Chesapeake City County holiday rentals

We found 963 holiday rentals — enter your dates for availability
Discover a selection of 37 homes, 16 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:13 Nov - 20 Nov

Beach
Room
Interior
Property grounds
Exceptional
(26 reviews)

Beach House on the Bay

Norfolk

8% off
AU$7,744
for 7 nights, 1 home
AU$1,106 per night
includes taxes & fees
Beach House on the Bay
Room
Private kitchen
Property grounds
Private kitchen
Exceptional
(15 reviews)

Convenient Beach Home, Beach Access Across Street

Norfolk

8% off
AU$6,748
for 7 nights, 1 home
AU$964 per night
includes taxes & fees
Convenient Beach Home, Beach Access Across Street
Living area
Exterior
Interior
Living area
Exceptional
(33 reviews)

Unique Country Farmhouse with Beautiful Courtyard

Moyock

8% off
AU$1,611
for 7 nights, 1 home
AU$230 per night
includes taxes & fees
Unique Country Farmhouse with Beautiful Courtyard
Living area
Pool
back porch
side bathroom for pool breaks
Excellent
(79 reviews)

Reunion Paradise! Spacious Luxury Home and Pool House

Virginia Beach

7% off
AU$8,848
for 7 nights, 1 home
AU$1,264 per night
includes taxes & fees
Reunion Paradise! Spacious Luxury Home and Pool House
Room
Interior
Exterior detail
Exterior
Exceptional
(12 reviews)

Private Guesthouse w/Full Kitchen

Moyock

8% off
AU$1,337
for 7 nights, 1 home
AU$191 per night
includes taxes & fees
Private Guesthouse w/Full Kitchen
Living area
Terrace/patio
Room
Interior
Exceptional
(26 reviews)

Country Escape Home in the Woods- Chesapeake, VA

Chesapeake

7% off
AU$1,655
for 7 nights, 1 home
AU$236 per night
includes taxes & fees
Country Escape Home in the Woods- Chesapeake, VA
Dining
Living area
Private kitchen
Living area
Exceptional
(17 reviews)

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

Norfolk

7% off
AU$2,360
for 7 nights, 1 home
AU$337 per night
includes taxes & fees
Beachside Escape 2-Bedroom Gem in Norfolk, Steps from the Sand, with AC and Wifi
Private kitchen
Interior
Interior
Private kitchen
Exceptional
(11 reviews)

Beautiful, modern furnished 3-bedroom, 2-bathroom cottage near attractions.

Portsmouth

7% off
AU$2,353
for 7 nights, 1 home
AU$336 per night
includes taxes & fees
Beautiful, modern furnished 3-bedroom, 2-bathroom cottage near attractions.
Room
Outdoor dining
Living area
Living area
Exceptional
(13 reviews)

Roomy House in Bayview Zoning Permit #STR25-00140

Norfolk

10% off
AU$1,697
for 7 nights, 1 home
AU$242 per night
includes taxes & fees
Roomy House in Bayview Zoning Permit #STR25-00140
Another morning view
Sunset view looking towards Bay
Canal view from back of lot (right)
This RV is not on the lot. It's an empty lot. Pic here is shown to indicate size
Wonderful
(7 reviews)

Waterfront RV Lot in Surfside Resort

Virginia Beach

5% off
AU$1,412
for 7 nights, 1 unit
AU$202 per night
includes taxes & fees
Waterfront RV Lot in Surfside Resort
Private kitchen
Terrace/patio
Exterior
Interior
Exceptional
(17 reviews)

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

Chesapeake

7% off
AU$1,510
for 7 nights, 1 room
AU$216 per night
includes taxes & fees
Country Escape Next DOOR Rental - Sleeps 6 - Stay upstairs in the trees
Exterior
Beach
Property grounds
Living area
Exceptional
(52 reviews)

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

Norfolk

7% off
AU$2,886
for 7 nights, 1 home
AU$412 per night
includes taxes & fees
Your own private beach with this charming 3-bedroom beachfront house!
Interior
Dining
Private kitchen
Room
Excellent
(25 reviews)

Cute Space Near TownCenter 15 Minutes from Beaches

Virginia Beach

5% off
AU$1,515
for 7 nights, 1 apartment
AU$216 per night
includes taxes & fees
Cute Space Near TownCenter 15 Minutes from Beaches
Dining table
Living room
1st bedroom Queen Bed
Coffee maker, French press and Electric kettle
Wonderful
(17 reviews)

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

Portsmouth

7% off
AU$2,419
for 7 nights, 1 home
AU$346 per night
includes taxes & fees
Portsmouth 3BR Near Casino, Comfy, Spacious Yard Stay, Sleeps 6!
Dining table
Porch
Interior
Living Room
Wonderful
(53 reviews)

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

Portsmouth

6% off
AU$1,649
for 7 nights, 1 apartment
AU$236 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:

  • Currituck County Welcome Center (10.7 mi / 17.3 km)
  • Virginia Beach National Golf Club (13.8 mi / 22.2 km)
  • Virginia Zoo (13.9 mi / 22.4 km)
  • Ocean Breeze Waterpark (19.6 mi / 31.5 km)
  • Chesapeake Golf Club (2.6 mi / 4.1 km)
  • TPC of Virginia Beach (13.8 mi / 22.2 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)
  • Mount Trashmore Park (14.4 mi / 23.2 km)
  • Norfolk Botanical Garden (16.6 mi / 26.6 km)
  • Little Creek Beach (19 mi / 30.5 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.

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