Chesapeake holiday homes

We found 5,055 holiday rentals — enter your dates for availability
Discover a selection of 38 homes, 16 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.

Holiday rentals with weekly discounts – Chesapeake

Showing deals for:30 Oct - 6 Nov

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Why visit Chesapeake

  • Natural beauty: Chesapeake offers lush parks and outdoor spaces perfect for family adventures and romantic getaways.
  • Local culture: Immerse yourself in the city's maritime history and charming local attractions that celebrate its unique heritage.
  • Vibrant community: Explore bustling neighbourhoods with a blend of urban vibes and relaxed local charm.
  • Family-friendly experiences: Enjoy a variety of activities and attractions suitable for all ages in this welcoming city.
  • Cultural excursions: Discover museums and historical sites that bring Chesapeake's rich past to life.

Top attractions in Chesapeake

Experience Chesapeake, Virginia, a charming city perfect for family, outdoor, and romantic holidays. Discover urban parks, maritime museums, and churches that highlight the local culture and history. Enjoy the blend of natural beauty and vibrant community spirit, making it an ideal destination for travellers seeking a mix of relaxation and exploration. Whether you’re on a family break or a romantic escape, Chesapeake offers a delightful and authentic American experience.

  • Chesapeake City Park: Enjoy a vibrant urban park with family-friendly spaces, expansive outdoor areas, and city charm for leisurely strolls and picnics.
  • Lake Drummond: Revel in romantic beach vibes, scenic lakeside views and outdoor serenity perfect for a memorable day out.
  • Chesapeake Arboretum: Explore a lush arboretum with winding paths, ideal for family outings and relaxed nature walks amidst diverse flora.

Things to do recommended for couples

Discover Chesapeake's hidden gems for a romantic escape. Enjoy a scenic drive along lush coastlines, savour local craft brews, and unwind with a quiet picnic under starlit skies. Experience true local charm for a memorable couple's retreat.

Things to do recommended for families

In Chesapeake, families can explore the stunning Great Dismal Swamp National Wildlife Refuge, perfect for hiking and birdwatching. Enjoy a day at the Chesapeake City Park, featuring playgrounds and picnic areas, or visit the Science Museum of Virginia for interactive exhibits that engage all ages.

Things to do recommended for groups

Explore the beautiful parks and waterways, such as Great Dismal Swamp, or enjoy a group outing at the Chesapeake City Park, complete with picnic areas and walking trails. Don't miss a visit to the local farmers' markets for fresh produce and artisanal goods.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Chesapeake

Whether you’re journeying with a group, as a family, with your pets, or seeking extended stays, be sure to sort by the appropriate priorities. Here are several Vrbo booking tips for you.

  • Traveling to Chesapeake with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Chesapeake with young kids: Traveling with little ones can be challenging. You want to ensure their comfort and safety, along with age-appropriate amenities like a private swimming pool. It’s also wise to consider how close you are to attractions that are family-friendly.
  • Taking your pets with you to Chesapeake: For many families, a trip isn’t truly complete without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chesapeake: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Chesapeake

Chesapeake, Virginia offers a charming blend of family-friendly and romantic experiences. Visitors can explore lush outdoor spaces, vibrant neighbourhoods, and local attractions that highlight the city’s unique character. From its scenic parks to its bustling local markets, Chesapeake is an ideal destination for diverse holiday experiences. Enjoy a perfect mix of nature, business vibes, and cultural excursions in this welcoming city.

  • Norfolk: Located a mere 10km from Chesapeake, Norfolk is a vibrant city that offers a delightful mix of outdoor adventures and cultural experiences. Visitors can stroll along the picturesque waterfront boardwalk, explore educational attractions such as museums, or indulge in shopping at local centres. The city's scenic beaches and lovely esplanade provide perfect spots for relaxation and recreation. Norfolk is particularly appealing for families and couples seeking a romantic getaway, with its charming tourist precinct serving as a hub for various activities and events.
  • Portsmouth: Just 8km from Chesapeake, Portsmouth is another inviting city that boasts a wealth of family-friendly and outdoor experiences. The boardwalk here is a popular destination for leisurely walks and stunning views, while the local shopping centres offer diverse retail options. Visitors will also find engaging educational attractions in the area. Portsmouth features beautiful beaches and an esplanade that enhance its appeal, making it an ideal spot for romantic outings or family adventures within its vibrant tourist precinct.
  • Ghent: Situated 11km from Chesapeake, Ghent is a charming neighbourhood known for its historic character and business-friendly atmosphere. The area is a hub of educational opportunities and features an array of shopping options. Ghent’s scenic boardwalk invites visitors to take in the coastal views, while its historic college university adds a unique charm. With its beautiful beaches and bustling tourist precinct, Ghent is an excellent choice for families and those looking to blend leisure with business pursuits.

Best time to go to Chesapeake

If you're planning a trip to Chesapeake, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January41.0°F (5.0°C)Light RainMostly SunnyAverage
February43.7°F (6.5°C)Light RainMostly SunnyAverage
March49.3°F (9.6°C)Light RainMostly SunnyAverage
April58.6°F (14.8°C)Light RainMostly SunnySlightly High
May67.1°F (19.5°C)Light RainMostly SunnyAverage
June75.2°F (24.0°C)Light RainMostly SunnySlightly High
July79.7°F (26.5°C)Light RainMostly SunnySlightly High
August78.4°F (25.8°C)Light RainMostly SunnyAverage
September73.6°F (23.1°C)Light RainMostly SunnyAverage
October64.0°F (17.8°C)Light RainMostly SunnySlightly Low
November52.9°F (11.6°C)Light RainMostly SunnySlightly Low
December46.4°F (8.0°C)Light RainMostly SunnySlightly Low

Booking with Vrbo is a breeze

Are you keen to save on your next getaway? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, simply use our filters to sort by price, location, and the type of holiday rental you prefer. We’re here to help you find the perfect accommodation for your adventure.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board is a handy tool designed for you to plan new adventures, refine your existing itineraries, or manage your bookings with ease. Your saved or reserved properties are conveniently organised into categories: Potential, Upcoming, and Current Trips. To check out the Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

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. Sandbridge Beach and Veterans United Home Loans Amphitheater at Virginia 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)
  • Virginia Beach National Golf Club (11.7 mi / 18.9 km)
  • Currituck County Welcome Center (15.9 mi / 25.6 km)
  • Ocean Breeze Waterpark (16.6 mi / 26.7 km)
  • Chesapeake Golf Club (3.8 mi / 6.1 km)
  • Cypress Point Country Club (10.1 mi / 16.3 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 (19.1 mi / 30.7 km)
  • Chesapeake City Park (3.5 mi / 5.6 km)
  • Town Point Park (5.4 mi / 8.8 km)
  • Portsmouth City Park (6.4 mi / 10.2 km)
  • Mount Trashmore Park (10 mi / 16.1 km)
  • Norfolk Botanical Garden (10.5 mi / 16.9 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 Bookabach 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? Bookabach 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 Bookabach 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 Bookabach. 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 Bookabach. 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 Bookabach, 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, Bookabach 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 Bookabach 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, Bookabach'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 Bookabach.
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 Bookabach 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 Bookabach, 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.