10/10 Excellent
Kathleen M.
2 Dec 2025
Kathleen M.
Stayed 2 nights in Nov 2025
Entire home
Historic Downtown Luxury • USNA • Waterfront
Holiday home with kitchen, 5-minute walk to U.S. Naval Academy
Photo gallery for Historic Downtown Luxury • USNA • Waterfront
Reviews
10 out of 10
Exceptional
5 bedrooms3+ bathroomsSleeps 10
Popular amenities
Explore the area
Annapolis, MD
- Place, Annapolis City Dock1 min walk
- Place, U.S. Naval Academy2 min walk
- Place, Maryland State House3 min walk
- Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)32 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 Single Bed
Other sleeping area
1 Single 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: 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.
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.
Blending coastal elegance with warm hospitality — we invite you to unwind and enjoy an authentic Annapolis stay.
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.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space
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House Rules
Check in after 4:00 PM
Minimum age to rent: 18
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Check-out instructions
The host requires you to 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 rubbish
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
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
About the area
Annapolis
Historic District, a neighbourhood in Annapolis, is home to this holiday home. The area's natural beauty can be seen at Jonas Green State Park and Sandy Point 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.
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
- Maryland State House - 3 min walk - 0.3 km
- St. John's College - 5 min walk - 0.4 km
Getting around
Restaurants
- The Choptank - 3 min walk
- Annapolis Market House - 2 min walk
- O'Brien's Oyster Bar & Seafood Tavern - 3 min walk
- Starbucks - 3 min walk
- Chick & Ruth's Delly - 5 min walk
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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