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Chesapeake Holiday Rentals

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Our top choices for Chesapeake holiday rentals

Secluded Ohio Forest Escape at Fuller's Fifty

Secluded Ohio Forest Escape at Fuller's Fifty
Patriot
10.0 out of 10, Exceptional, (89 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 AU$265
includes taxes & fees
23 June - 24 June
Secluded Ohio Forest Escape at Fuller's Fifty

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, (50 reviews)
"Great river view. Beds are comfy."
United States
Rebecca G.
The price is AU$200
includes taxes & fees
21 June - 22 June
Large Cabin with Stunning View - Fire Pit, Relax & Unwind

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, (22 reviews)
"Great place, clean cozy love the 2 bathrooms!!"
United States
Katherine D.
The price is AU$310
includes taxes & fees
21 June - 22 June
Cozy 2-bedroom apartment located next to St. Mary's Hospital!

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, (50 reviews)
"Very nice place to stay! We really enjoyed it! "
United States
Hannah M.
The price is AU$286
includes taxes & fees
21 June - 22 June
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.

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, (10 reviews)
"We really enjoyed our stay, perfect location for a visit to that part of Kentucky."
United States
Melinda K.
The price is AU$286
includes taxes & fees
21 June - 22 June
Charming 2-bedroom house located in beautiful wooded setting!

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

Modern Loft-Style Retreat Near Blenko Glass – Milton, WV
Milton
10.0 out of 10, Exceptional, (4 reviews)
"We enjoyed our stay. The apartment was clean, spacious, and comfortable! We will definitely stay here again!"
United States
Lauren P.
The price is AU$353
includes taxes & fees
20 June - 21 June
Modern Loft-Style Retreat Near Blenko Glass – Milton, WV

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, (124 reviews)
"Cozy Cabin is great. Highly recommend!"
United States
Jason M.
The price is AU$314
includes taxes & fees
25 June - 26 June
The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.

Pointer Palace

Pointer Palace
South Point
10.0 out of 10, Exceptional, (8 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 AU$261
includes taxes & fees
23 June - 24 June
Pointer Palace

The Bunkhouse

The Bunkhouse
Crown City
10.0 out of 10, Exceptional, (28 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 AU$318
includes taxes & fees
23 June - 24 June
The Bunkhouse

Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital

Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital
Huntington
8.8 out of 10, Excellent, (3 reviews)
"Everything was clean, tidy and pet friendly! We did have a little trouble with the lock, but the host took care of that right away. It was at times a little noisy but the sound spas helped with that. It was conveniently close to restaurants, we could walk to McDonald's for breakfast and coffee. Over all we enjoyed our stay!"
United States
Melissa K.
The price is AU$441
includes taxes & fees
30 June - 1 July
Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital

Whispering Pine's Cabin! NO CHECK-OUT LIST

Whispering Pine's Cabin! NO CHECK-OUT LIST
Patriot
10.0 out of 10, Exceptional, (1 review)
"Loved everything about this well kept cabin. The property is beautiful and secluded, but easily accessible. The cabin is comfortable and very thoughtfully stocked (in particular, the kitchen has every gadget, pot, pan, seasoning, coffee, creamer, you name it). The host, Kathy, is friendly and helpful. Will definitely be back and recommending to friends and family!"
United States
R
The price is AU$661
includes taxes & fees
20 July - 21 July
Whispering Pine's Cabin! NO CHECK-OUT LIST

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, (17 reviews)
"Had a great stay! Cool town!"
United States
Noah S.
The price is AU$227
includes taxes & fees
21 June - 22 June
Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland

The Black Nest • Modern Duplex w/ Porch

The Black Nest • Modern Duplex w/ Porch
Ashland
The price is AU$234
includes taxes & fees
13 July - 14 July
The Black Nest • Modern Duplex w/ Porch

THE LUXURY CABIN IN THE WOODS

THE LUXURY CABIN IN THE WOODS
Catlettsburg
10.0 out of 10, Exceptional, (232 reviews)
"Perfect weather enjoyed our stay "
United States
Kris C.
The price is AU$464
includes taxes & fees
27 June - 28 June
THE LUXURY CABIN IN THE WOODS

Rush Creek Camp, Lot # 03

Rush Creek Camp, Lot # 03
Rush
The price is AU$116
includes taxes & fees
1 July - 2 July
Rush Creek Camp, Lot # 03

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, (11 reviews)
"Every thing was great. "
United States
James G.
The price is AU$482
includes taxes & fees
12 July - 13 July
The Blue House – Eclectic Art Haven Near Marshall & Huntington’s Best Parks

Corner Cottage 2 bedroom pets welcome and close to downtown

Corner Cottage 2 bedroom pets welcome and close to downtown
Ashland
9.4 out of 10, Exceptional, (3 reviews)
"The host communicated promptly about pet friendly place. Home was great for my stay and needs."
United States
Jennifer A.
The price is AU$427
includes taxes & fees
2 July - 3 July
Corner Cottage 2 bedroom pets welcome and close to downtown

Secluded ranch home

Secluded ranch home
Ashland
10.0 out of 10, Exceptional, (19 reviews)
"Another great stay"
United States
Alix E.
The price is AU$458
includes taxes & fees
2 July - 3 July
Secluded ranch home

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 AU$427
includes taxes & fees
2 July - 3 July
Cozy Fonzie Flat

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 AU$634
includes taxes & fees
2 July - 3 July
Cozy With A Little Touch of Love
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

Everything you need to know about Chesapeake holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chesapeake holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesapeake. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake holiday rentals we have selected for you start as low as AU$200 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesapeake rentals

At Expedia, we put the best Chesapeake holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesapeake rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.