Owner Direct Vacation
Rentals in Chesapeake City

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

  1. Owner Direct
  2.  USA
  3.  Maryland
  4.  Chesapeake City

Explore the Best Chesapeake City Vacation Homes

Looking for the perfect place to stay in Chesapeake City? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Chesapeake City 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
New
House
Adventure Mobile
  • Air Conditioner
  • Security/Safety
  • Child Friendly
US
View Availability
New
House
Adventure Mobile
  • Air Conditioner
  • Security/Safety
  • Child Friendly
US
View Availability

Why Travelers Love Using
Owner Direct to
Find Chesapeake City 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.

Popular Neighborhoods for Chesapeake City Vacation Rentals

What are the best areas to stay in Chesapeake City

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

Sunday Feb 22

Chesapeake City, Maryland

Sun
weather icon
28.1°C
Mon
weather icon
28.2°C
Tue
weather icon
28.2°C
Wed
weather icon
28.1°C
Thu
weather icon
28.1°C
Fri
weather icon
28.0°C
Sat
weather icon
28.2°C

Common Vacation Rental Amenities Typical Vacation Rental Amenities

What sort of amenities will be available at your stay?

Our Chesapeake City 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

How to Reserve Your Chesapeake City 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.

Chesapeake City Vacation Rental FAQs

1. What are the top vacation rentals in Chesapeake City?

2. How many vacation rentals are available in Chesapeake City?

Currently, the total number of properties listed in 2026 is over 23 in the Chesapeake City area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chesapeake City.