Chesapeake City County holiday rentals

We found 969 holiday rentals — enter your dates for availability
Discover a selection of 36 homes, 15 apartments and other holiday rentals in Chesapeake City County that are perfect for your trip. Holiday rentals offer the best amenities for you and your friends, family or even pets, such as air conditioning and Wi-Fi. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Popular Chesapeake City County destinations on Stayz

Holiday rentals with weekly discounts – Chesapeake City County

Showing deals for:25 Dec - 1 Jan

Living area
Exterior
Interior
Dining
Exceptional
(39 reviews)

Unique Country Farmhouse with Beautiful Courtyard

Moyock

8% off
AU$2,020
for 7 nights, 1 home
AU$289 per night
includes taxes & fees
Unique Country Farmhouse with Beautiful Courtyard
Interior
Terrace/patio
Living area
Children’s area
Exceptional
(27 reviews)

Country Escape Home in the Woods- Chesapeake, VA

Chesapeake

7% off
AU$1,985
for 7 nights, 1 home
AU$284 per night
includes taxes & fees
Country Escape Home in the Woods- Chesapeake, VA
Canal view from back of lot (left)
Sunset view looking towards Bay
This RV is not on the lot. It's an empty lot. Pic here is shown to indicate size
Canal view from back of lot (right)
Wonderful
(8 reviews)

Waterfront RV Lot in Surfside Resort

Virginia Beach

5% off
AU$1,389
for 7 nights, 1 unit
AU$198 per night
includes taxes & fees
Waterfront RV Lot in Surfside Resort
Room
Private kitchen
Living area
Exterior
Exceptional
(5 reviews)

3BR Gem Near Rivers Casino – Comfort & Convenience

Portsmouth

11% off
AU$3,497
for 7 nights, 1 home
AU$500 per night
includes taxes & fees
3BR Gem Near Rivers Casino – Comfort & Convenience
Dining
Terrace/patio
Exterior
Private kitchen
Exceptional
(17 reviews)

Country Escape Next DOOR Rental - Sleeps 6 - Stay upstairs in the trees

Chesapeake

7% off
AU$1,502
for 7 nights, 1 room
AU$215 per night
includes taxes & fees
Country Escape Next DOOR Rental - Sleeps 6 - Stay upstairs in the trees
Property grounds
Beach
Living area
Living area
Exceptional
(60 reviews)

Your own private beach with this charming 3-bedroom beachfront house!

Norfolk

7% off
AU$3,393
for 7 nights, 1 home
AU$485 per night
includes taxes & fees
Your own private beach with this charming 3-bedroom beachfront house!
Coffee maker, French press and Electric kettle
Living room
1st bedroom Queen Bed
Dining table
Wonderful
(19 reviews)

Portsmouth 3BR Near Casino, Comfy, Spacious Yard Stay, Sleeps 6!

Portsmouth

7% off
AU$3,155
for 7 nights, 1 home
AU$451 per night
includes taxes & fees
Portsmouth 3BR Near Casino, Comfy, Spacious Yard Stay, Sleeps 6!
Kitchen
Porch
Living Room
Interior
Wonderful
(55 reviews)

Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

Portsmouth

6% off
AU$1,656
for 7 nights, 1 apartment
AU$237 per night
includes taxes & fees
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

Find the perfect holiday rental for your Chesapeake City County getaway

Learn about the unique charm of Chesapeake City County with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Chesapeake City County

Do you want to discover things to do while you're in town? Venture out of your cosy holiday rental and check out everything that makes Chesapeake City County a fun spot to go on holiday. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Virginia Zoo (13.9 mi / 22.4 km)
  • Ocean Breeze Waterpark (19.6 mi / 31.5 km)
  • Currituck County Welcome Center (10.7 mi / 17.3 km)
  • Virginia Beach National Golf Club (13.8 mi / 22.2 km)
  • Cypress Point Country Club (15.7 mi / 25.2 km)
  • Riverfront Golf Club (16 mi / 25.7 km)

Exploring the natural features in Chesapeake City County

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Chesapeake City County is a great place to get outside. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Sandbridge Beach (20.5 mi / 32.9 km)
  • Chesapeake City Park (6.5 mi / 10.4 km)
  • Town Point Park (11.6 mi / 18.7 km)
  • Dismal Swamp State Park (12.4 mi / 20 km)
  • Mount Trashmore Park (14.4 mi / 23.2 km)
  • Norfolk Botanical Garden (16.6 mi / 26.6 km)

Frequently asked questions

What is the best area to stay in Chesapeake City County when booking a holiday home?
Among the most popular destinations to book your holiday home in Chesapeake City County is Chesapeake. Set up home here and see its leading attractions, such as Greenbrier Mall and Chesapeake Square Mall.
What is the most popular type of holiday home accommodation in Chesapeake City County?
The most in-demand types of holiday homes in Chesapeake City County are houses. Searching for something different? Stayz has a variety of options to match the needs of our guests, so you'll see properties in all sizes, and for all budgets. The perfect home away from home is waiting for you — find yours today.
How much does it cost to rent a holiday home in Chesapeake City County?
A number of factors can influence how much you pay for a holiday home in Chesapeake City County, like the type of property, season and length of stay. But, all of our holiday homes have one thing in common — unbeatable value. Simply enter your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Chesapeake City County?
The average price for a holiday home near the beach in Chesapeake City County depends on when you'll be there and the type and size of property you're looking for. You can find prices quickly and easily on Stayz by entering the dates you'll be travelling. Then make use of the filter tool to select the number of bedrooms and amenities that you require, like WiFi, air conditioning and a pool.
What are popular home amenities in Chesapeake City County?
When it comes to home amenities that people are looking for in Chesapeake City County, a stovetop, a fridge and a microwave oven are at the top of the list. With Stayz holiday homes, you'll have options to suit your style and taste, whether you're going on a holiday with friends, family or even pets.
Are there large group holiday homes in Chesapeake City County?
Take your pick of five Stayz holiday homes in Chesapeake City County that can accommodate five or more people. You'll enjoy all the room and privacy you need to spend time with your favourite people — and nobody else.
What are the top attractions for families in Chesapeake City County?
There are loads of wonderful things to see and do with the family in Chesapeake City County, including:
  • Greenbrier Mall
  • Chesapeake City Park
  • Chesapeake Square Mall
Can I find two-bedroom holiday homes in Chesapeake City County?
Chesapeake City County has four two-bedroom holiday properties to select from. Go for a holiday home with all the comfort and privacy you need at a price that's hard to resist on Stayz.
Are there holiday homes with WiFi in Chesapeake City County?
Chesapeake City County has 11 holiday homes with WiFi, so you can stay connected during your holiday. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming Hollywood blockbusters to sending emails, these Stayz homes make it a breeze to go online.
How old do you have to be to rent a holiday home in Chesapeake City County?
The minimum required age is usually 16, 18 or 21. It can vary between properties on Stayz, so look at the rules of your chosen Chesapeake City County holiday home before booking.
How long can I rent a holiday home in Chesapeake City County for?
The amount of time you can stay in a Chesapeake City County holiday home for is up to the property. Just enter your preferred travel dates to browse available options that offer extended stays. They feature the things you need to make your extended holiday more convenient and comfortable, such as kitchens and air conditioning. Some holiday homes might also offer discounted weekly or monthly prices, so you can stay even longer for less.

More holiday ideas