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On-Site Parking, Steps to USNA Gate 3 and Private Patio at Historic Gatehouse

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Welcome to Gatehouse Annapolis! The thoughtfully-decorated home has many nods to the Naval Academy throughout.
The stately front of the Gatehouse Annapolis home, located across the street from USNA's Gate 3.
The spacious Anne Arundel suite is one of 5 bedrooms in the home, and has a Queen bed, vanity table and ceiling fan.
Welcome to the Gatehouse Annapolis - a rare find in Historic Annapolis.
Gather around the family room with the Flatscreen TV and watch the game. Go Navy!

Reviews

10 out of 10
Exceptional
5 bedrooms4+ bathroomsSleeps 103500 sq ft

Popular amenities

  • Onsite parking available
  • Kitchen
  • Air-conditioning
  • Outdoor barbecue
  • Deck or patio
  • Free Wi-Fi

Explore the area

View in a map
Annapolis, MD
  • Place, U.S. Naval Academy
    ‪1 min walk‬
  • Place, Maryland State House
    ‪6 min walk‬
  • Place, Annapolis City Dock
    ‪9 min walk‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪38 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Academy Room

1 Queen Bed

Anne Arundel Suite

1 Queen Bed

Capital View Suite

1 Queen Bed

College Walk

1 Queen Bed

Compass Rose

1 Double Bed

4 bathrooms, 1 half bathroom

2nd Floor Hall

Bathtub or shower · Toilet

3rd Floor Hall Bath

Toilet · Shower only

Anne Arundel EnSuite

Bathtub or shower · Toilet

Capital View EnSuite

Bathtub or shower · Toilet

Main Level Powder Room

Toilet

Spaces

Deck or patio
Kitchen

About this property

On-Site Parking, Steps to USNA Gate 3 and Private Patio at Historic Gatehouse

Experience the Difference: Professionally Managed by iTrip Annapolis

Historic Charm Across from the Naval Academy

Nestled in the heart of Downtown Annapolis, this spacious 5-bedroom, 4.5-bath historic brick row home is a rare gem. Located directly across from the U.S. Naval Academy's Gate 3, this home combines the charm of historic Annapolis with modern conveniences like on-site parking for 2-3 cars, a private patio, and generous living spaces.



Features You'll Love:

Navy-Inspired Elegance: Thoughtfully designed with nautical decor and a welcoming ambiance

Ample Space to Relax: Enjoy the spacious dining, living, and kitchen areas, perfect for entertaining family and friends

Convenient Parking: 2 Private parking spots behind the home make exploring Downtown Annapolis a breeze

Outdoor Oasis: Unwind on the private patio deck with dining for six, lounge chairs, and a BBQ grill.



Inquire about discounted extended stays!



Sleeping Arrangements (5 BR / 4.5 BA / Sleeps 10):

Anne Arundel Suite (2nd Floor): Queen bed, en-suite full bath

Academy Room (2nd Floor): Queen bed, full hall bath

Capital View Room (3rd Floor): Queen bed, en-suite full bath

College Walk Room (3rd Floor): Queen bed, shared hall bath

Compass Rose Room (3rd Floor): Full bed, shared hall bath



Additional Highlights:

Gourmet kitchen with ample counter space

Dining table seats 10-12 for large gatherings

Big screen Smart TVs and high-speed WiFi for entertainment

Luxury linens, starter toiletries, and boutique-level service

Easy keyless entry for a seamless check-in experience



Prime Location:

U.S. Naval Academy Gate 3: Just across the street!

Annapolis Waterfront: A short walk to shops, restaurants, and sights.

Washington, DC: 30 miles away.

Baltimore: 25 miles away.

House Rules:



Guests must be 25+ to book; no parties, pets, or smoking allowed.

Quiet hours must be observed to respect neighbors.

Check-in: 4:00 PM | Check-out: 11:00 AM.



Things to Note:

No Washer/Dryer: Plan accordingly for extended stays.

Steep Staircases: Guests with mobility challenges may want to consider alternative accommodations.

Owner's Suite: The locked-off private basement suite may be used by the owner on occasion but is not part of the rental space.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed, service animals permitted
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Annapolis

Located in Annapolis, this holiday home is in the city centre. Tose Family Tennis Center and Annapolis Harbor are worth checking out if an activity is on the agenda, while those in the mood for shopping can visit Annapolis City Dock and Bay Bridge Market Place Shopping Center. French Soldiers Monument and Helen Avalynne Tawes Garden are also worth visiting.
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Map
Annapolis, MD

What's nearby

  • U.S. Naval Academy - 1 min walk - 0.1 km
  • St. John's College - 2 min walk - 0.2 km
  • Maryland State House - 6 min walk - 0.6 km
  • William Paca House - 6 min walk - 0.6 km
  • Annapolis City Dock - 9 min walk - 0.8 km

Getting around

  • Odenton Station - 22 min drive
  • Fort Meade, MD (FME-Tipton) - 35 min drive

Restaurants

  • ‪Starbucks - ‬10 min walk
  • ‪Chick & Ruth's Delly - ‬9 min walk
  • ‪Annapolis Market House - ‬9 min walk
  • ‪Federal House - ‬10 min walk
  • ‪Buddy's Crabs & Ribs - ‬11 min walk

Frequently asked questions

Is On-Site Parking, Steps to USNA Gate 3 and Private Patio at Historic Gatehouse pet-friendly?

No, only service animals are welcome at the property.

How much does it cost to stay at On-Site Parking, Steps to USNA Gate 3 and Private Patio at Historic Gatehouse?

As of 4 May, 2026, prices found for a 1-night stay for 2 adults at On-Site Parking, Steps to USNA Gate 3 and Private Patio at Historic Gatehouse on 25 May, 2026 start from S$1,255, 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 On-Site Parking, Steps to USNA Gate 3 and Private Patio at Historic Gatehouse?

On-site parking is available at the property.

What time is check-in at On-Site Parking, Steps to USNA Gate 3 and Private Patio at Historic Gatehouse?

Check-in begins at 4:00 PM.

What time is check-out at On-Site Parking, Steps to USNA Gate 3 and Private Patio at Historic Gatehouse?

Checkout is at 11:00 AM.

Where is On-Site Parking, Steps to USNA Gate 3 and Private Patio at Historic Gatehouse located?

Located in the heart of Annapolis, this holiday home is steps away from U.S. Naval Academy and Hammond-Harwood House. Alumni Hall and St. John's College are also within 5 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 15 out of 15 reviews
Rating 8 - Good. 0 out of 15 reviews
Rating 6 - Okay. 0 out of 15 reviews
Rating 4 - Poor. 0 out of 15 reviews
Rating 2 - Terrible. 0 out of 15 reviews

9.4/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

From a partner site

10/10 Excellent

Ronny R.

Memory Maker

The house was wonderful! Great location and allowed our family to connect and make memories. Would book it again in a heartbeat!
Verified

10/10 Excellent

Noah B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Spacious property right by downtown Annapolis. Great hosts, very responsive!
Stayed 2 nights in Nov 2025
Verified

10/10 Excellent

Dawn K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had 10 of us (5 couples)and it was ample room for all of us. Very clean and stocked well. Kitchen was good size to prepare breakfas/brunch for all of us. Table seated all if us. Walking distance to everything. Great location. We enjoyed our stay
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Natalie V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Thank you for sharing your home with us. We really enjoyed our stay.. The property was very clean and comfortable for our large group. Would definitely rent again in the future.
Stayed 3 nights in Aug 2025
From a partner site

10/10 Excellent

Lorita R.

Great property for commissioning week

The property was perfect for my family during commissioning week. It has a great location and very close to the naval academy as well as downtown Annapolis. In addition, the property has everything that we needed to have an amazing time in Annapolis!
Verified

10/10 Excellent

Stephanie L.

Liked: Check-in, communication, location, listing accuracy
Disliked: Cleanliness
Appreciated the communication and quick resolution to an issue we had. Incredibly enjoyable place and AMPLE space in each bedroom. Great bathrooms. Great location.
Stayed 4 nights in Aug 2025
From a partner site

10/10 Excellent

Deborah

Excellent Stay at Gate House

We had a wonderful stay in this fabulous property. The location near gate 3 of USNA and the quick walk to downtown made it a perfect spot. The house was impeccably clean, comfortable and roomy. Cathy was exceptionally helpful throughout our booking process and stay. You will absolutely enjoy your stay!
Verified

10/10 Excellent

mered o.

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

Merd O

Great place to stay, open ,airy, very comfortable ! Everyone enjoyed their stay, and would highly recommend.
Stayed 5 nights in Oct 2023
Verified

10/10 Excellent

Joyce D.

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

Wedding weekend

A great location and plenty of room for visiting groups to be in and out. Clean and well provisioned. Parking was a great feature as well.
Stayed 4 nights in Sep 2024
Verified

10/10 Excellent

Margot D.

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

Great Stay

We had a great stay at the Gatehouse. Plenty of space to gather, plus quiet and comfortable bedrooms. Kitchen had everything we needed. 2 on-site parking spaces. Easy walks to town and the Naval Academy. Highly recommend.
Stayed 4 nights in Feb 2024
Verified

10/10 Excellent

Kimberly D.

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

Amazing experience and easy rental experience

This house was perfect for a girls weekend in Annapolis! The property was beautiful and spacious with everything we needed. The owner was super quick to respond with answers to questions and communicate with during the weekend. Location was excellent, and we were able to walk to everything we did in the downtown area.
Stayed 2 nights in Jun 2023
Verified

10/10 Excellent

Andy C.

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

Great extended weekend stay!

Our family had all traveled in for a wedding that used multiple venues around Annapolis. This property is perfectly placed for the short walks and drives to every place. The deck was nice to sit and chat the neighborhood was friendly. The amenities were excellent, not too much, exactly what you would expect. Clean well kept and nicely run. Thank you so much for our stay! It felt like a vacation at home away from home in a lovely setting!
Stayed 3 nights in May 2025
From a partner site

10/10 Excellent

Karen H.

Class of 1990 35th Reunion

This is our second stay at this amazing spacious home. The location is perfect. Can walk into town, the Academy and the stadium for the game. The process was simple and communication was great with trip. The home is super spacious with 5 bedrooms and 4 ½ bathrooms. Nicely decorated and super clean. We will look to stay here again and highly recommend. Thanks a bunch and Go Navy!
From a partner site

10/10 Excellent

Steve W.

Great stay in Annapolis

My wife and I just spent a long weekend at the Gatehouse with 3 other couples and had a wonderful time. The house was perfect! Centrally located and within easily walkable distance to the city dock, shops, bars and restaurants. We each had our own rooms, comfortable beds, and our own full bathroom with everything we needed. It was very clean, well stocked in the kitchen, and a huge dining room table for games at night. ITrip Annapolis was amazing to work with. We booked through VRBO but they were responsive, informative, and assessable throughout our stay. I will definitely go through ITrip the next time we need to rent a home!
Verified

10/10 Excellent

Verified traveller

Stayed 2 nights in Apr 2025

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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