Entire home

Prime Location Modern Comfort Steps to City Dock, Gate 1 w Bar & Parking

Photo gallery for Prime Location Modern Comfort Steps to City Dock, Gate 1 w Bar & Parking

A spacious living room with a large sofa set, a coffee table, and a staircase leading to an upper level.
A bar area with a wooden bar counter, multiple stools, and pendant lighting.
A historic ship docked at a harbor with a prominent white building with a dome in the background.
A two-story house with a red front and dark siding, a front porch, and a flag.
A living room with a sofa, a coffee table, and a dining area with a bar.

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Family fun awaits
    Top-rated for families.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Maryland State House

Popular amenities

  • Deck or patio
  • Free Wi-Fi
  • Air-conditioning
  • Kitchen
  • Refrigerator
  • Washing machine

Explore the area

View map
Annapolis, MD
  • Place, U.S. Naval Academy
    ‪1 min walk‬
  • Place, William Paca House
    ‪2 min walk‬
  • Place, Annapolis City Dock
    ‪5 min walk‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪39 min drive‬

Rooms & beds

3 bedrooms (sleeps 12)

2nd Floor Guestroom

2 Single Beds

Master Bedroom 1

1 Queen Bed

Master Bedroom 2

1 Queen Bed

Top Floor Bedroom

+1
5 Single Beds

2 bathrooms

Main Floor

Toilet · Shower only

Second Floor

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Number of living rooms

Add dates for prices

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About the area

Annapolis

Located in Annapolis, this holiday home is in the city centre. Hammond-Harwood House and John Smith House are local landmarks, and travellers looking to shop may want to visit Annapolis City Dock and Bay Bridge Market Place Shopping Center. French Soldiers Monument and Annapolis Maritime Museum are also worth visiting.
View more Holiday homes in AnnapolisOpens in a new window
Map
Annapolis, MD

What's nearby

  • U.S. Naval Academy - 1 min walk - 0.1 km
  • William Paca House - 2 min walk - 0.2 km
  • Annapolis City Dock - 5 min walk - 0.4 km
  • St. John's College - 5 min walk - 0.4 km
  • Maryland State House - 6 min walk - 0.6 km

Getting around

  • Odenton Station - 22 min drive
  • Fort Meade, MD (FME-Tipton) - 26 min drive

Restaurants

  • ‪The Choptank - ‬6 min walk
  • ‪Starbucks - ‬6 min walk
  • ‪The Red Bean - ‬7 min walk
  • ‪Iron Rooster - ‬4 min walk
  • ‪Middleton Tavern - ‬4 min walk

Frequently asked questions

Is Prime Location Modern Comfort Steps to City Dock, Gate 1 w Bar & Parking pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Prime Location Modern Comfort Steps to City Dock, Gate 1 w Bar & Parking?

As of 4 November 2026, prices found for a 1-night stay for 2 adults at Prime Location Modern Comfort Steps to City Dock, Gate 1 w Bar & Parking on 30 November 2026 start from NZ$4,161, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Prime Location Modern Comfort Steps to City Dock, Gate 1 w Bar & Parking?

On-site parking is available at the property.

What time is check-in at Prime Location Modern Comfort Steps to City Dock, Gate 1 w Bar & Parking?

Check-in begins at 4:00 PM.

What time is check-out at Prime Location Modern Comfort Steps to City Dock, Gate 1 w Bar & Parking?

Checkout is at 11:00 AM.

Where is Prime Location Modern Comfort Steps to City Dock, Gate 1 w Bar & Parking located?

Located in Historic District, this holiday home is within a 5-minute walk of John Smith House and Annapolis City Dock. William Paca House and Tose Family Tennis Center are just steps away.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 57 out of 62 reviews
Rating 8 - Good. 4 out of 62 reviews
Rating 6 - Okay. 0 out of 62 reviews
Rating 4 - Poor. 0 out of 62 reviews
Rating 2 - Terrible. 1 out of 62 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic location and amazing home with so much character!
Stayed 7 nights in Oct 2026
Response from VrboOwner on 13 October 2026
Thanks, Hilary! We hope you’ll come back and stay with us again. You are welcome back any time.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nothing but great things to say about our stay. House was clean, beautiful and well equipped. Communication with the host was excellent. Would have to say that having its own off street parking was the cherry on top. This is unheard of in Annapolis and makes unloading and loading effortless. Would highly recommend.
Stayed 3 nights in Oct 2026
Response from VrboOwner on 22 October 2026
Thanks, Llewellyn! We appreciate you and look forward to hosting you again.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Super comfortable! Cannot beat location. Love the main space for all to relax together. Cozy front porch! Will be back!!
Stayed 2 nights in Sep 2026
Response from VrboOwner on 28 September 2026
Thanks, Dawn! Glad you enjoyed everything and we hope to host you again soon.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property close to gate 1. Just like the pictures.
Stayed 4 nights in Sep 2026
Response from VrboOwner on 21 September 2026
Thanks, Chris. We hope we can host you again soon.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location for fun weekend in Annapolis! Place was very clean and well taken care of with all the amenities you need. Management was very responsive and communicative. Check-in and check-out were very easy and the property guide book was well thought out.
Stayed 3 nights in Aug 2026
Response from VrboOwner on 20 August 2026
Thanks, Reba! We would love to host you again any time.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home! Couldn’t have asked for a better location!
Stayed 3 nights in Jul 2026
Response from VrboOwner on 13 July 2026
Thanks, Mary. We hope to host you again! Sean
From a partner site

10/10 Excellent

Plebe parents weekend stay

The Anchor Inn house was perfect for two plebe families to spend quality time together at the end of plebe summer. The house is literally just outside the Academy wall so walking everywhere was a great bonus. There was plenty of room for everyone and the upper level “dorm” room was great. The hosts were very responsive to any issues we had. Highly recommend!!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location for a Thanksgiving holiday with the whole family!
Stayed 5 nights in Nov 2025
Response from VrboOwner on 12 December 2025
Thanks, Krista! We’re thrilled to hear that Anchor at Annapolis Inn was the perfect location for your Thanksgiving holiday with the whole family. We hope to welcome you back for another wonderful visit in the future!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a great house in a great location with off street parking in the historic district!!! The property was amazing, had plenty of room for all of the guests all within a few minutes walk to main street. It's great to be able to park your car and WALK to everything downtown Annapolis has to offer. We will be booking again!
Stayed 2 nights in Apr 2026
Response from VrboOwner on 1 May 2026
Thanks, Tim! So glad you enjoyed everything. We hope to host you again next time you’re here. Sean, iTrip Annapolis
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was adorable, clean and super comfortable! We loved having onsite parking for 2 cars. The location to downtown Annapolis was amazing.
Stayed 2 nights in Feb 2026
Response from VrboOwner on 23 February 2026
Thanks, Melissa! We hope to host you again soon. Sean, iTrip Annapolis
From a partner site

10/10 Excellent

Truly fantastic

We were here to celebrate the life of someone who was very dear to many people. The house was beyond perfect - warm, welcoming, and infused with great energy. The location could not be beat, either. Our whole family feels as though we have a home away from home now, in Annapolis, and look forward to returning in the future.
Response from VrboOwner on 7 April 2026
Thank you so much for such a lovely review. We do hope you will reach out to iTrip Annapolis in the future and book directly through us. We wish you safe travels, Cathy
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

Great location and easy check-in/out process.
Stayed 2 nights in Nov 2022
Response from VrboOwner on 11 November 2022
Thank you Joshua and we hope to host you again! - Cathy
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome location to walk everywhere! It’s a great set up for watching games and having family fun!
Stayed 3 nights in Nov 2025
Response from VrboOwner on 22 November 2025
Thanks, Paula! We’re thrilled to hear that Anchor at Annapolis Inn provided an awesome location for your stay. It’s fantastic that you enjoyed the setup for watching games and having family fun. We hope to welcome you back for another wonderful visit in the future! Melissa~iTripAnnapolis
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Third time to stay here. We are always pleased.
Stayed 4 nights in Oct 2025
Response from VrboOwner on 14 October 2025
Thanks, Cindy! We’re thrilled to hear that Anchor at Annapolis Inn continues to please you on your third stay. It’s wonderful to know that our property consistently meets your expectations. We look forward to welcoming you back for another great stay next time you’re in town! Melissa~iTrip Annapolis
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

Location was perfect - steps from down town and an easy walk to Eastport.
Stayed 3 nights in Aug 2022
Response from VrboOwner on 24 August 2022
Thank you Kate, we hope you will come back and stay at Anchor at Annapolis Inn again sometime! - Cathy
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay on the bay

Wonderful property in a great location. Very cool bar and fun spot to hang out.
Stayed 2 nights in Jun 2023
Response from VrboOwner on 29 June 2023
Nick, thank you for your kind review of Anchor at Annapolis Inn. We are happy to hear you enjoyed your stay. Please come back and stay with us again. Safe Travels! -Tiffany
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

Great location, plenty of space, fun house
Stayed 2 nights in Dec 2022
Response from VrboOwner on 15 December 2022
Thank you for the kind review of Anchor at Annapolis Inn Casey. We are happy to hear that you enjoyed your stay. We would love the opportunity to host you again. -Tiffany
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Miltary Bowl Trip

Fantastic property, amenities and most if all location, location, location!
Stayed 2 nights in Dec 2024
Response from VrboOwner on 14 January 2025
Hi Jimmy! Thank you for your positive feedback, this is a prime spot! We welcome you back anytime, Melissa~iTripAnnapolis
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding close by

Location was great for our needs House met all our needs and was very clean and very welcoming
Stayed 5 nights in Mar 2025
Response from VrboOwner on 18 March 2025
Thank you Brian & we welcome you back anytime! Melissa~iTripAnnapolis
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication

Great House great property management.

Great Property Management
Stayed 3 nights in Aug 2022
Response from VrboOwner on 8 September 2022
Thank you so much! The Anchor at Annapolis Inn is a great property! And thank you for your compliment of iTrip Vacations Annapolis! Come back and visit us again! Cathy
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Swim meet at the academy

Great location to the academy and shopping
Stayed 2 nights in Apr 2025
Response from VrboOwner on 3 June 2025
Hi Lori! Thank you for allowing us to host your stay & we are thrilled to know you enjoyed your time in the home! We welcome you back anytime, Melissa~iTripAnnapolis
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

Great location with plenty of space. Everything is in walking distance. Nicely decorated and well maintained property. Definitely recommend!
Stayed 3 nights in Nov 2022
Response from VrboOwner on 22 November 2022
Thank you Michele! We hope you will come back and stay at Anchor at Annapolis Inn. - Cathy
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy

Sisters+Spouses Getaway

The proximity to the naval academy, restaurants and shops on Main Street was great. Everything within walking distance.
Stayed 3 nights in Feb 2022
Response from VrboOwner on 15 February 2022
Thank you and we enjoyed hosting you as well!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay!

This was the perfect place for my group to stay while visiting for the Army Navy weekend. We had 6 adults and 2 teens and the location within walking distance of both downtown and the Yard were ideal for everyone to sightsee. The house was clean and well maintained, and the first floor (living room/bar/kitchen) made a great place for the group to gather and cook meals. I’d definitely recommend this him and stay here again.
Stayed 3 nights in Dec 2024
Response from VrboOwner on 14 January 2025
Thank you George & we welcome you back anytime! Melissa~iTripAnnapolis
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Gorgeous, cool historic home two blocks from USNA!

The property managers were very helpful, and the home was perfect for our family to relax, and sit on the porch, or around the cool bar in the family room. Such a beautiful historic home, and well-appointed for all the conveniences. We will stay here again!
Stayed 4 nights in Sep 2021
Response from VrboOwner on 22 October 2021
Kim thank you for staying with us at Anchor at Annapolis Inn. We look forward to hosting you again very soon!
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