176+ Rental Villas and Private Getaways in Chesapeake |
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  2. Virginia
  3. Norfolk - Virginia Beach
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Chesapeake Villa Rentals

About Chesapeake Vacation Rentals

There are more than 176 incredible getaway rentals that are available in Chesapeake. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Chesapeake.

BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Chesapeake, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Chesapeake. Places to stay near Chesapeake are 448.3 ft² on average, with prices averaging US $186 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Chesapeake. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.

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Top Private Villas, Resorts, and Rentals in Chesapeake

Type Count
Vacation Homes 64
Holiday Apartments 20
Cottages 2
Others 1
Unique Vacation Rentals 1

Use these Quick Filters to Find a Vacation Rental in Chesapeake

★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Chesapeake with BedroomVillas.

Weather in Chesapeake, VA

View the weather forecast for Chesapeake before booking your Chesapeake Vacation Rentals to confirm your best time to go.

December - February
High 62°F       Low 35°F
March - May
High 76°F       Low 41°F
June - August
High 90°F       Low 69°F
September - November
High 80°F       Low 44°F

Stay Near Chesapeake's Top Attractions

A Large Selection of Villas and Vacation Rentals from Around the World Chesapeake's Research Top Attractions For Your Vacation


Greenbrier Mall
Chesapeake Square Mall
Great Dismal Swamp National Wildlife Refuge
Chesapeake Conference Center
Chesapeake Veterans' Memorial
Chesapeake City Park
Chesapeake City Hall
Chesapeake Arboretum
Chesapeake Golf Club
Chesapeake Central Library
Jillian's Billiards
Portlock Galleries at SoNo
Oak Grove Lake Park
Float First
Cahoon Plantation Golf Course
Adventure Kayak Tours Day Tours
Lake Drummond
Chesapeake Regional Medical Center
Virginia Beach Boardwalk
Naval Station Norfolk

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Deep Creek South 145 Properties
Cahoon Plantation Golf Course 134 Properties
Chesapeake City County 126 Properties
Adventure Kayak Tours Day Tours 124 Properties
Portlock Galleries at SoNo 119 Properties
Chesapeake Veterans' Memorial 119 Properties
Chesapeake City Hall 118 Properties
Great Bridge 103 Properties
Western Branch North 70 Properties
South Norfolk 62 Properties
Greenbrier West 60 Properties
Greenbrier East 26 Properties

Complexes around Chesapeake, VA


Inn 3 Properties
Breakfast The Virginia Beach Business District 3 Properties
Stay America Suites Chesapeake Crossways Blvd 3 Properties
Comfort Norfolk 2 Properties
Econo Lodge Chesapeake Route 2 Properties
Breakfast Business Travelers 1 Properties
Rental 1 Properties

Frequently Asked Questions About Chesapeake?

What are the top hotels or resorts in Chesapeake?

We provide an array of great vacation destinations in Chesapeake. If you are looking to stay in or around the Chesapeake area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Chesapeake:

How many vacation rentals have private pools in Chesapeake?

We have 8 luxury villas and vacation rentals featuriung a private pool in and near Chesapeake. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel or resort in Chesapeake is best for families?

Searching for a family-friendly getaway in Chesapeake? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Chesapeake?

BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 176 in the Chesapeake area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Chesapeake. 

Nearby Neighborhood (7) 
Neighborhood Property Count
Greenbrier East Rental Villas and Private Getaways in Chesapeake, Virginia 26
Western Branch North Rental Villas and Private Getaways in Chesapeake, Virginia 70
Greenbrier West Rental Villas and Private Getaways in Chesapeake, Virginia 60
Great Bridge Rental Villas and Private Getaways in Chesapeake, Virginia 103
Deep Creek South Rental Villas and Private Getaways in Chesapeake, Virginia 145
Churchland Rental Villas and Private Getaways in Chesapeake, Virginia 63
Great Bridge East Rental Villas and Private Getaways in Chesapeake, Virginia 27

People Also Ask

There are 76 hotels in Chesapeake and 84 rentals

Recently Booked Hotels, Resorts, or Rentals in Chesapeake