10/10 Excellent
Keith C.
Dec 29, 2025
Liked: Cleanliness
Keith C.
Stayed 3 nights in Dec 2025
Entire home
Naval Academy Gate 1
Vacation home near U.S. Naval Academy in Annapolis
Choose dates to view prices
Photo gallery for Naval Academy Gate 1
Reviews
1010 out of 10
Exceptional
Entire home
2 bedrooms2 bathrooms97 sq m
Popular amenities
- Kitchen
- Washer
- Dryer
- Free WiFi
- Air conditioning
- Outdoor Space
Explore the area
Annapolis, MD
- Annapolis City DockPlace, Annapolis City Dock1 min walk
- U.S. Naval AcademyPlace, U.S. Naval Academy2 min walk
- Maryland State HousePlace, Maryland State House3 min walk
- Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)32 min drive
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About the area
Annapolis
Historic District stay.With a stay at this Historic District vacation home, you'll be steps from 14 Fleet Street and 48 Fleet Street. U.S. Naval Academy and Annapolis City Dock are also within half a mile (1 km).
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
- Maryland State House - 3 min walk - 0.3 km
- Hammond-Harwood House - 5 min walk - 0.4 km
Getting around
- Odenton Station - 23 min drive
- Fort Meade, MD (FME-Tipton) - 34 min drive
Restaurants
- The Choptank - 3 min walk
- Starbucks - 2 min walk
- O'Brien's Oyster Bar & Seafood Tavern - 2 min walk
- Buddy's Crabs & Ribs - 1 min walk
- Annapolis Market House - 2 min walk
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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.
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.
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
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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.
For extra flexibility, consider adding trip insurance for a nominal fee. It can cover you if you need to cancel at the last minute.
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Property amenities
Internet
- Available in the house: Free WiFi
Parking and transportation
- Parking on site
Kitchen
- Coffee/tea maker
- Cookware, dishware, and utensils
- Dishwasher
- Microwave
- Oven
- Refrigerator
- Stovetop
- Toaster
Dining
- Dining table
Bedrooms
- 2 bedrooms
- Bedsheets provided
Bathroom
- 1.5 bathrooms
- Hair dryer
- Towels provided
Living spaces
- Dining table
Entertainment
- Games
- Smart TV
Outdoor areas
- Fenced yard
- Gas grill
- Patio
Laundry
- Laundry facilities
- Washing machine
Work spaces
- Desk
- Desk chair
- Office
Comfort
- Air conditioning
- Heating
Pets
- No pets allowed
Suitability/Accessibility
- Smoking not allowed
Services and conveniences
- Iron/ironing board
Location highlights
- In the city center
Safety features
- Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
- Smoke detector (host has indicated there is a smoke detector on the property)
- First aid kit
- Fire extinguisher
- Deadbolt lock
General
- Unit size: 1,042 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
- No pets allowed
Children and extra beds
- Children are welcome.
Events
No events allowed
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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
- This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.
Property Registration Number RENT-002420-2024
Property is also known as
07f5612d-1e4b-46e3-aa40-d7856350a591
Naval Academy Gate 1 Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 9 out of 9 reviews
10 - Excellent
9
Rating 8 - Good. 0 out of 9 reviews
8 - Good
0
Rating 6 - Okay. 0 out of 9 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 9 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 9 reviews
2 - Terrible
0
10/10
Cleanliness
Reviews
10/10 Excellent
Sydnie M.
Sep 22, 2025
Liked: Cleanliness
Amazing venue. We spent our wedding night there and it was absolutely perfect and intimate. Thank you.
Sydnie M.
Stayed 2 nights in Sep 2025
10/10 Excellent
Cynthia K.
Sep 16, 2025
Liked: Cleanliness
This house was very centrally located. It was a great house and very clean. Couldn’t recommend it enough!
Cynthia K.
Stayed 4 nights in Sep 2025
10/10 Excellent
drew i., Baldwin, Ga
Jun 27, 2025
Liked: Cleanliness
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.
drew i.
Stayed 4 nights in Jun 2025
10/10 Excellent
Leigh H.
Jun 5, 2025
Liked: Cleanliness
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!
Leigh H.
Stayed 5 nights in May 2025
10/10 Excellent
Honoria A.
May 8, 2025
Liked: Cleanliness
Naval Academy Visit
Perfect for a quick weekend visit with our Midshipmen! Easy walking access to the Academy yard, shopping and dining.
Honoria A.
Stayed 2 nights in Apr 2025
10/10 Excellent
Dawn G.
May 4, 2025
Dawn G.
Stayed 2 nights in Apr 2025
10/10 Excellent
Allen H.
Dec 29, 2024
Liked: Cleanliness
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!
Allen H.
Stayed 3 nights in Dec 2024