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Chesapeake Vacation Rentals

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Check prices for these dates

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

Our top choices for Chesapeake vacation rentals

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 AED 350
AED 707 total
includes taxes & fees
7 Jul - 8 Jul
Secluded Ohio Forest Escape at Fuller's Fifty
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 AED 360
AED 577 total
includes taxes & fees
29 Jun - 30 Jun
Large Cabin with Stunning View - Fire Pit, Relax & Unwind
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 AED 349
AED 800 total
includes taxes & fees
28 Jun - 29 Jun
Cozy 2-bedroom apartment located next to St. Mary's Hospital!
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 AED 463
AED 798 total
includes taxes & fees
30 Jun - 1 Jul
The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.
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 AED 398
AED 737 total
includes taxes & fees
30 Jun - 1 Jul
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
Outdoor dining

Charming 2-bedroom house located in beautiful wooded setting!

Charming 2-bedroom house located in beautiful wooded setting!
Raceland
9.8 out of 10, Exceptional, (10 reviews)
"We really enjoyed our stay, perfect location for a visit to that part of Kentucky."
United States
Melinda K.
The price is AED 367
AED 729 total
includes taxes & fees
27 Jun - 28 Jun
Charming 2-bedroom house located in beautiful wooded setting!
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 AED 294
AED 578 total
includes taxes & fees
2 Jul - 3 Jul
Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland
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 AED 516
AED 807 total
includes taxes & fees
26 Jun - 27 Jun
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 AED 349
AED 1,143 total
includes taxes & fees
8 Jul - 9 Jul
Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes
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 AED 334
AED 481 total
includes taxes & fees
30 Jun - 1 Jul
Pointer Palace
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 AED 592
AED 1,203 total
includes taxes & fees
8 Jul - 9 Jul
THE LUXURY CABIN IN THE WOODS
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 AED 327
AED 595 total
includes taxes & fees
13 Jul - 14 Jul
The Black Nest • Modern Duplex w/ Porch
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 AED 643
AED 1,191 total
includes taxes & fees
29 Jun - 30 Jun
Secluded ranch home
TV, DVD player, books

Whispering Pine's Cabin! NO CHECK-OUT LIST

Whispering Pine's Cabin! NO CHECK-OUT LIST
Patriot
10.0 out of 10, Exceptional, (1 review)
"Loved everything about this well kept cabin. The property is beautiful and secluded, but easily accessible. The cabin is comfortable and very thoughtfully stocked (in particular, the kitchen has every gadget, pot, pan, seasoning, coffee, creamer, you name it). The host, Kathy, is friendly and helpful. Will definitely be back and recommending to friends and family!"
United States
R
The price is AED 735
AED 1,748 total
includes taxes & fees
12 Jul - 13 Jul
Whispering Pine's Cabin! NO CHECK-OUT LIST
Outdoor dining

Cozy Fonzie Flat

Cozy Fonzie Flat
Ashland
10.0 out of 10, Exceptional, (1 review)
"It was a very pleasant stay, it was well maintained and clean. The property manager answered my questions quickly and efficiently,also was very professional. As a Veteran it was nice to have a place that accepts pets. "
United States
James F.
The price is AED 569
AED 1,117 total
includes taxes & fees
28 Jun - 29 Jun
Cozy Fonzie Flat
Property grounds

Rush Creek Camp, Lot # 03

Rush Creek Camp, Lot # 03
Rush
The price is AED 184
AED 292 total
includes taxes & fees
18 Jul - 19 Jul
Rush Creek Camp, Lot # 03
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 AED 592
AED 1,748 total
includes taxes & fees
26 Jun - 27 Jun
Carroll Manor: RecentlyRenovated English Tutor. Sleeps 8
Living area

Corner Cottage 2 bedroom pets welcome and close to downtown

Corner Cottage 2 bedroom pets welcome and close to downtown
Ashland
9.4 out of 10, Exceptional, (3 reviews)
"The host communicated promptly about pet friendly place. Home was great for my stay and needs."
United States
Jennifer A.
The price is AED 569
AED 1,104 total
includes taxes & fees
7 Jul - 8 Jul
Corner Cottage 2 bedroom pets welcome and close to downtown
Property grounds

The Blue House – Eclectic Art Haven Near Marshall & Huntington’s Best Parks

The Blue House – Eclectic Art Haven Near Marshall & Huntington’s Best Parks
Huntington
10.0 out of 10, Exceptional, (13 reviews)
"Lovely and quiet location, comfortable, most stocked VRBO we’ve ever stayed in!"
United States
Lesly-Marie
The price is AED 551
AED 1,274 total
includes taxes & fees
12 Jul - 13 Jul
The Blue House – Eclectic Art Haven Near Marshall & Huntington’s Best Parks
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

DoubleTree by Hilton Huntington

DoubleTree by Hilton Huntington

10/10 Excellent
"Arrived VERY late and was so impressed and thankful that security met me in the parking garage to ensure my safety back into the hotel. THANK YOU!!"
Nancy 1-night trip
Posted 5 hours ago
DoubleTree by Hilton Huntington

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.