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Historic Downtown Luxury • USNA • Waterfront

Photo gallery for Historic Downtown Luxury • USNA • Waterfront

Interior
Interior
Interior
Living area
Living area

Reviews

10 out of 10
Exceptional
5 bedrooms3+ bathroomsSleeps 10

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washer
  • Air conditioning
  • Barbecue grill
  • Balcony

Explore the area

View in a 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

5 bedrooms (sleeps 10)

Bedroom

1 King Bed

Bedroom

1 King Bed

Bedroom

1 Queen Bed

Bedroom

1 Queen Bed

Bedroom

1 Twin Bed

Other sleeping area

1 Twin Bed

3 bathrooms, 1 half bathroom

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Spaces

Deck or patio
Kitchen
Balcony
Garden

About this property

Historic Downtown Luxury • USNA • Waterfront

Welcome to Fair Winds DTA (Downtown Annapolis): a beautiful, spacious, and sunlit historic home on gorgeous Prince George Street in the heart of downtown Annapolis. Less than a minute walk from both the vibrant waterfront and the Naval Academy’s Gate 1, this home’s location quite simply cannot be beat. It’s perfect for Naval Academy families and Annapolis visitors alike!

Blending coastal elegance with warm hospitality — we invite you to unwind and enjoy an authentic Annapolis stay.

Annapolis License: RENT-002655-2025

This beautifully restored historic home sits right in the heart of downtown Annapolis and waterfront bustle. Featuring five spacious bedrooms and 3.5 baths, it blends timeless charm with modern luxury. Every room is thoughtfully appointed with high-end finishes and authentic architectural details. Enjoy morning coffee or evening cocktails on the oversized patio overlooking the town — the perfect balance of history, elegance, and coastal serenity.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
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
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you complete the following before checking out:
Load and start the dishwasher
Strip any used beds
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights, lock the doors, and return the keys
Trash/Recycling bins are located out the back kitchen door / back patio on the side of the house. (Opposite side from entry).
See Welcome Book for additional check-out guidance.
Failure to complete these may result in a negative review from the host.

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
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

Annapolis

Historic District, a neighborhood in Annapolis, is home to this vacation home. The area's natural beauty can be seen at Chesapeake Bay and Jonas Green State Park, while The Colonial Players and Hammond-Harwood House are cultural highlights. French Soldiers Monument and Helen Avalynne Tawes Garden are also worth visiting.
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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 - 22 min drive
  • Fort Meade, MD (FME-Tipton) - 33 min drive

Restaurants

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

Frequently asked questions

Is Historic Downtown Luxury • USNA • Waterfront pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Historic Downtown Luxury • USNA • Waterfront?

As of May 5, 2026, prices found for a 1-night stay for 2 adults at Historic Downtown Luxury • USNA • Waterfront on Jun 12, 2026 start from $1,357, 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?

Onsite parking is available at the property.

What time is check-in at Historic Downtown Luxury • USNA • Waterfront?

Check-in begins at 4:00 PM.

What time is check-out at Historic Downtown Luxury • USNA • Waterfront?

Check-out is at 11:00 AM.

Where is Historic Downtown Luxury • USNA • Waterfront located?

Located in Historic District, this vacation home is within a 5-minute walk of Annapolis City Dock and U.S. Naval Academy. John Smith House and 14 Fleet Street are just steps away.

Reviews

10

Exceptional

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

Reviews

Verified

10/10 Excellent

Kathleen M.

Stayed 2 nights in Nov 2025

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