A quiet inn by the water is a fine way to see the Chesapeake. Here are bed and breakfasts on the Bay listed by Visit Maryland, the state tourism office.
Quick answer: Two bed and breakfasts on the Bay listed by Visit Maryland: Wades Point Inn on the Bay in St. Michaels, with 26 rooms and water views, and River Inn at Rolph’s Wharf near Chestertown, a 5-room B&B on the Chester River with a pool and beach bar. Visit Maryland also keeps a list of places to stay on the Eastern Shore.
Contents
- Wades Point Inn on the Bay, St. Michaels
- River Inn at Rolph’s Wharf, Chestertown
- More Places to Stay
- Want a Park Instead?
- Frequently asked questions
Wades Point Inn on the Bay, St. Michaels
Wades Point Inn – 10090 Wades Point Road, St. Michaels. 26 rooms, big grounds, shade trees, porches and water views. Phone 410-745-2500.[1]
River Inn at Rolph’s Wharf, Chestertown
River Inn – 1008 Rolph’s Wharf Road, Chestertown. A 5-room B&B on the Chester River, with a beach bar and a pool. Phone 410-778-6389.[2]
More Places to Stay
Visit Maryland keeps a list of places to stay on the Eastern Shore.[3] Check prices and dates with each inn.
Want a Park Instead?
For cabins and campsites, see our page on camping on the Chesapeake Bay.
Frequently asked questions
Are there B&Bs on the Chesapeake Bay? Yes. Visit Maryland lists inns such as Wades Point Inn and River Inn at Rolph’s Wharf.
How many rooms does Wades Point Inn have? 26.
Where is River Inn at Rolph’s Wharf? On the Chester River near Chestertown.
References
- [1] Visit Maryland, Wades Point Inn on the Bay – last checked 11/08/2026
- [2] Visit Maryland, River Inn at Rolph’s Wharf – last checked 11/08/2026
- [3] Visit Maryland, Places to Stay on the Eastern Shore – last checked 11/08/2026
Find St. Michaels and Chestertown on our map.