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Chesapeake Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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
10.0 out of 10, Exceptional, (32 reviews)
"It was a great place to stay."
United States
Mary Susan A.
The price is AED 349
AED 784 total
includes taxes & fees
27 Sep - 28 Sep
Cozy 2-bedroom apartment located next to St. Mary's Hospital!
Property grounds

2. 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)
"Great space for family gathering for our Marshall grad. Very cute, spacious and centrally located."
United States
Carrie S.
The price is AED 331
AED 1,076 total
includes taxes & fees
27 Sep - 28 Sep
Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes
Interior

3. The Park House A 5 Bedroom Retreat w/Game Room &

The Park House A 5 Bedroom Retreat w/Game Room &
Huntington
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful place, loved the decor and home away from home."
United States
Yvette H.
The price is AED 929
AED 2,525 total
includes taxes & fees
27 Sep - 28 Sep
The Park House A 5 Bedroom Retreat w/Game Room &
Dining

4. Huntington Modern History - 4BD, MU, DT, St Mary's

Huntington Modern History - 4BD, MU, DT, St Mary's
Huntington
10.0 out of 10, Exceptional, (12 reviews)
"It was a great, historic home. We loved how the owners have kept the original details and the space worked very well for a family of four. "
United States
Brian B.
The price is AED 784
AED 1,905 total
includes taxes & fees
27 Sep - 28 Sep
Huntington Modern History - 4BD, MU, DT, St Mary's
Interior

5. 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, (60 reviews)
"Very nice place to stay! We really enjoyed it! "
United States
Hannah M.
The price is AED 377
AED 706 total
includes taxes & fees
6 Oct - 7 Oct
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
Smart TV, fireplace

6. Espresso Maker & Modern Decor by Arena, University, Hospitals

Espresso Maker & Modern Decor by Arena, University, Hospitals
Huntington
10.0 out of 10, Exceptional, (3 reviews)
"The place was very cozy and had everything you would need for your stay"
United States
Kellie V.
The price is AED 342
AED 1,087 total
includes taxes & fees
27 Sep - 28 Sep
Espresso Maker & Modern Decor by Arena, University, Hospitals
Outdoor spa tub

7. 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, (14 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 511
AED 657 total
includes taxes & fees
27 Sep - 28 Sep
Charming Home with private Hot Tub and Fire Pit
Property grounds

8. 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 AED 264
AED 1,571 total
includes taxes & fees
27 Sep - 28 Sep
Cozy With A Little Touch of Love
Smart TV, fireplace

9. 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 AED 345
AED 1,092 total
includes taxes & fees
27 Sep - 28 Sep
Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital
Smart TV, video games

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

Convenient 1-BR - Fenced Backyard - Extended Stays wanted
Huntington
8.0 out of 10, Very good, (1 review)
The price is AED 213
AED 942 total
includes taxes & fees
28 Sep - 29 Sep
Convenient 1-BR - Fenced Backyard - Extended Stays wanted
Exterior detail

11. The Chessie Room - Historic Boutique Stay at Heritage Station

The Chessie Room - Historic Boutique Stay at Heritage Station
Huntington
The price is AED 545
AED 695 total
includes taxes & fees
1 Oct - 2 Oct
The Chessie Room - Historic Boutique Stay at Heritage Station
Smart TV, fireplace, books

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

Historic & Chic apartment by Arena, University, Hospital - Dog Friendly
Huntington
9.6 out of 10, Exceptional, (8 reviews)
"Very nicely decorated, cozy and clean."
United States
Yvette H.
The price is AED 375
AED 1,125 total
includes taxes & fees
5 Oct - 6 Oct
Historic & Chic apartment by Arena, University, Hospital - Dog Friendly
Smart TV

13. Entire Bldg w/6 Bedrooms across 4 Separate Apts - Group/Corporate Stay Downtown

Entire Bldg w/6 Bedrooms across 4 Separate Apts - Group/Corporate Stay Downtown
Huntington
The price is AED 2,020
AED 5,095 total
includes taxes & fees
27 Oct - 28 Oct
Entire Bldg w/6 Bedrooms across 4 Separate Apts - Group/Corporate Stay Downtown
Coffee/tea maker, fridge, microwave, oven

14. 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, (22 reviews)
"Great place to stay. Very modern and comfortable. Philip is a nice guy to deal with."
United States
Paul M.
The price is AED 364
AED 681 total
includes taxes & fees
29 Sep - 30 Sep
Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland
Outdoor dining

15. 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 624
AED 1,125 total
includes taxes & fees
3 Oct - 4 Oct
Cozy Fonzie Flat
Exterior

16. THE LUXURY CABIN IN THE WOODS

THE LUXURY CABIN IN THE WOODS
Catlettsburg
10.0 out of 10, Exceptional, (241 reviews)
"Host was great with communication, check in was a breeze and the property was beautiful. We caught about 30 fish in total between my husband and I. We will definitely be back!"
United States
Whitney M.
The price is AED 559
AED 1,102 total
includes taxes & fees
27 Sep - 28 Sep
THE LUXURY CABIN IN THE WOODS
TV, fireplace, books

17. 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)
"Enjoyed all the comfort of home."
United States
scott j.
The price is AED 511
AED 1,105 total
includes taxes & fees
4 Oct - 5 Oct
La'Chic Boutique Bungalow 3 Beds/1.5Baths
Property grounds

18. 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, (127 reviews)
"This was a great getaway with everything you could need great place for couples and family's."
United States
Andrew B.
The price is AED 463
AED 794 total
includes taxes & fees
27 Sep - 28 Sep
The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.
Interior

19. Charming 3BR Home - Near KDMC & Downtown

Charming 3BR Home - Near KDMC & Downtown
Ashland
8.8 out of 10, Excellent, (6 reviews)
"It was in a quiet neighborhood. The beds were comfortable."
United States
Judi
The price is AED 312
AED 621 total
includes taxes & fees
28 Sep - 29 Sep
Charming 3BR Home - Near KDMC & Downtown
Interior

20. 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 AED 1,074
AED 2,197 total
includes taxes & fees
29 Sep - 30 Sep
Spacious Historic 5-bedroom house in charming Barboursville with AC
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

8/10 Good
"nice property. parking is confusing"
Jennifer 1-night trip
Posted 23 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.