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.
A kitchen with a granite countertop, stainless steel appliances, a dining area with a table and chairs, a wooden cabinet, and a fireplace.
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.
A staircase with white railings, a wooden floor, and a light blue wall with decorative plates.

Reviews

10 out of 10
Exceptional

Highlights

  • Games
    A rare find - enjoy a variety of games available on-site.
  • Discover nearby landmarks
    Near Maryland State House

Popular amenities

  • Balcony
  • Barbecue
  • Air-conditioning
  • Refrigerator
  • Internet
  • Washing machine

Explore the area

View 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

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom

1 King Bed

Bedroom

1 King Bed

Bedroom

1 Queen Bed

Bedroom

1 Queen Bed

Bedroom

1 Single Bed

Other sleeping area

1 Single Bed

3 bathrooms, 1 half bathroom

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Spaces

Deck or patio
Kitchen
Balcony
Garden

Add dates for prices

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About the area

Annapolis

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.
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Map
Annapolis, MD

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

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.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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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

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

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
Response from VrboOwner on 16 September 2026
Thanks so much for the kind words! It was a pleasure to host you and we hope you return to beautiful Annapolis and stay with us again at Fair Winds!
Verified review

10/10 Excellent

Stayed 2 nights in Nov 2025
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