Chesapeake holiday rentals

We found 5,071 holiday rentals — enter your dates for availability
Discover a selection of 36 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:18 Dec - 25 Dec

Front left corner of home.
Beach
Pool
Newly expanded rear deck
Exceptional
(48 reviews)

Family vacation retreat w/ In-ground Pool with private Chesapeake Bay access!

Cape Charles

8% off
AU$8,387
for 7 nights, 1 home
AU$1,198 per night
includes taxes & fees
Family vacation retreat w/ In-ground Pool with private Chesapeake Bay access!
Interior
Living area
Living area
Living area
Exceptional
(54 reviews)

Salty Anchor oceanfront sunrise Carova4WD only! Pets not allowed!

Corolla

7% off
AU$5,703
for 7 nights, 1 home
AU$815 per night
includes taxes & fees
Salty Anchor oceanfront sunrise Carova4WD only! Pets not allowed!
Interior
Dining
Interior
Private kitchen
Exceptional
(25 reviews)

Brand New & Fully Renovated Luxury! 3 Min Walk From Your Peaceful Beach!

Norfolk

8% off
AU$4,130
for 7 nights, 1 home
AU$590 per night
includes taxes & fees
Brand New & Fully Renovated Luxury! 3 Min Walk From Your Peaceful Beach!
Only steps away from the ocean on Atlantic Ave
Living room with fire place
Room
Living room
Exceptional
(266 reviews)

Steps to the Ocean! Family and Dog Friendly North End Cottage w/ Rsrv Parking

Virginia Beach

7% off
AU$4,053
for 7 nights, 1 cottage
AU$579 per night
includes taxes & fees
Steps to the Ocean! Family and Dog Friendly North End Cottage w/ Rsrv Parking
Large kitchen fully equipped with everything you need.
Back yard looking at the water
Living area
Nice place to relax by the water
Exceptional
(86 reviews)

3 BEDROOM 2 BATH ON THE WATER

Norfolk

5% off
AU$3,125
for 7 nights, 1 home
AU$446 per night
includes taxes & fees
3 BEDROOM 2 BATH ON THE WATER
Dining
Property grounds
Interior
Property grounds
Exceptional
(81 reviews)

SEASIDE PRIVATE RETREAT!! 100-Acre Private WATERFRONT Home Stunning island views

Cape Charles

12% off
AU$3,850
for 7 nights, 1 home
AU$550 per night
includes taxes & fees
SEASIDE PRIVATE RETREAT!! 100-Acre Private WATERFRONT Home Stunning island views
Dining
Private kitchen
Room
Living area
Exceptional
(13 reviews)

Big Family Getaway - Walk to the Beach! Sleeps 10!

Hampton

23% off
AU$5,657
for 7 nights, 1 home
AU$808 per night
includes taxes & fees
Big Family Getaway - Walk to the Beach! Sleeps 10!
Front porch seating area
Entryway
Front of House
Dining room -- the downstairs bathroom is behind the barn door
Exceptional
(147 reviews)

Downtown Cape Charles Victorian, Dog-friendly, Short Walk to the Beach!

Cape Charles

7% off
AU$2,702
for 7 nights, 1 home
AU$386 per night
includes taxes & fees
Downtown Cape Charles Victorian, Dog-friendly, Short Walk to the Beach!
This 3,000 sq foot house is bright and spacious with unique architectural detail
Private kitchen
The living room has plenty of space to curl up and watch a movie.
Kitchen french doors open to patio for al fresco dining
Exceptional
(105 reviews)

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

Virginia Beach

7% off
AU$5,159
for 7 nights, 1 home
AU$737 per night
includes taxes & fees
Big Kitchen, Two Masters, Hot Tub, Short Walk from Croatan Beach
Room
Interior
Interior
Exterior
Exceptional
(17 reviews)

Private Guesthouse w/Full Kitchen

Moyock

8% off
AU$1,333
for 7 nights, 1 home
AU$190 per night
includes taxes & fees
Private Guesthouse w/Full Kitchen
Interior
Sunnybank Compound estate, 3 elevated acres with magnificent views, 3 buildings.
Large Swimming Pool & Kitty Pool / shower & entrance to Game Room & Pavalion.
Lobby
Exceptional
(69 reviews)

Majestic Oceanfront Estate w/ pool, hot tub, theater, elevator: Sunnybank-NC.com

Corolla

7% off
AU$9,494
for 7 nights, 1 home
AU$1,356 per night
includes taxes & fees
Majestic Oceanfront Estate w/ pool, hot tub, theater, elevator: Sunnybank-NC.com
Open kitchen and dining space with tons of seating
Breakfast nook with TV
Ottoman filled with board games for the family and lots of children's books
Shed packed with all you need! Bikes, floats, chairs, beach toys
Exceptional
(69 reviews)

Sweet Victorian Beach Cottage

Cape Charles

7% off
AU$3,053
for 7 nights, 1 home
AU$436 per night
includes taxes & fees
Sweet Victorian Beach Cottage
Living area
Stairs to front door/entryway.
Queen bed.
Dining
Exceptional
(74 reviews)

Beautiful 3 bedroom house minutes from the beach and First Landing State park

Virginia Beach

8% off
AU$4,965
for 7 nights, 1 home
AU$709 per night
includes taxes & fees
Beautiful 3 bedroom house minutes from the beach and First Landing State park
Living area
Dew Drop Inn
Living area
Outdoor dining
Exceptional
(217 reviews)

Carova Beach Canal Front Cottage 4x4 required Beach Parking Pass provided

Corolla

8% off
AU$2,396
for 7 nights, 1 cottage
AU$342 per night
includes taxes & fees
Carova Beach Canal Front Cottage 4x4 required Beach Parking Pass provided
Living area
Terrace/patio
Interior
Room
Exceptional
(27 reviews)

Country Escape Home in the Woods- Chesapeake, VA

Chesapeake

7% off
AU$1,682
for 7 nights, 1 home
AU$240 per night
includes taxes & fees
Country Escape Home in the Woods- Chesapeake, VA
Private kitchen
Exterior
Property grounds
Interior
Exceptional
(42 reviews)

Beach Cottage a short walk from the waves!

Corolla

8% off
AU$2,707
for 7 nights, 1 home
AU$387 per night
includes taxes & fees
Beach Cottage a short walk from the waves!
Living area
Living area
Private kitchen
Dining
Exceptional
(18 reviews)

Beachside Escape 2-Bedroom Gem in Norfolk, Steps from the Sand, with AC and Wifi

Norfolk

7% off
AU$2,589
for 7 nights, 1 home
AU$370 per night
includes taxes & fees
Beachside Escape 2-Bedroom Gem in Norfolk, Steps from the Sand, with AC and Wifi
Banquet hall
Store/Bar: Tuesday-Saturday 11am to 7pm or rent separately for events!
1896 Mansion
Cinderella room
Exceptional
(10 reviews)

1896 Historic Mansion with a general store

Newport News

8% off
AU$6,855
for 7 nights, 1 home
AU$979 per night
includes taxes & fees
1896 Historic Mansion with a general store
Terrace/patio
Living area
Living area
Dining
Exceptional
(10 reviews)

Welcome to Harper's Haven

Hampton

7% off
AU$1,953
for 7 nights, 1 home
AU$279 per night
includes taxes & fees
Welcome to Harper's Haven
Living area
Private kitchen
Exterior detail
Exterior detail
Exceptional
(19 reviews)

Lil' Ms. Clementine 2-bedroom home in Historic District with Golfcart option

Cape Charles

7% off
AU$3,061
for 7 nights, 1 home
AU$437 per night
includes taxes & fees
Lil' Ms. Clementine 2-bedroom home in Historic District with Golfcart option
7 Bedroom have a bath.
Tiki Pool, Waterfall, Blue Spa, Gas Grill, Volleyball, Yard Games, & Playground.
4200 Sq ft home, excellent location, awesome lighthouse views, sleeps 24.
Across from the Wild Horse Tour to see Mustangs from shipwrecks 500 yrs ago.
Exceptional
(142 reviews)

TIKI POOL & SPA, GOLF CART, KAYAK, WATERFALL, FIREPIT EXCELLENT LIGHTHOUSE VIEWS

Corolla

14% off
AU$6,069
for 7 nights, 1 home
AU$867 per night
includes taxes & fees
TIKI POOL & SPA, GOLF CART, KAYAK, WATERFALL, FIREPIT EXCELLENT LIGHTHOUSE VIEWS
Interior
Living area
Private kitchen
Exterior
Wonderful
(22 reviews)

Olde Hampton, right in the center of Hampton Roads 1

Hampton

11% off
AU$2,319
for 7 nights, 1 home
AU$331 per night
includes taxes & fees
Olde Hampton, right in the center of Hampton Roads 1
Private kitchen
Terrace/patio
Summer 2018
Side door. Vitex 'Chaste Tree' is 30 yrs old. Blooms in July.
Exceptional
(325 reviews)

Adorable Cottage In The Heart Of The Old Beach Area, Close To The Boardwalk.

Virginia Beach

8% off
AU$2,466
for 7 nights, 1 cottage
AU$352 per night
includes taxes & fees
Adorable Cottage In The Heart Of The Old Beach Area, Close To The Boardwalk.
Interior
Private kitchen
Room
Dining
Wonderful
(20 reviews)

Children's Dream House! Walk to the Beach!

Hampton

15% off
AU$3,344
for 7 nights, 1 home
AU$478 per night
includes taxes & fees
Children's Dream House! Walk to the Beach!

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • Ocean Breeze Waterpark (16.6 mi / 26.7 km)
  • Atlantic Fun Park (18.1 mi / 29.1 km)
  • Cypress Point Country Club (10.1 mi / 16.3 km)
  • Riverfront Golf Club (11.6 mi / 18.7 km)
  • TPC of Virginia Beach (11.7 mi / 18.9 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)
  • Mount Trashmore Park (10 mi / 16.1 km)
  • Norfolk Botanical Garden (10.5 mi / 16.9 km)
  • Norfolk Beaches (12.8 mi / 20.5 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.
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.
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 Stayz.
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.
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.
Are all fees included in the Chesapeake holiday homes prices shown on Stayz?
Stayz 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.
Are there any Chesapeake holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Chesapeake holiday homes?
You can find great discounts on holiday homes in Chesapeake on Stayz, 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.
Can I change or cancel my Chesapeake holiday home booking on Stayz?
To find Chesapeake holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Chesapeake?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Chesapeake holiday home?
Book your Chesapeake holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chesapeake?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Chesapeake to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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