Chesapeake, Charleston holiday accommodation: short-term house rentals & properties

Discover a selection of holiday rentals in Chesapeake that are perfect for your trip. Holiday rentals provide the amenities that you need and want for your stay with friends, family or just your pet, such as air conditioning and cable TV. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Chesapeake

Off grid Couples Cabin in Southern West Virginia

Sleeps 3 · 1 bedroom · 0+ bathrooms

Top rated rentals - Chesapeake

Premier Host

Great Spot for Families Visiting UC

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Book a holiday rental for your Chesapeake getaway

Learn about the unique charm of Chesapeake with a stay in a holiday home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Chesapeake

Are you searching for top things to see and do while you're in town? Venture out of your holiday home and experience everything that makes Chesapeake a fun place to get away to. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

Cabin Creek Quilts (5.4 mi / 8.6 km)
Coonskin Golf Course (12.2 mi / 19.6 km)

Exploring the natural features in Chesapeake

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Chesapeake is a great place to get out in nature. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

Kanawha State Forest (7 mi / 11.3 km)
Laidley Field (9.4 mi / 15.1 km)
Haddad Riverfront Park (10.3 mi / 16.6 km)
Little Creek Park (12.7 mi / 20.4 km)
Shawnee Sports Complex (16.2 mi / 26.1 km)
Daniel Boone Park (7.8 mi / 12.6 km)

Transport options to and around Chesapeake

Fly into Charleston, WV (CRW-Yeager), the closest airport, located 10.6 mi (17.1 km) from the city centre.

Frequently asked questions

How much does it cost to rent a holiday home in Chesapeake?

A number of factors influence what you’ll pay for your holiday home in Chesapeake, such as the length of stay, type of property and season. Still, all of our holiday homes have something in common — incredible value. Simply add your travel dates to find your ideal match.

How much does it cost to rent a beach house in Chesapeake?

The average price for a holiday home near the beach in Chesapeake depends on when you’re going and the size and type of property you’re searching for. You can easily and quickly find prices on Stayz by entering your destination and preferred travel dates. Then use the filters to pick the number of bedrooms and amenities essential to you, like a pool, WiFi and air conditioning.

What are the top attractions for families in Chesapeake?

Keep the kids occupied at these leading family-friendly attractions in Chesapeake:

West Virginia State Museum
Kanawha State Forest
Daniel Boone Park

How old do you have to be to rent a holiday home in Chesapeake?

We recommend checking with the Chesapeake holiday home you’d like on Stayz as the minimum age varies. However, it’s generally 16, 18 or 21.

How long can I rent a holiday home in Chesapeake for?

It really depends on the Chesapeake property. To browse a list of options offering extended stays, just type your travel dates and number of people into the Stayz search page. You can look forward to having the entire place to yourself, as well as comforts such as a fully-equipped kitchen, air conditioning and a yard where the kids can play. Keep your eyes peeled for any long-term stays that offer discounted weekly or monthly prices.