Historic Inn on the Eastern Shore

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

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
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.

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.

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, Lodge at Harbour Inn arranges hunting, fishing or crabbing experiences in a club-like atmosphere.

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.

The Inn at Perry Cabin
Historic Inn on the Eastern Shore

Take the wheel and sail the waters and dine on the freshest catch. Explore the quaint town of St. Michaels, a treasure-trove of shops. On Maryland's Frederick Douglass Driving Tour.

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

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. 

Chesapeake Charm, Point Lookout
St. Mary's
Porch overlooking water

Sleeping up to nine people, this house sits on a 15-acre crop farm on St. Jerome’s Creek, and provides crab pots, fishing rods and two kayaks for renters. You can stroll out onto your private dock to sip morning coffee, go crabbing, or jump in a boat (if you brought one).

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.

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.

Edge Hotel at Fager's Island
Ocean City
Hotel on the water
The Edge Hotel

These sophisticated rooms in 12 distinctive suites have one thing in common: the awe-inspiring views of the Bay through their expansive windows. There’s also easy access to Fager’s Island Restaurant, which has an extensive craft beer menu and second-to-none sunset views.

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.

Five Gables Inn and Spa
St. Michaels
Five Gables Inn and Spa, St. Michaels

This inn is located in four historic houses. Take a short walk to nearby shops and restaurants, or spend the day exploring the Chesapeake Bay on a charter boat. Go for a swim in the indoor pool, then stop by the sauna and steam room. Your four-legged friends can join you in one of the pet-friendly rooms. Visit off-season and take advantage of their special off-season packages.

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

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 letting embracing the beauty of the Chesapeake Bay.

Lighthouse Club Hotel
Ocean City
Lighthouse hotel

Book one of the stunning, bayfront suites at this Fager’s Island getaway for a unique perspective on OC. Escape for one of their winter romance and relax island escapes, or the famous New Year’s Eve Party Package. Or just make it that serene escape on your beach week adventure. You can’t go wrong at The Lighthouse.

Mariners Motel
Rock Hall

Simple, old-school, and awesome. If you’re looking to get away to Rock Hall, the Mariners Motel is perfect for families looking for a great place at a reasonable rate. Fishermen and outdoors enthusiasts will love the Mariner. It’s the perfect spot for Rockfish season, located right next door to the Rock Hall Marina. And after a long day on the water, the beautifully landscaped gazebo, complete with grills, is the perfect place to unwind.

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!

Hotel Atlantic
Atlantic Hotel

Since 1895, Hotel Atlantic has been welcoming travelers and sending them home with unforgettable memories. Nestled in the heart of “The Coolest Small Town in America,” and just a quick trip to Ocean City fun, Assateague escapes, and off-shore fishing adventures, the Hotel Atlantic is the perfect place in the perfect place.