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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Charming Historic Annapolis Home - Superior Downtown Location!!!

Bedrooms 2
Half Baths1
Property type townhome
Minimum Stay 2 - 8 nights


About the property

A touch of Manhattan meets Annapolis! Beautiful, completely renovated, historic home in the heart of Annapolis! Walk up one of the most photographed streets in Annapolis known for the “Painted houses of Pinkney”. Step off the old cobblestones and into this sleek, newly furnished home. This historic house is a true beauty and comes with all the convenience of being downtown; with less than a 1 minute walk to the United States Naval Academy’ Gate 1 entrance, Main St, and Ego Alley where you can watch the boats dock and enjoy the sunset. Dine at some of the finest restaurants in Maryland or find a quaint pub with great seafood as they are all within walking distance. This convenient location gives you instant access to sightseeing, shopping, boat cruises, and more. You can even walk or catch a local trolley to the Navy stadium in a matter of minutes to watch the game!

35 Pinkney was originally built in 1900 and the new hardwood floors throughout the house reflect the time along with the original wood beam ceilings. Tradition gives way to modern architecture as you enter the kitchen with its granite topped counters and contemporary styled appliances with every convenience provided to make you feel at home. This charming home sleeps up to 6 with 2 bedrooms with queen size beds on the upper floors, and a choice of the loft or plush queen size pullout sofa sleeper to accommodate two more guests.

The Lofted bedroom is accessed from the Master bedroom and is a fun room that is ideal for the kids to enjoy. The loft holds one more special feature for you. After a long day of taking in all the charm Annapolis has to offer, step outside to the rooftop deck where you can relax to the soft breezes and stars or wake up to the morning sun with a cup of coffee. From this vantage point, the only sounds you hear are the occasional boat horns from the bay or the bells from the church.

Historic downtown Annapolis is the ideal location for attending Naval Academy activities and games (Go NAVY!), St. Johns College events, boat shows, sailing regattas, weddings, reunions and romantic couple getaways. The Maryland State House located 2 blocks away is the oldest state capitol in continuous legislative use, dating to 1772. If your adventurous spirit desires more, Washington DC and Baltimore’s Inner Harbor are only a short drive away.

Available Commissioning Week 2018, 2019

The house is a certified rental property through the City of Annapolis.

More Details

Property Manager
Michelle DePew
Member since: 2014
Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
October 19, 2017


United States Naval Academy
Maryland State House
Boatyard Bar & Grill
Annapolis Towne Center
Chick and Ruth's Delly
Whole Foods Market
Carrol's Creek
Chart House
St. Mary's Roman Catholic Church
Annapolis Maritime Museum
Adam's Ribs
Metropolitan Kitchen & Lounge
"Unique menu and setting with great rooftop seating and occasional live music"
The Federal House Bar & Grille
Navy-Marine Corps Memorial Stadium
Pusser's Caribbean Grille
Castle Bay Irish Pub
Middleton Tavern
"Great downtown setting, with indoor and outdoor seating. There is a hidden secret on the top..."
Miss Shirley's
"Shared plates with modern unique food selection. "
City Dock Coffee
Annapolis Sailing School LLC.
Annapolis Summer Garden Theatre,Inc
"Wonderful outdoor plays, great summer time event"
United States Naval Academy
The Spice & Tea Exchange of Annapolis
William Paca House and Garden
Chuck E. Cheese's
Nearest Airport
24.4 Miles
Baltimore Washington International


Historic District Townhome Accommodation and Amenities

Property Type:
  • townhome
  • Guests provide their own meals
House Rules:
  • Check-in: 3:00 PM
  • /
  • Check-out: 11:00 AM
  • Max. occupancy: 6
  • Max. adults: 6
  • Min. age of primary renter: 25
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
  • No check in past 10 p.m. No loud house parties allowed.
Location Type:
  • Downtown
  • Family
  • Historic
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer ...
  • Hair Dryer
  • Heating ...
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking ...
  • Towels Provided
  • Washing Machine ...
  • Free Wifi
  • Coffee Maker
  • Dishes & Utensils ...
  • Dishwasher ...
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 6 people
  • 1 Bathroom
  • 1 Half Bath
  • Bathroom 1 - toilet , tub , Double Vanity Bathroom with full Shower
    Bathroom 2 - toilet , Main Floor Powder room
  • The Main floor has an updated powder room and the upstairs has a full bathtub and shower with updated double vanity. The Washer and Dryer are also located here.
  • 2 Bedrooms, Sleeps 6
  • Bedroom 1 - 1 queen , Guest Bedroom with a closet and dresser
    Bedroom 2 - 1 queen , Master Bedroom with walk-in closet, vanity and television
    Bedroom 3 - 1 king , Loft with daybed that pulls out into king size bed/ dresser
  • The house sleeps 6. There are two bedrooms on the upper floor. There is a choice of the sleeper sofa or the loft that will accommodate two other guests.
  • Satellite / Cable ...
  • Television ...
  • Balcony ...
  • Deck / Patio ...
  • wheelchair inaccessible
  • churches
  • live theater
  • marina
  • museums
  • restaurants
Leisure Activities:
  • boating
  • gambling casinos
  • outlet shopping
  • paddle boating
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • fitness center
  • groceries
  • hospital
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • hiking
  • jet skiing
  • kayaking
  • sailing
  • swimming
  • tennis
  • water skiing


Wonderful! 4.9/5 -
(39 traveler reviews)

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Charming Historic Annapolis Home - Superior Downtown Location!!!
average rating of 4.948718 based on 39 reviews

Perfect place. Perfect location

  • 5 of 5

Beautifully decorated. Could not have been better.

  • Submitted: Sep 10, 2017
  • Stayed: Sep 2017
  • Source: VRBO, from HomeAway
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Golden, CO U.S.A.

So nice!

  • 5 of 5

What a nice place! Updated and clean, and lots of amenities and well thought out! Nice extras, and little things that made it even better! Would stay here again for sure!

  • Submitted: Aug 13, 2017
  • Stayed: Aug 2017
  • Source: VRBO, from HomeAway
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Frederick, Md

Sweet house in a sweet spot!

  • 5 of 5

Loved this little house! Spectacular location! Cutest street. Super quiet. Charming and comfortable close to the dock! We were able to go out and sightsee for a while and then take a pit stop at the house before we headed out again.

Very clean, more than enough of everything provided. Watch your head if you're tall on the loft! We will definitely be back and totally recommend!

  • Submitted: Jul 10, 2017
  • Stayed: Jul 2017
  • Source: HomeAway
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A Perfect Stay!

  • 5 of 5

My husband and I stayed here with two of our adult children while we attended a wedding. So, I must say that my husband and I have stayed at VRBO/AirBNB/Home Away properties often but never have we stayed at one so convenient and well provisioned. The place is very charming, with a fully equipped kitchen, comfortable living room space and dining area. As a bonus, there is a lovely courtyard in the back with table and chairs where we had breakfast every morning. The two queen bedrooms and loft easily accommodated the four of us. The full bath on the second level was equipped with everyone one might need in a pinch and, in most cases, would have to go out and purchase such as shampoo, detergent, toothbrushes, bandaids, sunscreen etc., etc., etc. I have to say, it is so nice to be able to grab a bandaid for a cut on your finger rather than have to find a store and purchase a box that you really don't need because you have some at home! Everything was clean and organized. Using the TV was easy and intuitive. Also, I enjoyed browsing the Annapolis book that the owner thoughtfully left in the bedroom my husband and I used. It was our best stay ever.

  • Submitted: Jun 25, 2017
  • Stayed: Jun 2017
  • Source: VRBO, from HomeAway
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Wonderful - Couldn't ask for more!

  • 5 of 5

A fabulous rental in downtown Annapolis. The house has absolutely everything you could possibly need. The street is very quiet and restaurants, Naval Academy, shopping, and all of historic Annapolis is right outside your door.

Will absolutely visit again!

  • Submitted: May 20, 2017
  • Stayed: Apr 2017
  • Source: Vacation Rentals, from HomeAway
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Perfect stay in a truly perfect home

  • 5 of 5

If you are planning to visit Annapolis, you won't regret your stay in this home. Location is right in the middle of all the restaurants and attractions, but on a quiet side street so you don't have to deal with too much street noise. Inside of home is as other reviews have described, well thoughout and very comfortable. Our young children really loved the loft area.

Owner(Michelle) is great to deal with and even shipped us the jackets we left in the closet. Great home, book it!!!

  • Submitted: Apr 28, 2017
  • Stayed: Apr 2017
  • Source: HomeAway
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Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Refundable damage deposit $500
Cleaning Fee $150
Tax Rate 13.0%

Rates are subject to change until confirmed
Pets not allowed exceptions will be made for service dogs, Families welcome, Non smoking only
Commissioning week and Boat show have different cancellation policies, please inquire.
No check in past 10 p.m.
No loud parties or groups.

Manager's Cancellation Policy

  • 50% refund if canceled at least 14 days before arrival date.
  • 100% refund if canceled at least 30 days before arrival date.

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