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Chesapeake Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Chesapeake vacation rentals

A covered outdoor seating area with wicker furniture and a decorative wall with hanging plants.

1. 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)
"Great space for family gathering for our Marshall grad. Very cute, spacious and centrally located."
United States
Carrie S.
The price is ￥14,978
￥52,206 total
includes taxes & fees
Nov 1 - Nov 2
Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes
A fountain with water jets in a park area, surrounded by stone walls and greenery.

2. The Blue House/Eclectic Art /Huntington’s Best Parks/full refund 1 day out

The Blue House/Eclectic Art /Huntington’s Best Parks/full refund 1 day out
Huntington
10.0 out of 10, Exceptional, (23 reviews)
"Lovely and quiet location, comfortable, most stocked VRBO we’ve ever stayed in!"
United States
Lesly-Marie
The price is ￥12,061
￥39,732 total
includes taxes & fees
Nov 2 - Nov 3
The Blue House/Eclectic Art /Huntington’s Best Parks/full refund 1 day out
A living room with a patterned rug, a coffee table, and a bookshelf.

3. Espresso Maker & Modern Decor by Arena, University, Hospitals

Espresso Maker & Modern Decor by Arena, University, Hospitals
Huntington
10.0 out of 10, Exceptional, (4 reviews)
"The place was very cozy and had everything you would need for your stay"
United States
Kellie V.
The price is ￥14,662
￥48,521 total
includes taxes & fees
Nov 6 - Nov 7
Espresso Maker & Modern Decor by Arena, University, Hospitals
A living room with a sofa, coffee table, and a chandelier.

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

Historic & Chic apartment by Arena, University, Hospital - Dog Friendly
Huntington
9.2 out of 10, Wonderful, (9 reviews)
"Very nicely decorated, cozy and clean."
United States
Yvette H.
The price is ￥16,081
￥50,968 total
includes taxes & fees
Nov 12 - Nov 13
Historic & Chic apartment by Arena, University, Hospital - Dog Friendly
A living room with a sofa, coffee table, and a chandelier. There is a painting on the wall and a window with curtains.

5. Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital

Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital
Huntington
8.8 out of 10, Excellent, (3 reviews)
"Property was exactly as described. Wish we would have found it sooner. Will definitely be back. Nice cozy place and very affordable. "
United States
richie k.
The price is ￥16,239
￥53,800 total
includes taxes & fees
Nov 10 - Nov 11
Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital
A house with a welcoming entrance, a visible number '20' on the door, and a pathway leading to the front door.

6. The Park House A 5 Bedroom Retreat w/Game Room <br>*Newly renovated 100 yr old house<br>*Game room w/ pool table<br>*1K, 3Q, 2T Beds<br>*3 1/2 Bath

The Park House A 5 Bedroom Retreat w/Game Room <br>*Newly renovated 100 yr old house<br>*Game room w/ pool table<br>*1K, 3Q, 2T Beds<br>*3 1/2 Bath
Huntington
10.0 out of 10, Exceptional, (24 reviews)
"Beautiful place, loved the decor and home away from home."
United States
Yvette H.
The price is ￥42,426
￥117,337 total
includes taxes & fees
Nov 2 - Nov 3
The Park House A 5 Bedroom Retreat w/Game Room <br>*Newly renovated 100 yr old house<br>*Game room w/ pool table<br>*1K, 3Q, 2T Beds<br>*3 1/2 Bath
A wooden fence with decorative picket tops and string lights.

7. 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 ￥11,352
￥71,146 total
includes taxes & fees
Nov 3 - Nov 4
Cozy With A Little Touch of Love
A dining table with a woven basket containing a candle and a book. A fireplace with a tiled surround is visible in the background.

8. Huntington Modern History - 4BD, MU, DT, St Mary's

Huntington Modern History - 4BD, MU, DT, St Mary's
Huntington
10.0 out of 10, Exceptional, (14 reviews)
"It was a great, historic home. We loved how the owners have kept the original details and the space worked very well for a family of four. "
United States
Brian B.
The price is ￥28,961
￥80,697 total
includes taxes & fees
Nov 1 - Nov 2
Huntington Modern History - 4BD, MU, DT, St Mary's
A hot tub with a control panel and a wooden cabinet.

9. Charming Home with private Hot Tub and Fire Pit

Charming Home with private Hot Tub and Fire Pit
South Point
10.0 out of 10, Exceptional, (18 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 ￥22,072
￥28,851 total
includes taxes & fees
Nov 2 - Nov 3
Charming Home with private Hot Tub and Fire Pit
A kitchen with a granite countertop, a black faucet, and a window with a view of a forest.

10. 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, (63 reviews)
"Very nice place to stay! We really enjoyed it! "
United States
Hannah M.
The price is ￥21,599
￥37,031 total
includes taxes & fees
Nov 2 - Nov 3
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
A living room with a sofa, coffee table, and a chandelier.

11. Entire Bldg w/6 Bedrooms across 4 Separate Apts - Group/Corporate Stay Downtown

Entire Bldg w/6 Bedrooms across 4 Separate Apts - Group/Corporate Stay Downtown
Huntington
The price is ￥86,713
￥243,872 total
includes taxes & fees
Nov 9 - Nov 10
Entire Bldg w/6 Bedrooms across 4 Separate Apts - Group/Corporate Stay Downtown
A modern kitchen with a central island, built-in appliances, and pendant lighting.

12. 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, (24 reviews)
"Great place to stay. Very modern and comfortable. Philip is a nice guy to deal with."
United States
Paul M.
The price is ￥15,608
￥29,228 total
includes taxes & fees
Nov 1 - Nov 2
Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland
A covered porch with a wooden railing, a table with four chairs, and a hanging planter.

13. 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 ￥26,802
￥50,426 total
includes taxes & fees
Nov 4 - Nov 5
Cozy Fonzie Flat
A dining area with a round table, a vase with flowers, a lamp, and a potted plant.

14. Charming 3BR Home - Near KDMC & Downtown

Charming 3BR Home - Near KDMC & Downtown
Ashland
9.0 out of 10, Wonderful, (10 reviews)
"Very quiet location. The beds were super comfortable. Lots of room and close to restaurants. I messaged the host about check out and they responded within minutes. I would stay here again when we return."
United States
Shelia C.
The price is ￥18,131
￥36,399 total
includes taxes & fees
Nov 24 - Nov 25
Charming 3BR Home - Near KDMC & Downtown
A cozy living room with a fireplace, a dog lying on the floor, and a door leading outside.

15. Spacious Historic 5-bedroom house in charming Barboursville with AC

Spacious Historic 5-bedroom house in charming Barboursville with AC
Barboursville
10.0 out of 10, Exceptional, (2 reviews)
"Very cozy and nice place!"
United States
Joseph S.
The price is ￥46,116
￥99,552 total
includes taxes & fees
Nov 2 - Nov 3
Spacious Historic 5-bedroom house in charming Barboursville with AC
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with a wooden countertop.

16. The Cedar House -Cute, inviting, Charming and memorable.

The Cedar House -Cute, inviting, Charming and memorable.
Barboursville
The price is ￥22,561
￥46,270 total
includes taxes & fees
Nov 8 - Nov 9
The Cedar House -Cute, inviting, Charming and memorable.
A wooden porch with a swing, a bench, and a sign reading 'The Gathering Place.'

17. Tranquil Inn at The Barn 3 bedroom, 2 bathrooms, front and back porches

Tranquil Inn at The Barn 3 bedroom, 2 bathrooms, front and back porches
Crown City
The price is ￥28,379
￥46,825 total
includes taxes & fees
Oct 31 - Nov 1
Tranquil Inn at The Barn 3 bedroom, 2 bathrooms, front and back porches
A modern living room with a sofa, ottoman, and a flat-screen TV.

18. 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 ￥19,865
￥39,416 total
includes taxes & fees
Nov 8 - Nov 9
Modern Loft-Style Retreat Near Blenko Glass – Milton, WV
A wooden deck with a table and chairs, overlooking a calm lake with trees and buildings in the background.

19. 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, (58 reviews)
"It’s a wonderful place to stay so peaceful and relaxing hate to leave"
United States
Tess
The price is ￥15,466
￥24,766 total
includes taxes & fees
Nov 5 - Nov 6
Large Cabin with Stunning View - Fire Pit, Relax & Unwind
A wooden deck with a glass table and chairs, a thatched umbrella, and a grill.

20. 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, (23 reviews)
"We really enjoyed our stay, perfect location for a visit to that part of Kentucky."
United States
Melinda K.
The price is ￥15,766
￥31,458 total
includes taxes & fees
Nov 2 - Nov 3
Charming 2-bedroom house located in beautiful wooded setting!
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

TownePlace Suites by Marriott Ironton

TownePlace Suites by Marriott Ironton

10/10 Excellent
"Very clean and cozy beds! The breakfast here is one of the best I’ve ever had at any hotel! On weekends though it doesn’t start until 7am. We were up super early so it would have been nice if it started at 6am. No complaints on anything else."
Leslie 2-night trip
Posted 13 hours ago
TownePlace Suites by Marriott Ironton

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?

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.