Entire home

Historic Downtown Luxury • USNA • Waterfront

Photo gallery for Historic Downtown Luxury • USNA • Waterfront

An aerial view of a waterfront city with a large stadium, historic buildings, and a marina. - Historic Downtown Luxury • USNA • Waterfront (Annapolis)
A staircase with white railings, a wooden floor, and a light blue wall with decorative plates. - Historic Downtown Luxury • USNA • Waterfront (Annapolis)
A room with a white arched bookshelf filled with books, a framed certificate on the wall, and a white door with a window. - Historic Downtown Luxury • USNA • Waterfront (Annapolis)
A hallway with a radiator, a patterned rug, a white door leading outside, and a beige sofa. - Historic Downtown Luxury • USNA • Waterfront (Annapolis)
A kitchen with a granite countertop, stainless steel appliances, a dining area with a table and chairs, a wooden cabinet, and a fireplace. - Historic Downtown Luxury • USNA • Waterfront (Annapolis)
Close to Annapolis City Dock and U.S. Naval Academy, Historic Downtown Luxury • USNA • Waterfront provides amenities such as a garden. Guests can connect to free in-room WiFi.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms4 bathrooms

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Add dates for prices

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.

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • 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

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a village
  • In the city centre

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

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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 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.

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
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
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

About the area

Located in Annapolis, this holiday home is in the city centre. 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. Visit our Annapolis travel guide
View more Holiday homes in Annapolis
Map
Annapolis, MD

What's nearby

  • A well-manicured garden with a white gazebo, lush green trees, and a clear blue sky.
    William Paca House
    2 min walk - 0.2 km
  • A large building with ornate architecture, a cannon, and a sign reading "Bancroft Hall".
    U.S. Naval Academy
    2 min walk - 0.2 km
  • A grand hall with marble columns, a chandelier, and informational displays about historical rooms.
    Maryland State House
    3 min walk - 0.3 km
  • Annapolis City Dock
    1 min walk - 0.0 km
  • St. John's College
    5 min walk - 0.4 km

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
  • The Red Bean
    7 min walk
  • McGarvey's Saloon & Oyster Bar
    2 min walk
  • Iron Rooster
    2 min walk

Frequently asked questions

Is Historic Downtown Luxury • USNA • Waterfront pet-friendly?

No, pets are not allowed at this property.

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.

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Historic Downtown Luxury • USNA • Waterfront Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers 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.
More informationOpens in a new window
Rating 10 - Excellent. 2 out of 2 reviews
Rating 8 - Good. 0 out of 2 reviews
Rating 6 - Okay. 0 out of 2 reviews
Rating 4 - Poor. 0 out of 2 reviews
Rating 2 - Terrible. 0 out of 2 reviews

10

Cleanliness

10

Location

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We rented this home for a girls weekend so we could stay together while being close to downtown Annapolis, and it exceeded all of our expectations. The location is unbeatable, just a 1-2 minute walk to the waterfront and all the shops, restaurants, and attractions downtown has to offer.The house itself is a beautifully decorated historic home with plenty of space for our group to relax and enjoy our time together. The host was incredibly responsive, friendly, and helpful throughout our stay, making the entire experience seamless.We truly couldn't have asked for a better trip and highly recommend this property to anyone looking for a charming, comfortable place just steps from downtown Annapolis.
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Stayed 2 nights in Nov 2025