Chesapeake holiday lettings

We found 5,021 holiday rentals — enter your dates for availability

Discover a selection of 36 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.

Holiday rentals with weekly discounts - Chesapeake

Showing deals for:9 Jan - 16 Jan

Image gallery for Lovely 2 BR Condo in 4💎 Historic Golf Resort

Golf
9.2 out of 10, Wonderful, (20 reviews)
Wonderful
(20 reviews)

Lovely 2 BR Condo in 4💎 Historic Golf Resort

Williamsburg, VA

8% off
Price is £1,856
for 7 nights, 1 apartment
£265 per night
includes taxes & fees
Lovely 2 BR Condo in 4💎 Historic Golf Resort

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Find out more about Chesapeake

Find out more about Chesapeake

Why visit Chesapeake

  • Natural Escapes: Visit Chesapeake City Park and the Chesapeake Arboretum for beautiful green spaces and tranquil nature walks.
  • Cultural Attractions: Explore the maritime museum for a glimpse into the region's rich nautical history.
  • Family-Friendly Activities: Enjoy a range of recreational opportunities, from urban parks to entertainment arenas suitable for all ages.
  • Charming Neighbourhoods: Stroll through delightful neighbourhoods that showcase the warmth of local culture and hospitality.
  • Diverse Accommodation: Choose from a variety of rental options, including holiday homes, condos, and cosy cottages to suit your needs.

Popular types of accommodation in Chesapeake

Our platform showcases a variety of accommodation options in Chesapeake, including private holiday homes, condos, and charming cottages. Whether you're seeking a peaceful retreat or a family-friendly space, there's something for everyone. With our extensive selection of Chesapeake VA rentals, you can easily find the perfect rental homes to suit your needs. Explore the best of Chesapeake and enjoy a memorable stay with transparency and reassurance.

  • Houses: The top choice for visitors in Chesapeake, these homes offer a spacious and personalised stay for families, friends, or couples.
  • Condos: A popular option, condos provide modern amenities and shared facilities, ideal for a comfortable getaway.
  • Cottages: Charming and quaint, cottages in Chesapeake offer a cosy retreat, perfect for those seeking a peaceful escape.
  • Apartments: Convenient and well-equipped, apartments are a great choice for travellers looking for flexibility and independence.
  • Caravan Parks: A unique accommodation choice, caravan parks allow for a fun and adventurous stay amidst nature.**

Top attractions near Chesapeake

Chesapeake, Virginia, is an excellent destination for families and those seeking outdoor and urban experiences. Key attractions include urban parks, the maritime museum, and an entertainment arena, providing cultural and recreational activities for all ages. Don’t miss visiting Chesapeake City Park and the Chesapeake Arboretum for a taste of nature and relaxation. Whether you’re exploring with family or friends, Chesapeake promises a memorable getaway.

  • Regent University: A contemporary institution with a vibrant city atmosphere, Regent University offers cutting-edge facilities and engaging academic programmes, making it a unique spot for those interested in modern education and campus life.
  • Norfolk State University: A historically rich university that celebrates cultural diversity, Norfolk State University features impressive architecture and a lively community, providing insights into African American heritage and education.
  • Norfolk Scope: This dynamic entertainment venue hosts concerts, sports events, and family shows, making it a perfect destination for a fun-filled outing, suitable for all ages.

Things to do recommended for couples

Chesapeake offers delightful romantic experiences for couples. Enjoy a vibrant evening at The NorVa, just 3.7km away, filled with live music. Alternatively, indulge in the charm of Waters Edge Winery, located 5.6km from Chesapeake, where you can savour exquisite wines in a romantic setting.

Things to do recommended for families

Families can cheer on their favourite teams at Harbor Park, enjoy a peaceful day at Oak Grove Lake Park, or engage in fun-filled activities at Jillian's Billiards, all within the charming city of Chesapeake. Each venue promises unique experiences for all ages.

Things to do recommended for groups

Explore the vibrant Greenbrier Mall for shopping and entertainment, enjoy a round of golf at the scenic Chesapeake Golf Club, and catch a film with friends at the charming Commodore Theatre, located 3.1km from Chesapeake, perfect for family and romantic outings.

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

If you're travelling with a group, as a family, with your pets, or seeking extended stays, it's important to filter your options according to your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Chesapeake with a group: Think about how many bedrooms you'll require, as well as features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Chesapeake with young kids: Traveling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable facilities, such as 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 families, a holiday wouldn’t be the same without their beloved pet by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Chesapeake: If you're in search of holiday rentals featuring 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 accommodations. Don't forget to include options 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, is an ideal destination for families and outdoor enthusiasts alike. With its charming neighbourhoods and the stunning Chesapeake Bay, visitors can immerse themselves in a friendly atmosphere perfect for excursions and relaxation. Whether you're seeking a romantic getaway or a trendy urban experience, Chesapeake offers a delightful blend of activities and sights to explore. Enjoy the warmth of family homes and the vibrant local culture during your holiday in this fabulous city.

  • Norfolk: Situated a mere 3.7km from Chesapeake, Norfolk is a vibrant city brimming with family-friendly activities and outdoor adventures. The waterfront boardwalk offers a delightful space for leisurely strolls, while the bustling shopping centres cater to all your retail needs. Norfolk's educational attractions, including the renowned Nauticus maritime museum, provide both fun and learning. Visitors can also enjoy the scenic beaches and picturesque esplanade, making it a great spot for romantic outings or family days out.
  • Portsmouth: Located just 3.1km from Chesapeake, Portsmouth is another charming city that promises a wholesome experience for families and couples alike. Its inviting boardwalk and shopping centres make for an enjoyable day of exploration. Noteworthy attractions such as the historic Olde Towne district and the scenic esplanade offer glimpses into the area's rich heritage and natural beauty. With stunning views of the waterfront and easy access to lovely beaches, Portsmouth stands out as an ideal destination for outdoor enthusiasts.
  • South Norfolk: Nestled around the Chesapeake area, South Norfolk is a welcoming neighbourhood that captures the essence of family and outdoor experiences. With convenient access to a variety of shopping centres and a lovely boardwalk, it provides a perfect blend of leisure and recreation. The local attractions, including the beach and tourist precinct, are ideal for visitors seeking relaxation or adventure. South Norfolk's charming atmosphere and easy access to the esplanade make it a delightful stop during your vacation.

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

Are you hoping to save on your next holiday? If so, being flexible with your travel dates can be beneficial, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board provides you with a dedicated space to plan new getaways, pick up right where you paused, or review and arrange your itineraries. You can easily locate properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-gb/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. 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)
  • Virginia Beach National Golf Club (11.7 mi / 18.9 km)
  • Ocean Breeze Waterpark (16.6 mi / 26.7 km)
  • Atlantic Fun Park (18.1 mi / 29.1 km)
  • Cahoon Plantation Golf Course (3 mi / 4.8 km)
  • Chesapeake Golf Club (3.8 mi / 6.1 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)
  • 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)
  • Ocean View Beach (13.1 mi / 21.1 km)
  • Little Creek 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?
When considering a holiday rental in Chesapeake, Virginia, a popular area to stay is Great Bridge. This charming neighbourhood offers a blend of suburban tranquillity and convenient access to local attractions. Visitors can enjoy the scenic views along the Great Bridge Lock Park, where you can witness the fascinating operation of the locks and stroll along the waterfront trails. The area also features a variety of dining options and shops, making it a pleasant place for families and couples alike.

Another excellent option is the Greenbrier area, which is known for its vibrant shopping centres and restaurants. Here, you'll find the Greenbrier Mall, a popular spot for both shopping and entertainment. The neighbourhood is also close to several parks, such as the 24-acre Greenbrier Park, which is great for outdoor activities and picnics. With a range of holiday rentals available, visitors can choose from cosy homes to spacious apartments, ensuring there's something to suit every preference.
How much does it cost to rent a holiday home in Chesapeake?
Prices for holiday 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 holiday 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, travellers should consider the areas near the Elizabeth River and the nearby beaches of the Chesapeake Bay. The Great Bridge area, which is close to the water, offers a variety of waterfront properties with stunning views and convenient access to local marinas. Many of these homes come equipped with amenities such as private docks, outdoor seating areas, and spacious kitchens, ideal for families or groups looking to enjoy a relaxing getaway.

Another excellent option is the area around the Chesapeake Beach, where you can find charming beach houses that often feature direct beach access, outdoor showers, and terraces great for enjoying the coastal breeze. This locale is great for those who appreciate sandy shores and the opportunity for water sports, with rentals typically offering essentials like beach gear storage and barbecue facilities.
What is the most popular type of holiday rental accomodation in Chesapeake?
In Chesapeake, holiday houses are the predominant type of rental accommodation, with approximately 24 available throughout the area. These homes often feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups seeking a comfortable stay. Many holiday houses also include outdoor spaces, such as patios or gardens, great for relaxing after a day of exploring local attractions like the Chesapeake Arboretum or the Great Dismal Swamp National Wildlife Refuge.
Are there any family house rentals in Chesapeake?
In Chesapeake, Virginia, there are plenty of family-friendly house rentals available—about 19 in total. This city offers a welcoming environment for families, with many properties located in neighbourhoods close to parks and recreational facilities. Visitors can expect spacious living areas, full kitchens for preparing meals together, and outdoor spaces where children can play and explore.

Areas like Great Bridge and Deep Creek are particularly appealing, as they provide easy access to local attractions such as the Chesapeake City Park, which features playgrounds, walking trails, and picnic areas. Additionally, some homes may offer amenities like game rooms, private backyards, and even access to community pools, ideal for families looking to relax and bond during their stay.
Can I rent a holiday home with a pool or hot tub in Chesapeake?
In Chesapeake, there are several holiday homes available for rent that feature pools or hot tubs, with around 10 options to choose from. This charming city is known for its lush landscapes and waterways, providing a relaxing backdrop for travellers. Many of these rentals are situated in family-friendly neighbourhoods, where you can expect amenities such as private pools, outdoor entertaining areas, and hot tubs, great for unwinding after a day of exploring.
Can I find long-stay holiday rentals in Chesapeake?
A long-stay holiday rental in Chesapeake is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Chesapeake?
In Chesapeake, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these holiday homes feature amenities such as spacious backyards, allowing pets to roam freely, and comfortable living spaces with modern kitchens and laundry facilities for convenience.
Are there any remote work holiday rentals in Chesapeake?
In Chesapeake, Virginia, there is a solid selection of remote work holiday rentals available, with around 33 options to choose from. These properties are designed to cater to the needs of travellers looking to balance work and leisure. Many of the rentals come equipped with amenities such as Wi-Fi, dedicated workspaces including desks and ergonomic chairs, and often additional conveniences like computer monitors and safes for securing your devices. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chesapeake holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Chesapeake with parking available—perfect for families or travellers 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 holiday rental amenities typically include a kitchen equipped with essential appliances such as a microwave, refrigerator, and stovetop. Guests can expect cookware, dishware, and utensils to be provided, allowing for a convenient self-catering experience.
When is the best time to visit Chesapeake for a holiday rental?
The most popular time to visit Chesapeake for a holiday rental is during the peak season, which runs from May to July. This is when the area truly comes alive, offering a vibrant atmosphere superb for travellers. With the warm summer temperatures averaging in the high 20s to low 30s Celsius, visitors can indulge in an array of outdoor activities, from exploring beautiful parks and nature trails to enjoying water sports on the nearby Chesapeake Bay.

July, in particular, stands out as the pinnacle of tourist activity in Chesapeake. This month welcomes a lively crowd, with various events and festivals taking place that showcase the local culture and community spirit. It's an excellent time to connect with fellow travellers and immerse yourself in the region's offerings.

For those looking for more budget-friendly options, consider visiting in December. While it's the low season, this month offers a unique charm, complete with festive decorations and local holiday events. You can enjoy a quieter experience, taking in the sights at a leisurely pace and perhaps even finding some great deals on holiday rentals.
How early should I book a Chesapeake holiday rental?
Book your Chesapeake holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chesapeake?
In Chesapeake, Virginia, visitors can enjoy a variety of attractions that showcase the area's natural beauty and rich history. The Great Dismal Swamp National Wildlife Refuge offers a great experience for nature enthusiasts, featuring trails for hiking and biking as well as opportunities for birdwatching. Nearby, the Chesapeake City Park provides a lovely setting for picnics and outdoor activities, complete with playgrounds and scenic walking paths.

For history buffs, the Chesapeake Historical Society and the Great Bridge Battlefield & Waterways History Museum offer insights into the region's past, including its Civil War history. The city is also home to numerous parks and recreational areas, such as the Oak Grove Lake Park, which features a picturesque lake and walking trails.
Can I change or cancel my Chesapeake home rental booking on Vrbo?
To find Chesapeake holiday 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 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 travellers 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 cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Chesapeake holiday 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.

More holiday ideas

More holiday ideas