Chesapeake holiday rentals

We found 5,044 holiday rentals — enter your dates for availability

Discover a selection of 40 homes, 13 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.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, 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. Virginia Beach Town Center and Naval Station Norfolk 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)
  • Virginia Beach National Golf Club (11.7 mi / 18.9 km)
  • Ocean Breeze Waterpark (16.6 mi / 26.7 km)
  • Cahoon Plantation Golf Course (3 mi / 4.8 km)
  • Chesapeake Golf Club (3.8 mi / 6.1 km)
  • Lamberts Point Golf Course (8.2 mi / 13.1 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)
  • Chesapeake City Park (3.5 mi / 5.6 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)

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 home?
One of the most popular locations to book a holiday property in Chesapeake is Western Branch North. Discover a dream stay with Stayz and experience this area as a local.
What is the most popular type of holiday home accommodation in Chesapeake?
The most in-demand types of holiday homes in Chesapeake are houses. Ready for more choices? Stayz 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 home in Chesapeake?
A number of things can affect the price of a holiday home in Chesapeake, including the time of year, length of stay and property type. But, all Stayz 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 Stayz. 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 homes in Chesapeake?
Yes. There are. You’ll have your pick of 23 holiday homes that welcome pets in Chesapeake on Stayz. Our cuddly best friends need a getaway too, so simply use our search function for pet-friendly holiday homes 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 Stayz, and then spend carefree days splishing and splashing in a swimming pool that’s only for you.
What are popular home amenities in Chesapeake?
A fireplace, a swimming pool and a firepit head the list of most popular home amenities in Chesapeake. Whether you’re taking a trip alone, with a partner or a group of friends, Stayz can help you find a holiday home that suits your style with all the features you need.
Are there large group holiday homes in Chesapeake?
Take your pick of five Stayz 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 homes 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 homes in Chesapeake?
Yes, you can take your pick from nine one-bedroom homes in Chesapeake. Whether you’d like a cosy chalet or a fancy condo, Stayz’s one-bedroom homes 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 homes 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.
Are there holiday homes with WiFi in Chesapeake?
You’ll have a choice of 11 holiday homes with WiFi in Chesapeake. If you’d like to disconnect from daily life on your trip, but still need to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Chesapeake?
Chesapeake has 20 holiday homes where you can relax in air-conditioned comfort. To locate a stay on Stayz that offers this perk, enter your dates of travel and use the handy filters to select the “air conditioning” box.
How old do you have to be to rent a holiday home in Chesapeake?
The minimum required age is generally 16, 18 or 21. It can differ from property to property on Stayz, so check the rules of your preferred Chesapeake holiday home before booking your escape.
How long can I rent a holiday home in Chesapeake for?
How long you can rent a holiday home in Chesapeake varies according to the property. Simply enter your preferred travel dates to view a list of options offering extended stays. With plenty of creature comforts like full kitchens and air conditioning, as well as some offering weekly or monthly discounts, you’re sure to discover a terrific place to call your home away from home in Chesapeake.

Explore destinations around Chesapeake

People also search for

Ski holiday rentals in Park City
Standard Link for Park City
Beach holiday rentals in Virginia Beach
Standard Link for Virginia Beach
Ski holiday rentals in Breckenridge
Standard Link for Breckenridge

More Holiday Rentals ideas

San Diego Holiday Rentals
Standard Link for San Diego
Fraser Holiday Rentals
Standard Link for Fraser
Park City Holiday Rentals
Standard Link for Park City
Virginia Beach Holiday Rentals
Standard Link for Virginia Beach
Big Sky Holiday Rentals
Standard Link for Big Sky
Suffolk Holiday Rentals
Standard Link for Suffolk
Yosemite National Park Holiday Rentals
Standard Link for Yosemite National Park
Aspen Holiday Rentals
Standard Link for Aspen
Alpine Holiday Rentals
Standard Link for Alpine
Williamsburg Holiday Rentals
Standard Link for Williamsburg
Charlottesville Holiday Rentals
Standard Link for Charlottesville
Anaheim Holiday Rentals
Standard Link for Anaheim
Snowmass Village Holiday Rentals
Standard Link for Snowmass Village
Vail Holiday Rentals
Standard Link for Vail
Breckenridge Holiday Rentals
Standard Link for Breckenridge
McLean Holiday Rentals
Standard Link for McLean
Palm Springs Holiday Rentals
Standard Link for Palm Springs
Honolulu Holiday Rentals
Standard Link for Honolulu
Kailua-Kona Holiday Rentals
Standard Link for Kailua-Kona
Carmel Holiday Rentals
Standard Link for Carmel
Kailua Holiday Rentals
Standard Link for Kailua
Wilson Holiday Rentals
Standard Link for Wilson
Telluride Holiday Rentals
Standard Link for Telluride
Melbourne Holiday Rentals
Standard Link for Melbourne
Norfolk Holiday Rentals
Standard Link for Norfolk
Byron Holiday Rentals
Standard Link for Byron
Jackson Holiday Rentals
Standard Link for Jackson