Chesapeake Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Chesapeake holiday 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 AU$445
includes taxes & fees
18 Nov - 19 Nov
Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes
A modern living room with a dark wall, two wall-mounted lights, a patterned rug, a brown sofa with blue cushions, a black chair, and a window with curtains.

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 AU$345
includes taxes & fees
18 Nov - 19 Nov
The Blue House/Eclectic Art /Huntington’s Best Parks/full refund 1 day out
A house with a welcoming entrance, a visible number '20' on the door, and a pathway leading to the front door.

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

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 AU$1,073
includes taxes & fees
8 Nov - 9 Nov
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 dining table with a woven basket containing a candle and a book. A fireplace with a tiled surround is visible in the background.

4. 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.
Huntington Modern History - 4BD, MU, DT, St Mary's
A living room with a sofa, coffee table, and a chandelier.

5. 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 AU$2,077
includes taxes & fees
17 Nov - 18 Nov
Entire Bldg w/6 Bedrooms across 4 Separate Apts - Group/Corporate Stay Downtown
A living room with a patterned rug, a coffee table, and a bookshelf.

6. 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 AU$424
includes taxes & fees
18 Nov - 19 Nov
Espresso Maker & Modern Decor by Arena, University, Hospitals
A living room with a sofa, coffee table, and a chandelier.

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

Historic & Chic apartment by Arena, University, Hospital - Dog Friendly
Huntington
9.0 out of 10, Wonderful, (11 reviews)
"Very nicely decorated, cozy and clean."
United States
Yvette H.
The price is AU$433
includes taxes & fees
16 Nov - 17 Nov
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.

8. 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 AU$458
includes taxes & fees
16 Nov - 17 Nov
Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital
A bedroom with a bed, headboard, bedside tables, lamps, curtains, and a wall-mounted mirror.

9. 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 AU$606
includes taxes & fees
7 Nov - 8 Nov
Cozy With A Little Touch of Love
A hot tub with a control panel and a wooden cabinet.

10. 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 AU$249
includes taxes & fees
4 Dec - 5 Dec
Charming Home with private Hot Tub and Fire Pit
A spacious living room with a wooden dining table, leather sofas, and mounted deer heads.

11. 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, (64 reviews)
"Very nice place to stay! We really enjoyed it! "
United States
Hannah M.
The price is AU$282
includes taxes & fees
2 Dec - 3 Dec
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
A cozy living room with a fireplace, a dog lying on the floor, and a door leading outside.

12. 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 AU$848
includes taxes & fees
11 Nov - 12 Nov
Spacious Historic 5-bedroom house in charming Barboursville with AC
A dining area with a round table, a vase with flowers, a lamp, and a potted plant.

13. Charming 3BR Home - Near KDMC & Downtown

Charming 3BR Home - Near KDMC & Downtown
Ashland
9.2 out of 10, Wonderful, (11 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 AU$318
includes taxes & fees
1 Dec - 2 Dec
Charming 3BR Home - Near KDMC & Downtown
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with a wooden countertop.

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

The Cedar House -Cute, inviting, Charming and memorable.
Barboursville
The price is AU$409
includes taxes & fees
17 Nov - 18 Nov
The Cedar House -Cute, inviting, Charming and memorable.
A covered porch with a wooden railing, a table with four chairs, and a hanging planter.

15. 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 AU$431
includes taxes & fees
6 Nov - 7 Nov
Cozy Fonzie Flat
A wooden deck with a glass table and chairs, a thatched umbrella, and a grill.

16. 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 AU$274
includes taxes & fees
18 Nov - 19 Nov
Charming 2-bedroom house located in beautiful wooded setting!
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 AU$398
includes taxes & fees
15 Nov - 16 Nov
Tranquil Inn at The Barn 3 bedroom, 2 bathrooms, front and back porches
A wooden cabin with a red roof, surrounded by lush greenery and a calm lake.

18. THE LUXURY CABIN IN THE WOODS

THE LUXURY CABIN IN THE WOODS
Catlettsburg
10.0 out of 10, Exceptional, (244 reviews)
"Beautiful property well stocked pond and home was very clean."
United States
Eric H.
The price is AU$425
includes taxes & fees
8 Nov - 9 Nov
THE LUXURY CABIN IN THE WOODS
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 AU$215
includes taxes & fees
2 Dec - 3 Dec
Large Cabin with Stunning View - Fire Pit, Relax & Unwind
A rustic cabin with a fire pit and outdoor seating.

20. Secluded Ohio Forest Escape at Fuller's Fifty

Secluded Ohio Forest Escape at Fuller's Fifty
Patriot
10.0 out of 10, Exceptional, (100 reviews)
"Very beautiful place everything that you need to have a small getaway or a long getaway. "
United States
Anthony R.
The price is AU$303
includes taxes & fees
6 Dec - 7 Dec
Secluded Ohio Forest Escape at Fuller's Fifty
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

An outdoor seating area with wicker furniture and potted plants, surrounded by a wall with string lights.
DoubleTree by Hilton Huntington

DoubleTree by Hilton Huntington

DoubleTree by Hilton Huntington
Huntington

10/10 Excellent

Wonderful warm friendly hotel, The staff were very friendly and helpful, rooms and all areas very clean and high standard. I was travelling from Australia to see the Brantley Gilbert concert and the staff recommended some local restaurants and places to go in the town and answered any questions I had about the area. A special Thanks to staff member Tylor who arranged an early morning ride to the airport for me on my last day, and was extremely helpful for my entire stay. Great hospitality all...
Australia
Annika
Reviewed October 18, 2024
DoubleTree by Hilton Huntington

Find out more about Chesapeake

Everything you need to know about Chesapeake holiday rentals

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

Chesapeake holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake holiday rentals we have selected for you start as low as AU$214 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesapeake rentals

At Expedia, we put the best Chesapeake holiday 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 holiday.

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 holiday rental in Chesapeake?

Yes, there are holiday rentals close to the most popular sights in Chesapeake, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chesapeake has to offer?

2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.: This holiday home rental outside of Chesapeake is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most 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 wider area, you’ll find Mountain Health Arena and Pullman Square.

What are holiday rentals like in Chesapeake?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesapeake. Holiday rentals offer amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family getaway.