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Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard

Photo gallery for Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard

Are you ready for your Leave of Absence?
A special feature in Eastport - the generous patio with the extended private fenced backyard
Park up to 3 cars on the private drive along the side of the home.
The dining room table is one of many gathering places in the home.
The luxury bedding is the cherry on top of this beautifully decorated home.

Reviews

10 out of 10
Exceptional
2 bedrooms1+ bathroomSleeps 6

Popular amenities

  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill

Explore the area

View in a map
Annapolis, MD
  • Place, Annapolis Maritime Museum
    ‪5 min walk‬
  • Place, Annapolis Harbor
    ‪6 min walk‬
  • Place, U.S. Naval Academy
    ‪1 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪40 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Balcony King Bedroom

1 King Bed

Family room

1 Queen Sofa Bed

Front King Bedroom

1 King Bed

1 bathroom, 1 half bathroom

2nd Floor Hall Bath

Bathtub or shower · Toilet

Main Floor Powder Room

Toilet

Spaces

Deck or patio
Kitchen
Balcony
Number of living rooms

About this property

Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard

Experience the Difference: Professionally Managed by iTrip Annapolis

Available for Commissioning Week 2025!



Charming 1905 Eastport Duplex: Historic Character Meets Modern Comfort

Step into a beautifully-preserved piece of history with this charming 1905 duplex in the heart of Eastport. Offering a seamless blend of old-world charm and modern amenities, this home is perfect for families, professionals, or anyone seeking a cozy, yet stylish getaway.



Main Floor: The spacious open layout on the main floor includes a large living area, a dedicated office/desk space, and a convenient powder room. The inviting dining area opens to a gourmet kitchen, fully equipped with stainless steel appliances, perfect for cooking up a feast. The main floor also features a private, fenced backyard, ideal for relaxing or entertaining.



Upstairs: Two generously-sized King bedrooms provide a restful retreat, complete with luxury linens and a shared full bath. One bedroom boasts a private balcony overlooking the serene backyard and the front King bedroom has its own flatscreen TV and desk space. A bonus loft space offers additional room for kids or younger families to relax and enjoy their own shows.



Additional Features:

Parking for up to 3 cars

Private fenced backyard with a patio deck and and gas fire pit

Covered front porch, perfect for enjoying the neighborhood

Gas grill (propane included)

High-speed WiFi and a big-screen TVs for entertainment

Dedicated workspaces on each level for remote work or study

Full washer & dryer for your convenience

Dog-friendly



Perfect Location: Situated just steps away from Eastport's vibrant cafes, restaurants, and bars, this home offers easy access to everything the neighborhood has to offer. Water access for paddle boarding and kayaking (BYO) is just a short stroll away.



Plus, you're only:

1.5 miles from the U.S. Naval Academy

30 miles from Washington, D.C.

25 miles from Baltimore



House Rules:

No smoking, parties or events

Dogs ok if $150/per pet fee paid prior to checkin

Must be 25+ to book

Check-in: 4:00 pm | Check-out: 11:00 am

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About the area

Annapolis

Eastport, a neighbourhood in Annapolis, is home to this holiday home. Annapolis Maritime Museum and The Colonial Players are cultural highlights, and some of the area's landmarks include Kunta Kinte Plaque & Alex Haley Memorial and John Smith House. Looking to enjoy an event or a game while in town? See what's happening at Tose Family Tennis Center or Alumni Hall.
Map
Annapolis, MD

What's nearby

  • Annapolis Maritime Museum - 5 min walk - 0.4 km
  • Annapolis Harbor - 6 min walk - 0.6 km
  • U.S. Naval Academy - 1 min drive - 0.7 km
  • Maryland State House - 2 min drive - 1.4 km
  • Annapolis City Dock - 3 min drive - 1.8 km

Getting around

  • Odenton Station - 24 min drive
  • Fort Meade, MD (FME-Tipton) - 36 min drive

Restaurants

  • ‪Carrol's Creek Cafe - ‬7 min walk
  • ‪The Choptank - ‬18 min walk
  • ‪Boatyard Bar & Grill - ‬6 min walk
  • ‪O'Brien's Oyster Bar & Seafood Tavern - ‬19 min walk
  • ‪Annapolis Market House - ‬19 min walk

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 3 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

From a partner site

10/10 Excellent

Sarah A.

Amazing stay

We loved our stay, the house is so clean and beautifully decorated, the backyard is gorgeous!!! So easy to walk everywhere and the great added benefit of parking!
Response from VrboOwner on 20 Jun, 2025
Thanks, Sarah! We’re thrilled to hear you loved your stay at Leave of Absence and appreciated the clean and beautifully decorated house, as well as the gorgeous backyard. It sounds like the convenient location and parking made your visit even better. We’d love to host you again anytime you’re back in the area! Melissa~iTrip Annapolis
Verified

10/10 Excellent

William A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved our stay at this well located ‘walkable’ home. 5 stars all the way. Bed was comfortable, house was clean and well maintained. Would def book again.
Stayed 14 nights in Apr 2026
Response from VrboOwner on 11 May, 2026
Thanks, William! We are so glad you enjoyed your stay. We look forward to hosting you again soon. Sean, iTrip Annapolis
Verified

10/10 Excellent

Paul R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Sean was great and did everything to may our week stay very comfortable.
Stayed 16 nights in Jun 2025
Response from VrboOwner on 3 Aug, 2025
Thanks, Paul! We’re delighted to hear that Leave of Absence was comfortable for your week-long stay. Please come back and stay with us again next time you’re here. Melissa~ iTrip Annapolis
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