Where to stay around Chesapeake Bay, US?

Our 2018 property listings offer a large selection of 2,055 vacation rentals near Chesapeake Bay. From 976 houses to 325 condos, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chesapeake Bay for a holiday or a weekend are on VRBO.

What are the most popular destinations to visit in Chesapeake Bay?

There are many lovely places to stay for a holiday trip or just for a weekend in Chesapeake Bay. From VRBO travelers, the top most popular destinations to visit are:

  • Virginia Beach: 1,280 vacation rentals
  • Pennsylvania: 5,396 vacation rentals
  • Virginia: 5,623 vacation rentals
  • Williamsburg: 465 vacation rentals
  • Annapolis: 497 vacation rentals

And VRBO offers you the chance to discover many other popular destinations in Chesapeake Bay! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in Chesapeake Bay?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in Chesapeake Bay:

  • Virginia Beach: 1,280 rentals
  • Williamsburg: 465 rentals
  • Annapolis: 497 rentals
  • Baltimore: 250 rentals
  • Saint Michaels: 161 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Can I find easy-access vacation rentals when traveling by plane to Chesapeake Bay?

Yes of course. Our owners offer a large selection of vacation rentals near airports. The airports with a large selection of vacation rentals in Chesapeake Bay are:

  • Baltimore-Washington International Thurgood Marshall Airport (BWI): 675 vacation rentals
  • Penn Station Airport (ZBP): 272 vacation rentals
  • Newport News Williamsburg International Airport (PHF): 518 vacation rentals

For other airports, please use our search bar to access the selection of vacation rentals available.

Near which points of interest can I spend my holidays in Chesapeake Bay?

VRBO offers a large selection of rentals near lovely places in Chesapeake Bay. From VRBO travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Cape Charles Beach: 201 rentals
  • Baltimore Inner Harbor Marina: 293 rentals
  • Busch Gardens Williamsburg: 442 rentals
  • Colonial Williamsburg Visitor Center: 442 rentals
  • U.S. Naval Academy: 612 rentals

But there are many other points of interest around Chesapeake Bay listed on VRBO where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection.

The oceanfront setting of Eastern Shore is ready to explore

The ocean views and wildlife provide a pleasant backdrop to your vacation home in Eastern Shore. Travelers to this walkable city praise the sailing, seafood restaurants and bird watching. With a vacation rental, you get a home away from home—many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in and around Eastern Shore

Are you looking for attractions to see in the city? Travelers enjoy fun activities like boating and bird watching. Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Eastern Shore a one-of-a-kind vacation spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Layton's Chance Vineyard and Winery (12 mi / 19.3 km)
  • Hooper's Landing Golf Course (12.4 mi / 20 km)
  • Hog Neck Golf Course (15.6 mi / 25.1 km)
  • St. Michaels Winery (21.2 mi / 34.2 km)
  • Harrington Raceway and Casino (23.2 mi / 37.4 km)
  • Delaware State Fairgrounds (23.3 mi / 37.4 km)

Seasonal weather in Eastern Shore

Travelers enjoy Eastern Shore for its boating. If warm-weather activities are high on your list, July, June, August and September are the hottest months to visit, when temperatures average 88°F.

Exploring the beaches and other natural features in Eastern Shore

Travelers enjoy Eastern Shore for its seaside and wildlife. Whether you're looking for adventure or just want to appreciate the scenery, Eastern Shore is a great place to spend some time outside. Here are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Bill Burton Fishing Pier State Park (11 mi / 17.7 km)
  • Kiwanis Park (12.5 mi / 20.1 km)
  • Long Wharf Park (12.8 mi / 20.6 km)
  • Great Marsh Park (13 mi / 20.9 km)
  • Seaford Sports Complex (13.1 mi / 21.1 km)
  • Gateway Park (13.6 mi / 21.9 km)