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Chesapeake Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

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, (26 reviews)
"Beautiful place to stay. Exceptionally clean. Comfortable beds. Really enjoyed our stay."
United States
Sherry
The price is AED 349
AED 804 total
includes taxes & fees
15 Aug - 16 Aug
Cozy 2-bedroom apartment located next to St. Mary's Hospital!
Smart TV, fireplace

2. 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 AED 325
AED 1,123 total
includes taxes & fees
12 Aug - 13 Aug
Espresso Maker & Modern Decor by Arena, University, Hospitals
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, (16 reviews)
"Lovely and quiet location, comfortable, most stocked VRBO we’ve ever stayed in!"
United States
Lesly-Marie
The price is AED 397
AED 1,076 total
includes taxes & fees
19 Aug - 20 Aug
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, (54 reviews)
"Very nice place to stay! We really enjoyed it! "
United States
Hannah M.
The price is AED 377
AED 710 total
includes taxes & fees
10 Sep - 11 Sep
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)
"Great space for family gathering for our Marshall grad. Very cute, spacious and centrally located."
United States
Carrie S.
The price is AED 360
AED 1,171 total
includes taxes & fees
25 Aug - 26 Aug
Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes
Dining

6. Huntington Modern - Mins to DT, MU, St. Mary's

Huntington Modern - Mins to DT, MU, St. Mary's
Huntington
10.0 out of 10, Exceptional, (13 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.
Huntington Modern - Mins to DT, MU, St. Mary's
Smart TV, fireplace, books

7. 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)
"We had an amazing time. This cute apartment was so nice. Next visit, will have to go back and stay..Shari from Michigan "
United States
Shari W.
The price is AED 404
AED 1,225 total
includes taxes & fees
9 Sep - 10 Sep
Historic & Chic apartment by Arena, University, Hospital - Dog Friendly
Smart TV, fireplace

8. 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 325
AED 1,123 total
includes taxes & fees
12 Aug - 13 Aug
Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital
Outdoor spa tub

9. 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, (11 reviews)
"House was very clean and was in a quiet neighborhood. Enjoyed the hot tub after a day of baseball. Would definitely stay here again. "
United States
Karl S.
The price is AED 522
AED 680 total
includes taxes & fees
1 Sep - 2 Sep
Charming Home with private Hot Tub and Fire Pit
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, (22 reviews)
"Very nice property and reasonably priced. Great property manager! "
United States
Kathy M.
The price is AED 294
AED 578 total
includes taxes & fees
13 Aug - 14 Aug
Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland
Property grounds

11. 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 250
AED 1,641 total
includes taxes & fees
10 Sep - 11 Sep
Cozy With A Little Touch of Love
TV, fireplace, books

12. 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 AED 426
AED 1,054 total
includes taxes & fees
25 Aug - 26 Aug
La'Chic Boutique Bungalow 3 Beds/1.5Baths
Outdoor dining

13. 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, (16 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 737 total
includes taxes & fees
13 Aug - 14 Aug
Charming 2-bedroom house located in beautiful wooded setting!
Interior

14. 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 AED 290
AED 552 total
includes taxes & fees
23 Aug - 24 Aug
Charming 3BR Home - Near KDMC & Downtown
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 AED 463
AED 814 total
includes taxes & fees
14 Aug - 15 Aug
The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.
Exterior

16. 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 AED 559
AED 1,167 total
includes taxes & fees
12 Aug - 13 Aug
THE LUXURY CABIN IN THE WOODS
Outdoor dining

17. 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, (54 reviews)
"We loved the place—very quiet and super clean."
United States
Betsy L.
The price is AED 327
AED 543 total
includes taxes & fees
13 Aug - 14 Aug
Large Cabin with Stunning View - Fire Pit, Relax & Unwind
Outdoor dining

18. 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 1,191 total
includes taxes & fees
12 Aug - 13 Aug
Cozy Fonzie Flat
Desk, iron/ironing board, WiFi, bed sheets

19. 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 811 total
includes taxes & fees
7 Sep - 8 Sep
The Bunkhouse
Living area

20. 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 AED 661
AED 1,237 total
includes taxes & fees
8 Sep - 9 Sep
Corner Cottage 2 bedroom pets welcome and close to downtown
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

8/10 Good
"Door was super hard to open and very loud. Door to bathroom also barely opened - got stuck on floor. Other than that, quiet hotel and comfy beds."
Stephanie 1-night trip
Posted 2 hours ago
Fairfield Inn & Suites by Marriott 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?

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.