Discover a selection of 2,500 vacation rentals in Chesapeake, VA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $68 per night, and houses and condos are popular options for a stay in Chesapeake. Either way, you'll find a rental for everyone's needs.
Destination guide

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.

Things to do

Family fun in and around Chesapeake

If you’ve booked a Chesapeake vacation rental to accommodate the whole family, you’ll find plenty of Chesapeake attractions to match. Introduce your kids to the wonders of nature at the Chesapeake Arboretum – this 48-acre area erupts with lush native trees, and contains picnic areas, walking trails, and an historic 19th-century farmhouse. Older kids will be interested in the Chesapeake Planetarium, a modern white-domed downtown building offering free public shows on Thursdays. For a dreamy day trip, drive 20 miles northeast of Chesapeake to Virginia Beach, a small coastal city with miles of wide, sandy beachfront.


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.

Natural features

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.

How to get there

Traveling to and around Chesapeake

The nearest airport is in Norfolk, VA (ORF-Norfolk Intl.), located 10.1 mi (16.3 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Newport News, VA (PHF-Newport News - Williamsburg Intl.), which is 27.6 mi (44.5 km) away.

How many vacation rentals are available around Chesapeake, VA?

Our 2020 property listings offer a large selection of 2,745 vacation rentals around Chesapeake. From 1,707 house rentals to 532 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Chesapeake?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Chesapeake:

  • Greenbrier East: 39 vacation rentals
  • Whalehead Beach: 1,105 vacation rentals
  • Ocean Sands: 795 vacation rentals
  • Sandbridge: 250 vacation rentals
  • Corolla Light: 635 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Chesapeake?

Vrbo offers a large selection of vacation rentals near lovely places in Chesapeake. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Chesapeake Arboretum: 1,247 vacation rentals
  • Float First: 1,270 vacation rentals
  • Adventure Kayak Tours Day Tours: 1,246 vacation rentals
  • Chesapeake City Hall: 1,210 vacation rentals
  • Chesapeake Conference Center: 1,275 vacation rentals

But there are many other points of interest around Chesapeake listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Chesapeake?

Yes, of course. Vrbo has 1,707 Houses in Chesapeake. Our other popular types of vacation rentals in Chesapeake include:

  • Condos/Apartments: 532 rentals available
  • Cottages: 126 rentals available
  • Cabins: 126 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Townhouses and more.

Can I find a vacation rental with pool in Chesapeake?

Yes, you can select your preferred vacation rental with pool among our 1,661 vacation rentals with pool available in Chesapeake. Please use our search bar to access the selection of vacation rentals available.

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