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

Unique and Luxurious Accommodation for 6 in Eastport - Parking included for 6

Bedrooms 2
Half Baths1
Space 1,800 sq ft
Property type cottage
Minimum Stay 6 - 8 nights


About the property

Restored 1936 Waterman's Cottage - Off street parking for 6 - Walk to USNA

************* NEW LISTING - AVAILABLE NOW ************

SAILBOAT SHOW - $5500.00/wk

POWER BOAT SHOW - $5500.00/wk

CHRISTMAS - $5000.00/wk

COMMISSIONING WEEK 2018 still available - $4500-6300 per week depending on demand.

2018 - still available! $5000/week

2019 - rented!

2020 - still available

Eastport cottage sleeps 10

- 2 bedrooms with sleeping loft

- 1 full and 1 half bath

- 2 premium queen beds

- 1 pull-out queen sleeper

- 2 twins

Unique Features

- Walking distance to Naval Academy, downtown, shopping, restaurants and marinas

- Shower for two

- Off street parking for six

- Completely renovated in 2006

- Unique nautical property - tastefully furnished

- Small pets welcome on a case by case basis

- Designated vacation property - you will not share space with the owners personal belongings

Jump aboard the luxurious Annapolis Nautical Cottage and feel like your living aboard a yacht. With teak and holly floors in the kitchen, bathrooms and bedroom friends say they feel like they are on a boat. Located in the quaint Eastport community of Annapolis, Maryland you will find a small town atmosphere with access to the best restaurants and shopping the area has to offer. This cottage is principally used for vacationing friends and you will not have to share space with the owner's personal belongings. Closets, storage areas and drawers will be vacant and ready for use by visitors.

After a full day come home to your upscale Nautical Cottage and mosey down the slate walkway. An anchor door mat and boat bell will greet you at the side entrance of the gourmet kitchen. Tastefully styled custom cherry cabinets are fully stocked with everything you will need for your stay. From the commercial 4 burner gas stove with pot filler to the Keurig Coffee Maker we have you covered. Large pantry, french door refrigerator, granite countertops, microwave, island with breakfast seating, drop through trash receptacles, and dishwasher are a few of conveniences that make this kitchen handy to create amazing meals with simple clean up. Careful attention was paid to every detail in planning this space while keeping character of the nautical theme, with teak and holly floors paired with bead board gloss ceiling. Mahogany casement windows flood natural light while giving a view of sail boats rocking at the dock on Back Creek.

From the kitchen you can enter the covered deck and fenced backyard through the rear entrance. A lockable dog door has been installed at this entrance for the convenience of friends with small pets. Outdoor seating for 10 will suit most gatherings with a room to spare. Gas grill is easy to operate and conveniently located on covered deck. Natural gas supplies this grill so you will not be running out to refill. Bamboo offers privacy and you'll feel tucked away passing time in the backyard.

Impressive woodwork and built-ins adorn the lower level living room located just left of the kitchen. Model boats and cars line the shelves while framed maritime flags are displayed on bead board walls. Plop down on the slipcovered sofa and prop your feet on the backgammon table to surf the 100+ channels on the 60' Panasonic Plasma TV. Also here for your enjoyment are Apple compatible components such as a DVD player, stereo and surround sound. Large iMac with printer rests on the desk nook and is connected to high speed internet wirelessly.

From the living area you can enter the front rain porch where you can sit on the hanging swing and watch the world go by.

Powder room is conveniently located to living and kitchen area on the first floor. Cleat door grab opens bead board door to reveal the same teak and holly floor featured throughout the home.

If you have had enough exploring and socializing for the day then head upstairs where you will find a sitting room, two bedrooms, a sleeping loft, high end bathroom and upper deck with hot tub for four all concealed behind an electronic privacy door. Remotely lower or raise upper stairwell door for complete privacy. Unique buoy weight which operates door meshes with the nautical ambiance of the cottage. Railings are custom stanchions with rigging topped with a mahogany cap.

The main bathroom is simply amazing to get ready in! Mirrors everywhere coupled with natural light make seeing what you are doing and getting ready a breeze. Dual granite sinks sit on teak cabinetry with lots of storage. All of the mirrors on the left side of the bathroom open for storage. This bathroom is so easy to keep tidy it feels like it does it for you. The two person shower features a natural pebble floor with three shower heads and large glass front. Ample room for a couple to shower comfortably together without bumping into each other. A full sized washer and dryer is tucked away in the corner. No more lugging dirty clothes up and down the steps.

The upper sitting room is furnished with a queen size pull out sectional sofa with a lounge chaise on each end. Glance up to view the warm douglas fir ceiling and architecturally supportive sailboat shrouds. Climb the ladder to hang out in the sleeping loft which contains two twin beds. The same custom railings frame the loft and tie the room together. Skylight and plenty of windows fill this room with lots of natural sunshine.

Second Mate's Cabin contains a new luxury queen bed with a change of linens. Pine bead board dresses this room with a skylight to finish it off. Ample closet space and water views in the winter.

Open the large pocket door off of the sitting area to find the luxurious Stateroom with balcony. This sunken room has been designed to mimic a stateroom on a classic yacht (Trumpy). Step down the mahogany storage steps to find teak and holly floors throughout. Coffered bead board ceiling fastened with wood pegs add to the nautical charm of this bedroom. The built-in bed is custom made of mahogany and there are lots of nooks and crannies to store your belongings. Lay on the plush queen pillow top and view the sunrise over Back Creek from the wall of casement windows opposite of the bed. The remote control window shade allows you open or close the blind with ease. Built in bar with refrigerator comes in handy on the days you want to stay in bed. The top of the built in features an electrically retractable 44' Pioneer Elite with cable. Doors on each side of bed open to the huge walk through closet/dressing room. There is ample room with numerous shelves and rods for clothing storage as well as a mirror and lighting to get dressed. Step onto the private balcony to find the four person hot tub ready to help you relax. Bar height table with four chairs and an umbrella make this the perfect private spot to unwind.

Send us an email if you have questions or special requests. We look forward to sharing this unique property with you!

More Details

Property Manager
Member since: 2014
Speaks: english
Response time:
Within a few days
Response rate:
Calendar last updated:
April 13, 2018

About Wilmer

Hello! I love staying at the Annapolis cottage. There are always fun things going on around town and everyone is so laid-back. Currently I live and work in Wilmington, DE where I grew up. One of my passions is restoring homes and the Annapolis Nautical Cottage was my first project. I hope you enjoy it like I do.

Wilmer purchased this cottage in 2005

Why Wilmer chose Eastport

Business introduced me to Annapolis and the charm of the town kept me. I fell in love with how nice everyone was and wanted to stake my small claim in the community. I chose this cottage because of its' location, overall shape and size. I also liked the driveway and that the yard was large enough for the dogs. This property needed work though so I ended up gutting the entire place. Lots of time was spent on design and detail. The cottage is remodeled to resemble the interior of a boat. Teak and holly floors and the railings are custom stanchions with rigging. I hope you enjoy what I have done with the place and look forward to sharing it with you.

What makes this cottage unique

The interior of the cottage is designed to resemble the interior of a boat. The parking here is great too. This is a big deal in Annapolis where parking is scarce.


Eastport Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Guests provide their own meals
Floor Area:
  • 1800 sq ft
House Rules:
  • Max. occupancy: 10
  • pets considered
Location Type:
  • Downtown ...
  • Water View ...
  • Away From It All
  • Historic
  • Romantic
  • Spa
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning
  • Clothes Dryer
  • Heating
  • Internet ...
  • Linens Provided
  • Living Room
  • Parking ...
  • Towels Provided
  • Washing Machine
  • Coffee Maker ...
  • Dishes & Utensils
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Dining Area
  • 1 Bathroom
  • 1 Half Bath
  • First Floor Powder Room - toilet
    Second Floor Bathroom - toilet , shower
  • Second floor bathroom is equipped with a shower for two with multiple shower heads.
  • 2 Bedrooms, Sleeps 10
  • Stateroom - 1 queen
    Second Mate's Cabin - 1 queen
    Upper Sitting Room - 1 queen , Chaise sofa pulls out to queen bed
    Sleeping Loft - 2 twin/ single
  • DVD Player
  • Satellite / Cable ...
  • Stereo
  • Television ...
  • Balcony
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill
Pool / Spa:
  • Hot Tub ...
  • churches
  • festivals
  • health/beauty spa
  • live theater
  • marina
  • playground
  • restaurants
Leisure Activities:
  • antiquing
  • boating
  • miniature golf
  • outlet shopping
  • paddle boating
  • photography
  • shopping
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • fishing
  • freshwater fishing
  • kayaking
  • pier fishing
  • sailing
  • sound/bay fishing
  • tennis


5/5 -
(1 traveler review)

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Unique and Luxurious Accommodation for 6 in Eastport - Parking included for 6
average rating of 5.0 based on 1 reviews

Cool interior / great location

  • 5 of 5

My family stayed here for USNA 2nd Class Parent's Weekend in October 2014. The owners are very nice to deal with. We hosted a party for about 25 people and they were very accommodating, even offering to find extra tables and chairs if we needed them!

The interior is reminiscent of staying on a high end yacht. Great Eastport location - easy walk to The Boathouse and other restaurants. Perfect for boat show or a Navy weekend.

  • Submitted: May 19, 2015
  • Stayed: October 2014
  • Source: VRBO, from HomeAway
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Nearest Airport
25 Miles
Nearest Barpub
0.1 Miles
Eastport Davis Pub
Nearest Restaurant
0.1 Miles
Boatyard Bar & Grille and Lewnes Steak House
Nearest Beach
11 Miles
Sandy Point State Park

The Naval Academy, boating, downtown, shopping and restaurants are all less than a mile of the cottage. With numerous restaurants within a few blocks you are sure to find something to hit the spot if your hungry. Davis Pub is directly across the street and offers friendly service so much so that they were recently featured on Food Networks Diners, Drive-ins and Dives. Walk a couple blocks toward town to enjoy Boatyards Bar & Grill nightly specials and diversified menu which is sure to please everyone. Not only has Coastal Living named Boatyard as the best restaurant for sailors and boaters they have also been named to have the best crab cakes by Baltimore Magazine. Directly across the street is Lewnes Steak House who offer outstanding service while serving up delicious greek salads and arguably the best steaks in town. After your hunger has been tamed be sure to take a quick walk to the US Naval Academy.

United States Naval Academy Formation kicks off at noon weekdays during the academic year. Join a guided tour and view the rich history of the campus while supporting the Brigade of Midshipman. 100% of the admission profit goes directly back to helping midshipman. Cottage still available for Commissioning Week 2016.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $125
Refundable damage deposit $500
Pet Fee $100

Manager's Cancellation Policy

Please ask the manager or check their rental agreement when booking the property.