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

Walk/Boat Show, Downtown, Yacht Clubs, Capital, Naval Academy

Bedrooms 2
Half Baths1
Space 1,200 sq. ft.
Property type townhome
Minimum Stay 2 - 7 nights


About the property

Townhome, 2 Bedrooms, 1.5 Baths, (Sleeps 6)

The Property is a newly renovated 2 bedroom 1.5 bath town home located in a 10-unit historic 1880s building in the Eastport (Maritime Republic of Eastport “MRE”) section of Annapolis. Exposed factory brick, gas fireplace, oak floors, high ceilings, plantation shutters, granite-countered contemporary kitchen and spectacularly landscaped private terrace with grill and dining furniture. The home is exceedingly clean, efficient and well equipped with modern conveniences such as central air-conditioning, WiFi and automated garden irrigation & lighting. Unrestricted street parking and convenient keyless electronic front door lock.

Located on a lane that ends steps away at a waterfront park on the Chesapeake, offering unobstructed view of the Naval Academy. Walk, water taxi, bike or kayak to downtown Annapolis and Eastport restaurants, the Naval Academy, shops, nightlife, boat show and the Annapolis Yacht Club. One block from APS, Eastport Yacht Club, Severn Sailing Association and numerous marinas, yacht brokers and marine services.

First floor is a large open space with a dining area, fully equipped kitchen and breakfast bar, powder room and living room furnished with a tasteful mix of Asian antiques & rugs and classic European furniture & art. Bright and airy wall-wall sliders open from the living room to the cobble-stone terrace. 40' HD internet 'smart' TV, Bose stereo and a remote operated gas fireplace viewable from entire 1st floor.

Second Floor has two bedrooms, full bath with tub, washer/dryer and fully supplied linen closet. The master bedroom (with furnished balcony & 40 in LED TV) has a king size bed comprised of two x-long twin beds that may be separated, if preferred, a very large hanging closet and an extraordinary chest of draws. The second bedroom sleeps 4, having two sets of contemporary bunk beds, also with x-long twin mattresses, a hanging closet and two dressers.

Inspected & licensed by City of Annapolis.

Maryland DOE Lead Free Certification.

Historic Eastport Walking Tour #8 'Murphy's Row'.

Convenient PayPal available.

Keywords: Townhome

More Details

Member since: 2008
Speaks: english
Response time:
Within 2 days
Response rate:
Calendar last updated:
March 17, 2018

About Steven

I am a retired engineer/contractor/developer of electric power generation facilities globally and an active racing/cruising sailor. I grew up in CT and have resided in Boston, NY, Cairo and London. Home is now on Key Biscayne, an island suburb of Miami, FL. I have a grown son in NY and my wife & I have twin 7-year old boys. With our boys in school on Key Biscayne, as a family we now only get to visit Annapolis briefly in the spring. We spend our summers in New England cruising aboard our sailboat.

Steven purchased this townhome in 2007

Why Steven chose Eastport

I first came to Annapolis in 2006 to compete in a regatta and then later that spring in the Annapolis-Newport ocean race. I was seduced by Annapolis's history, beauty and European village feel. During free time I began a search of 'inner-city' areas. Eastport prevailed as being the most attractive, driving accessible and walkable location in which to live. Finding my home was pure luck - it offered everything in an easy-to-manage classic row house.

What makes this townhome unique

The property is our second home and as such, is furnished as a 'home', not an investment rental property. I am also fastidious about maintenance and cleanliness and spare no expense in the property's upkeep. This home has old world character with state-of-the-art comfort and convenience. It's in a great neighborhood with green space and the Bay just outside the door and some of the best restaurants in town around the corner. The Eastport neighborhood is not congested like the Historic district so parking is a non-issue yet it's only a brief walk or water taxi ride to downtown or the Academy.


Eastport Townhome Accommodation and Amenities

Property Type:
  • townhome
  • floor 1
Building Type:
  • building
  • Guests provide their own meals
Floor Area:
  • 1200 sq. ft.
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 6
  • Max. adults: 4
  • Children welcome
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only ...
Location Type:
  • Water View ...
  • Air Conditioning ...
  • Clothes Dryer
  • Fireplace ...
  • Hair Dryer
  • Heating
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Parking ...
  • Towels Provided ...
  • Washing Machine ...
  • Wireless Internet ...
  • Coffee Maker ...
  • Cooking Utensils ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Ice Maker
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Refrigerator ...
  • Stove ...
  • Toaster ...
  • Dining ...
  • Dining Area
  • seating for 6 people
  • 1 Bathroom
  • 1 Half Bath
    BATHROOM - toilet , combination tub/shower
  • POWDER ROOM: ground floor. FULL BATHROOM: 2nd floor with tub/shower, retractable cloths drying line, weigh scale and telescoping 5x cosmetic mirror. Both commodes are new Kohler 'comfort height' (16.5 in.) with elongated bowls.
  • 2 Bedrooms, Sleeps 6
  • MASTER BEDROOM - 1 king , King May be separated into 2 XL twins
    SECOND BEDROOM - 2 bunk bed , (4) XL sleeping surfaces
  • MASTER BEDROOM: King size beds (two joined XL twins which may be separated), full length mirror, Samsung 40 in. TV, large closet & chest of draws, furnished balcony. SECOND BEDROOM: Two sets of Bunk Beds (4 beds) extra-long, two dressers, 4 draws ea.
  • Books
  • CD Player
  • DVD Player ...
  • Satellite / Cable ...
  • Stereo ...
  • Television ...
  • Balcony ...
  • Deck / Patio ...
  • Lawn / Garden ...
  • Outdoor Grill ...
  • arboretum
  • churches
  • library
  • live theater
  • marina
  • museums
  • playground
  • recreation center
  • restaurants
  • synagogues
Leisure Activities:
  • boating
  • shopping
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • laundromat
Sports & Adventure Activities:
  • basketball court
  • cycling
  • kayaking
  • sailing
Electronic keypad front door lock - No keys required.


Exceptional! 5/5 -
(26 traveler reviews)

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Walk/Boat Show, Downtown, Yacht Clubs, Capital, Naval Academy
average rating of 5.0 based on 26 reviews

Great home and host

  • 5 of 5

This is a lovely home in a quiet neighborhood within walking distance to the action in Annapolis. The home is set up perfectly for a family or group of people visiting together; with modern set up of a smart home. We were within a minutes' walk to the water and restaurants in Eastport and about a 20 minute walk to downtown Annapolis. Great place to stay for a relaxing getaway! Parking was super easy, even on a Saturday afternoon and we never had issues. Steven was quick to respond to requests and inquiries and checked in after we arrived just to make sure we had everything we needed. Would absolutely recommend for another stay!

  • Submitted: Aug 29, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
Owner's Response: I am so pleased that my home, met your expectations. I look forward to your next visit. Thank you. Sincerely, Steven
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Charming, Peaceful, Perfect //

  • 5 of 5

We absolutely loved staying here! The kitchen was well stocked, the location was ideal and the condo was impeccably clean. You could tell that a lot of love went into preserving this unique slice of Annapolis and loved that we could walk to so many nearby restaurants to grab a drink to watch the sunset over the water. It was perfect and we can't wait to come back.

  • Submitted: Oct 25, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
Owner's Response: I am so pleased you appreciated and enjoyed the home. I look forward to your return. Sincerely, Steven
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USNA Commissioning-Graduation week Class of 2017

  • 5 of 5

Truly Wonderful... An outstanding Commissioning Week experience, Steven's home is beautiful, comfortable and elegant. Family and friends were totally impressed with all the special details: art paintings, mint soaps, plenty of linens, motion mirror and fully equipped Kitchen. Steve's essence, kindness and spirit is the special ingredient. Endless smiles and happy memories. Most definitely planning a return visit. Phenomenal Experience. ~thank you~moon family

  • Submitted: May 31, 2017
  • Stayed: May 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you. It was a pleasure hosting you and your family for Commissioning Week 2017. Congratulations to your son and best wishes for an exciting and rewarding future with the Navy. Thank you for your service to our nation. Sincerely, Steven
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Historic Eastport Beauty

  • 5 of 5

Our family had the pleasure of staying at Jeremy's Way located in beautiful Eastport which is minutes from Downtown Annapolis. Having the room to enjoy family & friends for dinner, the ability to take strolls through Eastport and catching the Water Taxi to Downtown Annapolis was extremely convenient. I was able to walk daily to 'The Yard' and Downtown, yet also able to drive quickly to stores and local attractions. Before she left for USNA, my daughter and I went to the end of Jeremy's Way and enjoyed the peaceful beauty of the water views and community garden.

As soon as we opened the door we felt welcomed and loved the open layout. This is not some 'rental property', it is the owner's vacation home and it is seen in the details of the antique furniture and lovely artwork. The beds are comfortable (to include the bunk bed mattresses) and the towels/linens are high quality. The kitchen is well-equipped to make wonderful meals, and the lovely patio is the perfect place to enjoy a cup of tea.

We are so thankful that we made reservations for Parents Weekend in August and get to stay in this lovely home again. Our daughter is also happy that she will be able to spend more time at Jeremy's Way when we come back to visit and celebrate her accomplishments.

Working with the owner has been extremely pleasant and he even quickly replied to emails during our stay to answer some questions we had regarding the local area. Thanks to him and his family for providing a comfortable stay, in a beautiful home, located in a gorgeous area!

  • Submitted: Jul 19, 2016
  • Stayed: June 2016
  • Source: VRBO, from HomeAway
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Kris S.

  • 5 of 5

We were lucky enough to find this beautiful home for our second trip to Annapolis. We have a midshipman at the Naval Academy and were looking for a home-away-from-home for the four years that we will be visiting the area. This home is close enough, and just far away enough (to escape the crowds) from USNA and Downtown Annapolis. We always were able to find a parking spot either adjacent or very near the home. Inside, it had everything that we were looking for. Full kitchen, 1 full bath and 1 half bath, a beautiful big master bedroom, and another bedroom with 4 bunk beds. In addition it has a place to have a sit-down dinner, a relaxing family room, and a great little patio to grill out. The neighborhood is quiet and everything we needed was close. The house has a fully stocked kitchen, linens, towels, ironing board, everything that you need to be comfortable for a day or a week. The home is clean and lovingly designed. Our several interactions with the owner Steven have been wonderful. He is very prompt in returning emails and is accommodating in every way. We had an effortless check-in with no problems at all. All information is provided either before you arrive and inside the home. We already have this home booked two more times for upcoming events at USNA!

  • Submitted: Jul 11, 2016
  • Stayed: May 2016
  • Source: VRBO, from HomeAway
Owner's Response: Your comfort at my home brings me great satisfaction. Thank you for sharing. All the best to you and your family as your son heads into his last couple years at the Academy. Sincerely, Steven
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29 Jeremy's Way

  • 5 of 5

My family and friends truly enjoy staying at this property. We park our cars and enjoy all of Eastport and Annapolis by foot. 29 Jeremy's Way is always kept in imacullate condition inside and out. It's a wonderful base location for sailing and sightseeing enthusiasts alike. The owner has been nothing but accommodating and helpful. We can't wait to schedule our next trip to Annapolis!

  • Submitted: Jul 10, 2016
  • Stayed: July 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you Ellen, Great having you and your family back again. Really enjoyed exchanging race reports on our respective children sailing Optimist regattas in different parts of the country. I'm sure we will meet someday at a regatta somewhere. Cheers, Steven
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United States Naval Academy
Boatyard Bar & Grill
Chart House
Annapolis Maritime Museum
Ruth's Chris Steak House
Pusser's Caribbean Grille
Carrol's Creek
Annapolis Yacht Club
Eastport Yacht Club
Severn Sailing Associates Jr Club
Annapolis Performance Sailing
Davis Pub
Lewnes Steakhouse
O'Leary's Seafood Restaurant
The Rockfish -- CLOSED
McGarvey's Saloon and Oyster Bar
Annapolis City Dock
Nearest Airport
25 Miles
Baltimore Washington International (BWI)
Nearest Barpub
0.25 Miles
Many: Boatyard Bar & Grill, Davis's Pub.
Nearest Ferry
0.25 Miles
Water Taxi to Downtown/USNA (2 short blocks away)
Nearest Train
25 Miles
Baltimore Washington International Airport -Amtrak
Nearest Motorway
3 Miles
Rt 50, Rt 97
Nearest Restaurant
0.25 Miles
Many: Ruth's Christ, Chart Hs, Lewnes, O'Leary's..
Nearest Beach
0.25 Miles
Chesapeake Bay
Car: not necessary

Stones throw to Annapolis Performance Sailing (APS), one short block to Eastport Yacht Club, Severn Sailing Association (SSA) and Annapolis Harbor Boatyard.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning $130

Rental rates are all-inclusive of taxes, fees, etc.
More than 4 occupants = additional $30 laundry service surcharge.

Owner's Cancellation Policy

  • Canceled bookings will not receive a refund