175+ Vacation Rentals in Chesapeake |
  1. USA
  2. Virginia
  3. Norfolk - Virginia Beach
  4. Chesapeake

Chesapeake Vacation Rentals, Hotels, & Places to Stay

About Chesapeake Vacation Rentals

There are more than 175 places to stay that are available in Chesapeake. These choices include hotels as well as other short-term private accommodations (including vacation rentals, cabins, condos, RVs, and more), have a wide selection of amenities at great prices, providing you with all the comforts of home or a touch of luxury. We like to help you find more room with Varoom when booking your property in Chesapeake.

Varoom features many last-minute deals on hotels, resorts and places to stay including many that are nearby. 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 Varoom's places in Chesapeake, you have the flexibility of comparing different options from multiple suppliers with a single click. Group deals, private pools, hot tubs, allows pets, or even those with huge master suite bedrooms with open-air showers? You can find vacation rentals and resorts as well as Airbnb-style properties in Chesapeake. Places to stay near Chesapeake are 445.15 ft² on average, with prices averaging US $184 a night.

Varoom helps you discover places to stay and suggests things to do to create great travel memories in Chesapeake. Prices listed are often found to be at a 30-40% discount versus the rack rates. Just search for your destination and secure your perfect place to stay today.

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Top Rental Accommodation Types in Chesapeake

Type Count
Vacation Homes 63
Holiday Apartments 20
Cottages 2

Use these Quick Filters to Find a Vacation Rental in Chesapeake

★ Pro Tip: Varoom is a meta travel and activities site, and as such we combine results from many of the leading travel websites, helping you compare the best places to stay and things to do in each market. Use the filter option to narrow down your selection and let us help you find more room to stay, play, and discover. Create new memories in Chesapeake today.

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

Top Attractions Around Chesapeake, VA

Varoom offers a large selection of top attractions around Chesapeake . Research things to do on your vacation before you visit Chesapeake.


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

Other Places to Stay in Chesapeake, VA


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 64 Properties
Greenbrier West 60 Properties
Jolliff 30 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 vacation rentals in Chesapeake?

We have scoured the web to find you options in Chesapeake. If you plan on staying near or in the Chesapeake area, consider one of the following places to stay for a week or more. Weekly stays are a great way to unwind and unplug. These places to stay have all been rated as one of the Top Places to Stay in Chesapeake:

How many vacation rentals have private pools in Chesapeake?

We have found 7 places to stay that feature a private swimming pool in or near Chesapeake. Some of the best places to stay that feature or have access to a swimming pool are:

Which vacation homes in Chesapeake are best for families?

If you are looking for a place to stay that is family-friendly in Chesapeake, check out one of the following places as all are highly-rated options and have received excellent reviews for families or groups staying in Chesapeake:

How many Varoom vacation rentals are available in Chesapeake?

Varoom updates its properties nightly to bring you a great selection of places to stay. Currently, the total number of properties listed by Varoom in 2025 is over 175 in the Chesapeake area, and still growing every day. When we combine listings from multiple websites and travel providers, Varoom can provide you with a diverse amount of choice of the best places to stay in Chesapeake. 

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

People Also Ask

There are 175 Chesapeake, VA Vacation Rentals

Recently Booked Vacation Rentals in Chesapeake