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8.2 / 10 Guest Rating

Inn on Main Annapolis

165 Main Street, Annapolis, us

Inn on Main Annapolis - main view

About the Property

Historic Bed and Breakfast in Annapolis

Charming Terrace and American Cuisine Restaurant
The Inn on Main Annapolis, a historic bed and breakfast near Annapolis Harbor, offers a delightful terrace for guests to relax and enjoy. Indulge in delicious American cuisine at the on-site restaurant, adding a flavorful touch to your stay.

Cozy Rooms with Modern Amenities
Each unit at the Inn on Main Annapolis features air conditioning, a flat-screen TV, and a private bathroom for your comfort. With added conveniences like a hair dryer and premium bed linen, your stay is sure to be cozy and relaxing.

Ideal Location for Exploring Annapolis
Conveniently situated near popular attractions like Carroll Park and Sports Legends Museum, as well as dining options, this charming bed and breakfast is perfect for travelers looking to explore Annapolis.

Book your stay at the Inn on Main Annapolis for a historic and memorable experience in Annapolis!

Facilities & Amenities

WiFi available
Free WiFi
Parking
Non-smoking rooms
Air conditioning
Restaurant
Heating
Terrace
Pets allowed
Hiking

Important Information

Check-in & Out

Check-in
Check-out11:00 AM

Property Notes

Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply. This property does not accommodate bachelor(ette) or similar parties. A deposit may be required at the property.

Check Room Availability

1 night · 2 adults

No rooms available

We couldn't find any available rooms for these dates and guests. Try adjusting your search criteria.

Guest Reviews

8.2
Excellent327 verified reviews
AI Summary

Guests highly rate the great location and frequently praise the delicious breakfast.

Categories

Cleanliness7.8
Service8.8
Location8.8
Room Quality7.2
Amenities8.3
Value for Money8.2
Food and Beverage8.8
Overall Experience7.8

Select topics to read reviews

C
ChristausUS
Verified booking
solo_traveller
Standard Room
Stayed in Feb 11, 2026

"We are here to please - said the owner at arrival and he did!"

9.0

We were a big party celebrating a big birthday and arriving nearly at the same time. The owner managed to assign the rooms to each of us taking all our requests into consideration. The roooms were very clean, the mattresses extremely comfortable, enough heating to survive the coldest night since years. We had a great breakfast in a separate area which was very nice. The location in a busy shopping and restaurant area close to the harbor is beautiful. Parking either on the street or in the offered parking lot without any problems.

It is a historic house in a historic area. So be aware of staires, rooms with wall view and bath tubs to climb in for a shower. However - it is very unique and charming and convinced us to come back!

Helpful?
G
GrallusUS
Verified booking
extended_group
Standard Room
Stayed in Jan 28, 2026

"Exceptional"

10.0

The staff was very friendly and helpful. The included breakfast was delicious and very convenient.

Helpful?
D
DaneusUS
Verified booking
couple
Standard Room
Stayed in Jan 20, 2026

"Exceptional"

9.0
Helpful?
K
KellyusUS
Verified booking
solo_traveller
Standard Room
Stayed in Jan 20, 2026

"Clean and comfortable rooms, wonderfully accomidating staff."

9.0

This was the perfect location and the staff was very accomidating. A really good value!

Just recognize that you are staying above the downtown area so it is not quiet at night, especially on weekends. If you understand that you're good to go!

Helpful?
P
PATRICKusUS
Verified booking
couple
Standard Room
Stayed in Jan 20, 2026

"Just a unique, romantic, and super memorable stay. We loved it."

9.0

Super convenient location and having the restaurant downstairs with a fabulous menu and B&B feature was top notch. We had no problem not having an elevator, but some people might not be in as good health as we were. The discount deal for parking with the local garage was a nice surprise too. The great customer care at check in by Tony was superior and made the visit extra special. Thanks so much.

We liked it all especially the ambiance and historical connection. Just so unique and romantic all in one place. There is always something that might not please the very picky client, but size of room and no elevator were actually a plus for us because it took us into days of yesteryears.

Helpful?
P
PauldeDE
Verified booking
couple
Standard Room
Stayed in Jan 19, 2026

"Top Preis-Leistung"

9.0

- Lage war top - sehr sauber - gutes FrĂĽhstĂĽck inbegriffen - Netter Empfang - das diner hatte eine riesige Speisekarte

Helpful?
S
SusanusUS
Verified booking
extended_group
Standard Room
Stayed in Jan 19, 2026

"Exceptional"

9.0
Helpful?
S
SarahusUS
Verified booking
couple
Standard Room
Stayed in Jan 19, 2026

"Exceptional"

9.0
Helpful?
S
SarahusUS
Verified booking
family_with_children
Standard Room
Stayed in Jan 19, 2026

"Ideally located for seeing downtown Annapolis with delicious breakfasts included to start your day!"

7.0

Location can’t be beat for Main St. Annapolis and proximity to the Naval Academy. The room adequately supported three adults, a child, and a large dog. Staff was very friendly. Several breakfast options included in stay was more than sufficient for morning fuel ups.

The room is advertised as having a kitchenette. While they had all the components of a kitchenette, the induction cooktop did not work and the sink in the kitchenette was broken and shooting water everywhere so we had to turn off water to the faucet. As to be expected when living above a bar, we could hear the sound of revelers late into the night.

Helpful?
J
JenniferusUS
Verified booking
couple
Standard Room
Stayed in Jan 19, 2026

"It was nice"

7.0

The location was great since it was right downtown and walking distance to everything so you don’t need to use your car. The staff was very nice and the breakfast was good

It was loud at times since it’s an above a restaurant and the windows in the to face a brick wall so it’s dark and small.

Helpful?