Inn of the Month
Diamond Collection
The Wayside Inn Bed & Breakfast
Ellicott City, MD (24 miles from Annapolis)
Hundreds of past guests agree: "This is the best Bed and Breakfast we have ever stayed in!"
Meadow Gardens Bed and Breakfast
Annapolis, MD
With a stay at Meadow Gardens Bed and Breakfast in Annapolis, you'll be within a 15-minute drive ...
Annapolis, MD
Flag House Inn
Annapolis, MD
With a stay at Flag House Inn in Annapolis, you'll be a 3-minute walk from William Paca House and...
Annapolis, MD
Scotlaur Inn Bed & Breakfast
Annapolis, MD
When you stay at Scotlaur Inn Bed & Breakfast in Annapolis, you'll be near the bay, just steps fr...
Laurel Grove Inn on the South River
Annapolis, MD
Located in Annapolis, Laurel Grove Inn on the South River is on a river, within a 15-minute drive...
Ivy Mansion at Dupont Circle
Washington, (27 miles from Annapolis)
With a stay at Ivy Mansion at Dupont Circle, you'll be centrally located in Washington, within a ...
Washington, (27 miles from Annapolis)
Found Places Capitol Hill Bed & Breakfast
Washington, (25 miles from Annapolis)
With a stay at Found Places Capitol Hill Bed & Breakfast, you'll be centrally located in Washingt...
Swann House Historic Dupont Circle Inn
Washington, (27 miles from Annapolis)
With a stay at Swann House Historic Dupont Circle Inn, you'll be centrally located in Washington,...
The Georgetown House
Washington, (28 miles from Annapolis)
Located in Washington (Georgetown), The Georgetown House is within a 10-minute drive of George Wa...
Birdhouse Bed and Breakfast
Washington, (26 miles from Annapolis)
Located in Washington (Northwest), Birdhouse Bed and Breakfast is within a 15-minute walk of Afri...
Washington, (26 miles from Annapolis)
Asante Sana Inn
Washington, (26 miles from Annapolis)
With a stay at Asante Sana Inn in Washington (Columbia Heights), you'll be within a 10-minute dri...
Tabard Inn
Washington, (27 miles from Annapolis)
With a stay at Tabard Inn in Washington (Dupont Circle), you'll be within a 10-minute drive of Wh...
Woodley Park Guest House
Washington, (28 miles from Annapolis)
A stay at Woodley Park Guest House places you in the heart of Washington, a 2-minute drive from E...
Washington, (28 miles from Annapolis)
Malolo Bed and Breakfast
Washington, (22 miles from Annapolis)
With a stay at Malolo Bed and Breakfast in Washington, you'll be within a 15-minute drive of Robe...
American Guest House
Washington, (27 miles from Annapolis)
With a stay at American Guest House, you'll be centrally located in Washington, within a 10-minut...
Embassy Circle Guest House
Washington, (28 miles from Annapolis)
With a stay at Embassy Circle Guest House in Washington (Dupont Circle), you'll be within a 5-min...
The Kalorama Guest House
Washington, (28 miles from Annapolis)
With a stay at The Kalorama Guest House, you'll be centrally located in Washington, a 5-minute dr...
Adam's Inn
Washington, (27 miles from Annapolis)
With a stay at Adam's Inn , you'll be centrally located in Washington, a 4-minute drive from Smit...
Carriage Guest House
Silver Spring, MD (24 miles from Annapolis)
With a stay at Carriage Guest House, you'll be centrally located in Silver Spring, within a 15-mi...
Silver Spring, MD (24 miles from Annapolis)
Eden Park Guest House
Takoma Park, MD (25 miles from Annapolis)
With a stay at Eden Park Guest House in Takoma Park, you'll be within a 15-minute drive of Montgo...
The Wayside Inn Bed & Breakfast
Ellicott City, MD (24 miles from Annapolis)
When you stay at The Wayside Inn Bed & Breakfast in Ellicott City, you'll be near the airport and...
The Columbia Inn at Peralynna Manor
Columbia, MD (25 miles from Annapolis)
Located in Columbia, The Columbia Inn at Peralynna Manor is in a rural location, a 4-minute drive...
Wilson House Bed & Breakfast
Baltimore, MD (24 miles from Annapolis)
Located in Baltimore (Downtown Baltimore), Wilson House Bed & Breakfast is within a 10-minute dri...
Houseboat Scorpius by SleepAfloat
Baltimore, MD (21 miles from Annapolis)
With a stay at this houseboat in Baltimore (Fells Point), you'll be within a 15-minute drive of N...
Rachael's Dowry Bed and Breakfast
Baltimore, MD (22 miles from Annapolis)
Located in Baltimore (Downtown Baltimore), Rachael's Dowry Bed and Breakfast is within a 15-minut...
1840s Carrollton Inn
Baltimore, MD (22 miles from Annapolis)
With a stay at 1840s Carrollton Inn in Baltimore (Downtown Baltimore), you'll be a 3-minute drive...
Bold and beautiful
Baltimore, MD (26 miles from Annapolis)
With a stay at Bold and beautiful in Baltimore, you'll be close to Mount Pleasant Golf Course and...
Baltimore, MD (26 miles from Annapolis)
Inn at 2920
Baltimore, MD (21 miles from Annapolis)
With a stay at Inn at 2920, you'll be centrally located in Baltimore, within a 15-minute drive of...
BlancNoir Bed & Breakfast
Baltimore, MD (22 miles from Annapolis)
Located in Baltimore (Little Italy), BlancNoir Bed & Breakfast is within a 15-minute walk of Nati...
Baltimore, MD (22 miles from Annapolis)
Miles River Guest House
Easton, MD (25 miles from Annapolis)
Located in Easton, Miles River Guest House is on a river, within a 10-minute drive of Historical ...
The Oaks Waterfront Inn
Easton, MD (24 miles from Annapolis)
Located in Easton, The Oaks Waterfront Inn is on the waterfront, within a 10-minute drive of St. ...
Bartlett Pear Inn
Easton, MD (28 miles from Annapolis)
With a stay at Bartlett Pear Inn in Easton, you'll be just steps from Avalon Theatre and Academy ...
Inn at 202 Dover
Easton, MD (28 miles from Annapolis)
With a stay at Inn at 202 Dover in Easton, you'll be within a 5-minute walk of Avalon Theatre and...
Hummingbird Inn
Easton, MD (28 miles from Annapolis)
When you stay at Hummingbird Inn in Easton, you'll be in the historical district, within a 10-min...
John L Stam House
Chestertown, MD (29 miles from Annapolis)
When you stay at John L Stam House in Chestertown, you'll be 11 minutes by foot from Washington C...
Inn at Mitchell House
Chestertown, MD (23 miles from Annapolis)
With a stay at Inn at Mitchell House in Chestertown, you'll be near the beach, and 11 mi (17.7 km...
Great Oak Manor
Chestertown, MD (27 miles from Annapolis)
With a stay at Great Oak Manor in Chestertown, you'll be next to a golf course, and 9.1 mi (14.6 ...
The Oxford Inn
Oxford, MD (27 miles from Annapolis)
Located in Oxford, The Oxford Inn is on a river, within a 15-minute drive of Oxford Museum and Th...
Oxford, MD (27 miles from Annapolis)
Sandaway Suites & Beach
Oxford, MD (27 miles from Annapolis)
With a stay at Sandaway Suites & Beach in Oxford, you'll be 0.3 mi (0.5 km) from Oxford Museum an...
Inn at Huntingfield Creek
Rock Hall, MD (18 miles from Annapolis)
With a stay at Inn at Huntingfield Creek in Rock Hall, you'll be on the waterfront, and 14.5 mi (...
Inn at Haven Harbour
Rock Hall, MD (19 miles from Annapolis)
With a stay at Inn at Haven Harbour in Rock Hall, you'll be on the waterfront, and 13.7 mi (22 km...
George Brooks House B&B
St Michaels, MD (20 miles from Annapolis)
Located in St. Michaels, George Brooks House B&B is within a 5-minute drive of St. Michaels Winer...
Parsonage Inn
St Michaels, MD (20 miles from Annapolis)
Located in St. Michaels, Parsonage Inn is within a 15-minute walk of Chesapeake Bay Maritime Muse...
St Michaels, MD (20 miles from Annapolis)
Lowes Wharf Marina Inn
Sherwood, MD (18 miles from Annapolis)
Located in Sherwood, Lowes Wharf Marina Inn is by the ocean, within a 15-minute drive of Tilghman...
Black Walnut Point Inn
Tilghman, MD (23 miles from Annapolis)
When you stay at Black Walnut Point Inn in Tilghman, you'll be by the sea and 8 minutes by car fr...
Tilghman, MD (23 miles from Annapolis)
Lazyjack Inn on Dogwood Harbor
Tilghman, MD (20 miles from Annapolis)
When you stay at Lazyjack Inn on Dogwood Harbor in Tilghman, you'll be on the waterfront and with...
Peaches and Dreams Bed and Breakfast
Cordova, MD (26 miles from Annapolis)
Located in Cordova, Peaches and Dreams Bed and Breakfast is in a rural location, within a 15-minu...
Cordova, MD (26 miles from Annapolis)
Featured Property
Recent reviews
The Inn on First Bed and Breakfast
$199 - $625
4.8 (243)
"My boyfriend and I had an amazing time in Napa, the Inn on First was our first bed an..."
The Inn on First Bed and Breakfast
$199 - $625
"My boyfriend and I had an amazing time in Napa, the Inn on First was our first bed an..."
Grey Gables Bed & Breakfast Inn
$127 - $300
4.8 (531)
"The inn is impeccably maintained & the attention to detail is amazing. We have be..."
Grey Gables Bed & Breakfast Inn
$127 - $300
"The inn is impeccably maintained & the attention to detail is amazing. We have be..."
The Inn at Forest Oaks
$99 - $159
5.0 (21)
"My husband and I stayed at The Inn at Forest Oaks for one night, and if we had had th..."