Experience

Located in the heart of downtown, the Flag House Inn affords guests easy access to all that Annapolis has to offer, just steps from our front door.

Our spacious common areas and carefully designed guest rooms offer tranquility mere steps away from the award-winning restaurants and nightlife of Annapolis. Our deliberate interior design incorporates original architectural features with fresh furnishings of the highest caliber. Every detail was carefully selected in order to deliver a uniquely memorable guest experience that reflects the character and history of Annapolis.

Inside the hotel

Set in an 1879 architectural masterpiece, the hotel was originally built by Welsh shipbuilder, Richard Owen Williams, as two personal residences. Blending historic beauty with the amenities of today, the hotel has been meticulously restored to provide you with a carefully curated stay, while maintaining the original architectural details of the duplex home.

Parlor Room

In the hotel’s Parlor Room , you will find no detail overlooked. The furnishings evoke a sense of 19th Century formal elegance. Located above the busy sidewalks of Randall Street, the lounge offers a wondrous and quiet respite for you to recharge, unwind, and delight in the refined sophistication of the Flag House Inn.

Dining Room

Hotel guests dine on the antique table tops in the hotel’s dining room that includes original design elements like crown molding and a three-dimensional fireplace.

The Reading Room

The Reading Room is a peaceful and exclusive retreat located on the hotel's first floor where guests may sip, savor, and indulge in this quintessentially Annapolis room defined by its bold colors and tastefully elegant design.

Breakfast

Guests are invited to join us for a farm-to-table breakfast experience designed and prepared by the hotel's chef with a Michelin-star background. The menu changes weekly, and includes mouth-watering concoctions such as a caviar-topped champagne omelette, a caprese tartine, and lobster quiche.

The Local Area

What you’ve heard is true! With Annapolis’ historic buildings that date back centuries, brick-lined streets, endless charm, and an unmatched culinary scene, you’ll find out quickly why Annapolis has been voted one of the most beautiful towns in America by Conde Nast Traveler. Our team is eager to offer our insider experience and help you uncover the best of our city.

Acqua al 2

236 Main Street, Annapolis, MD 21401 Visit Site

Located in the heart of Annapolis, Acqua al 2 offers an authentic Tuscan dining experience. Featuring a wide array of pasta dishes, hand-carved steaks, and fresh seafood, as well as an extensive Italian wine list, Acqua is perfect for a celebratory dinner, an intimate date night, or a low-key gathering with friends. Located a ten-minute walk from the hotel.

To Eat

Adam's on Fourth

424 Fourth St, Annapolis, MD 21403 Visit Site

Adam’s on Fourth is located in the heart of Eastport, which is known for its quirky nature and love for all things local. This new and fresh take on local has quickly gained a reputation for being one of the most popular spots in the maritime neighborhood of Eastport.

To Eat

Agave

106 Annapolis street Annapolis, MD 21401 Visit Site

The Mexican cantina vibes and outdoor patio are number one. Agave is an experience, not just another meal out. Come see for yourself!

To Eat

Annapolis Ice Cream Co.

196 Main St, Annapolis, MD 21401 Visit Site

Annapolis Ice Cream Company was founded on the ideals of crafting a premium, creamy, and homemade ice cream experience.

To See

Annapolis Sailing Cruises

80 Compromise Street, Annapolis, MD 21401 Visit Site

Located in the heart of the Chesapeake Bay is “America’s Sailing Capital.” Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay. Schooner Woodwind offers a fabulous sailing experience for all.

To See

Café Normandie

185 Main St. Annapolis, MD 21401 Visit Site

Open for nearly 40 years, Café Normandie combines French country cuisine with Maryland seafood specialties on the world-famous Main Street. Loved for its cozy atmosphere, and well-known for its typical French cuisine created and prepared by Award Winning Chef Jean-Louis.

To Eat

Chart House

300 Second St, Annapolis, MD 21403 Visit Site

Chart House is a Maryland treasure through and through. No matter what time of year you visit, you are assured not only the best seafood Annapolis has to offer, but also some of the best scenic dining in the northeast.

To Eat

Chessie's Wharf

609 Melvin Ave, Annapolis, MD 21401 Visit Site

A new, fun, and exciting taproom featuring nearly 40 draft beer selections and comfort food. A new offering located in West Annapolis owned and operated by RAR Brewing.

To Eat

Choptank - Annapolis

110 Compromise Street, Annapolis, MD 21401 Visit Site

With a spacious waterfront deck and rooftop, the Choptank is a classic fish and crab house serving Maryland’s famous cuisine, highlighted by steamed hard-shell blue crabs.

To Eat

City Dock and Ego Alley

Dock St, Annapolis, MD 21401 Visit Site

Mosey down Main Street from Church Circle to City Dock and you'll discover dozens of unique, locally-owned fashion boutiques and specialty gift shops tucked in between art galleries, pubs, restaurants and historic inns. Many of these small shop owners import their hand-crafted goods from far-off lands, just as town merchants have been doing for the past 350 years.

To See

Dry 85

193 B Main St, Annapolis, MD 21401 Visit Site

A bar and restaurant specializing in extraordinary drinks and modern twists on American comfort food.

To Eat

Eastport

Eastport, Annapolis, MD 21403 Visit Site

Take a water taxi from City Dock or shuffle across the Spa Creek Bridge to Eastport, the laid-back, maritime district of Annapolis.

To See

Forward Brewing

418 Fourth St. Annapolis, MD Visit Site

Located in the Annapolis neighborhood of Eastport, this nano-brewery and restaurant is emblematic of the Annapolis community – offering a fresh and local product using forward-thinking methods while honoring the local history where neighbors and visitors all feel welcome. Located a fifteen-minute walk from the hotel, or accessible by water taxi.

To See

Harold Black

236 Main St., Annapolis, MD 21401 Visit Site

Set in an old bank vault, Harold Black is a warm, intimate bar that is quiet enough to hear your conversation yet lively enough to keep you talking. Located a ten-minute walk from the hotel in the lower-level of Acqua al 2.

To See

InGrano

17 Annapolis St, Annapolis, MD 21401 Visit Site

InGrano’s extension into the realm of fine dining is not just about crafting delectable dishes; it's a celebration of their inviting boutique restaurant located in the West Annapolis neighborhood.

To Eat

Lemongrass

167 West St, Annapolis, MD 21401 Visit Site

Modern Thai cuisine in an easygoing atmosphere.

To Eat

Lewnes' Steakhouse

401 Fourth Street Annapolis, MD 21403 Visit Site

Lewnes' Steakhouse opened in 1994, specializing in USDA prime beef and exquisite seafood dishes. With a waitstaff dedicated to first-class service and an award-winning wine list with over 450 wine selections to pair with your meal, Lewnes' is the premier spot for special occasions or private dining.

To Eat

Main Street

Main St, Annapolis, MD 21401 Visit Site

A charming street full of a variety of unique boutiques, shops, and galleries you can browse to your heart’s content.

To See

Old Fox Books & Coffeehouse

35 Maryland Ave, Annapolis, MD 21401 Visit Site

Old Fox Books & Coffeehouse, where story lives, friends meet, and excellent coffee is served.

To See

Osteria 177

177 Main St, Annapolis, MD 21401 Visit Site

A restaurant that specializes in Italian coastal cuisine and spectacular wine.

To Eat

O’Leary’s Seafood

310 Third St, Annapolis, MD 21403 Visit Site

Serves some of the best seafood the city has to offer, freshly caught and cooked to perfection.

To Eat

Parley Room

25 State Circle Annapolis, MD 21401 Visit Site

A 1920s-style cocktail bar on State Circle overlooking the Maryland State House, the Parley Room prides itself on creating classic cocktails along with tasty charcuterie and shared plates. Located a five-minute walk from the hotel.

To See

Preserve

164 Main St, Annapolis, MD 21401 Visit Site

A casual and contemporary American restaurant with a focus on seasonal produce.

To Eat

Quiet Waters Park

600 Quiet Waters Park Rd, Annapolis, 21403 Visit Site

Enjoy trails winding through forests and past grassy fields, children’s playground, or picnic among 340 acres of beautiful park land.

To See

Red Red Wine Bar

189B Main St. Annapolis, MD 21401 Visit Site

Located in the middle of the action on Main Street, the 35+ wines by the glass and 120+ bottles pair perfectly with their elevated gourmet small-plates menu. Think of it as Maryland coastal meets California gourmet with a touch of New Orleans gluttony. Located a five-minute walk from the hotel.

To See

Ruth's Chris Steak House

301 Severn Avenue, Annapolis, MD 21403 Visit Site

Ruth’s Chris Steak House is located in the quaint, quiet neighborhood of Eastport in Annapolis, Maryland. Whether it’s a romantic steak dinner for two, an important business luncheon for 30 or more individuals, or a private party for six to 160 guests, Ruth's Chris Steak House will deliver superior service and an unforgettable dining experience in an atmosphere of warm, casual elegance.

To Eat

Sailor Oyster Bar

196 West St, Annapolis, MD 21401 Visit Site

Cozy, stylish spot serving up some of the best oysters & raw-bar fare in the region along with sandwiches, charcuterie & cocktails. Honoring the sailor and the sea.

To Eat

Seas the Bay - Private Sailing Charters

326 First Street, Ste 30, Annapolis, MD 21403 Visit Site

A sunset cruise, a romantic dinner, a family excursion, a wedding proposal….. Seas the Bay will help you design your special day in Annapolis.

To See

The Vineyards at Dodon

391 Dodon Rd, Davidsonville, MD 21035 Visit Site

The Vineyards at Dodon produces estate-grown wines. Tours and tastings are offered by appointment and Dodon has an active Wine Club.

To Eat

Tsunami

51 West St, Annapolis, MD 21401 Visit Site

Great place for eating sushi, having drinks with friends, and soaking up the special feeling of downtown’s West Street.

To Eat

U.S. Naval Academy

121 Blake Rd, Annapolis, MD 21402 Visit Site

The United States Naval Academy is a service academy located in the heart of Annapolis, Maryland. Established in 1845, it is the second oldest of the five U.S. service academies, and educates officers for commissioning primarily into the United States Navy and United States Marine Corps.

To See

Vin 909

909 Bay Ridge Ave, Annapolis, MD 21403 Visit Site

A restaurant and wine bar that serves fantastic farm-to-table New American cuisine.

To Eat

William Paca House

186 Prince George St, Annapolis, MD 21401 Visit Site

This five-part Georgian mansion was built in the 1760s by William Paca, one of Maryland’s four Signers of the Declaration of Independence and the state’s third Governor. Guided tours of the house, which features period furnishings and paintings, reveal the inner workings of an upper-class household in colonial and revolutionary Annapolis.

To See

Wrabyn Boutique

12 Annapolis St, Annapolis, MD 21401 Visit Site

Women's Clothing Boutique where you'll find a well edited selection of fine women's clothing, shoes, and accessories. The stylists at Wrabyn focus on helping clients explore, discover and curate a personal style that is uniquely theirs.

To See

Inside the hotel

Parlor Room

Dining Room

The Reading Room

Breakfast

The Local Area

Acqua al 2

Adam's on Fourth

Agave

Annapolis Ice Cream Co.

Annapolis Sailing Cruises

Café Normandie

Chart House

Chessie's Wharf

Choptank - Annapolis

City Dock and Ego Alley

Dry 85

Eastport

Forward Brewing

Harold Black

InGrano

Lemongrass

Lewnes' Steakhouse

Main Street

Old Fox Books & Coffeehouse

Osteria 177

O’Leary’s Seafood

Parley Room

Preserve

Quiet Waters Park

Red Red Wine Bar

Ruth's Chris Steak House

Sailor Oyster Bar

Seas the Bay - Private Sailing Charters

The Vineyards at Dodon

Tsunami

U.S. Naval Academy

Vin 909

William Paca House

Wrabyn Boutique

Come and experience Flag House Inn