Discover a selection of 6,000 holiday rentals in Chesapeake Bay that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at £ 150 per night, and houses and cottages are popular options for a stay in Chesapeake Bay. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Chesapeake Bay
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 features

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.

Can I find a vacation rental around Chesapeake Bay?

Yes, our 2021 property listings offer a large selection of 5,680 vacation rentals near Chesapeake Bay. From 2,948 houses to 254 cottages, 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.