Chesapeake vacation rentals

We found 5,065 vacation rentals — enter your dates for availability

Discover a selection of 36 homes, 12 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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Find out more about Chesapeake

Why visit Chesapeake

  1. Diverse Attractions: Chesapeake boasts urban parks, maritime museums, and entertainment arenas suitable for all ages.
  2. Outdoor Adventures: Enjoy scenic parks and outdoor activities that cater to families and nature enthusiasts.
  3. Charming Neighborhoods: Explore the rich history and vibrant local culture in Chesapeake's unique neighborhoods.
  4. Family-Friendly Accommodations: Choose from private vacation homes, cozy condos, and spacious apartments for a comfortable stay.
  5. Friendly Atmosphere: Experience warm hospitality from locals and a welcoming environment throughout your visit.

Popular types of accommodation in Chesapeake

If you're planning a getaway to Chesapeake, you're in for a treat with our variety of friendly vacation rentals. The most popular options include houses, cozy condos, and spacious apartments. Whether you're looking for a home rental or a vacation rental that fits your needs, Chesapeake has something for everyone. Discover the perfect rental in Chesapeake and enjoy a memorable stay with transparency and savings.

  • Houses: The top choice for travelers in Chesapeake, these homes offer spacious accommodations perfect for families, friends, or couples seeking a home-away-from-home experience.
  • Condos: A popular second option, condos provide modern amenities and often come with access to community facilities like pools and gyms.
  • Apartments: The third most sought-after option, apartments offer a convenient and budget-friendly stay for solo travelers or small groups.
  • Cottages: These charming getaways are perfect for those desiring a cozy and quaint atmosphere during their visit.
  • Caravan Parks: A unique and affordable option, caravan parks allow for outdoor experiences and community interactions.**

Top attractions near Chesapeake

Chesapeake, Virginia, offers a delightful vacation for families and outdoor enthusiasts alike. With attractions like urban parks, maritime museums, and entertainment arenas, there's something for everyone. Whether you're seeking cultural experiences or outdoor adventures, Chesapeake’s diverse points of interest ensure an enjoyable visit for travelers of all ages. Plan your trip to explore the vibrant local scene and make lasting memories!

  1. Regent University: A modern university featuring contemporary architecture and vibrant city vibes, Regent University offers a dynamic atmosphere for learning and exploration, just 6 miles from Chesapeake.
  2. Norfolk State University: This historic university is rich in culture, showcasing beautiful architecture and a lively campus life, located 6 miles from Chesapeake.
  3. Norfolk Scope: An entertainment arena that hosts various events, Norfolk Scope is perfect for family outings and entertainment experiences, situated 6 miles from Chesapeake.

Things to do recommended for couples

Ready for a romantic getaway in Chesapeake? Catch a live show at The NorVa, just 6 miles away, for a fun night out. Then, unwind at Waters Edge Winery, located 9 miles away, where you can savor exquisite wines in a cozy, romantic atmosphere.

Things to do recommended for families

Families visiting Chesapeake can catch a game at Harbor Park, unwind at Oak Grove Lake Park, and have a blast at Jillian's Billiards. Each spot offers unique experiences, ensuring a fun-filled adventure for everyone in the family.

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

No matter if you're traveling with a group, with family, bringing your pets along, or seeking extended stays, be sure to use filters that align with your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Chesapeake with a group: Think about how many bedrooms you require, as well as any additional features you might want, like a fully equipped kitchen or outdoor space for gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Chesapeake with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to attractions that are enjoyable for families.
  • Taking your pets with you to Chesapeake: For many, a family vacation feels incomplete without their furry companion. If you can relate, take a look at Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with 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 vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, 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 in and around Chesapeake

Chesapeake, Virginia, offers a delightful mix of family-friendly attractions and outdoor adventures, making it an ideal vacation spot. Explore its charming neighborhoods, rich history, and scenic parks, perfect for excursions with loved ones. Nearby cities add to the experience with a warm atmosphere, friendly locals, and plenty of vacation ideas. Whether you're seeking beautiful family homes or unique rental options, Chesapeake is sure to provide a memorable getaway for all types of travelers.

  • Norfolk: Norfolk is an exciting city located 6 miles away from Chesapeake, offering travelers a vibrant mix of family-friendly activities, outdoor adventures, and romantic spots. This bustling urban area features a picturesque waterfront boardwalk and a variety of shopping centers, making it a perfect destination for both leisure and retail therapy. Visitors can explore local landmarks such as the beautiful beaches and the scenic esplanade, as well as enjoy the lively tourist precinct filled with restaurants and entertainment options.
  • South Norfolk: Nestled within Chesapeake, South Norfolk is a charming village known for its family-oriented atmosphere and outdoor recreational opportunities. This inviting area boasts a delightful boardwalk and shopping centers, making it easy to spend a day exploring local boutiques and grabbing a bite to eat. Attractions nearby include stunning beaches and a vibrant tourist precinct, where visitors can immerse themselves in the local culture while enjoying the lovely esplanade that lines the waterfront.
  • Greenbrier East: Greenbrier East is a dynamic neighborhood situated within Chesapeake, ideal for families, business travelers, and city explorers alike. This area is home to several shopping centers and a convenient shopping mall, making it a go-to spot for those looking to indulge in retail therapy. Visitors can take advantage of the nearby esplanade, beautiful beaches, and the bustling tourist precinct, perfect for enjoying local cuisine and entertainment while soaking in the neighborhood's lively atmosphere.

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. Peak season runs in April and June to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

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

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock substantial savings. To discover a Vrbo property that suits your budget, use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner definitely has its perks! By enrolling in our travel rewards program, One Key, you can immediately access member discounts and earn as well as redeem OneKeyCash™ on eligible reservations. Sign up now and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, refine your existing plans, or manage your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

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?
Among the more popular locations to get a vacation home in Chesapeake is Western Branch North. Discover a dream stay on Vrbo and explore this area like a local.
What is the most popular type of vacation rental accommodation in Chesapeake?
Based on our data, apartments are considered the most popular type of property in Chesapeake. But that goes without saying, everyone's idea of an awesome stay is bound to be different. Vrbo has vacation homes with every size, shape and budget in mind, so you're bound to find your perfect match.
How much does it cost to rent a vacation rental in Chesapeake?
The average price for a vacation home in Chesapeake depends on several factors, including property type, length of stay and time of year. Whether you'd like a sprawling villa with room to move around or a cozy condo perfect for just you and the kids, just add your travel dates to find stays that offer great value.
How much does it cost to rent a beach house in Chesapeake?
When you travel and the style and size of the property will help determine the cost of your beachside escape. Click on your Chesapeake travel dates to see all your options on Vrbo. Can't live without a private pool? Use our filters to pick the features and amenities you want in your beach house.
Are there pet-friendly vacation rentals in Chesapeake?
Yes. Choose from 43 stays that roll out the welcome mat in Chesapeake on Vrbo. Our furry friends need to get away from it all too, so simply use our search function for pet-friendly vacation rentals to book a perfect pad where your puppy can get in on the family fun.
Can I rent a house with a pool in Chesapeake?
Add a whole other level of fun to your adventure by staying in one of the 21 houses with a private pool in Chesapeake. Use our handy search filter to find the kind of property you want on Vrbo, and then spend your downtime splashing about in a swimming pool that's just for you.
What are popular rental amenities in Chesapeake?
Some of the most popular rental amenities people search for in Chesapeake include a barbecue grill, a garden and a fireplace. Whether you're vacationing with buddies, family or even pets, Vrbo vacation properties provide the best amenities for making new memories with the people you cherish the most.
Are there large group vacation rentals in Chesapeake?
With 17 Chesapeake vacation properties that can accommodate a group of five or more people, you can bring a few extra pals or family members along. Whether you're planning an informal get-together or a celebratory event, Vrbo will help you find a comfy space to match the occasion.
Are there vacation rentals in Chesapeake that welcome kids?
With 43 family-friendly vacation homes to pick from in Chesapeake, there's never been a better time to introduce the kiddos to the pleasures of travel. Check our "Properties good for families" filter to view stays that come with amenities perfect for vacationing families, like kitchens, yards, entertainment units and bunk beds.
What are the top attractions for families in Chesapeake?
There are tons of fun things to see and do with the family in Chesapeake, including:

  • Chesapeake Square Mall
  • Oak Grove Lake Park
  • Greenbrier Mall

Are there one-bedroom vacation rentals in Chesapeake?
Yes, Chesapeake has 11 one-bedroom rentals on offer. Typically located in popular spots because of their compact size, a one-bedroom vacation property is great if you're getting away with a friend or your partner. And with comforts like laundry facilities and more privacy than a standard hotel, you'll be able to relax while enjoying this exciting destination.
Can I find two-bedroom vacation rentals in Chesapeake?
Gather your family and enjoy peace, privacy and comfort in one of the eight two-bedroom vacation rentals Chesapeake has to offer.
Are there vacation rentals with WiFi in Chesapeake?
Whether you'd like to stay in touch with world events, check emails or update your social media accounts, there are 21 vacation homes with WiFi in Chesapeake. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Chesapeake?
Select your dates and then make use of the filters to look for vacation rentals with air conditioning in Chesapeake on Vrbo. With 39 air-conditioned properties to choose from here, you can enjoy a comfy and cool stay.
How old do you have to be to rent a vacation rental in Chesapeake?
The minimum age is typically 16, 18 or 21. It can change from property to property on Vrbo, so look at the rules of your preferred Chesapeake vacation home before you book.
How long can I rent a vacation rental in Chesapeake for?
The amount of time you can rent a Chesapeake vacation home for is down to each property. Just put in your dates of travel to browse options offering longer term stays. They have all you require to make your extended vacation more comfortable such as air conditioning and laundries. Some vacation homes might also offer discounted weekly or monthly prices, so you can stay even longer for less.
Does Vrbo offer discounts for vacation homes in Chesapeake?
On Vrbo, you'll find incredible deals and discounts for Chesapeake. Browse our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you're looking for a mini getaway or an extended stay, Vrbo offers a variety of options for every style and budget.

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