Chesapeake Holiday Rentals

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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Chesapeake holiday rentals

Outdoor dining

Riverside Cabin

Riverside Cabin
Gallipolis
9.8 out of 10, Exceptional, (42 reviews)
"The property was in excellent condition facilities and beds were absolutely perfect the view over the river was spectacular the breakfast was delicious "
United States
Samuel H.
The price is HK$930
HK$1,412 total
includes taxes & fees
22 Feb - 23 Feb
Riverside Cabin
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, (80 reviews)
"It was a perfect spot for a quick getaway! "
United States
Patricia
The price is HK$619
HK$1,362 total
includes taxes & fees
18 Feb - 19 Feb
Secluded Ohio Forest Escape at Fuller's Fifty
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, (9 reviews)
"Very nice house in a very peaceful setting. Beds and furniture are comfortable too. Will be staying here again in the future"
United States
Barry M.
The price is HK$782
HK$1,560 total
includes taxes & fees
16 Feb - 17 Feb
Charming 2-bedroom house located in beautiful wooded setting!
Outdoor spa tub

Pointer Palace

Pointer Palace
South Point
10.0 out of 10, Exceptional, (4 reviews)
"An excellent place to stay. Clean, comfortable, in a safe feeling neighborhood. Probably the most thoughtfully appointed VRBO I've ever stayed in. "
United States
Jon W.
The price is HK$1,087
HK$1,407 total
includes taxes & fees
17 Feb - 18 Feb
Pointer Palace
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, (119 reviews)
"Cozy Cabin is great. Highly recommend!"
United States
Jason M.
The price is HK$985
HK$1,732 total
includes taxes & fees
16 Feb - 17 Feb
The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.
Living area

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, (14 reviews)
"Great place, clean cozy love the 2 bathrooms!!"
United States
Katherine D.
The price is HK$743
HK$1,669 total
includes taxes & fees
16 Feb - 17 Feb
Cozy 2-bedroom apartment located next to St. Mary's Hospital!
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, (37 reviews)
"Incredibly clean, with careful attention to details that make for a comfortable stay!"
United States
Liz M.
The price is HK$813
HK$1,514 total
includes taxes & fees
3 Mar - 4 Mar
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
Exterior

THE LUXURY CABIN IN THE WOODS

THE LUXURY CABIN IN THE WOODS
Catlettsburg
10.0 out of 10, Exceptional, (220 reviews)
"Perfect weather enjoyed our stay "
United States
Kris C.
The price is HK$1,321
HK$2,654 total
includes taxes & fees
16 Feb - 17 Feb
THE LUXURY CABIN IN THE WOODS
Property grounds

Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes

Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes
Huntington
9.4 out of 10, Exceptional, (6 reviews)
"Close to Marshall university, great communication, loved the fans and noise machines."
United States
Marsha Y.
The price is HK$727
HK$2,250 total
includes taxes & fees
8 Mar - 9 Mar
Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes
Property grounds

Relaxing 2 bdrm retreat. Mountain View w hottub & ATV option 5th night free

Relaxing 2 bdrm retreat. Mountain View w hottub & ATV option 5th night free
Crown City
9.8 out of 10, Exceptional, (27 reviews)
"Was nice "
United States
Joann M.
The price is HK$1,759
HK$2,908 total
includes taxes & fees
21 Feb - 22 Feb
Relaxing 2 bdrm retreat. Mountain View w hottub & ATV option 5th night free
Living area

4-bedroom, 2-bathroom house with AC in charming Ashland

4-bedroom, 2-bathroom house with AC in charming Ashland
Ashland
The price is HK$750
HK$1,522 total
includes taxes & fees
24 Feb - 25 Feb
4-bedroom, 2-bathroom house with AC in charming Ashland
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, (12 reviews)
"Had a great stay! Cool town!"
United States
Noah S.
The price is HK$625
HK$1,230 total
includes taxes & fees
16 Feb - 17 Feb
Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland
Fridge, microwave, oven, stovetop

Secluded ranch home

Secluded ranch home
Ashland
10.0 out of 10, Exceptional, (16 reviews)
"Another great stay"
United States
Alix E.
The price is HK$1,161
HK$2,292 total
includes taxes & fees
16 Feb - 17 Feb
Secluded ranch home
Internet, bed sheets

2 bedroom apartment in Ashland KY

2 bedroom apartment in Ashland KY
Ashland
The price is HK$500
HK$1,099 total
includes taxes & fees
16 Feb - 17 Feb
2 bedroom apartment in Ashland KY
Living area

Tranquil 2-bedroom apartment with AC in charming Ashland

Tranquil 2-bedroom apartment with AC in charming Ashland
Ashland
The price is HK$500
HK$1,099 total
includes taxes & fees
24 Feb - 25 Feb
Tranquil 2-bedroom apartment with AC in charming Ashland
Interior

Modern Loft-Style Retreat Near Blenko Glass – Milton, WV

Modern Loft-Style Retreat Near Blenko Glass – Milton, WV
Milton
The price is HK$938
HK$1,837 total
includes taxes & fees
16 Feb - 17 Feb
Modern Loft-Style Retreat Near Blenko Glass – Milton, WV
Living area

2 Bedroom Cottage in Charming Ashland KY

2 Bedroom Cottage in Charming Ashland KY
Ashland
The price is HK$663
HK$1,411 total
includes taxes & fees
24 Feb - 25 Feb
2 Bedroom Cottage in Charming Ashland KY
Dining

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, (6 reviews)
"Great house – everything is clean and new."
United States
JonathanK
The price is HK$1,565
HK$4,069 total
includes taxes & fees
22 Feb - 23 Feb
Huntington Modern - Mins to DT, MU, St. Mary's
Living area

Spacious, 2-Bedroom Unit with Laundry, Ashland KY-Near UK/KDMC Hospital!

Spacious, 2-Bedroom Unit with Laundry, Ashland KY-Near UK/KDMC Hospital!
Ashland
The price is HK$500
HK$1,221 total
includes taxes & fees
3 Mar - 4 Mar
Spacious, 2-Bedroom Unit with Laundry, Ashland KY-Near UK/KDMC Hospital!
TV, offices

The Market Place by Nest and Bloom <br>Suite 4 (5045)

The Market Place by Nest and Bloom <br>Suite 4 (5045)
Ashland
9.4 out of 10, Exceptional, (3 reviews)
"Clean, well furnished, easy to find"
United States
Kelly S.
The price is HK$703
HK$2,263 total
includes taxes & fees
13 Mar - 14 Mar
The Market Place by Nest and Bloom <br>Suite 4 (5045)
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

Delta Hotels by Marriott Huntington Mall

Delta Hotels by Marriott Huntington Mall

10/10 Excellent
"Clean room and towels. "
Robert 1-night trip
Posted 2 days ago
Delta Hotels by Marriott Huntington Mall

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:

  • View our selection of featured holiday rentals in Chesapeake
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  • Enter your travel dates to view the best deals on holiday rentals in Chesapeake while they last

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

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?

Unwind in a Spacious Kentucky Barndominium Ideal for Vacations and Events.: This holiday home rental outside of Chesapeake offers an indoor pool, a fireplace and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a patio and a selection of books.

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.