Compare Cheap 5 Star Hotels

When you stay at Wylder Tilghman Island in Tilghman, you'll be on the waterfront, within a 10-minute walk of Chesapeake Bay and Tilghman Watermen’s Museum.

With a stay at The Tilghman Island Inn in Tilghman, you'll be within a 5-minute walk of Chesapeake Bay and Tilghman Island Marina.

When you stay at this vacation home in Tilghman, you'll be on the waterfront, within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.

When you stay at Rod 'N' Reel Resort in Chesapeake Beach, you'll be on the waterfront, just steps from Chesapeake Beach Railway Museum and Rod n Reel Charter Fishing.

Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 5 minutes from Eastern Shore Hospital Center.

A stay at Inn at Perry Cabin places you in the heart of St. Michaels, within a 15-minute walk of Perry Cabin Park and Saint Michaels Town Hall.

A stay at Best Western Kent Narrows Inn places you in the heart of Grasonville, a 2-minute drive from Chesapeake Exploration Center and 7 minutes from Island Dog Park.

Located in Grasonville, Hyatt Place Kent Narrows & Marina is in the historical district, a 2-minute drive from Chesapeake Exploration Center and 7 minutes from Island Dog Park.

With a stay at Best Western Plus Easton Inn & Suites in Easton, you'll be within a 5-minute drive of Easton Cycle and Sport and Talbot Massage.

When you stay at The Tidewater Inn in Easton, you'll be in the historical district, just steps from Avalon Theatre and Talbot County Visitor Center.

Located in Stevensville, The Inn at Chesapeake Bay Beach Club is within a 15-minute drive of Chesapeake Bay and Chesapeake Bay Bridge.

With a stay at The Wildset in St. Michaels (Downtown St. Michaels), you'll be within a 5-minute walk of Higgins Yacht Yard and Marina and Saint Michaels Town Hall.