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10/10 Excellent
Sarah A.
Jun 8, 2025
Entire home
2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free
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Reviews
10 out of 10
Exceptional
2 bedrooms1+ bathroomSleeps 61500 sq ft
Popular amenities
Explore the area
Annapolis, MD
- Place, Annapolis Maritime Museum5 min walk
- Place, U.S. Naval Academy19 min walk
- Place, Annapolis City Dock2 min drive
- Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)34 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
About this property
2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free
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
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
Our prices include all fees. No hidden fees.
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Similar properties
2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free
2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free
- Kitchen
- Washer
- Dryer
- Pet friendly
10.0 out of 10, Exceptional, (42 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
Children
Children allowed: ages 0-17
Events
No events allowed
Pets
Pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
About the neighborhood
Annapolis
Eastport, a neighborhood in Annapolis, is home to this vacation 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.
Annapolis, MD
What's nearby
- Annapolis Harbor - 5 min walk - 0.4 km
- Annapolis Maritime Museum - 5 min walk - 0.4 km
- Annapolis Landing Marina - 9 min walk - 0.8 km
- U.S. Naval Academy - 19 min walk - 1.6 km
- Annapolis City Dock - 2 min drive - 1.4 km
Getting around
Restaurants
- The Choptank - 18 min walk
- Carrol's Creek Cafe - 7 min walk
- Boatyard Bar & Grill - 6 min walk
- O'Brien's Oyster Bar & Seafood Tavern - 19 min walk
- Buddy's Crabs & Ribs - 20 min walk
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Verified
10/10 Excellent
Paul R.
Jul 25, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Paul R.
Stayed 16 nights in Jun 2025
About the host
Hosted by iTrip Vacations Annapolis - Sean Degnan
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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