Compare Cheap 5 Star Hotels

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

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.

When you stay at St Michaels Inn in St. Michaels, you'll be in the historical district, within a 5-minute drive of St. Michaels Winery and Chesapeake Bay Maritime Museum.

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.

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.

When you stay at Days Inn & Suites by Wyndham Cambridge in Cambridge, you'll be near the beach, within a 5-minute drive of Bay Country Shop and Meredith House.

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.

Located in Grasonville, Holiday Inn Express Annapolis East-Kent Island by IHG is on a river, within a 10-minute drive of Queenstown Premium Outlets and Chesapeake Bay Environmental Center.