20 Best Romantic Fall Getaways in Maryland

Brampton Inn

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

Ideas in New England: Vermont, Massachusetts, New Jersey, < New Hampshire, Delaware

Flag House Inn

Right in the heart of historic Annapolis, Maryland, 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

Ideas by Occasion: Relax at a spa, Girls weekend, Birthday, Family, Honeymoon Weekend, All-Inclusive

Georgian House

Why visit historic sites in Annapolis when you can stay in one? One of the oldest residences in Annapolis, Georgian House is a unique bed and breakfast that predates the American Revolution. Guests visit the historic B&B from around the world and are greeted by a midshipman from the US Naval Academy, a unique feature of the B&B.

Another feature that makes the bed and breakfast stand out is that three Marylanders who signed the Declaration of Independence once stayed in the 260-year-old home. Guests will find rooms that ooze old-world charm in décor, but modern-day conveniences in terms of amenities at Georgian House.

Georgian House , 170 Duke of Gloucester Street, Annapolis, Maryland 21401, Phone: 410-263-5618

Weekend Inspiration: NC Getaways, Small Town Getaways, From Toronto, Oklahoma, From Jackson, From Louisville

Black Walnut Point Inn

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

West Coast Vacations: Oregon, From Seattle, Washington

Antrim 1844 Country House Hotel

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

Weekend Trips: Southwest Weekend Getaways, Arkansas, Idaho, Montana

Ship Watch Inn

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

Where to travel next: New England Getaways, Wisconsin, Kentucky, Illinois, NJ, Richmond, From NJ

Solomons Victorian Inn

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

California vacations: California Weekend Getaways, Southern California, Northern California, Lake Tahoe, From Los Angeles, From San Francisco, From San Diego

Stoney Creek Farm

It’s more than the name suggests – Stoney Creek is also an inn and retreat center located on the lush rolling hills of Washington County, Maryland. The historic home spares no comfort and is a wonderful place for guests to unwind, relax, and explore the rich American history that can be found there.

Minutes away from the historic towns of Hagerstown, Frederick, Harpers Ferry, and Shepherdstown, the inn boasts many sites and attractions that are fun for the whole family. The bed and breakfast has a warm, personal atmosphere that makes guests feel like they’re home while enjoying the comforts of the inn, including a stunning garden and rich interior and amenities.

Stoney Creek Farm, 19223 Manor Church Road, Boonsboro, MD 21713, Phone: 301-432-6272

The South USA Vacations: Mississippi, Georgia, Alabama, Florida, From New Orleans, Louisiana

Wilson House

A historic bed and breakfast in Baltimore, the Wilson House offers a unique getaway for guests. Behind the name of the B&B lies an interesting story: the home-converted-inn was the place William Jennings Bryant made the agreements that gave Woodrow Wilson the presidency in 1912. Guests will feel right at home in the friendly and comfortable atmosphere at Wilson House, which is perfect for a family vacation, business trip, or a romantic getaway for the weekend.

There are over 40 rooms in the inn, which has 12 bedrooms, twin parlors, a library, and a den with a sunroom. The original fittings such as the chandeliers and the eight fireplaces give the B&B a charming authenticity that guests will fall in love with.

Wilson House , 2100 Mt Royal Terrace Baltimore, MD 21217-4848, Phone: 410-383-6267

Bishop’s House

A warm, tranquil, and elegant bed and breakfast in Easton’s Historic District in Maryland, Bishop’s House is located on a gorgeous landscape with many towering trees shading the area dotted with stately homes. Within the house, guests can relax on the porch swing or on a rocker on the wraparound porch of the home, or unwind near the fish pond or fountain in the garden courtyard.

There are also drawing rooms with gas log fireplaces and a wide array of books, games, and other forms of amusement available for guests to take advantage of. Guests of Bishop’s House can cycle the beautiful countryside surroundings. If they’re bringing their own bike, they can use secure overnight bicycle storage, and if they are not, the B&B has a complimentary bike for guests to use.

Bishop’s House, 214 Goldsborough St, Easton, MD 21601, Phone: 410-820-7290

More ideas: Lutherville, Maryland

Elk Forge, a Romantic Getaway in Maryland for Couples

Located on five expansive acres of nature trails, gardens, and beautiful woods, Elk Forge is a gorgeous bed and breakfast minutes from Elkton, Newark, and greater Wilmington. Guests can hike or bike through the trails and enjoy nature in the calm surroundings.

The countryside inn offers a delightfully comfortable experience. A stay in any of the 14 luxurious rooms includes breakfast, private bathrooms, an in-room fireplace, comfortable mattresses, free high-speed internet, lush robes, and access to the outdoor hot tub. Elk Forge doubles as an on-site day spa that has various massages and body treatments on the menu.

Elk Forge, 807 Elk Mills Road, Elkton, MD 21921, Phone: 410-392-9007

The Wayside Inn

Located in Ellicott City, The Wayside Inn is the perfect bed and breakfast, as it serves as the ideal starting point to explore Baltimore, Annapolis, or Washington DC. The historic bed and breakfast, which was built circa 1780, is also perfect for a romantic and relaxing getaway and you don’t even have to leave the walls of the boutique inn.

The luxurious oasis is warm and comfortable, and it is the perfect combination of historic charm and modern amenities. Each room has free broadband Wi-Fi, flat screen TVs, large double spa jetted tubs, plush robes, and silky sheets. Breakfast is no small time event as guests are served a multi-course, gourmet breakfast.

The Wayside Inn, 4344 Columbia Road, Ellicott City, MD 21042, Phone: 410-461-4636

Osprey Point

The perfect fusion of a relaxed environment, luxurious accommodation, and elegant dining, Osprey Point Inn, Restaurant, and Marina is a great place for a waterside getaway. Near the Chesapeake Bay, the inn lies on the shore of Swan Creek in Rock Hall, Maryland.

Osprey Point has various accommodation options and amenities such as access to picnic areas and the surrounding grounds, a large swimming pool, and much more. A restaurant that serves contemporary American cuisine is located at the inn. Guests can also head down to the marina for an Eastern Shore boating experience fitted with modern bath house, floating docks, and fun both onboard and ashore.

Osprey Point, 20786 Rock Hall Avenue, Rock Hall, MD 21661, Phone: 410-639-2194

More ideas: Parkville, Maryland

River House Inn

River House Inn is a nationally registered Victorian home located on the banks of the breathtaking Pocomoke River in Snow Hill, Maryland just a 40-minute drive from Ocean City. The laidback bed and breakfast offers the perfect getaway to explore and unwind in Maryland’s Eastern Shore.

If guests are looking for a more active holiday, they will be pleased to learn the area is filled with activities perfect for nature lovers, including boating, canoeing, relaxing on the beach, exploring wildlife preserves, biking, fishing, or swimming. Other fun things to do include antiquing or playing golf on a beautiful course. River House Inn is nearby Assateague National Seashore, making it a perfect base point for exploration.

River House Inn, 201 E. Market Street, Snow Hill, MD 21863, Phone: 410-632-2722

Back Creek Inn Bed and Breakfast

Back Creek Inn Bed and Breakfast is located on the banks of Back Creek, a scenic waterway in southern Maryland that merges with the Chesapeake Bay and the Patuxent River. The B&B has been entertaining guests for over 28 years, and it has been a private residence for over 125 years, bringing together the perfect combination of old-time southern MD with modern conveniences.

Guests can ride around the neighborhood on complimentary bicycles or rent a kayak and explore the Chesapeake Bay. Guests can take a short walk to nearby gift shops, an art gallery and marine museum, restaurants, and wineries.

210 Alexander Lane, P.O. Box 520, Solomons Island, MD 20688-0520, Phone: 410-326-2022

Carmel Cove Inn

Located on the banks of Deep Creek Lake, Carmel Cove Inn is a hotel like no other. It offers guests a lakeside getaway that is comfortable, pampering, and friendly. Guests can play tennis, fish off the dock, relax by the campfire, borrow a bike for a ride around, play pool or read a book in the great room, or take a canoe out on the lake – all of these activities are complimentary of the inn.

There are 10 different rooms with private baths to choose from. All of the rooms are appointed with complimentary Wi-Fi, a flat screen TV, air conditioning, wonderful bath amenities, and ample privacy.

5 Vacation Way, McHenry, MD 21541, Phone: 301-387-0067

The Inn at Norwood

Built in 1906, The Inn at Norwood is a colonial revival home in the heart of historic Sykesville, Maryland. Retaining much of its original charm, the inn is an elegant, warm, and tranquil place where guests can get away from the bustle of their daily lives.

They are invited to relax on the front porch and people watch, as the inn conveniently overlooks the town, or take a walk and experience the hiking and bike trails, museums, antique shops, and festivals that Sykesville is known for. Each guest room has a private bath with whirlpool tubs, fireplaces, cable televisions, DVD players, and free Wi-Fi.

7514 Norwood Avenue, Sykesville, MD 21784, Phone: 410-549-7868

Whitehaven Hotel

The 19^th century Whitehaven Hotel is a charming riverfront hotel in Eastern Shore village. Located on the banks of the Wicomico River, it is a short drive away for guests looking to visit Ocean City, Assateague National Seashore, or Chincoteague Island. For those looking to relax and unwind, the hotel has eight rooms to choose from, each with a private bath.

Other room options include access to a screened porch and fireplaces. Complimentary kayaks are available for guests to use during their stay, and guests who are bringing their own boat can use the hotel dock. Having started out as a private home in 1810, the bed and breakfast has a lot of history behind it, and guests can spend hours exploring the house and the surrounding neighborhood.

2685 Whitehaven Road, Whitehaven, MD 21856, Phone: 410-873-3099

Inn BoonsBoro

One of the more luxurious inns in Boonsboro, Maryland, Inn BoonsBoro has amazing facilities and amenities, ensuring that guests who come will never have to leave the inn for home-like comfort. You’ll find luxurious sheets, cashmere throws, private bathrooms with heated tile floors and towel racks, and bath amenities by Cedar Ridge Soaps. There is also a personalized scent for each room that includes soap, shampoo, hair conditioner, shower gel, body lotion, and bath salts.

Every evening, guests can lounge in the common room and enjoy complimentary wine, fruit, cheese, and crackers. Guests are also given complimentary access to the nearby Fit In Boonsboro for a workout or to relax in the steam room/ sauna.

1 N. Main Street, Boonsboro, MD 21713, Phone: 301-432-1188

20 Best Romantic Fall Getaways in Maryland :