See all properties
Entire home

Historic Downtown Luxury • USNA • Waterfront

Vacation home near Annapolis City Dock in Annapolis

Choose dates to view prices

Photo gallery for Historic Downtown Luxury • USNA • Waterfront

An aerial view of a waterfront city with a large stadium, historic buildings, and a marina.
A kitchen with a granite countertop, stainless steel appliances, a dining area with a table and chairs, a wooden cabinet, and a fireplace.
A staircase with white railings, a wooden floor, and a light blue wall with decorative plates.
A room with a white arched bookshelf filled with books, a framed certificate on the wall, and a white door with a window.
A hallway with a radiator, a patterned rug, a white door leading outside, and a beige sofa.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms4 bathrooms

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Annapolis, MD
  • Place, Annapolis City Dock
    ‪1 min walk‬
  • Place, U.S. Naval Academy
    ‪2 min walk‬
  • Place, Maryland State House
    ‪3 min walk‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪39 min drive‬

Room options

You may also like

Ad
A balcony with a table set for two, overlooking a marina with boats.

Annapolis Waterfront Hotel, Autograph Collection

Historic District
  • Pet friendly
  • Free WiFi
  • Restaurant
  • Air conditioning
8.8 out of 10, Excellent, 1,003 reviews
The price is CA $301
CA $344 total
includes taxes & fees
Nov 8 - Nov 9
Annapolis Waterfront Hotel, Autograph Collection

About the area

Annapolis

Heart of Annapolis.A stay at this Historic District vacation home places you steps from Annapolis City Dock and a 5-minute walk from U.S. Naval Academy. John Smith House and 14 Fleet Street are also within half a mile (1 km).
View more Vacation homes in AnnapolisOpens in a new window

What's nearby

  • Annapolis City Dock - 1 min walk - 0.0 km
  • William Paca House - 2 min walk - 0.2 km
  • U.S. Naval Academy - 2 min walk - 0.2 km
  • Maryland State House - 3 min walk - 0.3 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
  • ‪Iron Rooster - ‬2 min walk
  • ‪McGarvey's Saloon & Oyster Bar - ‬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.

Similar properties

A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.
Historic Inns of Annapolis
Historic District
  • Pet friendly
  • Free WiFi
  • Restaurant
  • Air conditioning
4.5 out of 5, Wonderful, 2,060 reviews
The price is CA $115
CA $179 total
includes taxes & fees
Nov 26 - Nov 27
Historic Inns of Annapolis

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
  • Bed sheets 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

Location highlights

  • In a village
  • In the city center

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

  • No pets 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, and a smoke detector in each accommodation.

Property is also known as

30220

Frequently asked questions

How close is Historic Downtown Luxury • USNA • Waterfront to the airport?

This vacation home is 21 mi (33-min drive) away from the Fort Meade, MD (FME-Tipton) airport, the closest popular airport to the property.

How much does it cost to stay at Historic Downtown Luxury • USNA • Waterfront?

As of Oct 26, 2026, prices found for a 1-night stay for 2 adults at Historic Downtown Luxury • USNA • Waterfront on Nov 22, 2026 start from CA $686, 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.

Does Historic Downtown Luxury • USNA • Waterfront have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Historic Downtown Luxury • USNA • Waterfront to the beach?

This vacation home is 3.9 mi (9-min drive) from Carrs Beach and 4.2 mi (17-min drive) from Sparrows Beach. Don't forget your sunscreen!

Does Historic Downtown Luxury • USNA • Waterfront offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Historic Downtown Luxury • USNA • Waterfront?

No, there is no casino at this vacation home.

What time is check-in at Historic Downtown Luxury • USNA • Waterfront?

Check-in begins at 4:00 PM.

Is there free parking at Historic Downtown Luxury • USNA • Waterfront?

Free parking is not available at this vacation home.

Does Historic Downtown Luxury • USNA • Waterfront have a pool?

This vacation home does not have a pool.

Does Historic Downtown Luxury • USNA • Waterfront have a spa?

There are no spa services available at this vacation home.

How close is Historic Downtown Luxury • USNA • Waterfront to downtown Annapolis?

This vacation home is 0.3 mi away from Annapolis.

Historic Downtown Luxury • USNA • Waterfront Reviews

Reviews

10

Exceptional

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

10/10

Cleanliness

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

Explore More Ways to Travel with Travelocity