Owner Direct Vacation
Rentals in Chesapeake

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

  1. Owner Direct
  2.  USA
  3.  Virginia
  4.  Norfolk - Virginia Beach
  5.  Chesapeake

Explore the Best Chesapeake Vacation Homes

Looking for the perfect place to stay in Chesapeake? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Chesapeake 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 Vacation Rentals

What makes our vacation homes stand out?

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Verified Properties

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

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Value You Can Trust

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

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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

Popular Neighborhoods for Chesapeake Vacation Rentals

What are the best areas to stay in Chesapeake

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

Thursday Mar 12

Chesapeake, Virginia

Thu
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13.7°C
Fri
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6.3°C
Sat
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11.6°C
Sun
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12.1°C
Mon
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18.4°C
Tue
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5.6°C
Wed
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3.3°C

Common Vacation Rental Amenities Typical Vacation Rental Amenities

What sort of amenities will be available at your stay?

Our Chesapeake 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

How to Reserve Your Chesapeake 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.

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SEARCH PROPERTIES

Use filters for location, amenities, and budget.

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VIEW DETAILS

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

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BOOK SECURELY

Confirm your stay safely through our trusted travel partners.

Chesapeake Vacation Rental FAQs

What are the top vacation rentals in Chesapeake?

How many vacation rentals have private pools in Chesapeake?

There are 2 vacation rentals with private pools near Chesapeake. Top-rated homes that have access to a swimming pool include:

Which vacation homes in Chesapeake are best for families?

If you are looking for a family-friendly vacation home in Chesapeake, 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:

How many vacation rentals are available in Chesapeake?

Currently, the total number of properties listed in 2026 is over 181 in the Chesapeake area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chesapeake.