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

Vacation home near Annapolis City Dock in Annapolis

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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.
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.
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.
A neatly made bed with white linens, a colorful pillow, and a stack of white towels on the floor.
An outdoor dining area with tables and chairs under a blue awning, overlooking a waterfront with boats and buildings in the background.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms2 bathrooms139 sq m

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Annapolis, MD
  • Place, Annapolis Maritime Museum
    ‪5 min walk‬
  • Place, Annapolis Harbor
    ‪6 min walk‬
  • Place, Annapolis City Dock
    ‪3 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪40 min drive‬

Room options

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About the area

Annapolis

Eastport stay.At this Eastport vacation home, you'll be within a 5-minute walk of Annapolis Maritime Museum and Annapolis Harbor. Also, Spa Creek is within half a mile (1 km) and Kunta Kinte Plaque & Alex Haley Memorial is within 2 miles (3 km).
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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

  • ‪RaR Brewing - Chessie's Wharf - ‬5 min drive
  • ‪Taco Bell - ‬7 min drive
  • ‪Shika Sushi & Ramen - ‬7 min drive
  • ‪Starbucks - ‬20 min walk
  • ‪Boatyard Bar & Grill - ‬6 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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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Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

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

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

  • Smoking not allowed

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

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 welcome
  • Service animals 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
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
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector and a smoke detector in each accommodation.

Property is also known as

15632

Frequently asked questions

How close is Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard to the airport?

This vacation home is 21.8 mi (36-min drive) away from the Fort Meade, MD (FME-Tipton) airport, the closest popular airport to the property.

Does Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard to the beach?

This vacation home is 3.4 mi (8-min drive) from Carrs Beach and 3.4 mi (12-min drive) from Sparrows Beach. Don't forget your sunscreen!

Does Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard?

No, there is no casino at this vacation home.

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.

Is there free parking at Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard?

Free parking is not available at this vacation home.

Does Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard have a pool?

This vacation home does not have a pool.

Does Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard have a spa?

There are no spa services available at this vacation home.

How close is Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard to downtown Annapolis?

This vacation home is 0.9 mi away from Annapolis.

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

Reviews

10

Exceptional

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

10/10

Cleanliness

Reviews

Verified review

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
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!
From a partner site

10/10 Excellent

Neile M.

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
Verified review

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

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