Where to stay around Chesapeake Bay?

Our 2018 accommodation listings offer a large selection of 1,999 holiday lettings near Chesapeake Bay. From 976 houses to 325 condos, find unique self catering accommodation for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay near Chesapeake Bay is on HomeAway.

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

There are many lovely places to stay for a long holiday or just a weekend break in Chesapeake Bay. From HomeAway travellers, the popular destinations to visit are:

  • Virginia Beach: 1,313 holiday homes
  • Virginia: 5,229 holiday homes
  • Pennsylvania: 4,877 holiday homes
  • Williamsburg: 459 holiday homes
  • Delaware: 3,123 holiday homes

HomeAway offers you the possibility to discover many other popular destinations in Chesapeake Bay! Please use our search bar to access the selection of self catering accommodations available in other popular destinations.

What are the main cities to discover in Chesapeake Bay?

Whether you are travelling solo or with family and friends, here are the cities in Chesapeake Bay with the largest selection of holiday lettings for a perfect city break:

  • Virginia Beach: 1,313 holiday lettings
  • Williamsburg: 459 holiday lettings
  • Baltimore: 251 holiday lettings
  • Norfolk: 188 holiday lettings
  • Annapolis: 502 holiday lettings

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

Can I find easy access holiday homes when travelling by plane to Chesapeake Bay?

Yes of course. Our owners offer a large selection of self catering accommodations near to airports. Airports with a large selection of self catering accommodations in Chesapeake Bay are:

  • Leonardtown, MD (LTW-St. Marys County): 81 self catering accommodations
  • Cambridge, MD (CGE-Cambridge - Dorchester): 136 self catering accommodations
  • Baltimore-Washington International Thurgood Marshall Airport (BWI): 669 self catering accommodations

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

What are the most popular points of interest and landmarks to stay near in Chesapeake Bay?

HomeAway offers a large selection of holiday lettings near great places to visit in Chesapeake Bay. From HomeAway travellers, the top popular points of interest to stay for a holiday trip or just for a weekend are:

  • Fort George G. Meade: 821 holiday rentals
  • Perigeaux Vineyards and Winery: 80 holiday rentals
  • The Contemporary: 281 holiday rentals
  • Elk Neck State Park: 48 holiday rentals
  • Athena Vineyards and Winery: 113 holiday rentals

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

The oceanfront setting of Eastern Shore is ready to explore

The ocean views and wildlife provide a pleasant backdrop to your holiday home in Eastern Shore. Travellers to this walkable city praise the sailing, seafood restaurants and bird watching. With a holiday 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? Travellers enjoy fun activities like boating and bird watching. Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Eastern Shore a one-of-a-kind holiday spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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

Travellers 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 31°F.

Exploring the beaches and other natural features in Eastern Shore

Travellers 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 centre:

  • 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)