Chesapeake Holiday Rentals

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Holiday Rentals in Chesapeake

Quiet and cozy new townhome minutes from the mall exit.

9.8 out of 10, Exceptional, (19)
"The townhouse was very nice, clean and convenient. We were visiting family and it was so nice to be so close to them and everything we needed was only 5 to 10 minutes away. "
Quiet and cozy new townhome minutes from the mall exit.

Riverside Cabin with Homemade Breakfast

9.8 out of 10, Exceptional, (26)
"Cool cabin on the river. Clean inside. Fire pit was nice. Would stay again. "
The price is AU$214
includes taxes & fees
28 Nov - 29 Nov
Riverside Cabin with Homemade Breakfast

THE LUXURY CABIN IN THE WOODS

10.0 out of 10, Exceptional, (198)
"We spent four wonderful day on this lovely property. Spent every night around the fire and got better quality time than we had in years. The only complaint I have is that it was too short lived. I would definitely recommend this cabin to people looking for a wonderful experience or just a bit of peace and quiet. Great experience all around."
The price is AU$545
includes taxes & fees
1 Dec - 2 Dec
THE LUXURY CABIN IN THE WOODS

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

10.0 out of 10, Exceptional, (20)
"Definitely a great experience from start to finish. The property was clean, and exactly as described. The check in process was super easy. Definitely glad we booked here!"
The price is AU$268
includes taxes & fees
26 Nov - 27 Nov
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.

Secluded Ohio Forest Escape at Fuller's Fifty

10.0 out of 10, Exceptional, (42)
"Cool little cabin. Close to alot of the public hunting areas in south east OH. Only thing i would change if it was my cabin is I would invest in star link. "
The price is AU$288
includes taxes & fees
22 Dec - 23 Dec
Secluded Ohio Forest Escape at Fuller's Fifty

Cute little stone house on the hill

9.8 out of 10, Exceptional, (13)
"Nice little place. Would stay there again. Thanks for the hospitality!"
The price is AU$358
includes taxes & fees
30 Nov - 1 Dec
Cute little stone house on the hill

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

10.0 out of 10, Exceptional, (110)
"This cabin is simply outstanding in every aspect. The owners are wonderful people who went out of the way to make our stay a fantastic experience. I highly recommend the Cabin!"
The price is AU$370
includes taxes & fees
1 Dec - 2 Dec
The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.

4Bed/3Bath GREYSTONE COTTAGE

9.0 out of 10, Wonderful, (2)
"We rented this property while in town visiting family and it definitely served its purpose. However it is an older property (which I knew) with an older home comes problems. They need a new door and the basement had a wet spot. Otherwise good."
The price is AU$701
includes taxes & fees
29 Nov - 30 Nov
4Bed/3Bath GREYSTONE COTTAGE

Exceptionally clean, safe, private side by side duplex 3 minutes to stadium

10.0 out of 10, Exceptional, (3)
"We were visiting our son who attends marshall university. The house was located close to campus. We were provided with great directions and had some snacks provided for us whilevisiting. "
The price is AU$424
includes taxes & fees
25 Nov - 26 Nov
Exceptionally clean, safe, private side by side duplex 3 minutes to stadium

Enjoy the charm of Rush Kentucky on a quite and relax setting or go off-roading

8.8 out of 10, Excellent, (29)
"Our stay was great and the neighbors friendly. Sal was very responsive, helpful and made sure we had everything we needed. The place was very clean. I only gave our stay a 4 because some of the information was not correct and needs to be updated. It says that you have the grass next to the property but this has been turned into a RV campground. Not that it's a big deal there's plenty of space but that was not pictured and described Even though we don't have small children it did list a play...
Enjoy the charm of Rush Kentucky on a quite and relax setting or go off-roading

Creekside a piece of heaven

9.8 out of 10, Exceptional, (12)
"We came on a girls trip to see the mothman, it was a wonderful place to stay..beautiful house with great location. Thank you"
Creekside a piece of heaven

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

10.0 out of 10, Exceptional, (10)
"Great chance to get away. Very quiet and well furnished. Looking forward to my next stay here. "
The price is AU$263
includes taxes & fees
26 Nov - 27 Nov
This tiny cabin is a peaceful place complete with stocked pond and kayaks!

Urban Cottage:Homey & Convenient

10.0 out of 10, Exceptional, (9)
"We went to Huntington to visit family and decided on this property over getting a hotel room, and we are so glad we did. The house is very nice inside. The check-in process was painless. We had zero issues during our stay!"
Urban Cottage:Homey & Convenient

Impeccably Renovated Home Available in Russell

10.0 out of 10, Exceptional, (4)
"This place did not disappoint! It's very spacious and welcoming. My husband, grandkids, and I stayed and we all felt comfortable. Although we brought our own family games for game night, there were family games available to use which we enjoyed. My grandsons said they want to live in this house, lol. Seriously, this is a great home and the newly renovations are very modern and nice. My husband and I would definitely rent this home again when we travel to KY to visit our grandkids again. "
Impeccably Renovated Home Available in Russell

Secluded ranch home

10.0 out of 10, Exceptional, (8)
"We stayed a few nights with family and friends, and this place exceeded our expectations. It was super clean, the area was quiet, the manager was responsive, check-in was fast and easy. The layout was perfect for us, and the backyard area provided plenty of seating for outdoor adventures. You can't gogo wrong with this place!!issue"
The price is AU$464
includes taxes & fees
5 Dec - 6 Dec
Secluded ranch home

Low Key Living Hideaway

8.0 out of 10, Very good, (5)
"The stay was exactly as stated in the title. Just okay. This was my first time using VRBO & I reached out to the host & never heard back from her. We ended up being able to.get in but I would've like to have communicated with the host a few times during my stay. There were 3 remotes and we could only get 1 TV to work. That was in the bedroom with the bunk beds which we weren't even using. The driveway was very intimidating, this should have been stated in the description. "
Low Key Living Hideaway

The Runaway Retreat- No cleaning fee! Dogs & Kids stay Free!

10.0 out of 10, Exceptional, (36)
"Great space with an open floor plan, which was great for hanging out and chatting inside. The covered deck was perfect for having a coffee at the start of the day and for relaxing at night. All the necessities needed for an overnight stay were provided.and appreciated! Communication with the host was easy and helpful. "
The Runaway Retreat- No cleaning fee! Dogs & Kids stay Free!

Cozy With A Little Touch of Love

8.0 out of 10, Very good, (4)
"The host is very willing to work with you if problems arise or you have questions. Everything was clean, comfortable and quiet. I've got no complaints!"
The price is AU$410
includes taxes & fees
25 Nov - 26 Nov
Cozy With A Little Touch of Love

Cozy and quiet new townhome minutes from the mall exit.

9.6 out of 10, Exceptional, (10)
"We enjoyed our stay at this beautiful townhouse. The recommendations list was much appreciated as we were from out of town and not sure the best options close by. They had all the things you could need during the short story and easy to find location."
Cozy and quiet new townhome minutes from the mall exit.

Updated 2BR home in Huntington, WV

10.0 out of 10, Exceptional, (9)
"Very cute, clean, well stocked property just as pictured. Host was easy to communicate with and very responsive. We stayed here while our daughter visited Marshall-much nicer than being in a hotel. The neighborhood is in an older area of town."
Updated 2BR home in Huntington, WV
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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Other types of properties in Chesapeake you may be interested in

DoubleTree by Hilton Huntington

4.0 star property
8.6 out of 10, Excellent, (1000)
"enjoyable stay."
The price is AU$160
includes taxes & fees
1 Dec - 2 Dec
DoubleTree by Hilton Huntington

Fairfield Inn & Suites By Marriott Ashland

2.5 star property
8.2 out of 10, Very good, (599)
"The staff was extremely welcoming and made check in quick and easy. I highly recommend this hotel."
The price is AU$145
includes taxes & fees
27 Nov - 28 Nov
Fairfield Inn & Suites By Marriott Ashland

Fairfield Inn & Suites by Marriott Huntington

2.5 star property
9.2 out of 10, Wonderful, (879)
"Very clean and nice"
The price is AU$202
includes taxes & fees
27 Nov - 28 Nov
Fairfield Inn & Suites by Marriott Huntington
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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 Ritter Park. 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.