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Chesapeake Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Chesapeake vacation rentals

Fridge, microwave, oven, stovetop

Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland

Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland
Ashland
10.0 out of 10, Exceptional, (17 reviews)
"Had a great stay! Cool town!"
United States
Noah S.
The price is ￥12,939
￥25,459 total
includes taxes & fees
Jun 29 - Jun 30
Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland
Property grounds

Secluded Ohio Forest Escape at Fuller's Fifty

Secluded Ohio Forest Escape at Fuller's Fifty
Patriot
10.0 out of 10, Exceptional, (90 reviews)
"We really enjoyed the cabin. The host made us feel welcomed and was really nice and helpful. It’s the perfect couple getaway when you want to be secluded and enjoy nature. "
United States
Roynette
The price is ￥14,993
￥30,682 total
includes taxes & fees
Jul 8 - Jul 9
Secluded Ohio Forest Escape at Fuller's Fifty
TV

Cozy 2-bedroom apartment located next to St. Mary's Hospital!

Cozy 2-bedroom apartment located next to St. Mary's Hospital!
Huntington
10.0 out of 10, Exceptional, (22 reviews)
"Great place, clean cozy love the 2 bathrooms!!"
United States
Katherine D.
The price is ￥15,365
￥35,050 total
includes taxes & fees
Jun 29 - Jun 30
Cozy 2-bedroom apartment located next to St. Mary's Hospital!
Smart TV, video games

Convenient 1-BR - Fenced Backyard - Extended Stays wanted

Convenient 1-BR - Fenced Backyard - Extended Stays wanted
Huntington
The price is ￥7,765
￥40,351 total
includes taxes & fees
Jul 27 - Jul 28
Convenient 1-BR - Fenced Backyard - Extended Stays wanted
Outdoor dining

Large Cabin with Stunning View - Fire Pit, Relax & Unwind

Large Cabin with Stunning View - Fire Pit, Relax & Unwind
Gallipolis
9.8 out of 10, Exceptional, (50 reviews)
"Great river view. Beds are comfy."
United States
Rebecca G.
The price is ￥15,867
￥25,408 total
includes taxes & fees
Jul 1 - Jul 2
Large Cabin with Stunning View - Fire Pit, Relax & Unwind
Smart TV, fireplace

Espresso Maker & Modern Decor by Arena, University, Hospitals

Espresso Maker & Modern Decor by Arena, University, Hospitals
Huntington
10.0 out of 10, Exceptional, (1 review)
"Would recommend staying here to anyone! The host was gracious and accurate in response time to questions. Made us feel like we were at home! "
United States
Ashley H.
The price is ￥15,046
￥49,790 total
includes taxes & fees
Jul 16 - Jul 17
Espresso Maker & Modern Decor by Arena, University, Hospitals
Property grounds

Rush Creek Camp, Lot # 03

Rush Creek Camp, Lot # 03
Rush
The price is ￥8,087
￥12,841 total
includes taxes & fees
Jul 4 - Jul 5
Rush Creek Camp, Lot # 03
Outdoor dining

Charming 2-bedroom house located in beautiful wooded setting!

Charming 2-bedroom house located in beautiful wooded setting!
Raceland
10.0 out of 10, Exceptional, (11 reviews)
"We really enjoyed our stay, perfect location for a visit to that part of Kentucky."
United States
Melinda K.
The price is ￥16,174
￥32,272 total
includes taxes & fees
Jun 29 - Jun 30
Charming 2-bedroom house located in beautiful wooded setting!
Interior

2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.

2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
Kenova
10.0 out of 10, Exceptional, (50 reviews)
"Very nice place to stay! We really enjoyed it! "
United States
Hannah M.
The price is ￥17,516
￥32,448 total
includes taxes & fees
Jun 30 - Jul 1
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
Outdoor spa tub

Pointer Palace

Pointer Palace
South Point
10.0 out of 10, Exceptional, (9 reviews)
"The cleanliness and the small special items example the bottle of wine and snacks if we wanted them. Will definitely stay here again if we travel that way. "
United States
Elizabeth C.
The price is ￥13,586
￥20,056 total
includes taxes & fees
Jul 2 - Jul 3
Pointer Palace
3 bedrooms, iron/ironing board, free WiFi, bed sheets

The Black Nest • Modern Duplex w/ Porch

The Black Nest • Modern Duplex w/ Porch
Ashland
The price is ￥14,395
￥26,213 total
includes taxes & fees
Jul 28 - Jul 29
The Black Nest • Modern Duplex w/ Porch
Exterior detail

Carroll Manor: RecentlyRenovated English Tutor. Sleeps 8

Carroll Manor: RecentlyRenovated English Tutor. Sleeps 8
Ashland
9.6 out of 10, Exceptional, (14 reviews)
"Loved the decor… the house was spacious and comfortable! Our stay was fantastic!"
United States
Tom H.
The price is ￥26,063
￥77,171 total
includes taxes & fees
Jun 28 - Jun 29
Carroll Manor: RecentlyRenovated English Tutor. Sleeps 8
Property grounds

The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.

The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.
Catlettsburg
10.0 out of 10, Exceptional, (124 reviews)
"Cozy Cabin is great. Highly recommend!"
United States
Jason M.
The price is ￥20,379
￥35,660 total
includes taxes & fees
Jul 8 - Jul 9
The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.
Exterior

THE LUXURY CABIN IN THE WOODS

THE LUXURY CABIN IN THE WOODS
Catlettsburg
10.0 out of 10, Exceptional, (233 reviews)
"Perfect weather enjoyed our stay "
United States
Kris C.
The price is ￥26,056
￥52,973 total
includes taxes & fees
Jul 8 - Jul 9
THE LUXURY CABIN IN THE WOODS
Property grounds

The Bunkhouse

The Bunkhouse
Crown City
10.0 out of 10, Exceptional, (29 reviews)
"We really enjoyed staying there. The fishing was good. It was a very clean place to stay"
United States
Jennifer R.
The price is ￥22,742
￥35,717 total
includes taxes & fees
Jul 1 - Jul 2
The Bunkhouse
Property grounds

Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes

Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes
Huntington
9.6 out of 10, Exceptional, (8 reviews)
"Welcoming and clean. It has those little touches that made the stay even more enjoyable. Host responded to any questions. Would definitely stay again!"
United States
MARIANNE A.
The price is ￥15,365
￥50,315 total
includes taxes & fees
Jul 8 - Jul 9
Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes
Property grounds

Cozy With A Little Touch of Love

Cozy With A Little Touch of Love
Huntington
7.8 out of 10, Good, (6 reviews)
"Had a nice weekend stay here while in Huntington working. It was nice an quiet! Landlord was great!"
United States
Amanda P.
The price is ￥11,648
￥73,005 total
includes taxes & fees
Jul 10 - Jul 11
Cozy With A Little Touch of Love
Smart TV, fireplace

Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital

Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital
Huntington
8.8 out of 10, Excellent, (3 reviews)
"Everything was clean, tidy and pet friendly! We did have a little trouble with the lock, but the host took care of that right away. It was at times a little noisy but the sound spas helped with that. It was conveniently close to restaurants, we could walk to McDonald's for breakfast and coffee. Over all we enjoyed our stay!"
United States
Melissa K.
The price is ￥15,042
￥49,085 total
includes taxes & fees
Jul 28 - Jul 29
Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital
Fridge, microwave, oven, stovetop

Secluded ranch home

Secluded ranch home
Ashland
10.0 out of 10, Exceptional, (19 reviews)
"Another great stay"
United States
Alix E.
The price is ￥28,312
￥52,479 total
includes taxes & fees
Jun 29 - Jun 30
Secluded ranch home
Smart TV, fireplace, books

Historic & Chic apartment by Arena, University, Hospital - Dog Friendly

Historic & Chic apartment by Arena, University, Hospital - Dog Friendly
Huntington
9.8 out of 10, Exceptional, (7 reviews)
"Comfortable convenient to everything. It was a home away from home."
United States
Kimberly M.
The price is ￥16,497
￥52,287 total
includes taxes & fees
Jul 27 - Jul 28
Historic & Chic apartment by Arena, University, Hospital - Dog Friendly
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

Fairfield Inn & Suites by Marriott Huntington

Fairfield Inn & Suites by Marriott Huntington

10/10 Excellent
"Very nice breakfast selections."
Linda 1-night trip
Posted 6 hours ago
Fairfield Inn & Suites by Marriott Huntington

Find out more about Chesapeake

Search for holiday rentals in Chesapeake on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesapeake using one of the methods below:

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Frequently asked questions

Can I find a vacation rental in Chesapeake?

Yes, we give you a choice of vacation rentals close to the most popular local attractions in Chesapeake, or you can select a more secluded option if you'd like a relaxing place to stay.

What's the top vacation rental in Chesapeake?

2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.: This vacation home rental outside of Chesapeake is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

What can I see and do in Chesapeake?

Explore the area and family-friendly sights such as Camden Park Amusement Park, or get out into nature at a spot like Ohio River Valley. In the larger area, you’ll find Mountain Health Arena and Pullman Square.

What are vacation rentals like in Chesapeake?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Chesapeake. Vacation rentals offer extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for small groups.