174+ Luxury Vacation Rentals & Cabins in Chesapeake |
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  2. Virginia
  3. Norfolk - Virginia Beach
  4. Chesapeake

Chesapeake Cabin Rentals

About Chesapeake Vacation Rentals

There are more than 174 incredible getaway rentals that are available in Chesapeake. These choices include cabins, 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. Stay Close to Nature with Cabinns.ca and uncover great stays in Chesapeake.

Cabinns.ca features numerous last-minute deals on private villas, hotels, and cabin 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 Cabinns.ca 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 Cabinns.ca vacation rentals, resorts, and Airbnb-style properties in Chesapeake. Places to stay near Chesapeake are 447.71 ft² on average, with prices averaging CA $253 a night.

Cabinns.ca helps you find the ideal holiday rental to create a lifetime of 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 cabin retreat today.

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Top Cabin Rentals, Cottages, and Holiday Home Rentals in Chesapeake

Type Count
Vacation Homes 62
Holiday Apartments 20
Cottages 2
Others 1
Unique Vacation Rentals 1

Use these Quick Filters to Find a Vacation Rental in Chesapeake

★ Pro Tip: Cabinns.ca is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts 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 Cabinns.ca.

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

Activities Chesapeake Guest Reviews Local Attractions

A Large Selection of Cabins and Vacation Rentals from Around the World Chesapeake. Discover Top Attractions For Your Next Outdoor Adventure.


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 Nearby Cabin Rentals in these Cities & Neighborhoods


Deep Creek South 145 Properties
Cahoon Plantation Golf Course 134 Properties
Chesapeake City County 128 Properties
Adventure Kayak Tours Day Tours 124 Properties
Portlock Galleries at SoNo 119 Properties
Chesapeake Veterans' Memorial 119 Properties
Great Bridge 103 Properties
Western Branch North 70 Properties
South Norfolk 65 Properties
Greenbrier West 60 Properties
Jolliff 30 Properties
Greenbrier East 25 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 cabins, lake houses & summer homes 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 cabin resort or 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 cabin rentals and resorts have private pools in Chesapeake?

We have 7 cabins, luxury resorts, and holiday home rentals featuring 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 cabin rental, resort, or holiday home in Chesapeake is best for families?

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

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

Cabinns.ca offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.ca in 2025 is over 174 in the Chesapeake area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.ca 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 Cabins and Private Getaways in Chesapeake, Virginia 25
Western Branch North Rental Cabins and Private Getaways in Chesapeake, Virginia 70
Greenbrier West Rental Cabins and Private Getaways in Chesapeake, Virginia 60
Great Bridge Rental Cabins and Private Getaways in Chesapeake, Virginia 103
Deep Creek South Rental Cabins and Private Getaways in Chesapeake, Virginia 145
Churchland Rental Cabins and Private Getaways in Chesapeake, Virginia 63
Great Bridge East Rental Cabins and Private Getaways in Chesapeake, Virginia 27

People Also Ask

There are 76 hotels in Chesapeake and 82 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Chesapeake