Holiday Rentals in Chesapeake

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Holiday Rentals in Chesapeake

Hiding Place is near Montgomery colleges, hospital, NRG, & trails
8.8 out of 10, Excellent, (10)
"We loved this place!"
The price is €183
includes taxes & fees
19 Oct - 20 Oct
Hiding Place is near Montgomery colleges, hospital, NRG, & trails
River View
8.2 out of 10, Very good, (21)
"We enjoyed our stay. Thank you."
The price is €175
includes taxes & fees
15 Nov - 16 Nov
River View
RealTree Camo Cabin 2
8.4 out of 10, Very good, (6)
"Great stay! Recommending to my friends!"
The price is €100
includes taxes & fees
21 Oct - 22 Oct
RealTree Camo Cabin 2
Cozy River Cottage
2.0 star property
10.0 out of 10, Exceptional, (10)
"Great stay and good proximity"
The price is €179
includes taxes & fees
19 Oct - 20 Oct
Cozy River Cottage
Charming Apartment in CrossLanes
10.0 out of 10, Exceptional, (5)
"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! "
The price is €138
includes taxes & fees
16 Oct - 17 Oct
Charming Apartment in CrossLanes
Budget Spacious townhome with Gigabit Internet
10.0 out of 10, Exceptional, (3)
"Very clean house, love the beautiful scenery. Perfect vaca house thank you 😊"
The price is €262
includes taxes & fees
29 Oct - 30 Oct
Budget Spacious townhome with Gigabit Internet
The Boomer: sky, river, and mtn your postage stamp for a week of relaxation!
7.4 out of 10, Good, (10)
"We enjoyed our stay while exploring the area. Will recommend most definitely."
The price is €167
includes taxes & fees
16 Oct - 17 Oct
The Boomer: sky, river, and mtn your postage stamp for a week of relaxation!
Luxurious cabin, 6 mi HM trails, 12 mi Charleston
10.0 out of 10, Exceptional, (33)
"Great location nice clean cabin great host "
The price is €194
includes taxes & fees
20 Oct - 21 Oct
Luxurious cabin, 6 mi HM trails, 12 mi Charleston
Rosie's Cabin is an authentic log cabin located just 10 minutes from Charleston.
10.0 out of 10, Exceptional, (12)
"The cabin was very well made with so many amenities. "
The price is €284
includes taxes & fees
29 Oct - 30 Oct
Rosie's Cabin is an authentic log cabin located just 10 minutes from Charleston.
Remodeled townhouse - 5 mins from Shawnee Sports Complex!
7.8 out of 10, Good, (12)
"It was very pleasant , comfortable and convenient."
The price is €178
includes taxes & fees
16 Oct - 17 Oct
Remodeled townhouse - 5 mins from Shawnee Sports Complex!
Travelers Rest slps 5 Riverview, near NRG, trails, fishing. NRG, Falls, & more.
7.8 out of 10, Good, (10)
"Area is beautiful! Loved looking at the river and mountains! Wasn’t crazy about the set up of the house. Was only 2 bedrooms with a sleeper couch and bathroom is off of main bedroom. Easy check-in and communication was excellent. "
The price is €177
includes taxes & fees
16 Oct - 17 Oct
Travelers Rest slps 5 Riverview, near NRG, trails, fishing. NRG, Falls, & more.
Walking Distance to Shawnee Soccer Complex
9.6 out of 10, Exceptional, (10)
"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."
The price is €255
includes taxes & fees
18 Oct - 19 Oct
Walking Distance to Shawnee Soccer Complex
Cozy & Convenient - 20 Minutes to Charleston WV
9.6 out of 10, Exceptional, (7)
"Everything about this property was amazing"
The price is €131
includes taxes & fees
19 Oct - 20 Oct
Cozy & Convenient - 20 Minutes to Charleston WV
Off grid Couples Cabin in Southern West Virginia
8.0 out of 10, Very good, (3)
"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 "
The price is €126
includes taxes & fees
20 Oct - 21 Oct
Off grid Couples Cabin in Southern West Virginia
Charming 2-bedroom Bungalow - Close to Everything!
9.6 out of 10, Exceptional, (21)
"Me and 2 friends stayed here for a weekend of dirtbike riding on July 4th and it was exactly what we needed "
The price is €164
includes taxes & fees
19 Oct - 20 Oct
Charming 2-bedroom Bungalow - Close to Everything!
Royal Retreat Downtown-Convention Center
8.8 out of 10, Excellent, (25)
"Good location "
The price is €186
includes taxes & fees
17 Oct - 18 Oct
Royal Retreat Downtown-Convention Center
Historical land mark Gauley Bridge 1893 train station
9.4 out of 10, Exceptional, (3)
"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. "
The price is €129
includes taxes & fees
23 Oct - 24 Oct
Historical land mark Gauley Bridge 1893 train station
Cute 2 bed 1 bath with off street parking
7.4 out of 10, Good, (9)
"We enjoyed our few days stay here. it had everything we needed and the neighborhood is quiet."
The price is €203
includes taxes & fees
15 Nov - 16 Nov
Cute 2 bed 1 bath with off street parking
Prayer Mountain-Off Grid Farm spot#2
The price is €101
includes taxes & fees
22 Oct - 23 Oct
Prayer Mountain-Off Grid Farm spot#2
Remote Mountain A-Frame with BBQ Perfect for Nature Lovers in West Virginia
2.0 star property
The price is €125
includes taxes & fees
20 Oct - 21 Oct
Remote Mountain A-Frame with BBQ Perfect for Nature Lovers in West Virginia
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 €126 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 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.