptional, (14 reviews)
"Cute little space, served us perfect for a good resting spot for a couple of days. "
United States
kelly v.
The price is NZ$360
includes taxes & fees
1 June - 2 June
Relaxing 3-bedroom apartment with WiFi, AC in Crosslanes.

Charming 2-bedroom Bungalow - Close to Everything!

Charming 2-bedroom Bungalow - Close to Everything!
Charleston
9.6 out of 10, Exceptional, (37 reviews)
"Very clean, quiet and comfortable.I would definitely stay there again. It's close to shopping, gas, food and easily accessible from the highway. "
United States
Elvira
The price is NZ$316
includes taxes & fees
8 June - 9 June
Charming 2-bedroom Bungalow - Close to Everything!

Walking Distance to Shawnee Soccer Complex

Walking Distance to Shawnee Soccer Complex
Dunbar
9.6 out of 10, Exceptional, (14 reviews)
"Great space and lovely home. Host was very helpful and took care of all our needs."
United States
Chantel H.
The price is NZ$491
includes taxes & fees
29 May - 30 May
Walking Distance to Shawnee Soccer Complex

Cozy River Cottage

Cozy River Cottage
Dunbar
9.8 out of 10, Exceptional, (20 reviews)
"Exceptional place. Great location right on the river. Plenty of room."
United States
Jonathan K.
The price is NZ$364
includes taxes & fees
22 June - 23 June
Cozy River Cottage

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
9.0 out of 10, Wonderful, (21 reviews)
"Nice people great stay"
United States
John B.
The price is NZ$334
includes taxes & fees
9 June - 10 June
Cozy loft in private country setting 5 mins from downtown, Pet Friendly

Royal Retreat Downtown-Convention Center

Royal Retreat Downtown-Convention Center
Downtown Charleston
8.4 out of 10, Very good, (35 reviews)
"Check in was easy. The townhouse was perfect for our stay. It is in a great location, close to everything downtown. "
United States
Kelly M.
The price is NZ$359
includes taxes & fees
2 June - 3 June
Royal Retreat Downtown-Convention Center

Off grid Couples Cabin in Southern West Virginia

Off grid Couples Cabin in Southern West Virginia
Charleston
7.6 out of 10, Good, (4 reviews)
"In m opinion, if any place is going to call itself “Almost Heaven”, it should be this place. It was raining most of our visit and I still loved it. If you love animals and nature, this is the place. "
United States
Candra M.
The price is NZ$242
includes taxes & fees
31 May - 1 June
Off grid Couples Cabin in Southern West Virginia

Royal Retreat for corporate & family stay in Saint Albans area

Royal Retreat for corporate & family stay in Saint Albans area
St Albans
7.6 out of 10, Good, (68 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$364
includes taxes & fees
31 May - 1 June
Royal Retreat for corporate & family stay in Saint Albans area

Remote Mountain A-Frame with BBQ Perfect for Nature Lovers in West Virginia

Remote Mountain A-Frame with BBQ Perfect for Nature Lovers in West Virginia
Charleston
The price is NZ$231
includes taxes & fees
1 June - 2 June
Remote Mountain A-Frame with BBQ Perfect for Nature Lovers in West Virginia

“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, (3 reviews)
"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 NZ$320
includes taxes & fees
27 May - 28 May
“The Mountain View” is a welcoming apartment with AC in charming Boomer by river

Car camping Private Cemetary

Car camping Private Cemetary
Charleston
The price is NZ$112
includes taxes & fees
31 May - 1 June
Car camping Private Cemetary

Hillview - 3-bedroom house in peaceful Dunbar

Hillview - 3-bedroom house in peaceful Dunbar
Dunbar
10.0 out of 10, Exceptional, (1 review)
"Clean. Location was perfect and the host was to contact. Thanks "
United States
Douglas D.
The price is NZ$409
includes taxes & fees
28 May - 29 May
Hillview - 3-bedroom house in peaceful Dunbar
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, 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$208 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?

Luxurious getaway Home: This holiday home rental outside of Chesapeake offers a balcony, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What’s there to see and do in Chesapeake?

Explore the area and family-friendly sights such as Jefferson Park, or get out into nature at a spot like Kanawha State Forest. University of Charleston and West Virginia State Capitol Building 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.