Chesapeake Hotels, Resorts, and Rentals

About Chesapeake Vacation Rentals

There are more than 179 places to stay in Chesapeake that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Chesapeake.

Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Chesapeake, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Chesapeake. Places to stay near Chesapeake are 465.41 ft² on average, with prices averaging US $237 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Chesapeake with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.

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Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in Chesapeake

Type Count
Vacation Homes67
Holiday Apartments25
Cottages2
Others1
Unique Vacation Rentals1

Use these Quick Filters to Find a Vacation Rental in Chesapeake

★ Pro Tip: Hotala.co.nz has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay in Chesapeake.

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

Hotala.co.nz can help you find hotels, resorts, and rentals near many of Chesapeake's top attractions, neighborhoods, and points of interest.


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 149 Properties
Cahoon Plantation Golf Course 134 Properties
Adventure Kayak Tours Day Tours 124 Properties
Chesapeake City County 119 Properties
Portlock Galleries at SoNo 119 Properties
Chesapeake Veterans' Memorial 119 Properties
Chesapeake City Hall 118 Properties
Chesapeake Central Library 118 Properties
Western Branch North 71 Properties
Greenbrier West 66 Properties
South Norfolk 59 Properties
Greenbrier East 24 Properties

Frequently Asked Questions About Chesapeake?

What are the top hotels or resorts in Chesapeake?

You have a lot of choices in or near Chesapeake. If you need a hotel in the Chesapeake area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Chesapeake:

Which hotel or resort in Chesapeake is best for families?

If you are looking for a family-friendly hotel, resort, or vacation home in Chesapeake, check out one of the following places to stay as all are highly-rated accommodation choices with excellent reviews for families or groups staying in Chesapeake:

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

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2026 is over 179 in the Chesapeake area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Chesapeake.

Nearby Neighborhood (7) 

NeighborhoodProperty Count
Greenbrier East Hotel & Resort Deals in Chesapeake, Virginia 24
Greenbrier West Hotel & Resort Deals in Chesapeake, Virginia 66
Western Branch North Hotel & Resort Deals in Chesapeake, Virginia 71
Deep Creek South Hotel & Resort Deals in Chesapeake, Virginia 149
Churchland Hotel & Resort Deals in Chesapeake, Virginia 66
Great Bridge Hotel & Resort Deals in Chesapeake, Virginia 106
Great Bridge East Hotel & Resort Deals in Chesapeake, Virginia 27

People Also Ask

There are 71 hotels in Chesapeake and 92 rentals

Recently Booked Hotels, Resorts, or Rentals in Chesapeake