Chesapeake Holiday Rentals from €149: Search Short-Term Rentals

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

Cute little stone house on the hill : This holiday home rental outside of Chesapeake has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

Check Chesapeake holiday rental availability

Holiday Rentals in Chesapeake

"I liked how responsive the owners are and how quiet it is. The breakfasts are amazing - they give you a menu and bring it to your door when you want and it tastes great! The only downside is when it's super cold out, the floor gets cold, but they do run space heaters in addition to the regular heater and even put down extra rugs. The cabin is on stilts since it's right on the river so I think some insulation under the floor would make it perfect!"

includes taxes & fees

12 Jan - 13 Jan

"Very cozy, comfortable and clean. We love staying here and getting to be together for a couple days!"

includes taxes & fees

10 Jan - 11 Jan

5 bedrooms, iron/ironing board, free WiFi, bed sheets

"The house was very nice. The kitchen was not well organized. There was plenty of bedding and towels. My complaints are: water coming from the faucet was much too hot and should come with a warning or the temp be turned down. There should be a railing going into the basement. I am 78 yrs old and it was difficult getting down the steps! We were told to wash all towels before leaving and detergent would be provided. Well, the washer was full of stinky wet clothes that had obviously been there...

includes taxes & fees

10 Jan - 11 Jan

"Beautiful cabin! Worth the drive from VA. "

includes taxes & fees

10 Jan - 11 Jan

"Nice little place. Would stay there again. Thanks for the hospitality!"

includes taxes & fees

10 Jan - 11 Jan

"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"

includes taxes & fees

15 Jan - 16 Jan

"Exactly what we needed. House was clean and plenty of room"

includes taxes & fees

5 Feb - 6 Feb

"We enjoyed our stay although we had to leave for a family emergency early. Easy to get to. Clean and nice amenities. "

includes taxes & fees

10 Jan - 11 Jan

"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!"

includes taxes & fees

12 Jan - 13 Jan

"My boyfriend and I stayed here when visiting family. It felt like home and their little touches were really nice. We enjoyed our stay."

includes taxes & fees

18 Jan - 19 Jan

"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...

"We came on a girls trip to see the mothman, it was a wonderful place to stay..beautiful house with great location. Thank you"

"This was my second time staying at this place. It was just as perfect as the first time. Everything i need for a quick solo hunting trip. Ill be back again next year. "

includes taxes & fees

6 Feb - 7 Feb

"Nice location for our needs and able to accommodate all 7 of us comfortably Shower on the second floor did not have hot water and the basement bedroom was very cold Other than that, property was as depicted "

includes taxes & fees

12 Jan - 13 Jan

"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!"

"The renovations were very nice. It was up-to-date and felt like I was staying in a house I could live in. There was great lighting in the kitchen, nice appliances and plenty of cookware. Very spacious bedrooms, comfy beds and plenty of towels and blankets. And every room has a TV. Always a plus with kids. There was even a Christmas tree and decorations. We felt very much at home."

"This property was wonderful. Just tge rufht suze for my family and I. Very clean and up todate. The property manager was freindly and answered our questions fast. They even allowed us to check in early when we arrived sooner than planned. Will definitely be staying here again in the future!"

"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. "

"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. "

1 bedroom, in-room safe, iron/ironing board, WiFi

"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!"

includes taxes & fees

10 Jan - 11 Jan

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Other types of properties in Chesapeake you may be interested in

"Easy-to-use "

includes taxes & fees

17 Jan - 18 Jan

"Beautiful hotel"

includes taxes & fees

27 Jan - 28 Jan

"Alisha was wonderful at checkin and for my multiple questions throughout the night. My stay here was unplanned and I had to find somewhere to stay due to inclement weather. It ended up being a very relaxing evening after a stressful day. "

includes taxes & fees

12 Jan - 13 Jan

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, apart-hotels, 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 favorite 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 depends 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 €149 per night. Entering your travel dates in the search wizard you might find 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.

Recent reviews of Chesapeake properties

Delta Hotels by Marriott Huntington Mall

5/5 Excellent

"Alisha was wonderful at checkin and for my multiple questions throughout the night. My stay here was unplanned and I had to find somewhere to stay due to inclement weather. It ended up being a very relaxing evening after a stressful day. "

A verified traveller stayed at Delta Hotels by Marriott Huntington Mall

Posted 17 hours ago

5/5 Excellent

"I liked how responsive the owners are and how quiet it is. The breakfasts are amazing - they give you a menu and bring it to your door when you want and it tastes great! The only downside is when it's super cold out, the floor gets cold, but they do run space heaters in addition to the regular heater and even put down extra rugs. The cabin is on stilts since it's right on the river so I think some insulation under the floor would make it perfect!"

A verified traveller stayed at Riverside Cabin with Homemade Breakfast

Posted 10 days ago

5/5 Excellent

"The facility was exactly what one would want for a stay in the tri-state area. It was clean, quiet, safe, easy to access, comfortable, and the staff was great. Food, fuel and recreation areas are all not far. It was perfect for a quick stop to get some good rest at night and breakfast in the morning."

A verified traveller stayed at Ramada Limited Catlettsburg/Ashland

Posted 11 days ago

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?

Cute little stone house on the hill: This holiday home rental outside of Chesapeake has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.

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Holiday Rentals in Chesapeake

Plan, book, stay with confidence

Check Chesapeake holiday rental availability

Holiday Rentals in Chesapeake

Riverside Cabin with Homemade Breakfast

Riverside Cabin with Homemade Breakfast

THE LUXURY CABIN IN THE WOODS

THE LUXURY CABIN IN THE WOODS

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

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

Secluded Ohio Forest Escape at Fuller's Fifty

Secluded Ohio Forest Escape at Fuller's Fifty

Cute little stone house on the hill

Cute little stone house on the hill

Secluded ranch home

Secluded ranch home

4-bedroom vacation home short drive to Huntington Mall, Marshall, & St. Mary’s

4-bedroom vacation home short drive to Huntington Mall, Marshall, & St. Mary’s

La'Chic Boutique Bungalow 3 Beds/1.5Baths

La'Chic Boutique Bungalow 3 Beds/1.5Baths

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

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

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

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

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

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

Creekside a piece of heaven

Creekside a piece of heaven

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

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

4Bed/3Bath GREYSTONE COTTAGE

4Bed/3Bath GREYSTONE COTTAGE

Urban Cottage:Homey & Convenient

Urban Cottage:Homey & Convenient

Impeccably Renovated Home Available in Russell

Impeccably Renovated Home Available in Russell

Quiet and cozy new townhome minutes from the mall exit.

Quiet and cozy new townhome minutes from the mall exit.

Low Key Living Hideaway

Low Key Living Hideaway

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

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

Cozy With A Little Touch of Love

Cozy With A Little Touch of Love

Other types of properties in Chesapeake you may be interested in

Fairfield Inn & Suites By Marriott Ashland

Fairfield Inn & Suites By Marriott Ashland

DoubleTree by Hilton Huntington

DoubleTree by Hilton Huntington

Delta Hotels by Marriott Huntington Mall

Delta Hotels by Marriott Huntington Mall

Find out more about Chesapeake

Find out more about Chesapeake

Recent reviews of Chesapeake properties

Recent reviews of Chesapeake properties

Delta Hotels by Marriott Huntington Mall

Frequently asked questions