Historic Luxury Steps to USNA + Vibrant Waterfront

Annapolis, Maryland
$1275 avg/night Minimum Stay 14 Nights
Bed 5

Bed

Bath 4

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Night 14 nights

Min Stay

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.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    5 Bedrooms Bed Sheets Provided
  • KITCHEN

    Dishwasher Microwave Oven Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • INTERNET

    WiFi Available
  • OUTDOORS

    Barbecue Grill
  • BATHROOMS

    4 Bathrooms Hair Dryer Soap Toilet Paper Towels Provided
  • ENTERTAINMENT

    Smart TV
  • LIVING SPACES

    Fireplace
  • CLIMATE CONTROL

    Air Conditioning Heating
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 07:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Availability

Review Review

  • Shari D.

    Submitted Oct 2, 2025

    Stayed Sep 29, 2025

    House is great, and so close to everything. Host was exceptionally responsive and accommodating, and we lacked for nothing. Can’t say enough good things about it.

  • angela n.

    Submitted Jan 1, 2025

    Stayed Dec 29, 2024

    This house is amazing! The location is everything. The space so inviting. We loved curling up bythe fireplaces. The kitchen was stocked, beds super comfortable and towels soft. This was an amazing home and we are ready to book again! The host have been super friendly and helpful! You can not go wrong booking this home.

  • Submitted Jun 9, 2024

    Stayed Jun 6, 2024

    We stayed here for our niece’s wedding and the property was exactly as described in the listing. It was clean, well appointed and the location was steps from the wedding venue. Thank you for a wonderful stay!!

  • Noah B.

    Submitted May 12, 2024

    Stayed May 10, 2024

    Perfect location in Annapolis and an even better renovated house. Modern kitchen and bathrooms, spacious bedrooms, all while keeping the historic feel. Great property!

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Total

Includes taxes and fees
$1,275+
View details