We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

O'Callaghan Hotel Annapolis

174 West Street, Annapolis, MD 21401
Hotel amenities
Book on
TripAdvisor
Trusted partner. We work with Tingo to make your booking as easy as possible.
Secure payments. We use industry-leading practices to keep your information secure.
1 room 1 guest
Check In Check Out
Show Prices
Compare best prices from top travel sites
and 6 more sites!
Professional photos
O\\
View Map
Add Photo Write a Review

630 Reviews from our TripAdvisor Community

Rate and write a review
Roll over, then click to rate
  Click to rate
Traveler rating
    250
    195
    100
    59
    26
See reviews for
137
259
29
81
Rating summary
  • Location
    4.5 of 5 stars
  • Sleep Quality
    4 of 5 stars
  • Rooms
    4 of 5 stars
  • Service
    4 of 5 stars
  • Value
    4 of 5 stars
  • Cleanliness
    4 of 5 stars
Traveler tips help you choose the right room.   Room tips (94)
Date | Rating
  • Danish first
  • English first
  • German first
  • Italian first
  • Japanese first
  • Any
English first
  • All months
    (630)
  • Mar-May only
    (149)
  • Jun-Aug only
    (241)
  • Sep-Nov only
    (134)
  • Dec-Feb only
    (106)
All months
Dover, Delaware
Level Contributor
149 reviews
35 hotel reviews
common_n_hotel_reviews_1bd8 52 helpful votes
4 of 5 stars Reviewed 2 days ago NEW

I arranged a business meeting here recently. Beautiful hotel in Annapolis and a enjoyable 0.7 mile walk down to City Dock where there's shopping, dining and the water. Check-in process was great with Amanda at the desk. Welcoming smile and a cheerful personality. Take a moment to just gaze around and take in the architecture in the lobby. The restaurant... More 

Was this review helpful? Yes
Level Contributor
12 reviews
common_n_hotel_reviews_1bd8 6 helpful votes
3 of 5 stars Reviewed 2 days ago NEW

My husband and I booked this hotel for my birthday weekend in August. The location was fabulous with just a short walk to the main shops, restaurants, and ego alley waterfront. Upon arrival we parked underneath the valet driveway and paid to have our car parked. The lobby was clean and had a very nice historical charm. There was coffee... More 

Was this review helpful? Yes
Tulsa, Oklahoma
Level Contributor
7 reviews
5 hotel reviews
5 of 5 stars Reviewed 5 days ago NEW

Our family has stayed at O'Callaghans a couple of times and I can't say enough about how wonderful the staff are. The location is great and makes for a nice walk into downtown Annapolis. The rooms are spacious and beautiful. The restaurant is very accommodating and much better than we expected. Over all, we always have a pleasant stay and... More 

Was this review helpful? Yes
Robert R, General Manager at O'Callaghan Hotel Annapolis, responded to this review

Dear sealovingmomof3, The staff and I thank you for the wonderful review. It is always nice to hear from a guest that we have always provided them with wonderful service. We are glad you like that we are in walking distance to all Annapolis has to offer. I will sure to pass on your comments about the restaurant to our... More 

philadelphia
Level Contributor
4 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
3 of 5 stars Reviewed 6 days ago NEW

I chose this hotel based on overall reviews and found that on my stay it did not measure up. True the staff and location are great, the lobby and hallways are clean but once you get into your room it is a different matter. Room had a very musty smell so much so that we requested another room. Although the... More 

Was this review helpful? Yes
Robert R, General Manager at O'Callaghan Hotel Annapolis, responded to this review

Dear librtrav, Thank you for providing us with feedback on your stay. The staff and I are glad we met your needs for service. It is good to know the location met your needs. Thank you for the comments on the cleanliness of our public areas. I would like to apologize for the condition of the rooms we assigned to... More 

Martinsburg, West Virginia
1 review
4 of 5 stars Reviewed 1 week ago

The staff there was great. I really liked our valet, Gary Cooper. Hands down the best at his job and others as well. He went over and beyond for us. I stayed here with my mother and two sisters for the weekend. We love coffee and bring our own when staying out of town. When we noticed our 1 cup... More 

Was this review helpful? Yes
Robert R, General Manager at O'Callaghan Hotel Annapolis, responded to this review

Dear Christina L, Thank you for all the wonderful comments about our staff. Gary is truly an associate that goes above and beyond to make sure our guest are happy. I will definitely pass your comments on to him. I would like to thank you for the comments on the bar. They will help to correct service issues that we... More 

Bel Air, Maryland
Level Contributor
14 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
4 of 5 stars Reviewed 1 week ago

Gary Cooper, who works as a Valet, was hands down, the best employee in the whole hotel. When we got there, we found out that the in room coffee pot ws a single serve type deal that could only be used with an already pre-filled coffee pod. We love our coffee so much that we had actually brought our particular... More 

Was this review helpful? Yes 1
Robert R, General Manager at O'Callaghan Hotel Annapolis, responded to this review

Dear Candise B, Thank you for providing us with feedback from your stay. Gary Cooper is a service star. He is always willing to go the extra mile to please our guest. He also is a great team member and always willing to help other staff members. I will be sure to pass your comments on to him. We appreciate... More 

Middletown, Delaware
Level Contributor
2 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
4 of 5 stars Reviewed 1 week ago

We stayed for two nights and had adjoining rooms. My sister and I and my 1 year old stayed in room #1 and my mom and dad stayed in room #2. The service was excellent, and the hotel was very clean. Each of the staff members were attentive, and our needs were met immediately. The price was fantastic and location... More 

Was this review helpful? Yes
Robert R, General Manager at O'Callaghan Hotel Annapolis, responded to this review

Dear ErikaN4, Thank you for taking the time to tell us about your stay. We appreciate your comments on the staff and their service. We are glad you enjoyed your stay. Regards, Bob Russell More 

United States
Level Contributor
66 reviews
12 hotel reviews
common_n_hotel_reviews_1bd8 40 helpful votes
4 of 5 stars Reviewed 2 weeks ago

It's close enough to walk to the historic district, fish-market and Naval Academy-maybe a 20-minute walk to the Academy. Immaculately clean and comfortable rooms. Good prices (for Annapolis), especially with military discount. Restaurant is very good and the bar is friendly, cozy and away from the crowds. Live music is within a 5-minute walk to the Ram's Head on West... More 

Was this review helpful? Yes 1
Robert R, General Manager at O'Callaghan Hotel Annapolis, responded to this review

Dear Brian P, Thank you for taking the time to review us on Trip Advisor. We appreciate the wonderful comments on our rooms and location. It is great to hear that we are the go to place for you when in Annapolis. Hope to see you soon. Bob Russell More 

New York City, New York
1 review
5 of 5 stars Reviewed 2 weeks ago

The O’Callaghan Hotel in Annapolis, MD is a wonderful place to stay. It is elegant, beautifully styled, the rooms are large and the décor is classical. The staff was very accommodating and ready to serve. I would like to single out two people who really stood out among the rest as leaders. Sean Beasley, the Operations Manager was extremely helpful... More 

Was this review helpful? Yes
Robert R, General Manager at O'Callaghan Hotel Annapolis, responded to this review

Dear Harv A, Thank you for the kind review on Trip Advisor and for particularly pointing out Sean and Henry for their service. Thank you for complimenting the service they provided. We thank you for being our guest and sharing your positive comments. Hope to see you again soon. Bob Russell More 

Owings, Maryland
Level Contributor
4 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed 2 weeks ago

Our weekend celebrating our daughter's wedding at the O'Callaghan was wonderful from start to finish. Every employee we came in contact with or served us really made us feel that they cared about our business. The rooms were very clean and had the feel of Annapolis. If you are planning an Annapolis wedding, I highly recommend your family and friends... More 

Was this review helpful? Yes
Robert R, General Manager at O'Callaghan Hotel Annapolis, responded to this review

Dear Martha H, Greetings from O’Callaghan Hotel and thank you on your encouraging and supportive review! It is great and heart-warming to read of your experience during your stay with us and we are so pleased we were able to make your daughter’s wedding a memorable success. It makes all our hard work and effort worthwhile and sincere thank you... More 

Hotel Review Summarization

What travelers say

  • Valet parking(8)
  • Naval Academy(6)
  • Very good(4)
  • Main street(3)
Questions? Get answers from hotel staff and past guests. Ask a question

72 photos of this hotel

Traveler photos: See what travelers like you saw

Viewed
All traveler photos (52)
Viewed
Room/suite (11)
Viewed
Dining (2)
Viewed
Hotel & grounds (9)
Viewed
Bathroom (11)
Viewed
Pool/beach area (1)
Viewed
View from room (4)
Viewed
Other (14)

Management photos: Courtesy of the property manager

Viewed
All management photos (20)
Viewed
Room/suite (10)
Viewed
Hotel & grounds (4)
Viewed
Business center/function rooms (1)
Viewed
Other (5)
Check In Check Out
Prices are for 1 room, 2 adults
Show Prices
Hotels you might also like...
Travelers also viewed these Annapolis hotels
0.6 mi away
Historic Inns of Annapolis
Historic Inns of Annapolis
#5 of 21 in Annapolis
4.0 of 5 stars 779 reviews
0.1 mi away
Loews Annapolis Hotel
Loews Annapolis Hotel
#3 of 21 in Annapolis
4.0 of 5 stars 835 reviews
0.8 mi away
Annapolis Marriott Waterfront
Show Prices
Show Prices
Show Prices
0.2 mi away
Westin Annapolis
Westin Annapolis
#10 of 21 in Annapolis
4.0 of 5 stars 612 reviews
2.6 mi away
SpringHill Suites Annapolis
2.9 mi away
Courtyard by Marriott Annapolis
Show Prices
Show Prices
Show Prices
Questions? Get answers from hotel staff and past guests. Ask a question

Amenities

Enter dates for best prices
Check In Check In Check Out Check Out
Prices are for 1 room, 2 adults
Price Your Stay