Chesapeake Holiday Rentals

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Holiday Rentals in Chesapeake

THE LUXURY CABIN IN THE WOODS

10.0 out of 10, Exceptional, (200)
"This was perfect! Absolutely beautiful cabin, beautiful surroundings. We saw horses and Deers and squirrels and the pond my son-in-law and daughter fished in the pond. They had a blast. It was perfect. Will be renting again in the fall, because I can’t even imagine how gorgeous the leaves are going to be. The host is very accommodating very kind. We made a ton of fabulous memories. Thank you so much!My advice to others just do it!"
The price is AU$560
includes taxes & fees
25 Feb - 26 Feb
THE LUXURY CABIN IN THE WOODS

Riverside Cabin with Homemade Breakfast

9.8 out of 10, Exceptional, (30)
"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!"
The price is AU$268
includes taxes & fees
23 Feb - 24 Feb
Riverside Cabin with Homemade Breakfast

Superb British Colonial holiday home, greenhouse, outdoor deck, tropical garden

10.0 out of 10, Exceptional, (117)
"Was nice to have the family together. "
Superb British Colonial holiday home, greenhouse, outdoor deck, tropical garden

Urban Cottage:Homey & Convenient

10.0 out of 10, Exceptional, (10)
"The house was excellent great layout and really comfortable "
Urban Cottage:Homey & Convenient

Secluded Ohio Forest Escape at Fuller's Fifty

10.0 out of 10, Exceptional, (49)
"Great cabin, secluded and as advertised. Would recommend to stay. Host was responsive and had a great time. "
The price is AU$291
includes taxes & fees
23 Mar - 24 Mar
Secluded Ohio Forest Escape at Fuller's Fifty

Cozy 2-bedroom apartment located next to St. Mary's Hospital!

10.0 out of 10, Exceptional, (1)
"Great for short or long term stays. plenty of room and all amenities necessary for long stay."
The price is AU$339
includes taxes & fees
22 Feb - 23 Feb
Cozy 2-bedroom apartment located next to St. Mary's Hospital!

Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital

The price is AU$270
includes taxes & fees
17 Mar - 18 Mar
Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital

Cute little stone house on the hill

9.6 out of 10, Exceptional, (17)
"Highly recommend very clean will definitely book again !"
The price is AU$361
includes taxes & fees
28 Feb - 1 Mar
Cute little stone house on the hill

Cozy With A Little Touch of Love

8.4 out of 10, Very good, (5)
"I liked the homely feeling even though i am front out of town. The street was a bit narrow with limited parking."
The price is AU$418
includes taxes & fees
22 Feb - 23 Feb
Cozy With A Little Touch of Love

La'Chic Boutique Bungalow 3 Beds/1.5Baths

9.4 out of 10, Exceptional, (18)
"We enjoyed our stay although we had to leave for a family emergency early. Easy to get to. Clean and nice amenities. "
The price is AU$591
includes taxes & fees
3 Mar - 4 Mar
La'Chic Boutique Bungalow 3 Beds/1.5Baths

Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes

The price is AU$300
includes taxes & fees
23 Feb - 24 Feb
Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes

Highly Rated for Cleanliness, quiet/cozy space near St Mary's

10.0 out of 10, Exceptional, (3)
"Great place would come again"
The price is AU$281
includes taxes & fees
2 Mar - 3 Mar
Highly Rated for Cleanliness, quiet/cozy space near St Mary's

Quiet and cozy new townhome minutes from the mall exit.

9.8 out of 10, Exceptional, (21)
"The home was lovely and had everything we needed. The only thing which kept me from giving a 5-star review was an issue with cleaning. When we arrived, the house hadn't been cleaned. I contacted the property manager and they had somebody in the house cleaning within 30 minutes. They also gave us a partial refund. (There had been some miscommunication in letting the cleaner know that the previous renters had left.) There was a lot of dog hair in the house, but I think that was entirely a...
Quiet and cozy new townhome minutes from the mall exit.

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

10.0 out of 10, Exceptional, (22)
"Brennan, your host, provides everything you will need, except food, to have an enjoyable stay. This home is very cozy and clean. Located within a short distance to stores and restaurants. I highly recommend Ricky Top Pizza which is about 4 minutes away"
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.

Peaceful and Private Ranch

10.0 out of 10, Exceptional, (2)
"The house was very nice and well decorated "
Peaceful and Private Ranch

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

10.0 out of 10, Exceptional, (37)
"We had a fantastic stay over the holidays. The house was very easy to find, no issues getting into the property and it had everything we needed for a comfortable stay. We hope to return again some day. "
The Runaway Retreat- No cleaning fee! Dogs & Kids stay Free!

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"
Secluded ranch home

Aparthotel- Green Goddess by Arena/Univ/Hospital

The price is AU$290
includes taxes & fees
10 Mar - 11 Mar
Aparthotel- Green Goddess by Arena/Univ/Hospital

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

10.0 out of 10, Exceptional, (11)
"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. "
The price is AU$238
includes taxes & fees
23 Feb - 24 Feb
This tiny cabin is a peaceful place complete with stocked pond and kayaks!

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

10.0 out of 10, Exceptional, (4)
"Host was readily available for any questions i had. The lock system made me feel very secure. The apartment setting was very lovely and clean. Neighborhood was very quiet and locations close to downtown. "
The price is AU$273
includes taxes & fees
23 Mar - 24 Mar
Exceptionally clean, safe, private side by side duplex 3 minutes to stadium
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

Fairfield Inn & Suites by Marriott Huntington

2.5 star property
9.2 out of 10, Wonderful, (915)
"Very nice, and clean"
The price is AU$191
includes taxes & fees
23 Feb - 24 Feb
Fairfield Inn & Suites by Marriott Huntington

Delta Hotels by Marriott Huntington Mall

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Good clean room, easy place to stop for the night "
The price is AU$191
includes taxes & fees
16 Mar - 17 Mar
Delta Hotels by Marriott Huntington Mall

Fairfield Inn & Suites By Marriott Ashland

2.5 star property
8.2 out of 10, Very good, (615)
"Just needed an over night stay. Room was comfortable and clean"
The price is AU$159
includes taxes & fees
24 Feb - 25 Feb
Fairfield Inn & Suites By Marriott Ashland
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.

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?

Superb British Colonial holiday home, greenhouse, outdoor deck, tropical garden: This holiday home rental outside of Chesapeake offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.