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Naval Academy Gate 1

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2-bedroom, 1.5 bath on historic Fleet Street - just 1/2 block to the action in downtown Annapolis
Cozy family room with a queen sofa bed and room-darkening curtains
2-bedroom, 1.5 bath on historic Fleet Street - just 1/2 block to the action in downtown Annapolis
2-bedroom, 1.5 bath on historic Fleet Street - just 1/2 block to the action in downtown Annapolis
Primary bedroom with king bed and cathedral ceiling

Reviews

10 out of 10
Exceptional
2 bedrooms1+ bathroomSleeps 6

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Explore the area

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

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

2 Single Beds

Living room 1

1 Double Sofa Bed

1 bathroom, 1 half bathroom

Bathroom 1

Bathroom 2

Spaces

Deck or patio
Kitchen
Office
Dining area

About this property

Naval Academy Gate 1

This 2-bed, 1.5-bath townhome mixes modern renovations with 1900 classic charm. It's been lovingly decorated to accommodate 6 guests. You'll love the proximity to downtown Annapolis - simply walk one-half block to Main Street circle and Annapolis City Dock. You'll truly be in the middle of everything in this beautiful historic home!

Why guests love staying at 20 Fleet Street:

☼ Historic row home right in the heart of downtown Annapolis with tons of natural light and upgraded features, ideal for families, romantic getaways, or a group of friends visiting historic Annapolis, USNA, and other tourist sites
☼ Centrally located in downtown Annapolis, on historic Fleet Street, just 1/2 block from the action
☼ Two bedrooms: Primary: king bed; Guest: 2 twin beds
☼ The full bathroom is on the second level with both bedrooms and has a tub-shower combo; there is a half-bath on the main living area
☼ Kitchen with all major appliances, a drip coffee maker, kitchen supplies and tools and more
☼ Comfortable living room for watching movies and playing games, with a sliding glass door out to a private outdoor space
☼ Two outdoor spaces - one at the ground level is fully fenced with outdoor dining and a gas grill; the other is a fenced rooftop with outdoor dining
☼ Smart TV in the living room
☼ Fresh linens, towels, toiletries & essentials provided
☼ Professionally cleaned before each visit

​Look no further than this historic rowhome in downtown Annapolis!

Please note that there is no parking on Fleet Street. Guests are encouraged to park in nearby public parking garages.

We’ll follow up with a short online registration once you book. It’s fast, simple, and helps us prepare for your visit. Non-Airbnb guests will be asked to pay a small damage waiver OR refundable deposit.

For extra flexibility, consider adding trip insurance for a nominal fee. It can cover you if you need to cancel at the last minute.

20 Fleet Street is managed by a small, female-owned business. We're committed to making sure all of our guests feel welcome and have the best trip ever. Book your trip with confidence that not only will this property be amazing, but the service and attention you get will be, too.

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House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 10:00 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

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Smoking

Smoking is not permitted

Important information

You need to know

Property Registration Number RENT-002420-2024
Property # 4207439vb
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
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Annapolis

Located in Annapolis, this holiday home is in the city centre. The Colonial Players and Maryland Federation of Art are cultural highlights, and some of the area's attractions include French Soldiers Monument and Annapolis Maritime Museum. Helen Avalynne Tawes Garden and Maryland Hall for Creative Arts are also worth visiting.
View more Holiday homes in AnnapolisOpens in a new window
Map
Annapolis, MD

What's nearby

  • Annapolis City Dock - 1 min walk - 0.0 km
  • William Paca House - 2 min walk - 0.2 km
  • U.S. Naval Academy - 2 min walk - 0.2 km
  • Ego Alley - 3 min walk - 0.3 km
  • Maryland State House - 3 min walk - 0.3 km

Getting around

  • Odenton Station - 23 min drive
  • Fort Meade, MD (FME-Tipton) - 34 min drive

Restaurants

  • ‪Starbucks - ‬2 min walk
  • ‪The Choptank - ‬3 min walk
  • ‪The Red Bean - ‬5 min walk
  • ‪O'Brien's Oyster Bar & Seafood Tavern - ‬2 min walk
  • ‪Annapolis Market House - ‬2 min walk

Frequently asked questions

Is Naval Academy Gate 1 pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Naval Academy Gate 1?

As of 19 May 2026, prices found for a 1-night stay for 2 adults at Naval Academy Gate 1 on 21 August 2026 start from NZ$446, 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 Naval Academy Gate 1?

On-site parking is available at the property.

What time is check-in at Naval Academy Gate 1?

Check-in begins at 4:00 PM.

What time is check-out at Naval Academy Gate 1?

Checkout is at 10:00 AM.

Where is Naval Academy Gate 1 located?

Located in Historic District, this holiday home is within a 10-minute walk of 14 Fleet Street and U.S. Naval Academy. 48 Fleet Street and Annapolis City Dock are just steps away.

Reviews

10

Exceptional

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

10/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Keith C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Best feature is locationWorst feature is the living room feels crowded at 4 peopleOutdoor spaces would be nice in good weather.
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Cynthia K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This house was very centrally located. It was a great house and very clean. Couldn’t recommend it enough!
Stayed 4 nights in Sep 2025
Verified

10/10 Excellent

Sydnie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing venue. We spent our wedding night there and it was absolutely perfect and intimate. Thank you.
Stayed 2 nights in Sep 2025
Verified

10/10 Excellent

Honoria A.

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

Naval Academy Visit

Perfect for a quick weekend visit with our Midshipmen! Easy walking access to the Academy yard, shopping and dining.
Stayed 2 nights in Apr 2025
Response from VrboOwner on 19 June 2025
Thank you for your wonderful review! We’re so glad the location worked perfectly for your visit. We’d love to welcome you back anytime!
Verified

10/10 Excellent

Leigh H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our family enjoyed our stay so much! We were visiting for our Niece's graduation from the Naval Academy and it was absolutely perfect. We could walk to all the events and locations that our other family members were staying at. The set-up at this property is perfect and decor... inviting! The communication with the host was fantastic as well. Should we visit again, we'd definitely stay here!
Stayed 5 nights in May 2025
From a partner site

10/10 Excellent

Genevieve P.

Perfection

Had the privilege of spending time in this beautiful Annapolis house. It has every amenity you could ask for, charm, comfort and unbeatable location with access to downtown. Can’t wait to stay again!
Verified

10/10 Excellent

drew i.

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

Fantastic, will be go to spot everytime

Absolutely fantastic, just as advertised, clean, bed is comfy and twins are there if you need them. Location couldn't be better for Annapolis, you can easily take any left over crab cakes back to the house before heading out to the next location. 2 min walk to middle of down town Annapolis, and 5 min walk max to Gate 1 of the Naval Academy. owners were very responsive over text the questions we had. only down side is no parking, (but that is the deal anywhere in Annapolis). Go park at the Gott street deck and walk back or grab an Uber.
Stayed 4 nights in Jun 2025
Verified

10/10 Excellent

Allen H.

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

Military Bowl Football Game

Wonderful visit to Annapolis and great football game! This property is easily in walking distance of the Naval Academy, the Capital Building, and all the Main Street restuarants and shops. Great location!The rental was perfect, 2 bedrooms. One full bath and a second half bath. Worked great for our 4 adults. Large living area with a nice couch. Kitchen was well equipped; range, microwave, large fridge. Everything required if you planned to do any cooking, but I’d suggest the very short walk to the excellent local restaurants.Spiral staircase that leads upstairs to both bedrooms. My wife and I are 70 and we had no problem using it.Great response from the host, Mike. Our heat went out the second day. I messaged and he called almost immediately. He had a technician on site while we were out for dinner. Problem solved before we even had a chance to get cold! Great service!Overall I would highly recommend this property when visiting Annapolis!
Stayed 3 nights in Dec 2024
Verified

10/10 Excellent

brenna j.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Apr 2026
Verified

10/10 Excellent

Dawn G.

Stayed 2 nights in Apr 2025
Response from VrboOwner on 8 May 2025
Thank you for the 5-star review! It was a pleasure hosting you, and we'd love to welcome you back anytime!

About the host

Hosted by The House Kee, LLC

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Languages:

English

Premier Host

They consistently provide great experiences for their guests

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