Chesapeake vacation rentals

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Discover a selection of 35 homes, 18 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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Urban energy and lush wilderness in Virginia’s Chesapeake

Chesapeake is a large and buzzing city in Virginia, grouped around the mighty deep-blue Elizabeth River, which surges north into the Atlantic Ocean. The city is surrounded by nature and wilderness – from protected swampland to dense, leafy forests. Downtown Chesapeake offers independent and mall shopping, plenty of movie theaters, and a wealth of family-friendly restaurants. And with such a range of Chesapeake vacation rentals available – modern apartments, family homes, and historic townhouses – you’re sure to find the perfectly personalized place for you.

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)
  • Virginia Beach National Golf Club (11.7 mi / 18.9 km)
  • Signature at West Neck (12.7 mi / 20.5 km)
  • Heron Ridge Golf Club (14.3 mi / 23.1 km)

Swampland adventures and indulgent shopping

Nature lovers can explore the vast Great Dismal Swamp National Wildlife Refuge. This epic, Eden-like wilderness is covered in cypress, tupelo, and pine trees, with patches and pools of bird and amphibian-covered wetland. You can hike along the swamp trail, or venture to Lake Drummond – a circular freshwater lake in the middle of the swamp – which offers fishing and camping. Back in Chesapeake, shoppers can splurge at the modern Chesapeake Square mall – with its clothing and cosmetic stores – or take the family to Towne Place at Greenbrier, a flashy family shopping, entertainment, and dining destination.

Spring is a fine time to travel to Chesapeake

Chesapeake experiences a humid subtropical climate, which means hot, sun-struck, and humid summers – with bursts of heavy rainfall – and cool winters, which can see snow and freezing temperatures. A perfect time to book a Chesapeake vacation rental is in late spring – late April or May – when temperatures are balmy, and before the summer wave of travelers hits the city. During this season you’ll be able to engage in plenty of outdoor activities without overheating. Early fall is a fine time to visit too, particularly as the Chesapeake foliage sings with fiery reds and yellows.

Chesapeake’s wetland and wilderness areas

Chesapeake is bordered by the bustling high-rise studded metropolis of Norfolk to the north, the relaxed beachside city of Virginia Beach to the east, and the quaint heritage-rich city of Suffolk to the west. Southwest of Chesapeake, the Great Dismal Swamp stretches to the horizon, where the wetlands and thick forest house black bears, bobcats, and otters. Further east, the swamp gives way to the Cavalier Wildlife Management Area – full of songbirds, wild turkeys, rattlesnakes and white-tailed deer – which eventually breaks into the shimmering Back Bay waters, itself encased by wildlife refuges and state parks.

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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