Chesapeake vacation rentals

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your current months are March, 2024 and April, 2024.
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Discover a selection of 39 homes, 17 apartments, and other vacation rentals in Chesapeake that are perfect for your trip. Whether you’re staying in a vacation home with your kids and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a pool. 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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Delight in the beachside landscape of Chesapeake

The area's live music and theater scene are just a few of the reasons to vacation in Chesapeake. Travelers to this romantic city praise the shopping, restaurants and beaches. Naval Station Norfolk and Sandbridge Beach are just a couple of the must-sees in the area. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in and around Chesapeake

Are you hoping to discover top things to see and do in the city? Venture out of your cozy vacation rental and check out everything that Chesapeake has to offer. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Virginia Zoo (7.7 mi / 12.3 km)
  • Ocean Breeze Waterpark (16.6 mi / 26.7 km)
  • Cypress Point Country Club (10.1 mi / 16.3 km)
  • Riverfront Golf Club (11.6 mi / 18.7 km)
  • Virginia Beach National Golf Club (11.7 mi / 18.9 km)
  • Currituck County Welcome Center (15.9 mi / 25.6 km)

Exploring the beaches and other natural features in Chesapeake

Whether you're an adventurous traveler or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Chesapeake. Here are some of the area’s most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Sandbridge Beach (18.9 mi / 30.4 km)
  • Town Point Park (5.4 mi / 8.8 km)
  • Mount Trashmore Park (10 mi / 16.1 km)
  • Norfolk Botanical Garden (10.5 mi / 16.9 km)
  • Norfolk Beaches (12.8 mi / 20.5 km)
  • Ocean View Beach (13.1 mi / 21.1 km)

Seasonal weather in Chesapeake

If you're planning a vacation around warm-weather activities, July, August, June and September are the hottest months to visit, when temperatures average 77°F.

Traveling to and around Chesapeake

The nearest airport is in Norfolk Intl. Airport (ORF), located 10.1 mi (16.3 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Newport News - Williamsburg Intl. Airport (PHF), which is 27.6 mi (44.5 km) away.

Frequently asked questions

What is the best area to stay in Chesapeake when booking a vacation rental?

One of the most popular locations to book a vacation property in Chesapeake is Western Branch North. Discover a dream stay with Vrbo and experience this area as a local.

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

The most in-demand types of vacation rentals in Chesapeake are houses. Ready for more choices? Vrbo offers a variety of options to match the needs of our guests, so you'll see vacation homes in lots of shapes and sizes. The perfect fit is ready and waiting for you — grab yours today.

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

A number of things can affect the price of a vacation rental in Chesapeake, including the time of year, length of stay and property type. But, all Vrbo homes have something in common — excellent value. Simply add your travel dates to find your ideal fit.

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

When you travel and the size and style of the property will influence the cost of your beachside escape. Click on your Chesapeake travel dates to see your options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use our filters to select the features and amenities you need.

Are there pet-friendly vacation rentals in Chesapeake?

Yes. There are. You'll have your pick of 23 vacation rentals that welcome pets in Chesapeake on Vrbo. Our cuddly best friends need a getaway too, so simply use our search function for pet-friendly vacation rentals to book a place where your puppy can get in on the fun.

Can I rent a house with a pool in Chesapeake?

Add a new level of fun to your adventure by booking your family into one of the eight houses with a private pool in Chesapeake. Use our search filter to find the kind of property you want on Vrbo, and then spend carefree days splishing and splashing in a swimming pool that's only for you.

What are popular rental amenities in Chesapeake?

A fireplace, a swimming pool and a firepit head the list of most popular rental amenities in Chesapeake. Whether you're taking a trip alone, with a partner or a group of friends, Vrbo can help you find a vacation rental that suits your style with all the features you need.

Are there large group vacation rentals in Chesapeake?

Take your pick of five Vrbo properties in Chesapeake that can accommodate five or more guests. You'll enjoy all the privacy and room you need to hang out with your loved ones — and no one else.

Are there vacation rentals in Chesapeake that welcome kids?

With 23 family-friendly vacation homes to choose from in Chesapeake, now is a fantastic time to introduce the kids to the wonders of travel. Simply click on our "Properties good for families" filter box to search for stays loaded with amenities ideal for traveling families, like full kitchens, yards, entertainment areas and bunk beds.

What are the top attractions for families in Chesapeake?

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

  • Jillians Billiards
  • Oak Grove Lake Park
  • Chesapeake Arboretum

Are there one-bedroom vacation rentals in Chesapeake?

Yes, you can take your pick from nine one-bedroom rentals in Chesapeake. Whether you'd like a cozy chalet or a fancy condo, Vrbo's one-bedroom rentals are just right if you don't need loads of space. One of the major perks of having your own pad? You won't ever have to share your getaway with strangers.

Can I find two-bedroom vacation rentals in Chesapeake?

Pick from four two-bedroom properties in Chesapeake. Put your little ones in the second room or fill it with a couple of your best buddies. There's a spot for whoever's lucky enough to be joining your adventure.

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