Chesapeake holiday lettings

We found 5,012 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:23 Oct - 30 Oct

Image gallery for Beach access across street, East Beach

Private kitchen
10 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)

Beach access across street, East Beach

Norfolk

7% off
Price is £3,658
for 7 nights, 1 home
£523 per night
includes taxes & fees
Beach access across street, East Beach

Find spaces that suit your style

Why visit Chesapeake

  • Natural wonders: Discover the scenic Great Dismal Swamp National Wildlife Refuge, ideal for nature lovers and families.
  • Urban parks: Enjoy leisurely picnics and recreation at Chesapeake City Park, perfect for a day outdoors.
  • Cultural heritage: Visit charming local churches and delve into the city’s rich history at maritime museums.
  • Romantic waterfront: Unwind along the picturesque Elizabeth River, an enchanting spot for couples.
  • Diverse accommodation: Choose from cosy cottages, private vacation homes, and modern condos for your stay.

Popular types of accommodation in Chesapeake

Chesapeake, Virginia, is a captivating city rich in natural beauty and unique experiences. Visitors can explore the stunning Great Dismal Swamp, enjoy outdoor adventures at one of the many parks, or delve into local history at fascinating landmarks. When it comes to accommodation, you'll find a variety of options including houses, cosy cottages, and modern condos, making it easy to find the perfect rental for your stay in Chesapeake.

  • Houses: The top choice for visitors in Chesapeake, these homes offer a spacious and comfortable stay, perfect for families or groups.
  • Condos: A popular second option, condos provide modern amenities and often stunning views, ideal for couples or small families.
  • Cottages: Third in popularity, cottages offer a quaint and charming atmosphere, perfect for a peaceful getaway.
  • Apartments: Ranking fourth, apartments are convenient and well-equipped, making them a great choice for longer stays.
  • Caravan Parks: The fifth option, caravan parks offer a unique outdoor experience, ideal for those who enjoy nature.**

Top attractions near Chesapeake

Chesapeake, Virginia, offers a delightful mix of attractions perfect for families, outdoor enthusiasts, and couples seeking a romantic getaway. Visitors can explore urban parks for leisurely strolls, delve into the maritime museum to learn about local history, or visit charming churches that reflect the area’s culture. With a range of experiences tailored to all interests, Chesapeake is a wonderful destination to discover the beauty and heritage of this vibrant city.

  • Town Point Park: This urban park offers a serene escape with lush green spaces, picturesque waterfront views, and family-friendly activities. It's perfect for a leisurely stroll or a picnic while soaking up the vibrant city atmosphere.
  • USS Wisconsin BB-64: A majestic battleship turned maritime museum, visitors can explore its impressive decks and learn about naval history, immersing themselves in the rich culture and stories of those who served.
  • Douglas MacArthur Memorial: An engaging history museum dedicated to the life of General Douglas MacArthur, featuring exhibits and artefacts that reflect his significant contributions to military history and leadership.

Things to do recommended for couples

Chesapeake offers delightful experiences for couples. Enjoy a serene gondola ride through the picturesque canals of the Great Dismal Swamp, or take a romantic stroll at the Chesapeake City Park, where the sunset casts a magical glow over the water.

Things to do recommended for families

Families visiting Chesapeake can explore the fascinating Chesapeake Planetarium, enjoy outdoor fun at City Park, and discover wildlife at the Great Dismal Swamp National Wildlife Refuge, where kids can engage in nature trails and birdwatching activities.

Things to do recommended for groups

Explore the scenic Chesapeake Bay by taking a group kayak tour through its tranquil waters or enjoy a delightful afternoon at the Great Dismal Swamp, where you can hike and observe local wildlife. Don't miss the vibrant local cuisine at a nearby seafood restaurant for a true taste of Virginia.

*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 travelling with a group, family, pets, or planning for an extended stay, it's essential to filter your options according to your specific needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chesapeake with a group: Think about the number of bedrooms you require, along with features like a fully equipped kitchen or outdoor space for group gatherings. Luckily, you can easily filter for all these options, and more, on Vrbo.
  • Traveling to Chesapeake with young kids: Travelling with young children can be quite demanding. It’s important to prioritise their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Chesapeake: For many, a family holiday wouldn’t be the same without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most 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 offers for stays of a month or more, you've come to the perfect place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options 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 blend of family-friendly attractions and outdoor adventures. Visitors can explore the scenic Great Dismal Swamp National Wildlife Refuge, perfect for nature enthusiasts and families alike. The city's parks, such as Chesapeake City Park, provide ample space for picnics and recreation. For a romantic outing, the picturesque waterfront along the Elizabeth River is a lovely spot to unwind. With its friendly atmosphere and diverse experiences, Chesapeake is an excellent choice for your holiday.

  • Norfolk: Located a mere 10km from Chesapeake, Norfolk is a vibrant city known for its rich maritime history and bustling waterfront. Visitors flock to Norfolk for a variety of experiences, including family outings, romantic strolls, and outdoor adventures. The iconic boardwalk offers stunning views of the Elizabeth River, while the nearby beach provides a perfect spot for relaxation. Norfolk is home to a range of attractions, including museums and shopping centres, making it a delightful destination for all ages. Don’t miss the chance to explore the esplanade and indulge in the local dining scene.
  • Portsmouth: Just 8km from Chesapeake, Portsmouth is a charming city that embodies a friendly atmosphere ideal for families and couples alike. With its picturesque boardwalk and a variety of shopping options, Portsmouth invites visitors to enjoy leisurely strolls and engaging activities. The local beach and esplanade offer tranquil settings for relaxation and recreation. Cultural education opportunities abound, making this city both fun and enlightening. Portsmouth's vibrant tourist precinct ensures there’s always something happening, promising an enjoyable stay.
  • Greenbrier West: Nestled within Chesapeake, Greenbrier West is a welcoming neighbourhood perfect for families and business travellers. Its proximity to shopping malls and centres means you can easily indulge in retail therapy or enjoy a meal at various eateries. The area features a lovely boardwalk and is close to beautiful beaches, making it suitable for both leisure and exploration. Greenbrier West offers a blend of city life with a leisurely pace, ensuring a balanced and enjoyable experience during your visit.

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 simple

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

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform for planning your travels, allowing you to create new trips, resume your previous planning, or easily manage your itinerary. You can access your saved or booked properties, which are neatly organised under Potential, Upcoming, or Current Trips. To begin using Trip Boards, please 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. Sandbridge Beach 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)
  • 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 rental?
When considering a holiday rental in Chesapeake, Virginia, the Great Bridge area is often regarded as one of the best places to stay. This charming neighbourhood is known for its welcoming atmosphere and convenient access to various attractions. A highlight of Great Bridge is the Great Bridge Lock Park, where you can enjoy scenic views of the water and learn about the area's history. Another local gem is the Chesapeake Arboretum, which offers beautiful walking trails and picturesque gardens, superb for a leisurely stroll.

Another appealing option is the Greenbrier area, which boasts a vibrant shopping and dining scene, making it an excellent choice for those looking to explore local cuisine and retail therapy. Here, you can find the Greenbrier Mall, which features a variety of shops and eateries. Additionally, the nearby Chesapeake City Park provides ample green space for outdoor activities and relaxation.

In terms of properties, Chesapeake offers a range of holiday rentals, from cosy homes to spacious villas, ensuring there's something to suit every traveller's needs.
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, the area around the Chesapeake Bay offers some delightful options for travellers. The neighbourhoods close to the Bay, such as Great Bridge and South Norfolk, provide access to waterfront properties that often come with amenities like private docks, spacious decks, and stunning views of the water. Many rentals in these areas are designed for family gatherings, featuring large kitchens, outdoor grills, and ample living space for relaxation after a day at the beach.

In addition, the nearby Sandy Bottom Nature Park is a lovely spot for those who enjoy outdoor activities, and some properties in the region may even offer bicycles or kayaks for guests to use. For a balance of beach access and local culture, the proximity to downtown Chesapeake allows visitors to explore local restaurants and shops, making it a convenient and enjoyable destination for beach house rentals.
What is the most popular type of holiday rental accomodation in Chesapeake?
In Chesapeake, holiday houses are the most popular type of holiday rental, with around 120 available throughout the area. These spacious homes are great for families or larger groups, typically featuring multiple bedrooms, fully equipped kitchens, and often private outdoor spaces for relaxation. Many are situated near local parks and waterways, allowing guests to enjoy the natural beauty of the region. Additionally, there are about 48 apartments and 28 condos, which provide a more compact option for travellers looking for modern amenities and easy access to local attractions. Cottages, while less common with only 12 available, offer a quaint and charming stay, often located in quieter neighbourhoods.
Are there any family house rentals in Chesapeake?
In Chesapeake, Virginia, there are numerous family-friendly house rentals available, with around 21 properties to choose from. This charming city offers a variety of spacious homes, ideal for families looking to enjoy a comfortable stay. Many of these houses feature ample living areas, fully equipped kitchens, and outdoor spaces great for children to play. Additionally, amenities such as Wi-Fi and air conditioning ensure a pleasant experience for all guests.

The neighbourhoods in Chesapeake provide easy access to local attractions, including parks and recreational areas where families can partake in outdoor activities. Visitors can also explore the nearby Chesapeake Bay, known for its beautiful scenery and opportunities for fishing, boating, and picnics.
Can I rent a holiday home with a pool or hot tub in Chesapeake?
In Chesapeake, Virginia, there are several holiday homes available for rent that come with pools and hot tubs, with around 14 options to choose from. This charming city offers a variety of neighbourhoods where these properties can be found, including the scenic Great Bridge area, known for its picturesque waterfront, and the family-friendly Greenbrier district, which provides a suburban atmosphere.

Travellers can expect a range of amenities in these rentals, including private swimming pools, relaxing hot tubs, spacious outdoor areas for entertaining, and fully equipped kitchens ideal for preparing meals.
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, Virginia, there are several pet-friendly house rentals available, offering a variety of options for travellers with pets. Many of these rentals are equipped with modern amenities, including fully equipped kitchens, spacious living areas, and outdoor spaces where pets can roam freely. The homes often feature conveniences such as laundry facilities, Wi-Fi, and private gardens or patios, superb for enjoying the pleasant Virginia weather.

For those looking to explore the area, Chesapeake is home to several parks that welcome pets. The expansive Chesapeake City Park offers scenic walking trails, picnic areas, and a lovely environment for outdoor activities with your furry companions. Additionally, the nearby Great Dismal Swamp National Wildlife Refuge presents opportunities for hiking and wildlife observation, making it an ideal destination for nature-loving pet owners.
Are there any remote work holiday rentals in Chesapeake?
In Chesapeake, Virginia, there are numerous remote work-friendly holiday rentals available, with around 192 options to choose from. This thriving city offers a variety of accommodations that cater to the needs of remote workers. Many properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces, and comfortable seating areas, allowing for productive work sessions.

Travellers can expect additional features like safe in-room environments, access to printers for business needs, and sometimes even outdoor spaces for a refreshing break during work hours. The city is well-connected, providing access to local cafes and co-working spaces if a change of scenery is desired.

Chesapeake also boasts beautiful parks, waterways, and cultural attractions, making it an appealing destination for those looking to balance work and leisure. 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 include fully equipped kitchens, which allow guests to prepare their own meals, and onsite parking for convenience. Many rentals also feature coffee and tea makers, ensuring that travellers can enjoy a warm beverage at their leisure. Additionally, a number of properties are pet-friendly, accommodating those who wish to bring their furry companions along, and service animals are permitted as well.
When is the best time to visit Chesapeake for a holiday rental?
The peak season for holiday rentals in Chesapeake runs from May to July, with July being the most popular month for visitors. During this vibrant time, families and adventure seekers flock to the area to enjoy the warm, sunny weather, which averages around 25 to 30 degrees Celsius. This climate is great for outdoor activities such as kayaking, fishing, and exploring the stunning parks that dot the region.

With so many attractions nearby, including the scenic Elizabeth River and the beautiful Chesapeake Bay, you'll find plenty of opportunities for sightseeing and relaxation. The lively option during these months creates a sense of community, making it an excellent time to connect with fellow holidaymakers.

If you're looking for a more budget-friendly experience, consider visiting in December. While cooler temperatures, averaging around 5 to 10 degrees Celsius, may be less ideal for outdoor pursuits, the holiday season brings a unique charm to the area. You can enjoy festive decorations, local events, and seasonal activities without the crowds, allowing for a more tranquil exploration of Chesapeake's historic sites and natural beauty.

Ultimately, your ideal time to visit Chesapeake will depend on whether you prefer the bustling summer season filled with activities and excitement or the peacefulness of winter, where you can appreciate the area at a more leisurely pace.
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 explore a variety of attractions across its diverse neighbourhoods. The Great Dismal Swamp National Wildlife Refuge offers stunning natural beauty with opportunities for hiking, birdwatching, and kayaking, making it a must-visit for nature enthusiasts. For those interested in history, the Chesapeake City Park features a historic home and lovely walking trails, ideal for a leisurely afternoon.

The Chesapeake Arboretum is another highlight, showcasing beautiful gardens and walking paths that provide a peaceful escape from the hustle and bustle. Additionally, the area around Greenbrier is home to shopping centres and restaurants, offering a mix of modern conveniences and local dining options.
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 cabin or a beach house, 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 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.
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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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