Chesapeake vacation rentals

We found 5,043 vacation rentals — enter your dates for availability

Discover a selection of 40 homes, 13 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.

Vacation rentals with weekly discounts - Chesapeake

Showing deals for:Aug 7 - Aug 14

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Welcome to Croatan Beach, an upscale neighborhood away from the crowds.
9.4 out of 10, Exceptional, (99 reviews)
Exceptional
(99 reviews)

Big Kitchen, Two Masters, Hot Tub, Short Walk from Croatan Beach

Virginia Beach

9% off
Price is $1,559
$10,915 for 7 nights
All fees included
Big Kitchen, Two Masters, Hot Tub, Short Walk from Croatan Beach

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Find out more about Chesapeake

Why visit Chesapeake

  • Beautiful Chesapeake Bay: Enjoy relaxation and fun at the scenic Chesapeake Beach and surrounding bay area, perfect for outdoor enthusiasts.
  • Family-friendly activities: Discover a range of attractions suitable for families, providing memorable experiences for all ages.
  • Historic sites: Explore the rich history of local colleges, universities, and maritime museums that showcase Chesapeake's cultural heritage.
  • Diverse vacation rentals: Choose from cozy cottages to stylish condos, offering the comfort of home during your stay.
  • Nearby excursions: Venture into neighboring regions for trendy attractions and a friendly atmosphere, enhancing your Chesapeake visit.

Popular types of accommodation in Chesapeake

Planning a getaway to Chesapeake? You're in for a treat. Discover a variety of vacation rentals, from private homes and cozy cottages to stylish condos. Whether you're looking for Chesapeake Beach vacation rentals or charming options in nearby Charleston, we’ve got you covered. Enjoy the comfort and flexibility of home rentals while making lasting memories. Let’s find the perfect spot for your next adventure.

  • Houses: The top choice for visitors to Chesapeake, offering spacious and comfortable stays for families and groups.
  • Condos: A popular option for those seeking modern amenities and convenient locations, perfect for a relaxed getaway.
  • Cottages: Quaint and charming, these rentals provide a cozy atmosphere, ideal for couples or small families.
  • Apartments: A practical choice for solo travelers or couples, offering a home-like environment in the heart of the city.
  • Caravan Parks: An adventurous option for those looking to camp or stay in a mobile home setting amidst nature.**

Top attractions near Chesapeake

Chesapeake, Virginia, is an ideal destination for family-friendly, outdoor, and city-themed vacations. Visitors can explore a variety of points of interest, including urban parks, maritime museums, and historic colleges and universities. Whether you're seeking cultural experiences or outdoor adventures, Chesapeake offers a rich array of attractions that cater to families and solo travelers alike, making it a perfect spot for memorable getaways.

  • Norfolk State University: A historic college with rich cultural vibes, offering a unique glimpse into African American heritage and education. Visitors can explore its beautiful campus and enjoy various cultural events.
  • Norfolk Scope: An entertainment arena that hosts family-friendly events, concerts, and sports. It's a vibrant hub for entertainment, perfect for an exciting night out with loved ones.
  • Regent University: A modern college known for its picturesque campus and city vibes, offering opportunities to engage in various academic and community events.

Things to do recommended for couples

Planning a romantic getaway in Chesapeake? Enjoy live music at The NorVa, just 6 miles away, or savor fine wines at Waters Edge Winery, located 9 miles from the city. Both spots promise unforgettable experiences filled with romance and entertainment for couples.

Things to do recommended for families

Your family vacation in Chesapeake, Virginia, promises fun at Harbor Park, a lively sports stadium just 5 miles away. Enjoy the serene surroundings at Oak Grove Lake Park and unwind at Deep Creek Lock Park, both offering relaxation and wellness vibes for a perfect family day out.

Things to do recommended for groups

Groups in Chesapeake can enjoy a shopping spree at Greenbrier Mall, catch a movie at the cozy Commodore Theatre, and hit the greens at Chesapeake Golf Club for a fun day outdoors. Each spot offers a unique local vibe perfect for group bonding.

*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

If you're planning a trip with friends, family, pets, or looking for extended stays, be sure to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Chesapeake with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group get-togethers. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Chesapeake with young kids: Traveling with little ones can present some challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chesapeake: For many, a family vacation isn't truly complete without their furry companion by their side. If you can relate, 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 seeking vacation rentals with great deals 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 amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Chesapeake

Chesapeake, Virginia, offers a delightful blend of family-friendly activities and outdoor adventures. Visitors can explore the beautiful Chesapeake Beach and the scenic Chesapeake Bay area, perfect for relaxation and fun. With a variety of vacation rentals available, families can enjoy the comfort of home while discovering the local vibe. Nearby regions also provide trendy excursions and friendly atmospheres, making Chesapeake an ideal destination for memorable experiences.

  • Norfolk: Located 6 miles from Chesapeake, Norfolk is a vibrant city known for its rich maritime history and cultural attractions. Enjoy a family-friendly day at the Norfolk Waterfront, where you can stroll along the scenic boardwalk, visit the local shopping centers, and explore educational venues like the Nauticus maritime museum. The city's landmarks, including the beautiful beach and esplanade, make it an ideal destination for outdoor and romantic experiences, providing plenty of opportunities for relaxation and exploration.
  • Portsmouth: Just 5 miles away from Chesapeake, Portsmouth is a charming city with a welcoming atmosphere. Families and couples will appreciate its picturesque waterfront, perfect for outdoor activities. The boardwalk and shopping mall center offer plenty of options for shopping and dining. Notable attractions include the esplanade and beach, which are great for leisurely walks or picnics. Portsmouth's tourist precinct is also a highlight, showcasing local culture and history, making it a delightful stop on your vacation.
  • Greenbrier East: Nestled around the Chesapeake area, Greenbrier East is a suburban neighborhood that caters to families, business travelers, and city enthusiasts. With convenient access to shopping centers and a lively boardwalk, it's perfect for those looking to enjoy both leisure and commerce. The esplanade and nearby tourist precinct offer a blend of relaxation and entertainment, while the local beach provides a tranquil escape. Greenbrier East is an excellent choice for those wanting to experience the best of city life while enjoying a family-friendly 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

Looking to save on your next trip? Consider being flexible with your travel dates since prices can fluctuate. Plus, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers an easy-to-use platform for planning your travel. You can create new trips, continue from where you last paused, or manage your existing plans all in one place. Your saved or booked properties will be neatly organized under categories like Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/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, Virginia, United States of America when booking a vacation rental?
When looking for the best area to stay in Chesapeake, Virginia, you might want to consider the Great Bridge neighborhood. This charming area is known for its rich history and family-friendly atmosphere, making it an excellent choice for vacation rentals. One of the top attractions here is the Great Bridge Lock Park, where you can enjoy scenic views and learn about the area's historical significance. Additionally, the nearby Chesapeake City Park offers beautiful walking trails and recreational facilities, great for outdoor enthusiasts.

Another great option is the Greenbrier neighborhood, which boasts an abundance of shopping and dining options. This area is vibrant and convenient, with the Greenbrier Mall nearby, offering a variety of stores and eateries. You can also explore the beautiful amenities at the Chesapeake Arboretum, where you can immerse yourself in nature and enjoy peaceful walks among stunning gardens.
How much does it cost to rent a vacation home in Chesapeake?
Prices for vacation rentals in Chesapeake vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chesapeake to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chesapeake vacation house rentals?
You can find great discounts on house rentals in Chesapeake on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Chesapeake?
For renting a beach house in Chesapeake, Virginia, travelers should consider the area around the Chesapeake Bay. Specifically, the neighborhoods closer to the bay, such as Great Bridge and Indian River, offer a variety of vacation rentals that provide easy access to waterfront activities. Many of these properties come equipped with amenities such as private docks, outdoor decks, and spacious living areas, superb for enjoying the scenic views and relaxing by the water.

Additionally, the nearby Chesapeake Beach area features lovely homes that often include features like outdoor grills, fire pits, and access to sandy spots ideal for swimming and picnicking. The proximity to local parks and nature reserves like the Chesapeake Arboretum adds an extra layer of enjoyment for nature enthusiasts.

In terms of local attractions, the region boasts several parks and recreational areas, providing ample opportunities for hiking, fishing, and boating. Rentals in these neighborhoods frequently offer family-friendly amenities such as game rooms and fully stocked kitchens, making them suitable for both relaxed getaways and active vacations.
What is the most popular type of vacation rental accomodation in Chesapeake?
In Chesapeake, vacation houses are the most popular type of rental, with around 30 available throughout the city. These homes often come equipped with multiple bedrooms, spacious living areas, and full kitchens, making them ideal for families or groups. Many vacation houses also feature outdoor spaces like patios or backyards, providing a great spot for gatherings or enjoying the pleasant Virginia weather. Additionally, there are about 12 apartments and several condos and cottages, offering a variety of choices for travelers seeking a cozy stay.
Are there any family house rentals in Chesapeake?
In Chesapeake, Virginia, there are some family-friendly house rentals available—approximately 21 throughout the area. This charming city offers a variety of spacious homes suitable for families, many of which are equipped with full kitchens, ample living areas, and outdoor spaces ideal for children to play. Visitors will find amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay.

The local neighborhoods provide access to parks and recreational areas, great for family outings. Additionally, Chesapeake is close to attractions like the Great Dismal Swamp National Wildlife Refuge, where families can enjoy hiking and wildlife observation. See all family-friendly rentals in Chesapeake.
Can I rent a vacation home with a pool or hot tub in Chesapeake?
In Chesapeake, Virginia, there are several vacation homes available for rent that feature pools and hot tubs, with around 14 options to choose from. This city offers a variety of neighborhoods where these properties can be found, including the scenic areas near the Great Dismal Swamp and the waterfront properties along the Elizabeth River, which provide beautiful views and tranquil settings.

Travelers can expect a range of amenities in these rentals, such as private swimming pools, relaxing hot tubs, spacious outdoor areas for family gatherings, and fully equipped kitchens for convenient meal preparation. Many properties also include features like covered patios, barbecue grills, and easy access to local parks and recreational areas, enhancing the overall vacation experience.
Can I find long-stay vacation rentals in Chesapeake?
A long-stay vacation rental in Chesapeake is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Chesapeake?
In Chesapeake, travelers can find a variety of pet-friendly house rentals, with around 18 options available. The city offers a mix of charming neighborhoods, including Great Bridge and the scenic area near the Elizabeth River, where many of these rentals are located. Expect amenities such as spacious backyards, modern kitchens, and comfortable living spaces, ensuring a pleasant stay for both guests and their furry companions.

Nearby, the Chesapeake City Park provides ample opportunities for outdoor activities with pets, featuring walking trails and open green spaces. Additionally, the Dismal Swamp National Wildlife Refuge offers a beautiful natural setting for hiking and exploration, making it a great area for pet owners to enjoy the outdoors. See all pet-friendly rentals in Chesapeake.
Are there any remote work vacation rentals in Chesapeake?
In Chesapeake, Virginia, there are plenty of remote work vacation rentals available, with around 48 options to choose from. These properties cater specifically to travelers looking to balance work and leisure, featuring essential amenities such as high-speed internet, dedicated workspaces with desks and comfortable chairs, and often multiple bedrooms that allow for privacy and focus. Many rentals also include extra conveniences like fully equipped kitchens, laundry facilities, and outdoor spaces for relaxing after a day of work.

Chesapeake itself offers a charming mix of suburban living and outdoor activities, with nearby parks and waterways superb for breaks or after-work relaxation. The Great Dismal Swamp National Wildlife Refuge provides opportunities for hiking and birdwatching, making it an excellent area to unwind. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chesapeake vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chesapeake with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Chesapeake?
In Chesapeake, popular vacation rental amenities cater to a range of guest needs. Most rentals feature kitchens, allowing travelers to prepare meals during their stay. Onsite parking is commonly available, making it convenient for those traveling with vehicles. Many properties also include coffee and tea makers for a quick caffeine fix. Additionally, a number of rentals permit pets, accommodating travelers who wish to bring their furry companions along. Service animals are also welcomed, ensuring that guests with specific needs can enjoy their stay comfortably.
When is the best time to visit Chesapeake for a vacation rental?
The peak travel season in Chesapeake runs from May to July, making it a vibrant time for vacationers eager to enjoy the beautiful waterways and outdoor activities. July, in particular, is the most popular month, where visitors can bask in warm temperatures, often reaching the high 80s to low 90s Fahrenheit, ideal for boating, fishing, and exploring parks like Great Dismal Swamp National Wildlife Refuge.

During this bustling season, the city comes alive with various festivals and events, providing ample opportunities for entertainment and socializing. Travelers can also savor fresh seafood at local restaurants and take advantage of nearby attractions, ensuring a fulfilling and engaging experience.

For those looking for a more budget-friendly option, consider visiting Chesapeake in December. While this month may seem quieter, it offers a unique charm with festive holiday decorations and fewer crowds. Visitors can enjoy cozy accommodations and explore the area's historical sites without the hustle and bustle of peak season.
How early should I book a Chesapeake vacation rental?
Book your Chesapeake vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chesapeake, Virginia, United States of America?
In Chesapeake, Virginia, visitors can explore a variety of attractions across its diverse neighborhoods. The Great Dismal Swamp National Wildlife Refuge is a significant highlight, offering opportunities for hiking, birdwatching, and exploring the unique ecosystem. Nearby, the Chesapeake City Park features expansive green spaces, picnic areas, and a lake, making it superb for outdoor activities.

In the downtown area, visitors can discover the historic Chesapeake Square, which offers shopping and dining options, along with access to local events and festivals. Additionally, the Battlefield Park, commemorating the Civil War, provides educational opportunities and scenic walking trails.

For those interested in history, the Chesapeake Historic District showcases charming architecture and is close to the Chesapeake and Albemarle Canal, where visitors can enjoy walking paths along the water.
Can I change or cancel my Chesapeake home rental booking on Vrbo?
To find Chesapeake vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Chesapeake vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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