10/10 Excellent
Kathleen M.
Dec 2, 2025
Kathleen M.
Stayed 2 nights in Nov 2025
Entire home
Historic Downtown Luxury • USNA • Waterfront
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Photo gallery for Historic Downtown Luxury • USNA • Waterfront
Reviews
1010 out of 10
Exceptional
Entire home
5 bedrooms4 bathrooms
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 neighborhood
Annapolis
With a stay at this vacation home in Annapolis (Historic District), you'll be within a 5-minute walk of U.S. Naval Academy and Annapolis City Dock. .This vacation home is 0.1 mi (0.1 km) from John Smith House and 0.1 mi (0.1 km) from William Paca House.
What's nearby
- Annapolis City Dock - 1 min walk - 0.0 miles
- William Paca House - 2 min walk - 0.1 miles
- U.S. Naval Academy - 2 min walk - 0.1 miles
- Maryland State House - 3 min walk - 0.2 miles
- Hammond-Harwood House - 5 min walk - 0.3 miles
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
- O'Brien's Oyster Bar & Seafood Tavern - 3 min walk
- Buddy's Crabs & Ribs - 3 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.
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.
Make yourself comfortable in this air-conditioned vacation home, which features a fireplace. There's a private balcony. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wireless internet access is available to keep you connected.
Take in the views from a garden and make use of amenities such as barbecue grills.
Guests will find features like internet access and onsite parking.
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
- Spices
- Stovetop
- Toaster
Bedrooms
- 5 bedrooms
- Bedsheets provided
Bathroom
- 3.5 bathrooms
- Hair dryer
- Towels provided
Living spaces
- Fireplace
- Living room
Entertainment
- Books
- Games
- TV
Outdoor areas
- Balcony
- Barbecue grill
- Garden
Laundry
- Washing machine
Comfort
- Air conditioning
- Heating
Pets
- No pets allowed
Suitability/Accessibility
- Smoking not allowed
Services and conveniences
- Iron/ironing board
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)
- Fire extinguisher
General
- Garden
Policies
Check-in
Check-in time starts at 4:00 PM
Minimum check-in age: 18
Check-out
Check-out before 11:00 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
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.
Pets
Pets not 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
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
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
Property is also known as
30220
Historic Downtown Luxury • USNA • Waterfront Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travelers 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. 1 out of 1 reviews
10 - Excellent
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Rating 8 - Good. 0 out of 1 reviews
8 - Good
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Rating 6 - Okay. 0 out of 1 reviews
6 - Okay
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Rating 4 - Poor. 0 out of 1 reviews
4 - Poor
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Rating 2 - Terrible. 0 out of 1 reviews
2 - Terrible
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