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Vacation rentals in Chesapeake

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Top-rated vacation rentals in Chesapeake

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Home in Charleston

4.88 out of 5 average rating, 267 reviews

Historic Farmhouse by Nature Preserve

We welcome you to The Little House, sensitively restored and superbly furnished. Enjoy entire house and its 2.7 acres, adjacent to 52 acres of walking trails, while still in the heart of town. Ideal for nature-seekers and business travelers alike. Calm, quiet environs in which to read a book, or write one. One loft bedroom with one full bed + one (30" x 70") daybed. One pull-out loveseat in sitting room; 2 stored iBeds. Note all bedding details under Space. Re: pets: one dog allowed. No cats.

Sep 1 – 8

G$27,377 GYD per night

Guesthouse in Hurricane

4.98 out of 5 average rating, 105 reviews

Mountain Momma Homestead Cottage

A quaint studio guest house located in one of the many hollers of West Virginia. Less than 1 mile from I64, the house is roughly 300 sq. feet, centrally located between Charleston, New River Gorge, and Huntington. This guest house is equip with an outdoor space that includes a firepit and grill. It is located close to the main living quarters, but it is disconnected. The main living quarters do have dogs that are well behaved and quiet. If there are any questions, please feel free to reach out.

Feb 25 – Mar 4

G$16,765 GYD per night

Place to stay in Cross Lanes

4.96 out of 5 average rating, 139 reviews

Spectacular Storage Unit! 😉 Just Off I-64

Have you ever wondered what it would be like to stay overnight in a mini-storage? Probably not, lol! But if you've ever watched HGTV, you'll see that people across the country are creating short-term rentals out of all kinds of crazy things, from shipping containers and barns, to old warehouses. Well, in Cross Lanes WV, we took our cues from those folks on TV and created a short-term rental out of a storage unit! Conveniently located, just off I64, and only 1 mile to the Mardi Gras Casino.

Jul 10 – 17

G$18,251 GYD per night

Cottage in Charleston

4.87 out of 5 average rating, 183 reviews

Hunt Cottage-3 Miles from Downtown Charleston

Charming, remodeled private cottage completely surrounded by West Virginia nature! No neighbors in sight and less than 2 miles from I-64. Enjoy the peace and quiet of a cottage in the mountains only 3 miles from all bars, restaurants, and entertainment! Convenient to: CAMC General (2.5 miles) CAMC Memorial (5.3 miles) Thomas Memorial (7.7 miles) Airport (6.6 miles) Charleston Coliseum and Convention-Center (2.1 miles) University of Charleston (6.1 miles) Mardi Gras Casino (14 miles/20 minutes)

Mar 17 – 24

G$24,326 GYD per night

Guesthouse in Charleston

4.93 out of 5 average rating, 142 reviews

The Bear BnB - Pet friendly, 5 mins to downtown

Take it easy at this almost heaven hideaway. This adorable, Bear themed loft gives you the country setting you’re looking for and the convenience you need. Located just 5 minutes from downtown Charleston and just 3 minutes from Yeager Airport. Enjoy the peace and quiet of nature or hop downtown for an array of shopping and eatery selections. Tour the West Virginia State Capitol topped with its gorgeous gold dome or dive into WVs many adventures. Business or pleasure, you’ll love the Bear BNB.

Oct 17 – 24

G$25,415 GYD per night

Farm stay in Walton

4.94 out of 5 average rating, 196 reviews

Romantic Rustic Roost in Woodland Paradise

Only 40 minutes from the State Capitol, but delightfully secluded, the Rustic Roost is a converted cellarhouse transformed into a charming Glamping suite, located on a gorgeous 100 acre forest farm. Features include a queen size bed, mini-kitchenette, private deck and grilling area, fire pit, and a rather adorable "hillbilly en-suite" private bathroom. The property touts pristine mountain woodlands, fishing pond, myriad streams and creeks, and a magical waterfall grotto begging to be explored!

Aug 20 – 27

G$23,099 GYD per night

Cottage in Charleston

4.93 out of 5 average rating, 279 reviews

Peace Like A River

Freshly remodeled 2 bedroom cottage in North Charleston, West Virginia. Unwind with games, puzzles and books or take a hot bath in the claw-foot tub. You won't miss the TV when you can watch the sunset on the wrap around porch overlooking the Kanawha River. High-Speed Internet access is available to stay connected. You will be 10 minutes to The Charleston Coliseum and Appalachian Power Park. The Shawnee Sports Complex and WVSU are 7 minutes away. Come experience Peace Like a River!

Sep 8 – 15

G$23,274 GYD per night

Home in Charleston

4.83 out of 5 average rating, 24 reviews

Nature's Charm in Charleston

Welcome to our charming retreat near downtown Charleston, WV. Enjoy city life and peaceful woodland surroundings. Our cozy home offers a full-size bed, couch, 2 big TVs, free Wi-Fi, keyless entry and you can park two cars. Relax amid West Virginia's natural beauty, not far from Kanawha State Forest, or travel downtown for exciting events like Live on the Levee. We have complimentary coffee, snacks, popcorn, movies, bathroom amenities, a washer/dryer with detergent, and fabric softener.

Sep 10 – 17

G$11,417 GYD per night

Apartment in Charleston

4.97 out of 5 average rating, 106 reviews

Enjoy our Cozy Garage Apartment

You will love staying in this one bedroom garage apartment, located in the neighborhood of Kanawha City, in the south east section of Charleston , West Virginia. Situated on the Kanawha River, we are minutes from grocery stores and restaurants. We are less than 10 miles from downtown Charleston which has a lot to offer in cultural experiences and locally owned restaurants and businesses. Enjoy the neighborhood feel and enjoy the view of the mountains and the beautiful river.

Sep 25 – Oct 2

G$14,960 GYD per night

Home in Belle

4.94 out of 5 average rating, 62 reviews

Entire House with River Access/4.5 m to Charleston

Unwind in the serenity of this beautiful home, situated in the heart of the Appalachian Mountains, where you can gaze at the breathtaking Kanawha River and mountainous backdrop from the comfort of a covered patio. Includes access to the river for fishing or kayaking (gear not included). Minutes away from historic Charleston, offering a balance of access to city attractions with a scenic place to rest after adventuring. Close to Interstates 64, 77, and 79. No cleaning fee.

Mar 6 – 13

G$34,301 GYD per night

Place to stay in Edmond

4.94 out of 5 average rating, 190 reviews

The Eryie at Beauty Mountain

Located in the Heart of the New River Gorge National Park, this cozy, one bedroom loft has everything you need to relax after a long day of adventuring. Sleeps 4 with one bedroom with a full size bed and a seperate space with a single cot size bed. Also has a couch for a fourth guest. Fully stocked kitchen, and bathroom with fresh linens for your convenience. All beds have memory foam mattresses with washable mattress protectors. Enjoy the 50 inch flat screen Smart Tv.

Dec 13 – 20

G$19,376 GYD per night

Farm stay in Fayetteville

4.97 out of 5 average rating, 242 reviews

Gorgeous Guesthouse at Five Springs Farm

This charming farmhouse is the perfect retreat from which to stage your New River Gorge adventure. Built in 1850, this newly renovated farmhouse sits on a 171 acre working farm with stunning views. This is the only farm stay on a working farm in the Fayetteville area, is 10 minutes to town, and very close to all the area's amenities. It offers a quiet peaceful retreat to unwind and relax at the end of your busy day!

Mar 22 – 29

G$34,546 GYD per night

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Popular amenities for Chesapeake vacation rentals

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Other great vacation rentals in Chesapeake

Home in Charleston

4.92 out of 5 average rating, 24 reviews

Kanawha City House

Apr 28 – May 5

G$20,318 GYD per night

Guest suite in Charleston

4.84 out of 5 average rating, 57 reviews

Retreat in the mountains with new hot tub & deck.

May 29 – Jun 5

G$26,160 GYD per night

Home in Charleston

5.0 out of 5 average rating, 32 reviews

Venable single family house

May 2 – 9

G$20,739 GYD per night

Apartment in South Charleston

5.0 out of 5 average rating, 22 reviews

An All-Access Bookstore Vacation

Sep 27 – Oct 4

G$22,057 GYD per night

Home in Dunbar

4.96 out of 5 average rating, 97 reviews

Cozy bungalow in a quiet neighborhood

Oct 12 – 19

G$19,757 GYD per night

Apartment in Charleston

4.96 out of 5 average rating, 26 reviews

Easy walk to CAMC-2 BR Apt-Pet Friendly

Sep 12 – 19

G$20,068 GYD per night

Home in South Charleston

4.98 out of 5 average rating, 51 reviews

Wooded setting 10 mins to Charleston

Jan 27 – Feb 3

G$22,710 GYD per night

Cabin in Alum Creek

5.0 out of 5 average rating, 15 reviews

Cozy cabin, 6 mi HM trails, 12 mi Charleston

Aug 12 – 19

G$31,589 GYD per night

Destinations to explore