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Chesapeake Holiday Rentals

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Our top choices for Chesapeake holiday rentals

1. 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 HK$800
HK$2,536 total
includes taxes & fees
20 Sept - 21 Sept
Historic & Chic apartment by Arena, University, Hospital - Dog Friendly

2. 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 HK$1,985
HK$5,704 total
includes taxes & fees
20 Sept - 21 Sept
The Park House A 5 Bedroom Retreat w/Game Room &

3. 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, (31 reviews)
"It was a great place to stay."
United States
Mary Susan A.
The price is HK$745
HK$1,692 total
includes taxes & fees
20 Sept - 21 Sept
Cozy 2-bedroom apartment located next to St. Mary's Hospital!

4. The Blue House – Eclectic Art Haven in Huntington’s Best Parks

The Blue House – Eclectic Art Haven in Huntington’s Best Parks
Huntington
10.0 out of 10, Exceptional, (21 reviews)
"Lovely and quiet location, comfortable, most stocked VRBO we’ve ever stayed in!"
United States
Lesly-Marie
The price is HK$459
HK$1,801 total
includes taxes & fees
22 Sept - 23 Sept
The Blue House – Eclectic Art Haven in Huntington’s Best Parks

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 HK$805
HK$1,507 total
includes taxes & fees
1 Oct - 2 Oct
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.

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 HK$730
HK$2,414 total
includes taxes & fees
20 Sept - 21 Sept
Espresso Maker & Modern Decor by Arena, University, Hospitals

7. 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 HK$4,315
HK$11,571 total
includes taxes & fees
30 Sept - 1 Oct
Entire Bldg w/6 Bedrooms across 4 Separate Apts - Group/Corporate Stay Downtown

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 HK$565
HK$3,540 total
includes taxes & fees
20 Sept - 21 Sept
Cozy With A Little Touch of Love

9. 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 HK$745
HK$2,432 total
includes taxes & fees
20 Sept - 21 Sept
Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes

10. 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, (12 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 HK$1,036
HK$1,303 total
includes taxes & fees
1 Oct - 2 Oct
Charming Home with private Hot Tub and Fire Pit

11. 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 HK$455
HK$2,003 total
includes taxes & fees
19 Sept - 20 Sept
Convenient 1-BR - Fenced Backyard - Extended Stays wanted

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 HK$730
HK$2,414 total
includes taxes & fees
27 Sept - 28 Sept
Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital

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

The Chessie Room - Historic Boutique Stay at Heritage Station
Huntington
The price is HK$1,165
HK$1,484 total
includes taxes & fees
1 Oct - 2 Oct
The Chessie Room - Historic Boutique Stay at Heritage Station

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 HK$777
HK$1,454 total
includes taxes & fees
21 Sept - 22 Sept
Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland

15. 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 HK$2,528
HK$5,032 total
includes taxes & fees
21 Sept - 22 Sept
Spacious Historic 5-bedroom house in charming Barboursville with AC

16. THE LUXURY CABIN IN THE WOODS

THE LUXURY CABIN IN THE WOODS
Catlettsburg
10.0 out of 10, Exceptional, (240 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 HK$1,193
HK$2,457 total
includes taxes & fees
21 Sept - 22 Sept
THE LUXURY CABIN IN THE WOODS

17. 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 HK$1,334
HK$2,509 total
includes taxes & fees
19 Sept - 20 Sept
Cozy Fonzie Flat

18. 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 HK$745
HK$1,418 total
includes taxes & fees
20 Sept - 21 Sept
Charming 3BR Home - Near KDMC & Downtown

19. 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, (20 reviews)
"We really enjoyed our stay, perfect location for a visit to that part of Kentucky."
United States
Melinda K.
The price is HK$784
HK$1,565 total
includes taxes & fees
20 Sept - 21 Sept
Charming 2-bedroom house located in beautiful wooded setting!

20. 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 HK$1,090
HK$2,451 total
includes taxes & fees
4 Oct - 5 Oct
La'Chic Boutique Bungalow 3 Beds/1.5Baths
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

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 holiday rental in Chesapeake?

Yes, there are holiday rentals close to the most popular sights in Chesapeake, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chesapeake has to offer?

2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.: This holiday home rental outside of Chesapeake is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most 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 wider area, you’ll find Mountain Health Arena and Pullman Square.

What are holiday rentals like in Chesapeake?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesapeake. Holiday rentals offer amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family getaway.