Verified
10/10 Excellent
Kathleen M.
2 Dec, 2025
Kathleen M.
Stayed 2 nights in Nov 2025
Entire home
Historic Downtown Luxury • USNA • Waterfront
Photo gallery for Historic Downtown Luxury • USNA • Waterfront
Reviews
1010 out of 10
Exceptional
5 bedrooms3+ bathroomsSleeps 10
Popular amenities
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
- 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)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 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 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.
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.
Add dates for prices
Have a question?
BetaBetaGet instant answers with AI powered search of property information and reviews.
Similar properties
Historic 3 BR home and just forty yards from the US Naval Academy Barry Gate
Historic District
Historic 3 BR home and just forty yards from the US Naval Academy Barry Gate
Historic District
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
10.0 out of 10, Exceptional, (13 reviews)
10/10
Exceptional
(13 reviews)
Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!
Historic District
Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!
Historic District
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (26 reviews)
10/10
Exceptional
(26 reviews)
On-Site Parking, Steps to USNA Gate 3 and Private Patio at Historic Gatehouse
Annapolis
On-Site Parking, Steps to USNA Gate 3 and Private Patio at Historic Gatehouse
Annapolis
- Kitchen
- Free Wi-Fi
- Air-conditioning
- Outdoor space
10.0 out of 10, Exceptional, (15 reviews)
10/10
Exceptional
(15 reviews)
Brilliantly Updated Multi-Level Walkable to Navy Stadium & Close to Historic Downtown Annapolis
Admiral Heights
Brilliantly Updated Multi-Level Walkable to Navy Stadium & Close to Historic Downtown Annapolis
Admiral Heights
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
Parking at Randall House Across from USNA Gate 1
Historic District
Parking at Randall House Across from USNA Gate 1
Historic District
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.8 out of 10, Exceptional, (50 reviews)
9.8/10
Exceptional
(50 reviews)
Beautiful Blend of Restoration and Renovation in this Downtown Home
Historic District
Beautiful Blend of Restoration and Renovation in this Downtown Home
Historic District
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (20 reviews)
10/10
Exceptional
(20 reviews)
Admiral's Abode - Charming Retreat
Historic District
Admiral's Abode - Charming Retreat
Historic District
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
10.0 out of 10, Exceptional, (2 reviews)
10/10
Exceptional
(2 reviews)
All Newly-Designed Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis
Eastport
All Newly-Designed Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis
Eastport
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (5 reviews)
10/10
Exceptional
(5 reviews)
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Historic District
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Historic District
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
9.2 out of 10, Wonderful, (22 reviews)
9.2/10
Wonderful
(22 reviews)
Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks
Historic District
Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks
Historic District
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.8 out of 10, Exceptional, (64 reviews)
9.8/10
Exceptional
(64 reviews)
Updated historic home with parking; near Academy, college & harbor - central AC
Historic District
Updated historic home with parking; near Academy, college & harbor - central AC
Historic District
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
Prestigious Historic Annapolis home, parking for 5 cars, walk to everything!
Historic District
Prestigious Historic Annapolis home, parking for 5 cars, walk to everything!
Historic District
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
10.0 out of 10, Exceptional, (50 reviews)
10/10
Exceptional
(50 reviews)
Historic Annapolis Treasure
Historic District
Historic Annapolis Treasure
Historic District
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
9.6 out of 10, Exceptional, (5 reviews)
9.6/10
Exceptional
(5 reviews)
Panoramic Bay Views, Wraparound Decks, 1-Minute Walk to Beach
Arundel on the Bay
Panoramic Bay Views, Wraparound Decks, 1-Minute Walk to Beach
Arundel on the Bay
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (13 reviews)
10/10
Exceptional
(13 reviews)
Annapolis/Eastport 4 BR w/ Game room - Walk everywhere!
Eastport
Annapolis/Eastport 4 BR w/ Game room - Walk everywhere!
Eastport
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.6 out of 10, Exceptional, (5 reviews)
9.6/10
Exceptional
(5 reviews)
Beautiful waterfront home on The Chesapeake Bay with private dock & beach access
Bay Ridge
Beautiful waterfront home on The Chesapeake Bay with private dock & beach access
Bay Ridge
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
Annapolis
- Pool
- Hot tub
- Kitchen
- Washing machine
9.8 out of 10, Exceptional, (27 reviews)
9.8/10
Exceptional
(27 reviews)
Stunning 4 BR Home - Walking Distance to Stadium
Homewood
Stunning 4 BR Home - Walking Distance to Stadium
Homewood
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (2 reviews)
10/10
Exceptional
(2 reviews)
Cool 1870's home anchored in the Historic District with modern amenities.
Historic District
Cool 1870's home anchored in the Historic District with modern amenities.
Historic District
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (29 reviews)
10/10
Exceptional
(29 reviews)
Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!
Historic District
Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!
Historic District
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
9.8 out of 10, Exceptional, (35 reviews)
9.8/10
Exceptional
(35 reviews)
Downtown Annapolis Duke's House
Historic District
Downtown Annapolis Duke's House
Historic District
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)
Walk Everywhere From New Eastport Cape Cod with High-End finishes and Gourmet Kitchen
Eastport
Walk Everywhere From New Eastport Cape Cod with High-End finishes and Gourmet Kitchen
Eastport
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (3 reviews)
10/10
Exceptional
(3 reviews)
2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free
Historic District
2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free
Historic District
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.8 out of 10, Exceptional, (56 reviews)
9.8/10
Exceptional
(56 reviews)
Charming Annapolis Victorian
Homewood
Charming Annapolis Victorian
Homewood
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (73 reviews)
10/10
Exceptional
(73 reviews)
Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience
Homewood
Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience
Homewood
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (57 reviews)
10/10
Exceptional
(57 reviews)
Historic Chapel Views, Steps to USNA Gate 1 with Private Patio and Off-Site Parking
Historic District
Historic Chapel Views, Steps to USNA Gate 1 with Private Patio and Off-Site Parking
Historic District
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (57 reviews)
10/10
Exceptional
(57 reviews)
Boutique Historic Cedar Home 2 blocks from the Waterfront, USNA and Main Street
Historic District
Boutique Historic Cedar Home 2 blocks from the Waterfront, USNA and Main Street
Historic District
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (4 reviews)
10/10
Exceptional
(4 reviews)
Annapolis Bayfront Home
Bay Ridge
Annapolis Bayfront Home
Bay Ridge
- Pool
- Hot tub
- Kitchen
- Washing machine
10.0 out of 10, Exceptional, (2 reviews)
10/10
Exceptional
(2 reviews)
Historic Eastport! Steps from restaurants, retail, and more.
Eastport
Historic Eastport! Steps from restaurants, retail, and more.
Eastport
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (8 reviews)
10/10
Exceptional
(8 reviews)
Beachfront Home Minutes to Downtown Annapolis Dogs OK
Annapolis
Beachfront Home Minutes to Downtown Annapolis Dogs OK
Annapolis
- Ocean view
- Kitchen
- Washing machine
- Dryer
9.8 out of 10, Exceptional, (40 reviews)
9.8/10
Exceptional
(40 reviews)
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
Property # 4927787vb
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
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 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.
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
- Starbucks - 3 min walk
- The Choptank - 3 min walk
- O'Brien's Oyster Bar & Seafood Tavern - 3 min walk
- Annapolis Market House - 2 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 9 May, 2026, prices found for a 1-night stay for 2 adults at Historic Downtown Luxury • USNA • Waterfront on 10 Aug, 2026 start from S$1,581, 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 Historic Downtown Luxury • USNA • Waterfront?
On-site 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?
Checkout is at 11:00 AM.
Where is Historic Downtown Luxury • USNA • Waterfront located?
Located in Historic District, this holiday 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 labelled.
Learn moreOpens in a new windowRating 10 - Excellent. 1 out of 1 reviews
10 - Excellent
1
Rating 8 - Good. 0 out of 1 reviews
8 - Good
0
Rating 6 - Okay. 0 out of 1 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 1 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 1 reviews
2 - Terrible
0
Reviews
About the host
Your host
Tell us how we can improve our siteShare feedback
