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Entire home

Historic Downtown Luxury • USNA • Waterfront

Vacation home in Annapolis, 5-minute walk to U.S. Naval Academy

Photo gallery for Historic Downtown Luxury • USNA • Waterfront

Terrace/patio
Interior
Interior
5 bedrooms, iron/ironing board, free WiFi, bed sheets
Interior
A short walk from U.S. Naval Academy, Historic Downtown Luxury • USNA • Waterfront provides amenities like a garden. Guests can connect to free in-room WiFi.

Entire home

5 bedrooms4 bathrooms

Popular amenities

  • Kitchen
  • Fireplace
  • Washer
  • Dryer
  • Barbecue grill
  • Outdoor Space
The current price is ￥36,085
￥80,960 total
includes taxes & fees
Nov 5 - Nov 6

Add dates for prices

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: 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.

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 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

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

About the neighborhood

Map
MD, Annapolis

What's nearby

  • Annapolis City Dock - 1 min walk - 0.0 km
  • U.S. Naval Academy - 2 min walk - 0.2 km
  • Maryland State House - 3 min walk - 0.3 km
  • Annapolis Maritime Museum - 19 min walk - 1.6 km
  • Navy-Marine Corps Memorial Stadium - 3 min drive - 2.1 km

Getting around

  • Odenton Station - 22 min drive
  • Fort Meade, MD (FME-Tipton) - 33 min drive

Restaurants

  • ‪The Choptank - ‬3 min walk
  • ‪O'Brien's Oyster Bar & Seafood Tavern - ‬3 min walk
  • ‪Starbucks - ‬3 min walk
  • ‪Annapolis Market House - ‬2 min walk
  • ‪McGarvey's Saloon & Oyster Bar - ‬2 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 Nov 4, 2025, prices found for a 1-night stay for 2 adults at Historic Downtown Luxury • USNA • Waterfront on Nov 5, 2025 start from ￥36,085, excluding 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.

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?

Check-out is at 11:00 AM.

Where is Historic Downtown Luxury • USNA • Waterfront located?

Located in Historic District, this vacation 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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