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

Bedrooms 2
Half Baths1
Property type townhome
Minimum Stay 2 - 7 nights


Half Baths
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 a few hours
Response rate:
Calendar last updated:
January 9, 2017

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 Annapolis

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.


Exceptional! 5/5 -
(23 traveler reviews)

Walk/Boat Show, Downtown, Yacht Clubs, Capital, Naval Academy
average rating of 5.0 based on 23 reviews

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: Jun 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: Jul 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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TLC in Annapolis

  • 5 of 5

Only 2500 characters allowed on this review-how am I going to give this residence due justice with that limited amount of characters? I guess one word could sum up the entire weekend; FABULOUS! Honestly, the pictures of Steve's place are not good enough. It is extremely clean, comfortable, spacious, and warm. The gas fireplace was definitely an added bonus. The sailors from Eckerd were able to put their dry suits, gloves, hats, and shoes around the fire and dry them without using the dryer. They wanted to save electricity, which was nice! After the cold and rainy days they had on the water, they also wanted to get as close to the fire as possible. Because we were all so tired, we decided to do take out and eat in the residence. The restaurant, Boatyard Grill, is so close that it took about 10 minutes to drive there and back. Great for hungry sailors. The food was delicious and plentiful and the dining accommodations were superb. As soon as we ate, we all wanted to sleep. The sailors loved the water pressure in the shower and all were able to take nice, hot showers without running out of hot water. Everyone had plenty of clean towels and washcloths too. Nice to have, especially with sailors. After using a wet towel all day, it is nice to have clean and dry towels. Although I was pleased with the accommodations and the fact that they were better than I imagined and the location was perfect, I was extremely touched by Steve's email conversations with me prior to arriving. I enjoyed learning about his family and his take on good restaurants and sailing in Annapolis. I felt like I was important to him because I was a person and not because I was renting his beautiful residence. I felt connected to his place and it made me appreciate the hard work he and his wife have put into the home to make it cozy and homey for all. It was fun to imagine the pitter-patter of little feet running upstairs and jumping or not jumping into the bunk beds. Maybe easily climbing into the bunk beds, would be a better way to put it. Do not want to get the little ones into trouble. My husband and I took a stroll out of the back door through the condo complex and found it to be very nice. The entire neighborhood was also very nice. I am looking forward to returning to Annapolis when the weather is warmer. I hope that we are able to stay in Steve's place too. Annapolis for us, would not be the same unless we were able to stay at Steve's. Thanks again Steve! You a #1 host!

  • Submitted: Mar 23, 2016
  • Stayed: Mar 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you! It was a pleasure having you and you are welcome any time. Be sure your daughter sticks with that sailing passion - I'll watch for her on the ICSA website. Cheers, Steven
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Wonderful home, great host!

  • 5 of 5

I frequently travel to Annapolis for business, and have stayed in nearly a dozen rentals in Eastport, and this is one of my favorites! It's absolutely spotless and well-appointed. It has a great kitchen with everything you could possibly need for cooking - I tend to eat most my meals at the rental property, and it's great to have a kitchen that easily rivals what I have at my own home. It's also great tech wise - super fast wireless, great TVs.

Most of all though, Steven is a great host. He's great at communicating, prompt with information, and attentive. He also shares great local information, and truly makes you feel like family instead of just a renter. He gets the ultimate gold star for being extra kind and sending me a knick knack from the home that I had taken a shine to. Wow, right? Talk about service.

Can't wait to stay here next time.

  • Submitted: Nov 3, 2015
  • Stayed: Sep 2015
  • Source: VRBO, from HomeAway
Owner's Response: Dear Anna, It was an absolute pleasure having you. I am also pleased that as a result of your stay, we have established a standing relationship with your Foundation which allows for expedited booking of your visiting representatives. Thank you and look forward to your return to Annapolis. Cheers, Steven
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Classy and Convenient Eastport Home

  • 5 of 5

We stayed at Steven's home while visiting our Plebe for Parent Weekend. The home is immaculate and beautifully decorated with upscale amenities. It is well stocked with just about anything you could need.

Our family of six was able to spread out and relax because of its well thought out design and many special touches. We especially loved the patio area with the beautiful plantings and lighting. The smart, high definition television was a hit with the teenagers and adults alike. This home is conveniently located in a charming, home-like neighborhood of Eastport, yet we were able to walk to the downtown Annapolis and the Naval Academy in about 12-15 minutes. The drive was under 5 minutes. Parking in the area is free and easy to find. Steven was wonderful to work with before, during, and after our visit. He made us feel like welcomed guests rather than just vacation renters. We would love to come back again and again during future visits to Annapolis.

  • Submitted: Aug 25, 2015
  • Stayed: Aug 2015
  • Source: VRBO, from HomeAway
Owner's Response: Thank you. It was an absolute pleasure having you. Best wishes to you and your family. Cheers, Steven
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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

Eastport Townhome Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
USNA Commissioning Week
May 20 2017 - May 26 2017
7 night minimum stay
Flat fee
My Standard Rate
2 night minimum stay

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

Please ask the owner or check their rental agreement when booking the property.
Enter dates for accurate pricing
Available arrival
Available stay (no arrival)


Eastport Townhome Accommodation and Amenities

Property Type:
  • townhome
  • floor 1
Building Type:
  • building
  • Guests provide their own meals
Floor Area:
  • 1200 sq. ft.
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 ...
  • non smoking only ...
  • pets not allowed
  • 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.

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