Entire home
Historic Luxury Steps to USNA + Vibrant Waterfront
Photo gallery for Historic Luxury Steps to USNA + Vibrant Waterfront





Reviews
1010 out of 10
Exceptional
Popular amenities
- Washing machine
- Air-conditioning
- Barbecue grill
- Internet access
- Fireplace
- Barbecue grill
Rooms & beds
5 bedrooms (sleeps 10)
Bedroom 1
1 King Bed
Bedroom 2
1 Queen Bed
Bedroom 3
1 Queen Bed
Bedroom 4
1 Queen Bed
Bedroom 5
2 Single Beds
4 bathrooms
Bathroom 1
Bathroom 2
Bathroom 3
Bathroom 4
About this property
Historic Luxury Steps to USNA + Vibrant 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 downtown 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!
The Space
Step inside this beautifully restored home and be greeted by the original fireplace, updated to gas power to provide instant ambiance for the well appointed living and dining rooms. The living room has comfortable seating and a large flat-screen TV, while the adjacent dining room seats 8 to 10 comfortably. The fully equipped kitchen has stainless steel appliances, granite countertops, a gas oven range, fully stocked pantry and every appliance you could want to whip up a memorable meal for your guests. The kitchen even includes its own gas fireplace to add ambience to your meal prep!
Upstairs on the second floor you’ll find three bedrooms, including one featuring a full view of beautiful Prince George Street below as well as a large flat-screen TV. The second floor also features a laundry room with a back staircase leading to the kitchen for late-night snacking. This floor features two spa-inspired full baths, one with a luxurious bathtub to relieve stress any time of day. Look out on the state Capitol building as you head up to the third floor for two more bedrooms, one with beautiful views of Prince George Street, as well as another luxurious full bath.
Fair Winds also features outdoor living at its finest. The front porch allows for cozy seating and people-watching along Prince George Street over a glass of wine. Meanwhile, a beautiful brick courtyard in the rear features cafe lights, an electric retractable awning and outside dining. A gas grill is available to create your own outdoor feast to be enjoyed surrounded by centuries-old brick in this oasis of privacy in the very heart of downtown Annapolis.
If your priority is “location, location, location,” Fair Winds has that and more. Annapolis’s restaurants and shops are mere steps away, as are its wonderful historic sites. You won’t believe how close you are to everything – and by the time your stay at this beautiful property is over, you’ll feel like a local.
The Space
Step inside this beautifully restored home and be greeted by the original fireplace, updated to gas power to provide instant ambiance for the well appointed living and dining rooms. The living room has comfortable seating and a large flat-screen TV, while the adjacent dining room seats 8 to 10 comfortably. The fully equipped kitchen has stainless steel appliances, granite countertops, a gas oven range, fully stocked pantry and every appliance you could want to whip up a memorable meal for your guests. The kitchen even includes its own gas fireplace to add ambience to your meal prep!
Upstairs on the second floor you’ll find three bedrooms, including one featuring a full view of beautiful Prince George Street below as well as a large flat-screen TV. The second floor also features a laundry room with a back staircase leading to the kitchen for late-night snacking. This floor features two spa-inspired full baths, one with a luxurious bathtub to relieve stress any time of day. Look out on the state Capitol building as you head up to the third floor for two more bedrooms, one with beautiful views of Prince George Street, as well as another luxurious full bath.
Fair Winds also features outdoor living at its finest. The front porch allows for cozy seating and people-watching along Prince George Street over a glass of wine. Meanwhile, a beautiful brick courtyard in the rear features cafe lights, an electric retractable awning and outside dining. A gas grill is available to create your own outdoor feast to be enjoyed surrounded by centuries-old brick in this oasis of privacy in the very heart of downtown Annapolis.
If your priority is “location, location, location,” Fair Winds has that and more. Annapolis’s restaurants and shops are mere steps away, as are its wonderful historic sites. You won’t believe how close you are to everything – and by the time your stay at this beautiful property is over, you’ll feel like a local.
Add dates for prices
Have a question?
Get instant answers with AI powered search of property information and reviews.
Similar properties

Spacious Annapolis Abode: 507 Schley Rd Vacation Rental, Minutes from Downtown!
Admiral Heights
Spacious Annapolis Abode: 507 Schley Rd Vacation Rental, Minutes from Downtown!
Admiral Heights
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
9.6 out of 10, Exceptional, (10 reviews)
9.6/10
Exceptional
(10 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)

96 Five Star Reviews located in the City of Annapolis in a quiet neighborhood!
Annapolis
96 Five Star Reviews located in the City of Annapolis in a quiet neighborhood!
Annapolis
- Hot tub
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (99 reviews)
10/10
Exceptional
(99 reviews)

Historic Downtown Luxury • USNA • Waterfront
Historic District
Historic Downtown Luxury • USNA • Waterfront
Historic District
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)

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)

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)

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)

Two Historic Rowhomes in Downtown Annapolis
Historic District
Two Historic Rowhomes in Downtown Annapolis
Historic District
- Kitchen
- Washing machine
- Dryer
- Pet-friendly

Gather, Relax & Explore — Townhome 1 Block from State Capitol Building with Backyard & Parking
Historic District
Gather, Relax & Explore — Townhome 1 Block from State Capitol Building with Backyard & Parking
Historic District
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (37 reviews)
10/10
Exceptional
(37 reviews)

Historic Renovated Home in the Heart of Downtown
Historic District
Historic Renovated Home in the Heart of Downtown
Historic District
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
10.0 out of 10, Exceptional, (115 reviews)
10/10
Exceptional
(115 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, (36 reviews)
9.8/10
Exceptional
(36 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
9.0 out of 10, Wonderful, (24 reviews)
9.0/10
Wonderful
(24 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)

Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
Annapolis
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
Annapolis
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (56 reviews)
10/10
Exceptional
(56 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)

Walkable to Main Street at Seashell in the City with 2 parking spots
Historic District
Walkable to Main Street at Seashell in the City with 2 parking spots
Historic District
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.8 out of 10, Exceptional, (56 reviews)
9.8/10
Exceptional
(56 reviews)

New Luxury Townhome Near Downtown Annapolis with Multiple EnSuite Bedrooms and Parking
Annapolis
New Luxury Townhome Near Downtown Annapolis with Multiple EnSuite Bedrooms and Parking
Annapolis
- Kitchen
- Washing machine
- Dryer
- Pet-friendly

Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W/D
Bay Ridge
Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W/D
Bay Ridge
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi

Spacious Historic Home with Private Parking in the Heart of Downtown Annapolis
Historic District
Spacious Historic Home with Private Parking in the Heart of Downtown Annapolis
Historic District
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (5 reviews)
10/10
Exceptional
(5 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)

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)

Beautiful Historic Annapolis home just a few minutes walk from Main Street
Historic District
Beautiful Historic Annapolis home just a few minutes walk from Main Street
Historic District
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
10.0 out of 10, Exceptional, (14 reviews)
10/10
Exceptional
(14 reviews)

Secluded Cozy Cottage in Historic Downtown
Historic District
Secluded Cozy Cottage in Historic Downtown
Historic District
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
9.6 out of 10, Exceptional, (20 reviews)
9.6/10
Exceptional
(20 reviews)

Heart of Historic District!
Historic District
Heart of Historic District!
Historic District
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
9.8 out of 10, Exceptional, (173 reviews)
9.8/10
Exceptional
(173 reviews)

Historic Downtown Annapolis Gem Steps to USNA and Main St with Private Patio and Parking
Historic District
Historic Downtown Annapolis Gem Steps to USNA and Main St with Private Patio and Parking
Historic District
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (26 reviews)
10/10
Exceptional
(26 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, (41 reviews)
9.8/10
Exceptional
(41 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, (65 reviews)
9.8/10
Exceptional
(65 reviews)

Steps to Chesapeake Bay! 'Callaway Drive Retreat'
Shady Side
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
Shady Side
- Kitchen
- Washing machine
- Outdoor space
- Microwave
9.2 out of 10, Wonderful, (7 reviews)
9.2/10
Wonderful
(7 reviews)

Sailor's Retreat! Perfect home for the getaway weekend. Best location!
West Annapolis
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
West Annapolis
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (30 reviews)
10/10
Exceptional
(30 reviews)
About the area
Annapolis
Historic District, a neighbourhood in Annapolis, is home to this holiday home. John Smith House and William Paca House are local landmarks, and travellers looking to shop may want to visit Annapolis City Dock and Bay Bridge Market Place Shopping Center. Looking to enjoy an event or a game while in town? See what's happening at Tose Family Tennis Center or Alumni Hall.
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) - 29 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
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. 5 out of 5 reviews
10 - Excellent
5
Rating 8 - Good. 0 out of 5 reviews
8 - Good
0
Rating 6 - Okay. 0 out of 5 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 5 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 5 reviews
2 - Terrible
0
10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Tell us how we can improve our siteShare feedback
