Chesapeake holiday lettings

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your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 39 homes, 17 apartments and other holiday rentals in Chesapeake that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and garden. Whatever you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

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  • All the privacy of home
    Enjoy full kitchens, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Delight in the beachside landscape of Chesapeake

The area's live music and theatre scene are just some of the reasons to come on holiday to Chesapeake. Travellers to this romantic city praise the shopping, restaurants and beaches. Naval Station Norfolk and Sandbridge Beach are just a couple of the must-see attractions in the area. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Chesapeake

Do you want to find things to do in the area? Venture out of your cosy holiday rental and check out everything that makes Chesapeake a fun place to get away to. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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 active traveller or just want to appreciate the scenery, Chesapeake is a great place to spend some time outside. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • 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 holiday around warm-weather activities, July, August, June and September are the hottest months to visit, when temperatures average 25°C.

Travelling to and around Chesapeake

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

Frequently asked questions

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

One of the most popular locations to book a holiday 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 holiday rental accommodation in Chesapeake?

The most in-demand types of holiday 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 holiday 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 holiday rental in Chesapeake?

A number of things can affect the price of a holiday 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 holiday rentals in Chesapeake?

Yes. There are. You'll have your pick of 23 holiday 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 holiday 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 holiday rental that suits your style with all the features you need.

Are there large group holiday 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 holiday rentals in Chesapeake that welcome kids?

With 23 family-friendly holiday 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 travelling 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 holiday rentals in Chesapeake?

Yes, you can take your pick from nine one-bedroom rentals in Chesapeake. Whether you'd like a cosy 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 holiday 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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