Chesapeake Vacation Rentals

Check prices for these dates

In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Vacation Rentals in Chesapeake

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

Secluded Ohio Forest Escape at Fuller's Fifty

10.0 out of 10, Exceptional, (65)
"Great cabin, secluded and as advertised. Would recommend to stay. Host was responsive and had a great time. "
$100 nightly
The price is $100
Sep 1 - Sep 2
Total with taxes and fees
Secluded Ohio Forest Escape at Fuller's Fifty
THE LUXURY CABIN IN THE WOODS
Exterior

THE LUXURY CABIN IN THE WOODS

10.0 out of 10, Exceptional, (211)
"Amazing place to stay! Plenty of space for our family. we will definitely be visiting again!"
$306 nightly
The price is $337
Sep 1 - Sep 2
Total with taxes and fees
THE LUXURY CABIN IN THE WOODS
Riverside Cabin with Homemade Breakfast
Outdoor dining

Riverside Cabin with Homemade Breakfast

9.8 out of 10, Exceptional, (39)
"Clean cabin with a great breakfast!"
$176 nightly
The price is $181
Aug 29 - Aug 30
Total with taxes and fees
Riverside Cabin with Homemade Breakfast
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
Fridge, microwave, oven, stovetop

2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.

10.0 out of 10, Exceptional, (27)
"Great place to stay!"
$184 nightly
The price is $205
Sep 1 - Sep 2
Total with taxes and fees
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
This tiny cabin is a peaceful place complete with stocked pond and kayaks!
Terrace/patio

This tiny cabin is a peaceful place complete with stocked pond and kayaks!

10.0 out of 10, Exceptional, (22)
"The Bunkhouse was the perfect spot for us during our visit to the area. Clean, cozy, and with all the amenities of home, with the addition of beautiful surroundings. We're already planning our next trip back!"
$185 nightly
The price is $185
Aug 31 - Sep 1
Total with taxes and fees
This tiny cabin is a peaceful place complete with stocked pond and kayaks!
The Eagle's Nest: 5Beds/3Baths Beautiful Craftsman Home
5 bedrooms, iron/ironing board, free WiFi, bed sheets

The Eagle's Nest: 5Beds/3Baths Beautiful Craftsman Home

9.8 out of 10, Exceptional, (21)
"A great property; warm, cozy and accommodating. "
The Eagle's Nest: 5Beds/3Baths Beautiful Craftsman Home
"Stay Steps from Marshall - Your Home in Huntington!"
Sport court

"Stay Steps from Marshall - Your Home in Huntington!"

3.0 out of 10, (4)
"Relatively clean except for the floors. Can see improvements that they’ve been making. The TV in the main room does not work even though we changed the batteries in the remote never got a response from the property manager. The AC that is advertised is only a small bedroom unit in the whole apartment "
"Stay Steps from Marshall - Your Home in Huntington!"
GOLIATH RENTALS. 3-bedroom house in Rush KY. 0.1 miles from trailhead
Fridge, microwave, oven, stovetop

GOLIATH RENTALS. 3-bedroom house in Rush KY. 0.1 miles from trailhead

$238 nightly
The price is $270
Sep 15 - Sep 16
Total with taxes and fees
GOLIATH RENTALS. 3-bedroom house in Rush KY. 0.1 miles from trailhead
Diamond Creek Cabin - Sleeps up to 6
2 bedrooms, iron/ironing board, free WiFi, bed sheets

Diamond Creek Cabin - Sleeps up to 6

10.0 out of 10, Exceptional, (1)
"Excellent place to rest and reset. Quiet and remote. Loved our stay there. Set in the middle of the woods. Hope to return soon. "
Diamond Creek Cabin - Sleeps up to 6
Cozy 2-bedroom apartment located next to St. Mary's Hospital!
Living area

Cozy 2-bedroom apartment located next to St. Mary's Hospital!

9.8 out of 10, Exceptional, (9)
"Great for short or long term stays. plenty of room and all amenities necessary for long stay."
$190 nightly
The price is $214
Sep 1 - Sep 2
Total with taxes and fees
Cozy 2-bedroom apartment located next to St. Mary's Hospital!
Ohio River Manor House<br>Experience the peace and quiet of a country residence!
Fridge, microwave, oven, stovetop

Ohio River Manor House<br>Experience the peace and quiet of a country residence!

9.8 out of 10, Exceptional, (81)
"The house and grounds are absolutely beautiful and very comfortable. Perfect for a retreat or reunion. We had a wonderful experience!"
Ohio River Manor House<br>Experience the peace and quiet of a country residence!
Hot Tub, Fire Pit: Lake-View Catlettsburg Getaway!
Internet, bed sheets

Hot Tub, Fire Pit: Lake-View Catlettsburg Getaway!

10.0 out of 10, Exceptional, (3)
"Place was very clean and a nice little place to enjoy with a little campfire and nice overlook of the lake "
Hot Tub, Fire Pit: Lake-View Catlettsburg Getaway!
Relaxing 2 bdrm retreat. Mountain View w hottub & ATV option 5th night free
Property grounds

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

10.0 out of 10, Exceptional, (22)
"The property great! I highly recommend!"
Relaxing 2 bdrm retreat. Mountain View w hottub & ATV option 5th night free
Secluded ranch home
Dining

Secluded ranch home

10.0 out of 10, Exceptional, (12)
"A nice place with a neat layout & the backyard was great for the dog to run freely off leash."
$249 nightly
The price is $282
Sep 3 - Sep 4
Total with taxes and fees
Secluded ranch home
Cozy 2-Bdrm Cabin Fox Den- near Greenbo Lake State Park
Smart TV, books

Cozy 2-Bdrm Cabin Fox Den- near Greenbo Lake State Park

10.0 out of 10, Exceptional, (7)
"Seemed new very clean, nice amenities. "
Cozy 2-Bdrm Cabin Fox Den- near Greenbo Lake State Park
The Park House by Nest and Bloom
Exterior detail

The Park House by Nest and Bloom

10.0 out of 10, Exceptional, (9)
The Park House by Nest and Bloom
Pointer Palace
Fridge, microwave, oven, stovetop

Pointer Palace

10.0 out of 10, Exceptional, (1)
"Very clean and very organized, you'll notice the attention to detail in almost every corner of the home. "
$148 nightly
The price is $148
Sep 9 - Sep 10
Total with taxes and fees
Pointer Palace
The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.
Property grounds

The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.

10.0 out of 10, Exceptional, (118)
"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 "
$199 nightly
The price is $219
Sep 1 - Sep 2
Total with taxes and fees
The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.
La'Chic Boutique Bungalow 3 Beds/1.5Baths
TV, fireplace, books

La'Chic Boutique Bungalow 3 Beds/1.5Baths

9.4 out of 10, Exceptional, (24)
"We enjoyed our stay although we had to leave for a family emergency early. Easy to get to. Clean and nice amenities. "
La'Chic Boutique Bungalow 3 Beds/1.5Baths
Hot Tub, Fire Pit: Lake-view Catlettsburg Getaway!
Apartment (0 Bedroom) | Interior

Hot Tub, Fire Pit: Lake-view Catlettsburg Getaway!

3.0 star property
Hot Tub, Fire Pit: Lake-view Catlettsburg Getaway!
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

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 $100 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

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?

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 Ritter Park. 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.