Historic Inn on the Eastern Shore
The Inn at Perry Cabin by Belmond

Chesapeake Bay Resorts

By Jennifer Ajello

Relax and rejuvenate at some of the Bay’s finest resorts and spas.

Historic Inn on the Eastern Shore
The Inn at Perry Cabin by Belmond

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.

Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina
With a spa, golf club and proximity to outdoor activities, this resort has something for everyone.

On the Choptank River in Cambridge, this 400-acre resort gives you access to one of the state’s best golf courses, The River Marsh Golf Club, as well as one of its most charming towns.

Rod N' Reel Resort
Chesapeake Beach
resort on the water

You’ll go for the picturesque views of the Bay and Calvert Cliffs, but you’ll stay for the three restaurants and spa. Bring a group to go fishing on a large charter fleet. There’s also gaming—via video tab pull machines and bingo—as well as an array of other outdoor activities.

The Inn at Herrington Harbour
Rose Haven
The Inn At Herrington Harbour

Pampering goes green at the Inn at Herrington Harbour, an “Eco-Lifestyle” Marina Resort. Enjoy the private beach, Olympic-sized swimming pool, playground and eco walking trails. There’s even more opportunity to relax in the outdoor hot tubs, and to enjoy nature and the water on a kayak or paddleboard available for use by inn guests.

St. Michaels Harbour Inn
St. Michaels
Inn on Harbor
St. Michaels Harbour Inn

Stay in the waterfront rooms and indulge in dining and spa services in this lovely bayside town. The resort offers complimentary bicycles, an outdoor pool, pet-friendly rooms and a resort shuttle. The resort offers an outdoor pool, pet-friendly rooms, a resort shuttle and bicycles for complimentary use by inn guests. For outdoor lovers, the Lodge at Harbour Inn arranges hunting, fishing or crabbing experiences in a club-like atmosphere.

Island Inn & Suites on St. George Island
Piney Point
St. George Island Inn and Suites

With your own private terrace from which you can watch the sun rise over St. George Creek, this Inn is the definition of relaxation. If you’re looking for adventure, go for a pedal or a paddle quest. The resort offers free use of kayaks and bicycles. At the end of the day, head to The Ruddy Duck Seafood and Ale House for delicious local seafood.

The Inn at Perry Cabin
St. Michaels
Historic Inn on the Eastern Shore
The Inn at Perry Cabin by Belmond

Come to Maryland’s Eastern Shore where your cares will melt away on the shores of the Miles River. The tranquil view, the water’s constant flow and leaves rustling in the wind will be the only things competing for your attention. The Inn at Perry Cabin is the premier resort on Maryland’s Eastern Shore. 

The Inn at the Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club

The Inn is beautifully appointed with high end furnishings, amenities and views of the Chesapeake Bay. The beautifully appointed Inn provides views of the Chesapeake Bay and offers wellness-focused treatments at the full service spa and salon. A gourmet cafe and Knoxie’s Table Restaurant are on site, using locally grown produce. Consider booking “The Barn,” which features 18 guest rooms overlooking four acres of gardens, courtyards, fountains and activity lawns.

Cove Point Lighthouse
Light house and cottage

For a unique place to rest your head, stay in a refurbished lighthouse keeper’s house. Located at one of the narrowest points on the Chesapeake Bay, the views from here to the Eastern Shore are breathtaking. Though the lighthouse grounds are open to the public during limited hours, there’s a private beach for renters. Best of all, revenue from the rental supports the Calvert Marine Museum.

Inn at Huntingfield Creek
Rock Hall
Brick Inn
Inn at Huntingfield Creek

Water and nature lovers will find paradise here. Take a relaxing walk on the nearby trails through meadows and forests, then return to your guest room or fully-furnished private cottage. Visit the nearby Waterman’s Museum and learn about one of Maryland’s most vital and historic industries, then stop at Waterman’s Crab House and Dock Bar to taste the succulent seafood resulting from that labor.

Historic Kent Manor Inn
Beautiful manor
Kent Manor Inn

This stunning waterfront property, first built in 1820 and refurbished, sits on 220 acres of farmland, woods and waterfront, with 24 guest rooms. Wander the grounds for picturesque water views and gardens. The inn provides a fresh complimentary deluxe continental breakfast for guests, and there’s a Sunday champagne brunch buffet, too.

Camp Merryelande
St. Mary’s
Camp Merryelande, St. Mary's County

Snuggled into the pine trees on the sandy shore of the Potomac River, Camp Merryelande (yes, with three “e”s) is an island escape just a short drive from Baltimore and D.C. Located on St. George’s Island in St. Mary’s County, you can choose a campsite on the beach, or one of the fantastic cabins, the largest of which can accommodate up to 24 guests. At Camp Merryelande, the extra “e”s are for excellent!

Smith Island Inn
Smith Island Inn Front Entrance
Smith Island Inn

Outside magazine called the Smith Island Inn one of its “28 Best Trips of 2016,” and it’s little wonder why. With stunning views from this harbor front vista, a stay at the Smith Island Inn means becoming an islander for a few days and embracing the beauty of the Chesapeake Bay.

Inn at the Canal
Chesapeake City
Inn porch overlooking canal
Inn at the Canal

If you’ve never made the trip to Chesapeake City, a historic, walkable town on the banks of the Elk River, you need to change that soon. And there’s no better place to stay than the Inn at the Canal. This seven-room Victorian B&B is just steps away from the Ben Cardin C&D Canal Trail, and a short drive to Chateau Bu-De, where fine wines meet gorgeous views of the Bohemia River and vineyard. Plan your trip now!