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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 hallway with a radiator, a patterned rug, a white door leading outside, and a beige sofa. - 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 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)
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)
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
The current price is AU$2,717
includes taxes & fees
10 Aug - 11 Aug

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

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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Meeting facility
Historic Inns of Annapolis
Historic District
  • Pet-friendly
  • Free Wi-Fi
  • Restaurant
  • Air-conditioning
9.0 out of 10, Wonderful, 1,907 reviews
The price is AU$198
includes taxes & fees
20 July - 21 July
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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

Historic District, a neighbourhood in Annapolis, is home to this holiday home. Chesapeake Bay Bridge is a notable landmark, and the area's natural beauty can be seen at Chesapeake Bay and Sandy Point State Park. 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 white building with a dome, surrounded by lush greenery and a well-maintained garden with pathways and benches.
    William Paca House
    2 min walk - 0.2 km
  • A grand hall with ornate columns, a large staircase, and flags.
    U.S. Naval Academy
    2 min walk - 0.2 km
  • A waterfront cityscape with a prominent clock tower, a marina with boats, and a mix of historic and modern buildings.
    Ego Alley
    3 min walk - 0.3 km
  • A statue on a pedestal labeled "DEKALB" in front of a brick building with a clock tower.
    Maryland State House
    3 min walk - 0.3 km
  • Annapolis City Dock
    1 min walk - 0.0 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
  • McGarvey's Saloon & Oyster Bar
    2 min walk
  • Chick & Ruth's Delly
    5 min walk
  • Middleton Tavern
    1 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 15 July 2026, prices found for a 1-night stay for 2 adults at Historic Downtown Luxury • USNA • Waterfront on 10 Aug 2026 start from AU$2,717, 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.

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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. 1 out of 1 reviews
Rating 8 - Good. 0 out of 1 reviews
Rating 6 - Okay. 0 out of 1 reviews
Rating 4 - Poor. 0 out of 1 reviews
Rating 2 - Terrible. 0 out of 1 reviews

Reviews

Verified

10/10 Excellent

Kathleen M.

Stayed 2 nights in Nov 2025