Where to Stay Along the Great Chesapeake Bay Loop



Featured Places

The Inn at Perry Cabin
The Inn at Perry Cabin
Image Credit: Belmond
Academy Bed and Breakfast - Annapolis
Academy Bed and Breakfast - Annapolis
Image Credit: Academy Bed and Breakfast

From five-star resorts with all the amenities to charming Bed & Breakfasts in walkable bayfront towns to cabins in state parks, and even lighthouses you can rent-- along the Great Chesapeake Bay Loop, your overnight options are limitless. Extend your Chesapeake Bay experience into the night by selecting a place to stay that matches your adventures of the day.

There are so many options.  Start with these lists to explore your nighttime accommodation choices:

Chesapeake Beach Resort and Spa

1 Chesapeake Bay Resorts

Spoil yourself on the banks of the beautiful Chesapeake Bay. Whether it’s getting a facial or massage, playing golf, fishing or simply watching the water lap gently to the shore, you are certain to find a resort or spa to give you that much-needed break. Here are some options that will make your dream vacation truly spectacular.

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Rosewood Manor in Port Tobacco

2 Places to Stay in Southern MD

Southern Maryland on the Western Shore offers the charm of the Chesapeake and good old-fashioned Southern hospitality, just around the corner from Baltimore and D.C. Get away for a weekend to one of these charming retreats and you’ll want to lose yourself for a lifetime.

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The Monaco Baltimore Hotel

3 Places to Stay in Central Maryland

Five-star luxury in the heart of Baltimore Harbor, quiet retreats nestled in Maryland’s nearby horse country, historic B&Bs by the Annapolis City Dock—in Maryland’s iconic Central Region, your home away from home, and the getaway of your dreams are right next door.

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The Robert Morris Inn

4 Places to Stay on the Eastern Shore

Whether you’re planning a romantic retreat, a shopping safari, a camping trip with the kids or even an old west adventure, Maryland’s Eastern Shore can put you up for your perfect getaway.

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Chesapeake Bay Sunset Image Credit: motoxdms-instagram-

5 More About the Great Chesapeake Bay Loop

To help you plan your Chesapeake Bay adventure, here’s some suggestions to get the most memories per mile:

Travel Around the Chesapeake Bay Loop

Quintessential Chesapeake Bay Towns

Experiences Along the Great Chesapeake Bay Loop

Trip Suggestions for the Great Chesapeake Bay Loop

About the Great Chesapeake Bay Loop

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