Owner Direct Vacation
Rentals in Chesapeake City County

The Best Owner Direct Vacation Rentals in Chesapeake City County. Explore thousands of vacation home rentals, large cabins, and villas near Chesapeake City County

Explore the Best Chesapeake City County Vacation Homes

Looking for the perfect place to stay in Chesapeake City County? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Chesapeake City County character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.

  • vacation rentals
  • luxury villas
  • beachfront homes
  • pet-friendly rentals
  • condos

Why Travelers Love Using
Owner Direct to
Find Chesapeake City County Vacation Rentals

What makes our vacation homes stand out?

check-mark

Verified Properties

Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.

check-mark

Value You Can Trust

Compare a range of properties and find fair, transparent pricing—no hidden fees.

check-mark

Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

More Places to Stay Near Chesapeake City County

Popular Neighborhoods for Chesapeake City County Vacation Rentals

What are the best areas to stay in Chesapeake City County

Discover the top neighborhoods in Chesapeake City County and choose a place that suits your stay.

Tuesday Jun 2

Chesapeake City County, Virginia

Tue
weather icon
16.9°C
Wed
weather icon
18.1°C
Thu
weather icon
19.6°C
Fri
weather icon
23.3°C
Sat
weather icon
24.4°C
Sun
weather icon
26.1°C
Mon
weather icon
26.9°C

Common Vacation Rental Amenities Typical Vacation Rental Amenities

What sort of amenities will be available at your stay?

Our Chesapeake City County vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.

Indoor Amenities

  • indoor-amenities-kitchenFully equipped kitchens
  • indoor-amenities-living-areaSpacious living areas with streaming TVs
  • indoor-amenities-wifiComplimentary Wi-Fi
  • indoor-amenities-acAir conditioning and heating
  • indoor-amenities-washerIn-unit washer and dryer
  • indoor-amenities-bedPlush bedding and comfortable furniture

Outdoor Amenities

  • outdoor-amenities-balconyBalconies or patios with coastal views
  • outdoor-amenities-poolPrivate or shared pools
  • outdoor-amenities-bbqBBQ grills and outdoor dining areas
  • outdoor-amenities-parkingOn-site parking
  • outdoor-amenities-beachEasy access to beaches and attractions

More Vacation Rentals You May Like Near Chesapeake City County

How to Reserve Your Chesapeake City County Vacation Rental

Booking Made Simple

Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.

search-icon

SEARCH PROPERTIES

Use filters for location, amenities, and budget.

compare-icon

VIEW DETAILS

Check photos, reviews, and features for your top picks.

bed-icon

BOOK SECURELY

Confirm your stay safely through our trusted travel partners.

travel-tips

Travel Trips for Visiting Chesapeake City County

What should you know when planning a trip to St. Augustine?
  • Book early
    for popular festivals and spring weekends.
  • Pack layers
    Florida weather can change quickly.
  • Stay hydrated
    and plan beach days around midday heat.
  • Explore early
    to avoid crowds at major attractions.
Transportation Around St. Augustine?
  • Driving
    Most convenient for exploring the city and coast.
  • Trolley & Shuttle Tours
    Great for sightseeing and hopping between landmarks.
  • Walking
    The downtown historic district is pedestrian-friendly.
Local Etiquette
  • Respect historic sites and marked paths.
  • Standard U.S. tipping (15–20%) applies.
  • Quiet hours are observed in residential and beachfront areas.

Chesapeake City County Vacation Rental FAQs

What are the top vacation rentals in Chesapeake City County?
How many vacation rentals have private pools in Chesapeake City County?

There are 3 vacation rentals with private pools near Chesapeake City County. Top-rated homes that have access to a swimming pool include:

Which vacation homes in Chesapeake City County are best for families?

If you are looking for a family-friendly vacation home in Chesapeake City County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chesapeake City County:

How many vacation rentals are available in Chesapeake City County?

Currently, the total number of properties listed in 2026 is over 184 in the Chesapeake City County area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chesapeake City County.