Title: Historic Downtown Luxury • USNA • Waterfront - Latest Reviews, Deals & Photos 2026 - Expedia.ca

[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&selected=122315355&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false)

Entire home

# Historic Downtown Luxury • USNA • Waterfront

Vacation home with kitchen, 5-minute walk to U.S. Naval Academy

## Photo gallery for Historic Downtown Luxury • USNA • Waterfront

![Interior - Historic Downtown Luxury • USNA • Waterfront (Annapolis)](https://images.trvl-media.com/lodging/123000000/122320000/122315400/122315355/0ff6f8d8.jpg?impolicy=resizecrop&rw=598&ra=fit)

![Terrace/patio - Historic Downtown Luxury • USNA • Waterfront (Annapolis)](https://images.trvl-media.com/lodging/123000000/122320000/122315400/122315355/7f358fef.jpg?impolicy=resizecrop&rw=297&ra=fit)

![Interior - Historic Downtown Luxury • USNA • Waterfront (Annapolis)](https://images.trvl-media.com/lodging/123000000/122320000/122315400/122315355/be665276.jpg?impolicy=resizecrop&rw=297&ra=fit)

![Fridge, microwave, oven, stovetop - Historic Downtown Luxury • USNA • Waterfront (Annapolis)](https://images.trvl-media.com/lodging/123000000/122320000/122315400/122315355/w1200h799x0y0-fc18d27a.jpg?impolicy=resizecrop&rw=297&ra=fit)

![TV, fireplace, books - Historic Downtown Luxury • USNA • Waterfront (Annapolis)](https://images.trvl-media.com/lodging/123000000/122320000/122315400/122315355/b779842d.jpg?impolicy=resizecrop&rw=297&ra=fit)

- Overview
- Location
- Amenities
- Policies

Close to U.S. Naval Academy, Historic Downtown Luxury • USNA • Waterfront provides amenities like a garden. Guests can connect to free in-room WiFi. 

## Reviews

10

Exceptional

### Entire home

5 bedrooms4 bathrooms

## Popular amenities

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

## Add dates for prices

Check-in

Check-out

Travellers

## 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

## Similar properties

![Property grounds](https://images.trvl-media.com/lodging/77000000/76580000/76579700/76579660/18f7d789.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium)

### Charming Downtown 3rd Floor 1 Bedroom Apt

Historic District

- Kitchen
- Washer
- Dryer
- Free WiFi

9.8

Exceptional

20 reviews

CA $235

CA $423 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Hotel-Search?startDate=2026-01-22&endDate=2026-01-23&selected=76579660&PinnedHotelID=76579660&HadPinnedHotel=true&regionId=-1&adults=2)

![Exterior](https://images.trvl-media.com/lodging/88000000/87580000/87576400/87576375/e0fc6398.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium)

### Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Admiral Heights

- Kitchen
- Washer
- Dryer
- Pet friendly

10

Exceptional

48 reviews

CA $492

CA $638 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Hotel-Search?startDate=2026-01-28&endDate=2026-01-29&selected=87576375&PinnedHotelID=87576375&HadPinnedHotel=true&regionId=-1&adults=2)

![TV, offices](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/b24c0f35.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium)

### Wright's Cottage- Pet's Welcome & EV Charging

Annapolis

- Kitchen
- Washer
- Dryer
- Pet friendly

9.2

Wonderful

16 reviews

[](https://www.expedia.ca/Hotel-Search?startDate=2026-02-04&endDate=2026-02-05&selected=105549011&PinnedHotelID=105549011&HadPinnedHotel=true&regionId=-1&adults=2)

![Property grounds](https://images.trvl-media.com/lodging/49000000/48630000/48624300/48624274/acffe7be.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium)

### ★ Midcentury Modern Getaway ★ Prime Location ★

Historic District

- Kitchen
- Washer
- Dryer
- Air conditioning

10

Exceptional

35 reviews

[](https://www.expedia.ca/Hotel-Search?startDate=2026-02-04&endDate=2026-02-05&selected=48624274&PinnedHotelID=48624274&HadPinnedHotel=true&regionId=-1&adults=2)

![Marina](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w1024h447x0y118-8b5ab4ef.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium)

### Secluded Cozy Cottage in Historic Downtown

Historic District

- Kitchen
- Washer
- Dryer
- Pet friendly

9.6

Exceptional

16 reviews

CA $412

CA $758 total

includes taxes & fees

Feb 2 - Feb 3

[](https://www.expedia.ca/Hotel-Search?startDate=2026-02-02&endDate=2026-02-03&selected=92565863&PinnedHotelID=92565863&HadPinnedHotel=true&regionId=-1&adults=2)

![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/76e5fee9.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium)

### Flag House Inn

Historic District

- Free WiFi
- Air conditioning
- Breakfast available
- Parking available

9.4

Exceptional

85 reviews

CA $251

CA $286 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Hotel-Search?startDate=2026-01-26&endDate=2026-01-27&selected=27530544&PinnedHotelID=27530544&HadPinnedHotel=true&regionId=-1&adults=2)

![Bar (on property)](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/6d339134.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium)

### 86 State Circle - Luxury Boutique Hotel

Historic District

- Free WiFi
- Air conditioning
- Parking available
- Laundry

10

Exceptional

3 reviews

CA $404

CA $461 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Hotel-Search?startDate=2026-01-26&endDate=2026-01-27&selected=115964505&PinnedHotelID=115964505&HadPinnedHotel=true&regionId=-1&adults=2)

![Reception](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/f2cc9e28.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium)

### Kent Island Resort

Stevensville

- Pool
- Parking included
- Free WiFi
- Air conditioning

9.2

Wonderful

131 reviews

CA $163

CA $230 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Hotel-Search?startDate=2026-01-28&endDate=2026-01-29&selected=194102&PinnedHotelID=194102&HadPinnedHotel=true&regionId=-1&adults=2)

![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/986ce82e.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium)

### The Inn at Chesapeake Bay Beach Club

Stevensville

- Pool
- Spa
- Parking included
- Free WiFi

9.4

Exceptional

434 reviews

CA $216

CA $275 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Hotel-Search?startDate=2026-02-01&endDate=2026-02-02&selected=12402244&PinnedHotelID=12402244&HadPinnedHotel=true&regionId=-1&adults=2)

![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/76a0c2be.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium)

### Annapolis Waterfront Hotel, Autograph Collection

Historic District

- Pet friendly
- Free WiFi
- Restaurant
- Air conditioning

8.8

Excellent

899 reviews

CA $258

CA $294 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Hotel-Search?startDate=2026-02-15&endDate=2026-02-16&selected=5075&PinnedHotelID=5075&HadPinnedHotel=true&regionId=-1&adults=2)

## 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

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 area

Historic District, a neighborhood in Annapolis, is home to this vacation home. The area's natural beauty can be seen at Jonas Green State Park and Sandy Point 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](https://www.expedia.ca/Annapolis.dx6034082)

[View more Vacation homes in Annapolis](https://www.expedia.ca/Annapolis-Private-Vacation-Homes.d6034082-aaPrivateVacationHomes.Travel-Guide-Accommodation)

![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&center=38.976933,-76.48478&zoom=13&channel=expedia-HotelInformation&maptype=roadmap&scale=1&path=color:0xFFFFF|weight:2|fillcolor:0x005AEB7F|enc:%7Dp%7ClFzlyqM%3FS%3FS%40U%3FS%40Q%40S%3FSBS%40U%40S%40SBSBSBQBSBSBQBSDSDQBSDQDQDQDQFQDSFQFODQHQFQFOFQHOFOHOFOHOHOJMHOHOHMJMHMJMJMJMJKJKJMJKJKLKJILKLKJILILILILGLILGLGLINELGLELGNENELELENCNCLCNENANELANANANANALAN%3FN%3FN%3FN%3FL%3FN%3FN%40N%40N%40N%40L%40N%40NDN%40LDNBNBLBNDLDNDLDNFLDLFLDNHLFLFLHLFLHJHLHLHLJJJLHJJJJLJJLJJJJJLHLJLJLHNJJHNHNHLHNHNHNFNHNFNHPFNFPFPFPFNDPFRDPFPDPDPBPDRDPBRDRBPBRBRBRBP%40R%40RBR%40T%40R%40R%40R%3FP%40R%3FT%3FR%3FR%3FR%3FR%3FRAR%3FRARARARATCRARAPCRCRCPCRCREPCREPERCREPEPGPEPGPEPGPGPGNGRGNINGPILGPININILININILKLINKLKLIJKLKLKJKJMJKLKJMHKJMHMJMFKJMFMHMFMHMFOFMFMFMDOFMDODMDOBMDOBOBMDO%40OBOBM%40O%40O%40O%40O%3FO%3FM%40O%3FO%3FOAO%3FM%3FOAOAOAOAMCOCOAOEMCOCOEMCMEOEOEMGMEMGOGMGMGMIMGMIMGMKMGKKMIMKKIMKKMKKKKKKKMKMKKKMIMKMIOIMIOKOIMIOGOIOGOIQGOGOGSIOEQGQGQEQGQEQEQEQESCSEQESCQCSCSCQCSCSCQASASAUCS%3FSASAS%3FSAS%3FS%3FS&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=kML6veEHc_yqWl-t4RAVJDRox7Y=)

Annapolis, MD

### What's nearby

- ![William Paca House](https://images.trvl-media.com/place/6077398/3bb55f17-d86c-421e-a447-1c41c2d30660.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high)  
William Paca House  
2 min walk \- 0.2 km
- ![U.S. Naval Academy featuring military items, interior views and heritage architecture](https://images.trvl-media.com/place/6077390/365a14c8-731b-4cc4-a5d7-9baf0c5edd8f.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high)  
U.S. Naval Academy  
2 min walk \- 0.2 km
- ![Maryland State House featuring heritage elements and interior views](https://images.trvl-media.com/place/6077394/efd8bda7-e742-4ff4-a0c4-f5be726abcf9.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high)  
Maryland State House  
3 min walk \- 0.3 km
- ![Thurgood Marshall Memorial](https://images.trvl-media.com/place/553248621532662279/8ac54644-28c2-41e0-bf87-529e7072ce96.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high)  
Thurgood Marshall Memorial  
5 min walk \- 0.5 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
- Annapolis Market House  
2 min walk
- O'Brien's Oyster Bar & Seafood Tavern  
3 min walk
- Buddy's Crabs & Ribs  
3 min walk

## Frequently asked questions

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

### How much is parking?

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

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

### Where is Historic Downtown Luxury • USNA • Waterfront located?

## Have a question?

Beta

Get instant answers with AI powered search of property information and reviews.

Ask a question

## 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 information](https://www.expedia.ca/lp/b/content-guidelines)

10 - Excellent

1

8 - Good

0

6 - Okay

0

4 - Poor

0

2 - Terrible

0

## Reviews

### 10/10 Excellent

#### Kathleen M.

Dec 2, 2025

##### Kathleen M.

Stayed 2 nights in Nov 2025