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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
Premier Partner

This VRBO partner has demonstrated and is committed to fast response times, the best rates, and a great traveler experience.

Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
December 12, 2017


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


Exceptional! 5/5 -
(42 traveler reviews)

95% Complete
4% Complete
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Charming Historic Annapolis Home - Superior Downtown Location!!!
average rating of 4.952381 based on 42 reviews

Perfect stay!

  • 5 of 5

The House was perfect for our wedding weekend. The townhouse was fully stocked and so convenient. Thank you so much!

  • Submitted: Nov 20, 2017
  • Stayed: November 2017
  • Source: VRBO, from HomeAway
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It was perfect. Close to downtown and clean!

  • 5 of 5

Nice place. Easy commute to everywhere in Annapolis be it by foot or car. Perfect for what we needed!

  • Submitted: Nov 2, 2017
  • Stayed: October 2017
  • Source: HomeAway
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Cozy & Well Appointed in Great Location

  • 5 of 5

We (two adult couples) loved staying here as we attended a wedding at the Naval Academy. It was the perfect location - walkable to the Academy as well as great restaurants & shops and the harbor. Also walkable to conveniences like CVS. It's located on such a pretty cobblestone street. The inside was clean and well appointed, and it felt cozy & peaceful. Two parking passes were provided for surrounding streets, which certainly came in handy. Highly recommend.

  • Submitted: Oct 12, 2017
  • Stayed: September 2017
  • Source: VRBO, from HomeAway
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Perfect place. Perfect location

  • 5 of 5

Beautifully decorated. Could not have been better.

  • Submitted: Sep 10, 2017
  • Stayed: September 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: August 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: July 2017
  • Source: HomeAway
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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


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $150
Damage Deposit $500

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.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.