Romantic Fall & Winter Getaways in Maryland

A mile away from Chestertown, a historic arts and entertainment district in Maryland, Brampton Inn is the perfect place to have a memorable Eastern Shore vacation. Ornithology lovers will adore the location, as it is one of the best birding areas in the US.

Other activities include biking, kayaking, and exploring the Chesapeake region. The Garfield Center for the Arts and Washington College are just a few of the nearby sites in the waterfront town. Accommodation ranges from a choice of guest rooms and secluded cottages – all with en-suite bathrooms and unparalleled privacy.

Brampton Inn, 25227 Chestertown Road, Chestertown, MD 21620, Phone: 410-778-1860, Map

Right in the heart of historic Annapolis, Flag House Inn lies amidst the museums, restaurants, shops, and sites for which Annapolis is famed. Within walking distance, guests will find the US Naval Academy, the Annapolis waterfront, William Paca House, the Hammond-Harwood and Chase Lloyd Houses, and the Maryland State House, among other attractions.

A stay at the inn comes with a full home-cooked breakfast, comfortable king-size beds, free on-site parking, and private bathrooms with each room. The innkeepers can help guests plan their day according to their interests, even suggesting restaurants for a particular palette or providing a booklet with information on nearby museums, tours, and sails.

Flag House Inn, 26 Randall Street, Annapolis, MD 21401, Phone: 410-280-2721

Flanked by the Choptank River and the Chesapeake Bay, Black Walnut Point Inn is a serene place for guests to go to when searching for an uninterrupted, peaceful getaway. The six-acre estate boasts a beautiful inn and manicured lawn and gardens, and 52 acres of a bird sanctuary surround it.

Guests are encouraged to relax with a good book on a hammock or chaise lounge and unwind as the waves and waterfront view take over them. If you’re interested in perfecting the art of doing nothing, activities include lounging by the pool, playing croquet on the great lawn, fishing off the dock, or flying a kite.

Black Walnut Point Inn, 4417 Black Walnut Point Road, PO Box 308, Tilghman Island, MD 21671, Phone: 410-886-2452

Nestled at the foothills of the Catoctin Mountains in Taneytown, Maryland, Antrim 1844 Country House Hotel is a magnificent estate built in 1844. The 450-acre land is rich in history, much of which is preserved for guests to experience today. The architecture of the house is sure to take guests to another era; everything from the towering white columns on the grand porch to the 14-foot ceilings in the identical drawing rooms is intact.

Guests will have a wonderful time exploring nooks and crannies without ever leaving Antrim, which is now a boutique 40-room country house hotel. Guests can enjoy fine dining in the restaurant, quench their thirst with something from the expansive wine cellar, browse the gift shop, relax in the swimming pool, or play a round of tennis, croquet, horseshoes, or badminton.

Antrim 1844 Country House Hotel, 30 Trevanion Road, Taneytown, MD 21787, Phone: 410-756-6812

Located on the edge of the Chesapeake and the Delaware Canal, Ship Watch Inn allows guests to do just that: watch ships. It is one of the only bed and breakfasts in South Chesapeake City and is situated in a great location for guests who are looking to spend their vacation right on the waterfront.

All of the rooms at the inn have breathtaking panoramic views of the waterfront as well as an outdoor deck with private access, allowing guests to enjoy the view, catch some rays, and just relax during their getaway. Other amenities include an outdoor hot tub right by the waterside. Guests can get VIP perks at the nearby local restaurant, The Chesapeake Inn Restaurant and Marina.

Ship Watch Inn, 401 1st Street, Chesapeake City, MD 21915, Phone: 410-885-5300

Enjoy the ultimate Chesapeake Bay bed and breakfast experience at Solomons Victorian Inn. Located on the beautiful Solomons Island by the flowing Chesapeake Bay, the inn affords guests a magnificent view of the harbor from every room. Start the day with a delicious three-course European style breakfast from the inn’s airy porch and then enjoy the day lounging at the inn or actively exploring the surrounding area. Yacht building is a famed activity in the area.

Additional activities include biking, boating, jogging, or going on a walk. Guests can learn about the history and culture of the surrounding area by visiting the Calvert Marine Museum, the Drum Point Lighthouse, or the J.C. Lore Oyster House, which is the perfect place to better understand the local oyster industry and the role it has played in Solomons Island history.

Solomons Victorian Inn, 125 Charles Street, P.O. Box 759, Solomons, MD 20688, Phone: 410-326-4811