Chesapeake Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Chesapeake

Smart TV, fireplace, video games, DVD player
Secluded Ohio Forest Escape at Fuller's Fifty

Secluded Ohio Forest Escape at Fuller's Fifty

Patriot
10.0 out of 10, Exceptional, (78)
"It was a perfect spot for a quick getaway! "
United States
Patricia
$174 nightly
The price is $174
Dec 8 - Dec 9
Total with taxes and fees
Secluded Ohio Forest Escape at Fuller's Fifty
Outdoor dining
Riverside Cabin with Homemade Breakfast

Riverside Cabin with Homemade Breakfast

Gallipolis
9.8 out of 10, Exceptional, (41)
"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.
$176 nightly
The price is $181
Dec 7 - Dec 8
Total with taxes and fees
Riverside Cabin with Homemade Breakfast
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, (5)
"Throughly enjoyed our stay at the home! It was very accommodating and comfortable. And very convenient for our local family to visit."
United States
Doug & Sandra N.
$183 nightly
The price is $202
Dec 6 - Dec 7
Total with taxes and fees
Charming 2-bedroom house located in beautiful wooded setting!
Fridge, microwave, oven, stovetop
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, (29)
"Love the property and the way it was made up nice and clean comfortable and just far enough away from everything to be peaceful"
United States
Wanda W.
$160 nightly
The price is $178
Dec 7 - Dec 8
Total with taxes and fees
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
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)
"It was jus what we needed for our fishing trip plenty of parking and peaceful close to everything as well will stay again next year "
United States
Josh P.
$201 nightly
The price is $222
Dec 7 - Dec 8
Total with taxes and fees
The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.
Fridge, microwave, oven, stovetop
Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital

Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital

Huntington
8.0 out of 10, Very Good, (1)
"Upon arrival everything looks great. We had no issues until Bedtime. Im not sure if the room isnt booked alot bit our covers were dusty. . I have pretty bad allergies so i was nervous. Then around 10pm the people upstairs were so loud.. Walking around on a Harwood floor. Moving Furniture. This happened every night. We didnt sleep much! Even w. The sound machine provided. If your a heavy sleeper you are fine! "
United States
Ashli S.
$226 nightly
The price is $254
Dec 31 - Jan 1, 2026
Total with taxes and fees
Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital
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, (11)
"Great place, clean cozy love the 2 bathrooms!!"
United States
Katherine D.
$190 nightly
The price is $214
Dec 8 - Dec 9
Total with taxes and fees
Cozy 2-bedroom apartment located next to St. Mary's Hospital!
Interior
Convenient 1-BR - Fenced Backyard - Extended Stays wanted

Convenient 1-BR - Fenced Backyard - Extended Stays wanted

2.0 star property
Huntington
$215 nightly
The price is $242
Dec 9 - Dec 10
Total with taxes and fees
Convenient 1-BR - Fenced Backyard - Extended Stays wanted
Property grounds
Rush Creek Camp, Lot # 03

Rush Creek Camp, Lot # 03

Rush
$70 nightly
The price is $79
Dec 5 - Dec 6
Total with taxes and fees
Rush Creek Camp, Lot # 03
Fridge, microwave, oven, stovetop
Pointer Palace

Pointer Palace

South Point
10.0 out of 10, Exceptional, (4)
"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.
$172 nightly
The price is $172
Dec 22 - Dec 23
Total with taxes and fees
Pointer Palace
Microwave, oven, stovetop, dishwasher
Cozy & Modern 1-Bedroom Downstairs Apartment with King Bed + Queen Sofa Bed

Cozy & Modern 1-Bedroom Downstairs Apartment with King Bed + Queen Sofa Bed

South Point
10.0 out of 10, Exceptional, (2)
"Property was clean, comfortable and inviting! Would highly recommend to anyone visiting the area"
United States
Anson S.
$252 nightly
The price is $252
Dec 31 - Jan 1, 2026
Total with taxes and fees
Cozy & Modern 1-Bedroom Downstairs Apartment with King Bed + Queen Sofa Bed
Outdoor dining
The Bunkhouse

The Bunkhouse

Crown City
10.0 out of 10, Exceptional, (28)
"Great place! Quiet and peaceful lots of wildlife. Very relaxing weekend."
United States
Shelley R.
$206 nightly
The price is $210
Dec 8 - Dec 9
Total with taxes and fees
The Bunkhouse
1 bedroom, in-room safe, iron/ironing board, WiFi
Cozy With A Little Touch of Love

Cozy With A Little Touch of Love

Huntington
7.8 out of 10, Good, (6)
"I liked the homely feeling even though i am front out of town. The street was a bit narrow with limited parking."
United States
Nate
$409 nightly
The price is $459
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy With A Little Touch of Love
Private kitchen
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, (2)
"Very quiet, clean, nice house "
United States
Karen S.
$238 nightly
The price is $269
Dec 11 - Dec 12
Total with taxes and fees
Corner Cottage 2 bedroom pets welcome and close to downtown
Dining
Secluded ranch home

Secluded ranch home

Ashland
10.0 out of 10, Exceptional, (14)
"Another great stay"
United States
Alix E.
$258 nightly
The price is $292
Dec 6 - Dec 7
Total with taxes and fees
Secluded ranch home
Fridge, microwave, oven, stovetop
Cozy Fonzie Flat

Cozy Fonzie Flat

Ashland
10.0 out of 10, Exceptional, (1)
"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.
$256 nightly
The price is $290
Dec 5 - Dec 6
Total with taxes and fees
Cozy Fonzie Flat
Dining
Huntington Modern History - 4BR MU, DT, St Marys

Huntington Modern History - 4BR MU, DT, St Marys

Huntington
10.0 out of 10, Exceptional, (5)
"Great house – everything is clean and new."
United States
JonathanK
$454 nightly
The price is $469
Dec 7 - Dec 8
Total with taxes and fees
Huntington Modern History - 4BR MU, DT, St Marys
Exterior
THE LUXURY CABIN IN THE WOODS

THE LUXURY CABIN IN THE WOODS

Catlettsburg
10.0 out of 10, Exceptional, (218)
"Great property with good catch and release fishing, would stay at again."
United States
Dave S.
$308 nightly
The price is $340
Dec 22 - Dec 23
Total with taxes and fees
THE LUXURY CABIN IN THE WOODS
Terrace/patio
Modern Comfort Near KDMC: 3BR Home w/ Workspace & Coffee Bar

Modern Comfort Near KDMC: 3BR Home w/ Workspace & Coffee Bar

Coal Grove
$201 nightly
The price is $201
Dec 5 - Dec 6
Total with taxes and fees
Modern Comfort Near KDMC: 3BR Home w/ Workspace & Coffee Bar
Interior
Carroll Manor: RecentlyRenovated English Tutor. Sleeps 8

Carroll Manor: RecentlyRenovated English Tutor. Sleeps 8

Ashland
9.8 out of 10, Exceptional, (11)
"Beautiful house with all of the accommodations to make us comfortable for our stay!"
United States
Darrin I.
$296 nightly
The price is $345
Dec 5 - Dec 6
Total with taxes and fees
Carroll Manor: RecentlyRenovated English Tutor. Sleeps 8
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

10/10 Excellent
"Staff were so kind and uplifting!"
Ray Gregor 3-night trip
Posted 1 day ago
Fairfield Inn & Suites by Marriott Huntington

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 $172 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.

Explore a world of travel with Expedia

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?

The Eagle's Nest:5 bed 3BathBeautiful Craftsman Home: This vacation home rental outside of Chesapeake offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You can relax into your vacation with a garden 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 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.