Photo by Kaylee Spinhirn

Cottages in Chesapeake

Sun 16 Nov
Sat 22 Nov
November 2025
15
December 2025

Free cancellation options if plans change

Unlock travel rewards with One Key

Save more with Member Prices

Check prices for these dates

Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov
In one month
12 Dec - 14 Dec
In two months
9 Jan - 11 Jan

Cottages in Chesapeake

Top neighbourhoods in Chesapeake

Greenbrier East

Chesapeake's Greenbrier East neighbourhood has lots of places to visit, such as Greenbrier Mall and Jillian's Billiards.

Greenbrier

The Greenbrier neighbourhood has lots to see, including Greenbrier Mall and Chesapeake Arboretum.

Greenbrier West

The Greenbrier West neighbourhood has lots to see, including Bowlero Chesapeake and Rivercrest Play Area.

South Norfolk

Chesapeake's South Norfolk neighbourhood offers attractions, including Portlock Galleries at SoNo.

Great Bridge

The Great Bridge neighbourhood has lots to see, including Chesapeake City Hall and Chesapeake Golf Club.

Top landmarks in Chesapeake

Greenbrier Mall
Greenbrier Mall

Greenbrier Mall

If you want to give your credit card some exercise, head out to Greenbrier Mall in Greenbrier East. Why not take a stroll along the beaches and watch the sunset while you're here?

See properties in Greenbrier Mall
Chesapeake Square Mall
Chesapeake Square Mall

Chesapeake Square Mall

If you want to give your credit card some exercise, head out to Chesapeake Square Mall in Western Branch North.

See properties in Chesapeake Square Mall
Chesapeake Conference Center
Chesapeake Conference Center

Chesapeake Conference Center

After visiting Chesapeake Conference Center, make a plan to see the other sights and activities in Chesapeake. Experience the area's great live music and acclaimed theatre scene.

See properties in Chesapeake Conference Center
Oak Grove Lake Park
Oak Grove Lake Park

Oak Grove Lake Park

After visiting Oak Grove Lake Park, make a plan to see the other sights and activities in Chesapeake. Experience the area's acclaimed theatre scene or attend a sporting event.

See properties in Oak Grove Lake Park
Chesapeake Regional Medical Center

Chesapeake Regional Medical Center

Chesapeake Regional Medical Center is a hospital in Greenbrier West.

See properties in Chesapeake Regional Medical Center
Chesapeake City Park

Chesapeake City Park

Chesapeake City Park is just one of the places to see in Chesapeake, so why not enjoy the other things to explore during your travels? Stroll along the area's beautiful beaches or experience its acclaimed theatre scene.

See properties in Chesapeake City Park

Learn more about Chesapeake

A city of contrasts where urban pleasures meet natural wonders. Catch live music at the Chesapeake Conference Centre before exploring the Great Dismal Swamp National Wildlife Refuge's mysterious wetlands. Oak Grove Lake Park offers family-friendly trails where locals fish in peaceful seclusion. The Chesapeake Arboretum's 48 acres showcase native trees along winding paths that feel miles from civilisation. Shopping enthusiasts can browse Greenbrier Mall's offerings, though savvy visitors head to local farmers' markets for regional specialities. The city's waterfront areas reveal its maritime heritage, with inlets and waterways that once served as crucial trade routes. Don't miss the wildlife viewing platforms where patient observers spot eagles and herons in their natural habitat.

See all hotels in Chesapeake
Hidden Gems.

#trovember #chesapeake #virginia #november #fall #golden #hiddengems
Photo by Sarah Chiricosta

Find out more about Chesapeake

There's a lot visitors like about Chesapeake, especially its beaches and restaurants. You might find the perfect souvenir at Greenbrier Mall or Chesapeake Square Mall. And while you're here, be sure to stop by Chesapeake Conference Center and Chesapeake Arboretum.