Where to stay around Chesapeake Bay?

Our 2018 accommodation listings offer a large selection of 1,877 holiday lettings near Chesapeake Bay. From 958 houses to 244 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: 1,312 holiday homes
  • Virginia: 5,208 holiday homes
  • Pennsylvania: 4,775 holiday homes
  • Maryland: 5,887 holiday homes
  • Williamsburg: 370 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: 1,312 holiday lettings
  • Williamsburg: 370 holiday lettings
  • Baltimore: 244 holiday lettings
  • Norfolk: 181 holiday lettings
  • Annapolis: 482 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): 76 self catering accommodations
  • Cambridge, MD (CGE-Cambridge - Dorchester): 133 self catering accommodations
  • Baltimore-Washington International Thurgood Marshall Airport (BWI): 621 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: 776 holiday rentals
  • Perigeaux Vineyards and Winery: 79 holiday rentals
  • The Contemporary: 248 holiday rentals
  • Elk Neck State Park: 42 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.

Delight in the sea landscape of Eastern Shore

The sea, beaches and wildlife display a scene truly unique to Eastern Shore. Well-known for its sailing, seafood and boating, this walkable city won't disappoint. Thinking of staying in a rental home? Holiday rentals often feature a full kitchen, Internet access and maybe even a fireplace.

Attractions in and around Eastern Shore

Have time to spare and looking for things to do around Eastern Shore? Local attractions include Coco's Funhouse, Salisbury Zoo and Grand Prix Amusements. If some outdoor time is on the agenda, soak up some sun at Maryland Beach and Ocean City Beach or experience the natural beauty of Bill Burton Fishing Pier State Park and Long Wharf Park. Fun activities in the city include Wye Landing, Cedar Hill Marina and Rolphs Wharf Marina. During your stay, you may want to visit Great Marsh Park, Martinak State Park or Adkins Arboretum. Also while in town, you can visit Harriet Tubman Underground Railroad National Historical Park, Pemberton Historical Park or Chesapeake Bay Environmental Center.