Holiday Rentals in Chesapeake

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Our top choices for Chesapeake holiday rentals

RealTree Camo Cabin 2

RealTree Camo Cabin 2
Clendenin
8.6 out of 10, Excellent, (7 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 €109
includes taxes & fees
8 Mar - 9 Mar
RealTree Camo Cabin 2

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, (38 reviews)
"Great location and had everything we needed. "
United States
Noah B.
The price is €205
includes taxes & fees
29 Mar - 30 Mar
Luxurious cabin, 6 mi HM trails, 12 mi Charleston

Charming Apartment in CrossLanes

Charming Apartment in CrossLanes
Charleston
10.0 out of 10, Exceptional, (7 reviews)
"Great little place for 1 or 2 people. The only problem we had was the way Google maps brought us in. Once we figured out the roads in the neighborhood, we really had no issues. Our hostess was very quick to respond the one question we had. If in the area again, we would pick this spot over a hotel any time."
United States
Amy S.
The price is €138
includes taxes & fees
8 Mar - 9 Mar
Charming Apartment in CrossLanes

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 €166
includes taxes & fees
9 Mar - 10 Mar
Hiding Place is near Montgomery colleges, hospital, NRG, & trails

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, (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 €156
includes taxes & fees
9 Mar - 10 Mar
The Boomer: sky, river, and mtn your postage stamp for a week of relaxation!

Cozy & Convenient - 20 Minutes to Charleston WV

Cozy & Convenient - 20 Minutes to Charleston WV
Quick
9.6 out of 10, Exceptional, (7 reviews)
"Everything about this property was amazing"
United States
Corey
Cozy & Convenient - 20 Minutes to Charleston WV

Near Kanawha River & ATV Trails: Home w/ Deck!

Near Kanawha River & ATV Trails: Home w/ Deck!
3.0 star property
Belle
The price is €301
includes taxes & fees
7 Mar - 8 Mar
Near Kanawha River & ATV Trails: Home w/ Deck!

Cozy River Cottage

Cozy River Cottage
Dunbar
9.8 out of 10, Exceptional, (17 reviews)
"It was great for a quiet get away"
United States
sallie c.
The price is €179
includes taxes & fees
8 Mar - 9 Mar
Cozy River Cottage

River View

River View
Boomer
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 €172
includes taxes & fees
6 Mar - 7 Mar
River View

Historical land mark Gauley Bridge 1893 train station

Historical land mark Gauley Bridge 1893 train station
Gauley Bridge
9.0 out of 10, Wonderful, (9 reviews)
"This is just the coolest place! You have everything you need and the building is beautiful. We had a great stay and definitely would recommend. "
United States
Kathryn J.
The price is €129
includes taxes & fees
10 Mar - 11 Mar
Historical land mark Gauley Bridge 1893 train station

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 €255
includes taxes & fees
6 Mar - 7 Mar
Ivy Branch Cottage - Danville

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, (20 reviews)
"Nice people great stay"
United States
John B.
The price is €206
includes taxes & fees
4 Apr - 5 Apr
Cozy loft in private country setting 5 mins from downtown, Pet Friendly

Walking Distance to Shawnee Soccer Complex

Walking Distance to Shawnee Soccer Complex
Dunbar
9.6 out of 10, Exceptional, (12 reviews)
"Great space and lovely home. Host was very helpful and took care of all our needs."
United States
Chantel H.
The price is €249
includes taxes & fees
8 Mar - 9 Mar
Walking Distance to Shawnee Soccer Complex

Royal Retreat Downtown-Convention Center

Royal Retreat Downtown-Convention Center
Downtown Charleston
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
9 Mar - 10 Mar
Royal Retreat Downtown-Convention Center

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 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 €126
includes taxes & fees
6 Mar - 7 Mar
Off grid Couples Cabin in Southern West Virginia

ADULT ONLY Naughty Pines log cabin located in South Charleston, WV

ADULT ONLY Naughty Pines log cabin located in South Charleston, WV
South Charleston
9.8 out of 10, Exceptional, (19 reviews)
"It was a great time for me and my wife to celebrate our anniversary"
United States
Robbie E.
The price is €435
includes taxes & fees
8 Mar - 9 Mar
ADULT ONLY Naughty Pines log cabin located in South Charleston, WV

“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, (2 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 €165
includes taxes & fees
9 Mar - 10 Mar
“The Mountain View” is a welcoming apartment with AC in charming Boomer by river

Royal Retreat for corporate & family stay in Saint Albans area

Royal Retreat for corporate & family stay in Saint Albans area
St Albans
7.8 out of 10, Good, (64 reviews)
"Nice property and after some communication issues all was well for the time we were there. "
United States
Kay G.
The price is €187
includes taxes & fees
29 Mar - 30 Mar
Royal Retreat for corporate & family stay in Saint Albans area

Travelers Rest slps 5 Riverview, near NRG, trails, fishing. NRG, Falls, & more.

Travelers Rest slps 5 Riverview, near NRG, trails, fishing. NRG, Falls, & more.
Boomer
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 €177
includes taxes & fees
6 Mar - 7 Mar
Travelers Rest slps 5 Riverview, near NRG, trails, fishing. NRG, Falls, & more.

Budget Spacious townhome with Gigabit Internet

Budget Spacious townhome with Gigabit Internet
Charlton Heights
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 €245
includes taxes & fees
18 Mar - 19 Mar
Budget Spacious townhome with Gigabit Internet
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 €172 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 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.