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From118US$ /night
Check-in
26Oct2025Select date
Check-out
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Rooms and Guests2 Guests, 1 Room
Key details

Hotel Overview

165 Main Street, Annapolis, Maryland, United States, 21401

Inn On Main Annapolis - Bed & Breakfast in historic district near Maryland State House

Located in the heart of Annapolis's historic district, this family-owned bed and breakfast has operated since 1964 alongside Chick & Ruth's Delly, making them the oldest family-owned businesses of their type in the area. The property offers free WiFi throughout, air conditioning, a terrace, and an on-site restaurant. Guests have access to a business center, express check-out, and complimentary newspapers in the lobby. The hotel is a short walk from the Maryland State House of Delegates, US Naval Academy, City Dock, and St. John's College. Baltimore-Washington International Airport is 34 km away.

Additional perks of the hotel

Complimentary à la carte breakfast served at Chick & Ruth's Delly

Terrace with garden furniture and garden views

Express check-out service

Complimentary newspapers in lobby

Business center access

Accommodation Options

The property offers double and twin rooms with private bathrooms. All rooms include air conditioning, free WiFi, flat-screen TVs, telephones, and carpeted flooring. Some rooms feature DVD players. Bathrooms are equipped with showers, bathtubs (in some rooms), hairdryers, and free toiletries.

Other conveniences

AM/FM alarm clocks in all rooms

Wardrobes for storage

Heating system

Private bathrooms with showers

Hairdryers provided

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Choose Your Room

Our listed hotels offer a variety of room types—double rooms, family suites, or deluxe options—all with features like breakfast, flexible cancellation policies, and exclusive deals.
Twin Room Extra Bed
2 persons
11 m² 
2 Single beds
Shower
Air conditioning
King Room
2 persons
17 m² 
1 King-size bed
Shower
Bathtub
Queen Room
2 persons
14 m² 
1 King-size bed
Shower
Heating
Double Room
2 persons
11 m² 
1 Double bed
Shower
Heating
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Transportation Tips

Transportation Options

City Centre
Annapolis300 m
Airports
Baltimore (BWI) 40.4 km
Ronald Reagan Washington National (DCA) 59.5 km
Train
Union Station Marc Washington 45.6 km
Bus
Bus stop300 m

Amenities

Thoughtful hotel amenities for a comfortable stay

General

  • No smoking on site
  • Free Wi-Fi
  • Parking
  • Pets allowed
  • Luggage storage
  • Coffee shop

Sports & Fitness

  • Wind surfing
  • Canoeing
  • Hiking
  • Cycling
  • Fishing

Services

  • Tours/Ticket assistance
  • Welcome drink
  • Happy hour

Dining

  • Restaurant
  • Dinner
  • Packed lunches

Children

  • Children's menu

Spa & Leisure

  • Live entertainment

Room features

  • Air conditioning
  • Heating
  • Terrace
  • Garden furniture

Bathroom

  • Free toiletries

Media

  • Flat-screen TV
  • AM/FM alarm clock

Room decor

  • Carpeted floor
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Hotel Location

165 Main Street, Annapolis, Maryland, United States, 21401
Map view
165 Main Street, Annapolis, Maryland, United States, 21401
Nearby
University
United States Naval Academy Museum
450 m
Public Building
Maryland State House
450 m
19 Maryland Ave
Hammond-Harwood House
450 m
199 Duke of Gloucester St
St. Anne's Episcopal Church
450 m
Museum
William Paca Garden
450 m
107 Duke of Gloucester St
Charles Carroll House
450 m
Church
Banneker-Douglass Museum
450 m
22 Maryland Ave
Chase Lloyd House
450 m
Main Street
Annapolis Historic District
450 m
Museum
Big Brice House
450 m
Annapolis
The Kunta Kinte Alex Haley Memorial
450 m
Prince George St.
Little Brice House
450 m
118 Maryland Ave
US Naval Academy Museum
450 m
Annapolis
Thurgood Marshall Memorial
110 m
40 West St
Mission Escape Rooms
450 m
Museum
Historic Annapolis Museum and Store
200 m
Gallery
Maryland Federation of Art
130 m
Church
Saint Mary Catholic Church
350 m
43 Pinkney St
Hogshead
190 m
60 College Ave
St. John's College
360 m
Gallery
ARTFX Gallery of Fine Crafts and Arts
480 m
1 City Dock
Susan Campbell Park
450 m
Main Street
450 m
Restaurants
Annapolis Ice Cream Company
100 m
196 Main St
Potato Valley Cafe
140 m
47 State Cir Ste 100
The Red Bean
170 m
220 Main St
City Dock Coffee
260 m
18 Market Space
City Dock Cafe
260 m
18 Market Space
Storm Brothers Ice Cream Factory
340 m
130 Dock St
Sammys Downtown Deli
310 m
47 Randall St
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Check-in
26Oct2025Select date
Check-out
27Oct2025Select date
Rooms and Guests2 Guests, 1 Room