Destination guide

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.

Natural highlights

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)
How to get there

Travelling to and around Eastern Shore

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 15.2 mi (24.5 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Georgetown, DE (GED-Sussex County), which is 26.9 mi (43.2 km) away.

If you prefer train travel, you can make your way to Perryville Station.

Where to stay near Chesapeake Bay?

Our 2019 accommodation listings offer a large selection of 6,168 holiday rentals near Chesapeake Bay. From 2,554 Houses to 315 Cabins, find unique holiday homes for you to enjoy a memorable stay with your family and friends. The best place to stay near Chesapeake Bay for a long holiday or a weekend break is on Stayz.

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 Stayz travellers, the popular destinations to visit are:

  • Washington DC: 1,991 holiday rentals
  • Bumpass: 220 holiday rentals
  • Del Haven: 17 holiday rentals
  • New Jersey: 9,233 holiday rentals
  • Northeast Virginia Beach: 667 holiday rentals

Stayz offers you the possibility to discover many other popular destinations in Chesapeake Bay! Please use our search bar to access the selection of holiday rentals 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 rentals for a perfect city break:

  • Washington DC: 1,991 holiday homes
  • Bumpass: 220 holiday homes
  • Philadelphia: 1,099 holiday homes
  • Dewey Beach: 2,006 holiday homes
  • Ocean View: 2,251 holiday homes

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 holiday homes near to airports. Airports with a large selection of rentals in Chesapeake Bay are:

  • Ronald Reagan Washington National Airport (DCA): 2,026 holiday houses
  • Baltimore-Washington International Thurgood Marshall Airport (BWI): 726 holiday houses
  • Dulles International Airport (IAD): 248 holiday houses

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

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

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

  • Verizon Wireless Virginia Beach Amphitheater: 1,459 holiday rentals
  • Jungle Jim's River Safari Water Park: 4,381 holiday rentals
  • Barclay Farmstead Museum: 1,131 holiday rentals
  • Rehoboth Beach Boardwalk: 2,878 holiday rentals
  • Belmont Golf Course: 140 holiday rentals

But there are many other points of interest around Chesapeake Bay listed on Stayz 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 homes.

Explore destinations around Chesapeake Bay

Washington DC
1,991 holiday rentals
220 holiday rentals
1,099 holiday rentals
Dewey Beach
2,006 holiday rentals
Ocean View
2,251 holiday rentals
564 holiday rentals
Virginia Beach
1,604 holiday rentals
158 holiday rentals
28 holiday rentals
Ruther Glen
129 holiday rentals
46 holiday rentals
Chesapeake City
32 holiday rentals
1,902 holiday rentals
2,580 holiday rentals
Ocean City
5,416 holiday rentals
Cape May
1,992 holiday rentals
98 holiday rentals
3,296 holiday rentals
Chincoteague Island
206 holiday rentals
Silver Spring
1,821 holiday rentals