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Chesapeake Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Chesapeake vacation rentals

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
9.8 out of 10, Exceptional, (20 reviews)
"Had a great stay! Cool town!"
United States
Noah S.
$135 nightly
The price is $157
Jul 5 - Jul 6
Total with taxes and fees
Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland
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, (91 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
$191 nightly
The price is $191
Jul 13 - Jul 14
Total with taxes and fees
Secluded Ohio Forest Escape at Fuller's Fifty
TV

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)
"Maybe the cleanest place we’ve ever stayed. Easy check-in and quick communication. The apartment everything a traveler needs, including a new toothbrush, which was fantastic since I’d forgotten mine. I’d very definitely recommend staying there. "
United States
Rebecah C.
$192 nightly
The price is $216
Jul 1 - Jul 2
Total with taxes and fees
Cozy 2-bedroom apartment located next to St. Mary's Hospital!
Smart TV, video games

Convenient 1-BR - Fenced Backyard - Extended Stays wanted

Convenient 1-BR - Fenced Backyard - Extended Stays wanted
Huntington
$218 nightly
The price is $245
Jul 27 - Jul 28
Total with taxes and fees
Convenient 1-BR - Fenced Backyard - Extended Stays wanted
Outdoor dining

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.
$153 nightly
The price is $157
Jul 1 - Jul 2
Total with taxes and fees
Large Cabin with Stunning View - Fire Pit, Relax & Unwind
Smart TV, fireplace

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.
$274 nightly
The price is $308
Jul 16 - Jul 17
Total with taxes and fees
Espresso Maker & Modern Decor by Arena, University, Hospitals
Property grounds

Rush Creek Camp, Lot # 03

Rush Creek Camp, Lot # 03
Rush
$70 nightly
The price is $79
Jul 1 - Jul 2
Total with taxes and fees
Rush Creek Camp, Lot # 03
Outdoor dining

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, (11 reviews)
"We really enjoyed our stay, perfect location for a visit to that part of Kentucky."
United States
Melinda K.
$181 nightly
The price is $200
Jul 5 - Jul 6
Total with taxes and fees
Charming 2-bedroom house located in beautiful wooded setting!
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, (51 reviews)
"Very nice place to stay! We really enjoyed it! "
United States
Hannah M.
$179 nightly
The price is $200
Jul 5 - Jul 6
Total with taxes and fees
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
Outdoor spa tub

Pointer Palace

Pointer Palace
South Point
10.0 out of 10, Exceptional, (9 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.
$124 nightly
The price is $124
Jul 1 - Jul 2
Total with taxes and fees
Pointer Palace
3 bedrooms, iron/ironing board, free WiFi, bed sheets

The Black Nest • Modern Duplex w/ Porch

The Black Nest • Modern Duplex w/ Porch
Ashland
$139 nightly
The price is $162
Jul 19 - Jul 20
Total with taxes and fees
The Black Nest • Modern Duplex w/ Porch
Exterior detail

Carroll Manor: RecentlyRenovated English Tutor. Sleeps 8

Carroll Manor: RecentlyRenovated English Tutor. Sleeps 8
Ashland
9.6 out of 10, Exceptional, (14 reviews)
"Loved the decor… the house was spacious and comfortable! Our stay was fantastic!"
United States
Tom H.
$406 nightly
The price is $474
Jul 5 - Jul 6
Total with taxes and fees
Carroll Manor: RecentlyRenovated English Tutor. Sleeps 8
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, (124 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.
$198 nightly
The price is $218
Jul 1 - Jul 2
Total with taxes and fees
The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.
Exterior

THE LUXURY CABIN IN THE WOODS

THE LUXURY CABIN IN THE WOODS
Catlettsburg
10.0 out of 10, Exceptional, (233 reviews)
"Perfect weather enjoyed our stay "
United States
Kris C.
$289 nightly
The price is $318
Jul 7 - Jul 8
Total with taxes and fees
THE LUXURY CABIN IN THE WOODS
Property grounds

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.
$215 nightly
The price is $219
Jul 1 - Jul 2
Total with taxes and fees
The Bunkhouse
Property grounds

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)
"Welcoming and clean. It has those little touches that made the stay even more enjoyable. Host responded to any questions. Would definitely stay again!"
United States
MARIANNE A.
$276 nightly
The price is $310
Jul 8 - Jul 9
Total with taxes and fees
Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes
Property grounds

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.
$400 nightly
The price is $449
Jul 2 - Jul 3
Total with taxes and fees
Cozy With A Little Touch of Love
Smart TV, fireplace

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.
$274 nightly
The price is $308
Jul 8 - Jul 9
Total with taxes and fees
Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital
Fridge, microwave, oven, stovetop

Secluded ranch home

Secluded ranch home
Ashland
10.0 out of 10, Exceptional, (19 reviews)
"Another great stay"
United States
Alix E.
$288 nightly
The price is $327
Jul 1 - Jul 2
Total with taxes and fees
Secluded ranch home
Smart TV, fireplace, books

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

Historic & Chic apartment by Arena, University, Hospital - Dog Friendly
Huntington
9.8 out of 10, Exceptional, (7 reviews)
"Comfortable convenient to everything. It was a home away from home."
United States
Kimberly M.
$288 nightly
The price is $323
Jul 13 - Jul 14
Total with taxes and fees
Historic & Chic apartment by Arena, University, Hospital - Dog Friendly
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

Comfort Inn Barboursville near Huntington Mall area

Comfort Inn Barboursville near Huntington Mall area

10/10 Excellent
"The room was clean and the bed comfortable."
Jason 1-night trip
Posted 21 hours ago
Comfort Inn Barboursville near Huntington Mall area

Find out more about Chesapeake

Everything you need to know about Chesapeake vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesapeake vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chesapeake in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $157 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chesapeake rentals

At Expedia, we put the best Chesapeake vacation 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 vacation.

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 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.