10 Great Chesapeake Bay Hotels and Inns

The hotels and inns located along the Chesapeake Bay offer a magical and unforgettable experience for all ages. Extending 200 miles along the Eastern Shore of Maryland, the Chesapeake Bay provides spectacular waterfront views and great opportunities for outdoor recreation. With so many small towns and waterfront destinations to explore, you could spend a lifetime visiting this region and keep discovering something new. Following is a guide to some of the best places to stay overnight along the bay. Accommodations range from large luxury resorts to cozy bed and breakfasts. These properties are all located in unique destinations along the waterfront with beautiful views and access to boating and swimming. (Listed in alphabetical order)

01 of 10

Back Creek Inn

Back Creek Inn
© Back Creek Inn

Solomons, MD. Located in the heart of historic southern Maryland, the Bed & Breakfast is nestled along Back Creek, a scenic waterway that merges with the Patuxent River and the Chesapeake Bay. Seven guest rooms are available. The property is beautifully landscaped. Sailing and motorized boating guests may dock at one of the two slips available at the Inn's dock. Read traveler reviews and compare rates on TripAdvisor

02 of 10

Chesapeake Beach Resort and Spa

Chesapeake Beach Resort and Spa
© Chesapeake Beach Resort and Spa

Chesapeake Beach, MD.  The resort's Rod 'N' Reel Marina is known as the “Charter Fishing Capital of Maryland” with the largest charter fishing fleet on the Chesapeake Bay. The waterfront property features 72 guest rooms, two restaurants, a full-service spa, a 120-slip marina, an indoor heated swimming pool, a fitness center, a gaming and bingo room, and meeting and banquet space. Kayaks, canoes, paddle boards, and bicycles are available to rent. There is a boardwalk and a water park nearby.

03 of 10

Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina

Hyatt Regency Cambridge
© Rachel Cooper

Cambridge, Maryland. The 400-room luxury resort is set on the banks of the Choptank River, a major tributary of the Chesapeake Bay, on the Eastern Shore of Maryland. Hotel guests enjoy sailing, fishing, swimming, golf, biking, spa treatments and fine dining. Nearby attractions include Historic Cambridge, Blackwater Wildlife Refuge, St. Michaels, and the Harriet Tubman Museum. Read more about the Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina.

 

04 of 10

The Inn at Herrington Harbour

The Inn at Herrington Harbour
© The Inn at Herrington Harbour

Rose Haven, MD. The 33 room inn offers a relaxing, rejuvenating experience on the Chesapeake Bay. Enjoy the views from your front porch rocking chair, take a stroll through the beautifully landscaped gardens and roam the private beach. Amenities include a swimming pool, gym, sauna, and tennis courts. Read traveler reviews and compare rates on TripAdvisor

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05 of 10

The Inn at Osprey Point

Inn at Osprey Point
© Inn at Osprey Point

Rock Hall, MD. The Inn at Osprey Point is an Eastern Shore waterfront property with charming accommodations and the Osprey Point Restaurant. The main inn has seven rooms, the Osprey Annex, has six rooms and the beautifully renovated Farmhouse has four bedrooms. The property has a large swimming pool and excellent views of the Chesapeake Bay with romantic sunsets. Nearby activities include visiting the Eastern Neck Wildlife Refuge, fishing and sailing charters, shopping, and more. Read traveler reviews and compare rates on TripAdvisor

06 of 10

Inn at Perry Cabin

Inn at Perry Cabin
© Inn at Perry Cabin

St. Michaels, MD. The 78 room waterfront inn sits on the edge of St. Michaels, a beautiful historic town on the Maryland Eastern Shore. The Inn at Perry Cabin provides a romantic setting with lovely accommodations, an award-winning restaurant, a top-rated spa, a zero-edge pool, Afternoon Tea, and activities such as fitness classes, craft sessions, wine tastings, kayaking and open-air movie nights. Sailing and boating activities are offered daily. Read traveler reviews and compare rates on TripAdvisor

07 of 10

Lowes Wharf Marina Inn

Lowes Wharf Marina Inn
© Lowes Wharf Marina Inn

Sherwood, MD. Located along the Chesapeake Bay between St. Michael's and Tilghman Island, the 10-room inn offers waterfront guest rooms, a restaurant, patio bar, a marina, sunset cruises, crabbing, kayaking, bicycling and more. Read traveler reviews and compare rates on TripAdvisor

08 of 10

Sandaway Waterfront Bed and Breakfast

Sandaway Waterfront Bed and Breakfast
© Sandaway Waterfront Bed and Breakfast

Oxford, MD. The charming Bed & Breakfast features waterfront guest rooms with porches overlooking the Tred Avon River, Choptank River, and Chesapeake Bay. Guests especially enjoy the waterfront lawn and private sandy beach. The towns of St. Michaels, Easton, and Cambridge are only a short drive or ferry ride away offering a variety of dining, shopping, and recreational activities. Read traveler reviews and compare rates on TripAdvisor

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09 of 10

Solomons Victorian Inn

Solomons Victorian Inn
© Solomons Victorian Inn

Solomons, MD. This lovely Queen Anne Victorian style Bed & Breakfast is set on the southern tip of Solomon's Island with magnificent views of the harbor from every room. Seven guest rooms are available. You can easily walk to many restaurants and the town's famous Tiki Bar. Nearby attractions include the Calvert Marine Museum, Drum Point Lighthouse, Ann Marie Gardens, Saint Mary’s City, and Sotterley Plantation. Read traveler reviews and compare rates on TripAdvisor

10 of 10

Wades Point Inn on the Bay

Wades Point Inn on the Bay
© Wades Point Inn on the Bay
Inns & Bed and Breakfasts
4.6

St. Michaels, MD.  The charming 26-room historic inn is located just minutes from St. Michaels on the Chesapeake Bay. The property has four distinctly different buildings to meet a variety of needs. A 5-room farmhouse is available for family groups and can sleep up to 13 people. Visitors enjoy biking, bird and wildlife viewing, kayaking, and swimming on site. The property is conveniently located near a variety of restaurants, the Chesapeake Bay Maritime Museum and a variety of marinas with water sports activities. Read traveler reviews and compare rates on TripAdvisor

More About the Chesapeake Bay and the Maryland Eastern Shore

The Maryland Eastern Shore extends hundreds of miles between the Chesapeake Bay and the Atlantic Ocean and is a popular vacation destination. The historic towns, beaches and beautiful natural areas offer a variety of recreational activities such as boating, swimming, fishing, bird watching, biking and golf. The resort communities along the Eastern Shore host wonderful annual events including waterfront festivals, seafood festivals, boating regattas and races, fishing tournaments, boat shows, museum events, arts and crafts shows, and more. See a guide to the Cities and Towns Along the Chesapeake Bay.