Chesapeake vacation rentals

We found 21 vacation rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
May 2024
June 2024
Discover a selection of vacation rentals in Chesapeake that are perfect for your trip. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll find the amenities you need and want, which might include a fireplace and a washer and dryer. Whatever you're looking for, you'll be able to choose a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

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Choose a vacation rental for your Chesapeake getaway

Experience the unique character of Chesapeake with a stay in a vacation home rental. You'll find plenty to explore during your stay in the area. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Chesapeake

Are you hoping to find things to do in the area? Venture out of your cozy vacation rental and experience everything that makes Chesapeake a fun spot to vacation. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Camden Park Amusement Park (4.5 mi / 7.2 km)
  • El Haijj Salon & Spa (2.2 mi / 3.6 km)
  • Pump Up The Fun (8.8 mi / 14.2 km)
  • Esquire Country Club (10.7 mi / 17.3 km)
  • Sundowner Golf Course (13.8 mi / 22.3 km)
  • Sandy Creek Golf Course (14.7 mi / 23.6 km)

Exploring the natural landscape of Chesapeake

Whether you're an adventurous traveler or just want to spend some time taking in the scenery, Chesapeake is a great spot to appreciate mother nature. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Beech Fork State Park (10.3 mi / 16.6 km)
  • Armco Park (12.7 mi / 20.4 km)
  • Ritter Park (1.8 mi / 2.9 km)
  • Village of Barboursville Park (8.9 mi / 14.3 km)
  • Central Park (10.3 mi / 16.6 km)
  • Virginia Point Park (7.5 mi / 12 km)

Traveling to and around Chesapeake

The nearest airport is in Huntington, WV (HTS-Tri-State), located 6.7 mi (10.9 km) from the city center.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Chesapeake?

Based on our data, farmhouses are the most desirable vacation rental type in Chesapeake. But as you know, everyone's idea of the perfect stay can vary. Vrbo has vacation rentals of all shapes and sizes, and we'll help you discover your perfect match.

How much does it cost to rent a vacation rental in Chesapeake?

The average price for a vacation home in Chesapeake can vary depending on factors including season, property type and length of stay. Whether you're thinking about a sprawling villa with space for the whole family or a quaint cabin that's perfect for two, just add your dates of travel to discover some great-value stays.

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

Prices for beach houses in Chesapeake can differ depending on the style and size of the property and time of year you're traveling. All you need to do is enter your travel dates into Vrbo and the number of guests to view your rental options and prices. From there you can use our filter tool to narrow your search by ratings, nearby activities, amenities and more.

What are the top attractions for families in Chesapeake?

Keeping the kids occupied during your Chesapeake vacation is child's play with these cool family-friendly attractions:

  • Camden Park Amusement Park
  • Pump Up The Fun
  • Huntington Museum of Art

How old do you have to be to rent a vacation rental in Chesapeake?

It's advisable to check with the Chesapeake vacation home you're looking at on Vrbo as the age limit differs. However, typically it's 16, 18 or 21.

How long can I rent a vacation rental in Chesapeake for?

The length of time you can book a vacation rental in Chesapeake varies according to the property. Simply enter your preferred travel dates to view a list of options offering extended stays. With many creature comforts like air conditioning and kitchens, as well as some offering weekly or monthly discounts, you're sure to discover somewhere perfect to call your home away from home in Chesapeake.