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

St. Michael's, Talbot County

Chesapeake Bay Resorts

By Jennifer Ajello

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

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

St. Michael's, Talbot County

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.

1
Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina
Cambridge
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.

2
Rod N' Reel Resort
resort on the water

You’ll go for the picturesque views out over the bay of Calvert Cliffs, but you’ll stay for the three restaurants and spa. Bring a group out 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.

3
The Inn at Herrington Harbour
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 with the complimentary kayaks and paddleboards.

4
St. Michaels Harbour Inn
Inn on Harbor
St. Michaels Harbour Inn

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

5
Island Inn & Suites on St. George Island
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. But if you’re looking for adventure, go for a pedal or a paddle quest, with the resort’s free use of kayaks and bikes. At the end of the day, head to The Ruddy Duck Seafood and Ale House for delicious local seafood.

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

St. Michael's, Talbot County

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. 

7
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.  Enjoy spa services.  Or consider booking "The Barn," which features another 18 guest rooms overlooking four acres of gardens, courtyards, fountains and activity lawns. 

8
Cove Point Lighthouse
Calvert County
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 of the Chesapeake Bay, the views here are breathtaking. Though the functioning lighthouse still welcomes guests, there’s a private beach for renters. Best of all, revenue from the rental supports the Calvert Marine Museum.

9
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.

10
Historic Kent Manor Inn
Stevensville
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.

11
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!

12
Smith Island Inn
Ewell
Smith Island Inn
TripAdvisor

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.

13
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 an easy stroll to Chateau Bu-De, where classic French cooking meets unforgettable Chesapeake flavors. Plan your trip now!