Chesapeake Vacation Rentals

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Check prices for these dates

Tonight
Dec 5 - Dec 6
Tomorrow
Dec 6 - Dec 7
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Vacation Rentals in Chesapeake

5 bedrooms, iron/ironing board, free WiFi, bed sheets
The Eagle's Nest:5 bed 3BathBeautiful Craftsman Home

Vacation Home in Ashland

9.8 out of 10, Exceptional, (22)
"A great property; warm, cozy and accommodating. "
United States
Kevin C.
The price is ￥27,759
￥56,779 total
includes taxes & fees
Dec 16 - Dec 17
The Eagle's Nest:5 bed 3BathBeautiful Craftsman Home
Fridge, microwave, oven, stovetop
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.

Vacation Home in 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.
The price is ￥13,996
￥27,649 total
includes taxes & fees
Dec 15 - Dec 16
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
Living area
Cozy 2-bedroom apartment located next to St. Mary's Hospital!

Apartment in Huntington

10.0 out of 10, Exceptional, (11)
"Great place, clean cozy love the 2 bathrooms!!"
United States
Katherine D.
The price is ￥14,733
￥33,110 total
includes taxes & fees
Dec 10 - Dec 11
Cozy 2-bedroom apartment located next to St. Mary's Hospital!
Exterior
THE LUXURY CABIN IN THE WOODS

Cabin in Catlettsburg

10.0 out of 10, Exceptional, (218)
"Great property with good catch and release fishing, would stay at again."
United States
Dave S.
The price is ￥26,209
￥52,656 total
includes taxes & fees
Dec 22 - Dec 23
THE LUXURY CABIN IN THE WOODS
Outdoor dining
Charming 2-bedroom house located in beautiful wooded setting!

Vacation Home in 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.
The price is ￥15,508
￥31,286 total
includes taxes & fees
Dec 6 - Dec 7
Charming 2-bedroom house located in beautiful wooded setting!
Smart TV, fireplace, video games, DVD player
Secluded Ohio Forest Escape at Fuller's Fifty

Cabin in Patriot

10.0 out of 10, Exceptional, (78)
"It was a perfect spot for a quick getaway! "
United States
Patricia
The price is ￥12,282
￥27,015 total
includes taxes & fees
Dec 8 - Dec 9
Secluded Ohio Forest Escape at Fuller's Fifty
Property grounds
Relaxing 2 bdrm retreat. Mountain View w hottub & ATV option 5th night free

Cabin in Crown City

9.8 out of 10, Exceptional, (26)
"This is the 2nd time we’ve stayed here and we love it! What a beautiful and peaceful place to stay. Feels like our own little world when we’re there. We definitely didn’t want to leave. We will be back! Everything was perfect.. Awesome place! "
United States
chris p.
The price is ￥34,904
￥57,708 total
includes taxes & fees
Dec 12 - Dec 13
Relaxing 2 bdrm retreat. Mountain View w hottub & ATV option 5th night free
Exterior detail
The Park House by Nest and Bloom

Vacation Home in Huntington

10.0 out of 10, Exceptional, (12)
"Very nice house. We enjoyed our stay. Hosts were attentive and friendly."
United States
Patricia M.
The Park House by Nest and Bloom
Property grounds
Enjoy the charm of Rush Kentucky on a quite and relax setting or go off-roading

Vacation Home in Rush

9.0 out of 10, Wonderful, (36)
"Excellent place to stay, great location. Cant wait to go back! "
United States
Lydia J.
Enjoy the charm of Rush Kentucky on a quite and relax setting or go off-roading
Exterior
Urban Cottage:Homey & Convenient

Vacation Home in Huntington

9.8 out of 10, Exceptional, (18)
"Great stay "
United States
Chris P.
Urban Cottage:Homey & Convenient
Terrace/patio
RiverSuite1 - A mesmerizing river & bridge view.

Condo in Russell

2.0 star property
10.0 out of 10, Exceptional, (7)
"The house was beautiful!!! The view was amazing!! The host was very friendly!!’ We would stay there again!!! Thank you for letting enjoy the house!!!"
United States
Cindy F.
RiverSuite1 - A mesmerizing river & bridge view.
Outdoor dining
Riverside Cabin with Homemade Breakfast

Cabin in 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.
The price is ￥15,358
￥24,514 total
includes taxes & fees
Dec 7 - Dec 8
Riverside Cabin with Homemade Breakfast
Fridge, microwave, oven, stovetop
CLEAN 2-bedroom cozy apartment Huntington. Spacious and accomodating!

Apartment in Huntington

2.0 star property
CLEAN 2-bedroom cozy apartment Huntington. Spacious and accomodating!
Fridge, microwave, oven, stovetop
Pointer Palace

Vacation Home in 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.
The price is ￥21,556
￥28,224 total
includes taxes & fees
Dec 6 - Dec 7
Pointer Palace
Interior
The Bluegrass Bungalow: New Constructed Sleeps 8: 6 beds 2.5 baths. Handicap ass

Vacation Home in Ashland

10.0 out of 10, Exceptional, (1)
"Very nicely decorated 2 bedroom/2 bathroom home in a great location. Owners are great to work with."
United States
Greg T.
The Bluegrass Bungalow: New Constructed Sleeps 8: 6 beds 2.5 baths. Handicap ass
Interior
Carroll Manor: RecentlyRenovated English Tutor. Sleeps 8

Vacation Home in 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.
The price is ￥27,759
￥56,779 total
includes taxes & fees
Dec 16 - Dec 17
Carroll Manor: RecentlyRenovated English Tutor. Sleeps 8
Exterior
Circa 1891 Historic Governors Inn now available for private stays or events

Vacation Home in Ashland

10.0 out of 10, Exceptional, (2)
"Beautifully restored home with a great layout for a large group. "
United States
Rebekah B.
Circa 1891 Historic Governors Inn now available for private stays or events
Exterior
4Bed/3Bath GREYSTONE COTTAGE

Vacation Home in Ashland

9.4 out of 10, Exceptional, (8)
"great for a quick stop."
United States
William M.
The price is ￥27,759
￥67,447 total
includes taxes & fees
Dec 8 - Dec 9
4Bed/3Bath GREYSTONE COTTAGE
Fridge, microwave, oven, stovetop
Charming home where you can enjoy "Small Town Living" close to everything

Vacation Home in Barboursville

2.0 star property
10.0 out of 10, Exceptional, (1)
"House is convenient to Marshall University, Huntington, the mall and much more. Hosts have thought of everything to make your stay comfortable. "
United States
Cathy M.
Charming home where you can enjoy "Small Town Living" close to everything
Apartment (0 Bedroom) | Interior
Hot Tub, Fire Pit: Lake-view Catlettsburg Getaway!

Apartment in Catlettsburg

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

Fairfield Inn & Suites By Marriott Ashland

Fairfield Inn & Suites By Marriott Ashland

10/10 Excellent
"Staff was excellent, the room was clean, I just had two issues, the carpet at the doorway was all ripped up, the second issue when pulling into the place it looks like there's zero maintenance being done on the building."
KURT 1-night trip
Posted 2 days ago
Fairfield Inn & Suites By Marriott Ashland

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:

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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.