Talbot County’s Romantic Hideaways

Quiet Time is the Right Time to Get Away

With miles of spectacular waterfront and small towns defined by charming tree-lined brick sidewalks, exclusive Talbot County is the ideal backdrop for a relaxing romantic getaway on the Chesapeake Bay. Located on Maryland's Eastern Shore, less than a 90-minute drive from Washington, D.C. and three hours from Philadelphia, arriving here is a breeze.

It’s always a good time to visit, but there’s something especially beautiful during the quiet, colder season when couples can stroll uncrowded streets in postcard pretty villages, hike and bike along miles of nature trails, as well as savor the unspoiled beauty of the waterfront.

From low-key inns to luxurious waterfront resorts to historic house rentals there’s a place to stay for every mood.  Best of all, Talbot County’s hospitality industry adheres to the strictest standards to protect guests from COVID-19, so you can truly indulge in a worry-free escape.  Here are some of the area’s most romantic offerings.

EASTON

The Tidewater Inn and Tidewater House

The Tidewater Inn, the grand dame of historic downtown Easton, has made it easier than ever to enjoy a romantic getaway with the new premier suites (refurbished in 2020) and the recently debuted Terrasse Spa, a luxury retreat that features unique treatments, such as a soothing CBD hemp massage. For even more privacy, hole up across the street at one of the five spacious suites at the circa 1874 Tidewater House, such as the two story Safari Suite with a romantic fireplace. Both properties offer knock ‘n drop contact-less room service from Hunter’s Tavern, the beloved Eastern Shore restaurant that offers classics with a modern twist, including Chesapeake rockfish served with a green curry sauce.

Hummingbird Inn

There are six individually designed rooms at this bed and breakfast housed within a Victorian in the heart of Easton.  One of the most romantic is the Easton Room, which features a claw foot tub and a working fireplace, along with a bay window.  This nearly one-acre property shaded by a magnificent magnolia is a wonderland of sorts with a trickling fountain and hidden benches. Come evenings the wide porch transforms to make room for a romantic happy hour under the stars with music and wine— there’s even a porch swing! 

OXFORD

Robert Morris Inn

Set along the waterfront in town, Robert Morris Inn makes for a picturesque stay.  The property, built in 1710, is America’s oldest full service inn. Rooms exude colonial charm with details like heart pine floors and original mantels. The inn’s atmospheric tavern with its wooden beams, brick walls, and large fireplace is headed up by an Englishman (the chef and co-owner), who serves up what’s often described as the county’s finest fish and chips, along with his signature oyster pot pie with a flakey pastry crust.

Sandaway Suites & Beach

Set on a stunning stretch of beach overlooking the Chesapeake Bay, couples can book their very own cottage or villa (some with full kitchens) for complete privacy. It’s here, at this adults-only property, where you can slow your pace and cozy up together on a porch overlooking the water, push off for a bike ride around the quaint town, or, when the weather cooperates, hop in kayaks to explore the nearby waterways.

ST. MICHAELS

The Inn at Perry Cabin

One of America’s most luxurious properties, the Inn at Perry Cabin exudes casual refinement.  Choose a suite with a terrace and fireplace for your very own 900-square-foot waterfront pied-a-terre.  Couples who want to hang out with their four-legged besties can select a garden suite, located in the main circa 1812 inn, with a furnished patio and separate entrance.  STARs, the resort’s acclaimed restaurant, takes locally-sourced food to a new level, tapping ingredients from area watermen and farmers, as well as its very own gardens and orchards.  Newly installed dining greenhouses stationed along the waterfront ensure safe, private, and very romantic dinners for two.

Hambleton Inn Bed & Breakfast

This 1860 beauty is flanked by a stand of crepe myrtles at the foot of Honeymoon Bridge. (Can it get any more romantic?). The inn has its own boat slips, dock and a fire pit that overlooks St. Michaels Harbour, the perfect place to sip a cocktail as the sun goes down. Each of the seven suites is unique, some have water views, many have fireplaces and one even has a dreamy copper soaking tub. Breakfasts are next level with treats like French crepes and eggs dusted with caviar.

The Parsonage Inn and the George Brooks House

The Parsonage Inn is a St. Michaels icon, a 19th century brick home with distinctive pointy slate roof.  Several of the eight rooms have private decks and fireplaces, while the Dodson King Suite has its own private entrance.  The B&B’s sister (or should we say brother?) property the George Brooks House is nestled on eight acres at the quiet end of town. Most guestrooms feature romantic four-poster beds. Some have Jacuzzis and fireplaces. Borrow bikes to explore the town’s Nature Trail, which weaves along the waterfront over a covered bridge.

Old Brick Inn

This inn’s 20 rooms are spread over three buildings, all in the heart of historic St. Michaels.  One of the early 19th century buildings actually hosted General Robert E. Lee at one point in history. Details like jetted tubs, double showers, and fireplaces make this inn extra romantic.  Couples can hole up for days in the Chesapeake Suite, an 800-square-foot guestroom with a fireplace, a Jacuzzi built for two, a spacious sitting room and a fridge, without ever setting eyes on the world until you’re good and ready.

Aida’s Victoriana Inn

This 1865-era Victorian mansion with slate mansard roof has Adirondack chairs staggered along the lawn overlooking the harbor and Navy Point (home to the Chesapeake Bay Maritime Museum).  Period details have been retained throughout the inn, like elaborate wainscoting, arched cornices and glass transoms. Some of the seven rooms have wood burning fireplaces and four-poster beds. Warm breakfast (including fluffy blueberry pancakes) is served daily, while Friday nights include a complimentary happy hour.

St. Michaels Harbour Inn, Marina & Spa

Located on the marina in St. Michaels, this resort offers plenty of romantic perks in its 52 rooms, like spa tubs and private waterfront decks. You can arrange for the ultimate harbor hideaway by booking the Commodore’s Quarters, a loft-like space that has private access and a two-person shower. Downstairs, Harrison’s Harbour Lights serves up Chesapeake Bay treats like cream of crab soup, rockfish bites freckled with Old Bay, and traditional oyster stew served beside stone fireplaces. Come with a boat?  No worries.  There are 50 slips at the marina waiting for you.

TILGHMAN ISLAND

Tilghman Island Inn

The new owners of the 20-room Tilghman Island Inn are a dynamic husband/wife duo.  He’s a chef known to serve creative spins on classics, such as a grilled Caesar salad with oyster “croutons,” at the restaurant overlooks a waterway still plied by local fisherman. She’s a landscape architect that has created a green oasis that relies on native plantings. Rooms are simple, chic, and modern, and should you arrive by boat, there’s a boat slip waiting.

Wylder Hotel Tilghman Island

Almost all of the 54 rooms at this historic property (which started life in 1898 as a boarding house) have private outdoor porches, most with a water view. Nine acres of waterfront ensures plenty of space to spread out, sip a drink by the fire pit, pump your legs on the tree swing, and stroll along the dock. Sample the fruits of the Chesapeake Bay like blue crab hush puppies and local oyster po’ boy sandwiches prepared by an award-winning chef at Tickler’s Restaurant, which has indoor and outdoor waterfront dining.

AROUND THE COUNTY

Vacation Rentals

For the most private getaway of all, you can book a vacation rental for a weekend, a week, a month — or more. No matter how long you choose to stay, you can rest assured life on the Shore will renew your spirit.  From waterfront estates to cozy cabins to historic homes in town, Tidewater Vacations, Eastern Shore Vacation Rentals, and A Historic St. Michaels Vacation have you covered. 

For a complete list of Talbot County’s lodging options, click here.