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Chesapeake Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Chesapeake vacation rentals

TV

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

Cozy 2-bedroom apartment located next to St. Mary's Hospital!
Huntington
9.8 out of 10, Exceptional, (25 reviews)
"Beautiful place to stay. Exceptionally clean. Comfortable beds. Really enjoyed our stay."
United States
Sherry
The price is ￥15,520
￥35,229 total
includes taxes & fees
Jul 31 - Aug 1
Cozy 2-bedroom apartment located next to St. Mary's Hospital!
Smart TV, fireplace, books

2. 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.
Historic & Chic apartment by Arena, University, Hospital - Dog Friendly
Property grounds

3. 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, (15 reviews)
"Lovely and quiet location, comfortable, most stocked VRBO we’ve ever stayed in!"
United States
Lesly-Marie
The price is ￥19,849
￥50,701 total
includes taxes & fees
Aug 12 - Aug 13
The Blue House – Eclectic Art Haven Near Marshall & Huntington’s Best Parks
Interior

4. 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, (53 reviews)
"Very nice place to stay! We really enjoyed it! "
United States
Hannah M.
The price is ￥17,693
￥32,602 total
includes taxes & fees
Aug 10 - Aug 11
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
Property grounds

5. 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 ￥16,664
￥52,815 total
includes taxes & fees
Aug 24 - Aug 25
Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes
Outdoor spa tub

6. Charming Home with private Hot Tub and Fire Pit

Charming Home with private Hot Tub and Fire Pit
South Point
10.0 out of 10, Exceptional, (10 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 ￥22,708
￥29,570 total
includes taxes & fees
Aug 2 - Aug 3
Charming Home with private Hot Tub and Fire Pit
Smart TV, fireplace

7. 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 ￥15,193
￥48,880 total
includes taxes & fees
Aug 2 - Aug 3
Espresso Maker & Modern Decor by Arena, University, Hospitals
Smart TV, video games

8. Convenient 1-BR - Fenced Backyard - Extended Stays wanted

Convenient 1-BR - Fenced Backyard - Extended Stays wanted
Huntington
The price is ￥13,723
￥48,442 total
includes taxes & fees
Aug 2 - Aug 3
Convenient 1-BR - Fenced Backyard - Extended Stays wanted
Property grounds

9. 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 ￥11,109
￥72,984 total
includes taxes & fees
Aug 13 - Aug 14
Cozy With A Little Touch of Love
Coffee/tea maker, fridge, microwave, oven

10. 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, (21 reviews)
"Very nice property and reasonably priced. Great property manager! "
United States
Kathy M.
The price is ￥13,070
￥25,716 total
includes taxes & fees
Jul 31 - Aug 1
Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland
TV, fireplace, books

11. La'Chic Boutique Bungalow 3 Beds/1.5Baths

La'Chic Boutique Bungalow 3 Beds/1.5Baths
Ashland
9.4 out of 10, Exceptional, (29 reviews)
"Cozy, clean house. Will rent again. "
United States
C. Loden A.
The price is ￥20,585
￥48,384 total
includes taxes & fees
Aug 29 - Aug 30
La'Chic Boutique Bungalow 3 Beds/1.5Baths
Smart TV, fireplace

12. Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital

Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital
Huntington
8.8 out of 10, Excellent, (3 reviews)
"Property was exactly as described. Wish we would have found it sooner. Will definitely be back. Nice cozy place and very affordable. "
United States
richie k.
The price is ￥15,193
￥49,579 total
includes taxes & fees
Aug 23 - Aug 24
Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital
Exterior

13. THE LUXURY CABIN IN THE WOODS

THE LUXURY CABIN IN THE WOODS
Catlettsburg
10.0 out of 10, Exceptional, (237 reviews)
"it made our golf trip really great"
United States
Dennis H.
The price is ￥24,996
￥51,330 total
includes taxes & fees
Aug 11 - Aug 12
THE LUXURY CABIN IN THE WOODS
Outdoor dining

14. 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, (13 reviews)
"We really enjoyed our stay, perfect location for a visit to that part of Kentucky."
United States
Melinda K.
The price is ￥16,337
￥32,597 total
includes taxes & fees
Aug 4 - Aug 5
Charming 2-bedroom house located in beautiful wooded setting!
Property grounds

15. 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, (125 reviews)
"This was our 2nd stay in the cozy cabin. It's a favorite of ours and we'll definitely return!"
United States
Michael S.
The price is ￥20,585
￥35,840 total
includes taxes & fees
Aug 2 - Aug 3
The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.
Outdoor dining

16. 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 ￥27,773
￥52,252 total
includes taxes & fees
Aug 4 - Aug 5
Cozy Fonzie Flat
Living area

17. Corner Cottage 2 bedroom pets welcome and close to downtown

Corner Cottage 2 bedroom pets welcome and close to downtown
Ashland
9.0 out of 10, Wonderful, (4 reviews)
"The host communicated promptly about pet friendly place. Home was great for my stay and needs."
United States
Jennifer A.
The price is ￥29,407
￥54,476 total
includes taxes & fees
Aug 9 - Aug 10
Corner Cottage 2 bedroom pets welcome and close to downtown
Interior

18. Charming 3BR Home - Near KDMC & Downtown

Charming 3BR Home - Near KDMC & Downtown
Ashland
8.0 out of 10, Very Good, (1 review)
"Very quiet location. The beds were super comfortable. Lots of room and close to restaurants. I messaged the host about check out and they responded within minutes. I would stay here again when we return."
United States
Shelia C.
The price is ￥12,906
￥24,572 total
includes taxes & fees
Aug 13 - Aug 14
Charming 3BR Home - Near KDMC & Downtown
Interior

19. Spacious Historic 5-bedroom house in charming Barboursville with AC

Spacious Historic 5-bedroom house in charming Barboursville with AC
Barboursville
10.0 out of 10, Exceptional, (2 reviews)
"Very cozy and nice place!"
United States
Joseph S.
The price is ￥50,285
￥105,107 total
includes taxes & fees
Aug 26 - Aug 27
Spacious Historic 5-bedroom house in charming Barboursville with AC
Property grounds

20. Secluded Ohio Forest Escape at Fuller's Fifty

Secluded Ohio Forest Escape at Fuller's Fifty
Patriot
10.0 out of 10, Exceptional, (92 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 ￥14,997
￥31,007 total
includes taxes & fees
Aug 3 - Aug 4
Secluded Ohio Forest Escape at Fuller's Fifty
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

Rodeway Inn

Rodeway Inn

8/10 Good
"Very nice motel, courteous staff, but there was no coffee maker in the room, the wifi code was not offered and loud noises in the back parking at night."
Mary Anne 3-night trip
Posted 12 hours ago
Rodeway Inn

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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Look no further and take a look at our great range of rental properties in Chesapeake!

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?

Charming 3BR Home - Near KDMC & Downtown: This vacation home rental outside of Chesapeake is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.