Entire home

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

A modern living room with a flat-screen TV, wooden console, two round side tables, a sofa, and a staircase with a railing. - Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard (Annapolis)
A neatly made bed with white linens, a colorful pillow, and a stack of white towels on the floor. - Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard (Annapolis)
A modern living room with a sofa, two side tables, a coffee table, a blue armchair, a staircase, and a wall with a mirror and two signs. - Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard (Annapolis)
An outdoor dining area with tables and chairs under a blue awning, overlooking a waterfront with boats and buildings in the background. - Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard (Annapolis)
A modern bedroom with a dark wooden desk, a round mirror, a lamp, a chair, a small round table, and a wooden staircase leading to a balcony with a view of trees. - Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard (Annapolis)
Close to Annapolis City Dock, Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard provides amenities, such as a firepit and laundry facilities. Guests can connect to free in-room WiFi.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms2 bathrooms139 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning

Add dates for prices

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

    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 ($150 non-refundable pet fee per pet paid prior to checkin)



    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

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Dishwasher
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator

Dining

  • Dining table

Bedrooms

  • 2 bedrooms

Bathroom

  • 1.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo

Living spaces

  • Dining table
  • Living room

Entertainment

  • TV

Outdoor areas

  • Balcony
  • Firepit
  • Gas grill

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Things to do

  • Bicycle parking
  • Bicycle storage

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)

General

  • Bicycle parking
  • Bicycle storage
  • Recycling
  • Unit size: 1,500 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome

Events

No events 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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

About the area

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 John Smith House and William Paca House. Looking to enjoy an event or a game while in town? See what's happening at Tose Family Tennis Center or Alumni Hall. Visit our Annapolis travel guide
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Map
Annapolis, MD

What's nearby

  • A large building with ornate architecture, a cannon, and a sign reading "Bancroft Hall".
    U.S. Naval Academy
    1 min drive - 0.7 km
  • A town with historic buildings, a prominent church steeple, and a weather vane atop a building.
    Maryland State House
    2 min drive - 1.4 km
  • Annapolis Maritime Museum
    5 min walk - 0.4 km
  • Annapolis Harbor
    6 min walk - 0.6 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

  • The Choptank
    18 min walk
  • Boatyard Bar & Grill
    6 min walk
  • Royal Farms
    7 min walk
  • Iron Rooster
    20 min walk
  • McGarvey's Saloon & Oyster Bar
    20 min walk

Frequently asked questions

Is Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard?

On-site parking is available at the property.

What time is check-in at Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard?

Check-in begins at 4:00 PM.

What time is check-out at Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard?

Checkout is at 11:00 AM.

Where is Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard located?

Located in Eastport, this holiday home is within 1 mi (2 km) of Annapolis Maritime Museum and Annapolis City Dock. Annapolis Harbor and Spa Creek are also within 15 minutes.

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Reviews

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

10

Exceptional

10

Cleanliness

10

Location
Rating 10 - Excellent. 4 out of 4 reviews
Rating 8 - Good. 0 out of 4 reviews
Rating 6 - Okay. 0 out of 4 reviews
Rating 4 - Poor. 0 out of 4 reviews
Rating 2 - Terrible. 0 out of 4 reviews

Reviews

Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
From a partner site

10/10 Excellent

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!
From a partner site

10/10 Excellent

We loved Leave of Absence!

We had a wonderful month at Leave of Absence...the house is in a perfect location to walk restaurants, or to the water to launch the kayak, or just to walk around the charming Eastport neighborhood. The beds are super comfortable and the kitchen is stocked with everything you need (and more) if you enjoy gourmet cooking. We also enjoyed the beautifully landscaped back yard with dining area and grill. The management company was very responsive to any problems we encountered......special shout out and thank you to Kathy and Greg!! We will be back! Neile and Steven Martin