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Historic Eastport! Steps from restaurants, retail, and more.

Photo gallery for Historic Eastport! Steps from restaurants, retail, and more.

A waterfront view with a prominent building with a dome, a marina with boats, and a modern building with a glass roof.
A waterfront building named 'Chart House' with large windows and a flat roof, surrounded by boats.
A modern kitchen with white cabinets, a stainless steel refrigerator, a central island with stools, and pendant lighting.
A modern kitchen with a central island, bar stools, and a dining area with a leather sofa and coffee table.
A teal building with a black awning labeled "O'LEARY'S SEAFOOD".

Reviews

10 out of 10
Exceptional

Highlights

  • Family fun awaits
    Top-rated for families.
  • Ping pong onsite
    A rare find — challenge friends and family to endless matches.
  • Discover nearby landmarks
    Walk to William Paca House
4 bedrooms4 bathroomsSleeps 10

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
    ‪6 min walk‬
  • Place, Annapolis City Dock
    ‪17 min walk‬
  • Place, U.S. Naval Academy
    ‪18 min walk‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪40 min drive‬

Rooms & beds

4 bedrooms (sleeps 10)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Beds

Bedroom 4

1 Queen Bed

Living Room 1

1 Double Sofa Bed

4 bathrooms

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Bathroom 3

Soap · Towels provided · Toilet · Shower only · Shampoo

Bathroom 4

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Kitchen
Separate dining area
Number of living rooms
Dining area

About this property

Historic Eastport! Steps from restaurants, retail, and more.

Virtual tour: https://cquh.short.gy/eastportretreat

Welcome to our charming Eastport retreat in Annapolis, Maryland – where historic charm meets modern comfort! Nestled in the heart of the maritime district, our VRBO promises an unforgettable stay surrounded by nautical vibes, vibrant culture, and a welcoming community. Situated just steps away from the scenic shores of the Chesapeake Bay, stroll into downtown Annapolis, where you'll discover renowned restaurants, quaint boutiques, and historic landmarks like the U.S. Naval Academy.

Step into our thoughtfully decorated space that seamlessly combines contemporary amenities with coastal-inspired decor. The cozy living area invites you to unwind after a day of exploration, complete with plush furnishings and maritime accents. The fully equipped kitchen beckons culinary enthusiasts to whip up a delicious meal using local ingredients or simply enjoy a morning coffee in the private backyard.

The bedrooms boast comfortable beds dressed in crisp linens, ensuring a restful night's sleep. Immerse yourself in the coastal ambiance of the tastefully decorated space.

Explore Eastport's unique character by taking a leisurely stroll along the waterfront, where sailboats sway in the gentle breeze. Indulge in the culinary scene with a variety of seafood restaurants, local pubs, and charming cafes, each offering a taste of the Chesapeake Bay's bounty. Just steps to Boatyard Bar & Grill, Forward Brewing, O'Learys Seafood, Lewnes Steakhouse, Chart House, Ruth's Chris, Annapolis Canoe and Kayak Rentals, Annapolis Pirate Adventures, and more!

For history buffs, the historic district of Annapolis is a short walk away, showcasing colonial architecture, museums, and the iconic Naval Academy. Don't miss the opportunity to take a boat tour or catch a water taxi to experience the city from a different perspective.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 3:00 PM
Minimum age to rent: 18
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: limit 2 total
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Smoking

Smoking is not permitted
No bachelor or bachelorette parties.
No guns, drugs, or illegal substances. No smoking on the property.
Quiet hours: 9pm-8am

Important information

You need to know

Property # 3795169vb
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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

About the area

Annapolis

Eastport, a neighbourhood in Annapolis, is home to this holiday home. Kunta Kinte Plaque & Alex Haley Memorial and John Smith House are local landmarks, and travellers looking to shop may want to visit Annapolis City Dock and Bay Bridge Market Place Shopping Center. Travelling with kids? Consider Annapolis Maritime Museum, or check out an event or a game at Tose Family Tennis Center.
View more Holiday homes in AnnapolisOpens in a new window
Map
Annapolis, MD

What's nearby

  • Annapolis Harbor - 3 min walk - 0.3 km
  • Annapolis Maritime Museum - 6 min walk - 0.6 km
  • Annapolis City Dock - 17 min walk - 1.5 km
  • U.S. Naval Academy - 18 min walk - 1.6 km
  • Maryland State House - 20 min walk - 1.7 km

Getting around

  • Odenton Station - 24 min drive
  • Fort Meade, MD (FME-Tipton) - 32 min drive

Restaurants

  • ‪The Choptank - ‬16 min walk
  • ‪Starbucks - ‬19 min walk
  • ‪Boatyard Bar & Grill - ‬4 min walk
  • ‪Carrol's Creek Cafe - ‬6 min walk
  • The Red Bean

Frequently asked questions

Is Historic Eastport! Steps from restaurants, retail, and more. pet-friendly?

Yes, this property allows pets (limit 2 total).

How much is parking at Historic Eastport! Steps from restaurants, retail, and more.?

On-site parking is available at the property.

What time is check-in at Historic Eastport! Steps from restaurants, retail, and more.?

Check-in begins at 3:00 PM.

What time is check-out at Historic Eastport! Steps from restaurants, retail, and more.?

Checkout is at 11:00 AM.

Where is Historic Eastport! Steps from restaurants, retail, and more. located?

Located in Eastport, this family-friendly Annapolis holiday home is within a 10-minute walk of Annapolis Harbor, Annapolis Maritime Museum and Spa Creek. U.S. Naval Academy is 1.3 mi (2.1 km) away.

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. 9 out of 9 reviews
Rating 8 - Good. 0 out of 9 reviews
Rating 6 - Okay. 0 out of 9 reviews
Rating 4 - Poor. 0 out of 9 reviews
Rating 2 - Terrible. 0 out of 9 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Caroline J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

great location

We really enjoyed our stay here. We were in town for our daughter's wedding at the Maritime Museum. The house and its location were perfect.
Stayed 2 nights in Oct 2024
Verified review

10/10 Excellent

Michael M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great accomodation

This is a wonderful home with all the amenities you can imagine. I would highly recommend this property for a great stay.
Stayed 6 nights in Apr 2024
Verified review

10/10 Excellent

Gosia H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family reunion

Great location, beautiful home, and easy communication with the owners. Highly recommend.
Stayed 2 nights in Jun 2024
Verified review

10/10 Excellent

Wayne F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent House

Location and house were super nice. Clean and updated. Great neighborhood. Owner was fantastic to work with. Highly recommend.
Stayed 3 nights in Dec 2024
Verified review

10/10 Excellent

Jeffrey G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

USNA Baseball Weekend

We really enjoyed our stay and the house was perfect for our family. All the amenities we needed were available and the hosts were very helpful and prompt when we had a question about the TV. We would definitely return in the future
Stayed 5 nights in Apr 2024
Verified review

10/10 Excellent

Colleen O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house is clean and well stocked. Beds clean and comfy. The kitchen is nice and has all you need to cook. Enough bedrooms to have privacy. Do not park in front of red lines on curb.
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

Keith Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cal 25 Nationals

Could not say enough on how ell we were taken care of nad every thing at the home was perfect
Stayed 5 nights in Sep 2024
Verified review

10/10 Excellent

Rhonda H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Feeling the Love at The Love Shack

Our family enjoyed our stay during our 5 day visit to Annapolis. We used all of the amenities and all of the spaces in this beautiful, well maintained and fully equipped home designed and dedicated to making guests feel welcome. ❤️
Stayed 4 nights in May 2024
Verified review

10/10 Excellent

Donna V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The location and layout of this home was absolutely perfect! Our family could walk to all the Eastport and Annapolis destinations which was very helpful as we were vacationing with a toddler. The home was clean, well-equipped and offered plenty of room to spread out and relax. The basement was a particular asset as different generations like to watch different TV shows at night. Loved the drop zone at the side door and the backyard offered shade in the afternoon for the little one to frolic in a little splash pool we brought with us. Would definitely stay here again!
Stayed 5 nights in Jul 2026

About the host

Hosted by Connor Bell

Host profile image
Welcome to our slice of paradise! We take immense pride and joy in welcoming guests to our cherished retreat. There's something truly magical about sharing our space with travelers from around the world, and we want to give you a glimpse into why hosting on VRBO has become such a rewarding and fulfilling experience for us.

First and foremost, hosting on VRBO allows us to open our doors to a diverse array of guests, each with their unique stories and backgrounds. The connections we've made with people from different corners of the globe have enriched our lives in ways we could have never imagined. From sharing local tips to learning about traditions and customs from our guests, the cultural exchange is a constant source of inspiration and a reminder of the beautiful tapestry that is the global community.

One of the key reasons we choose VRBO is the platform's commitment to providing a home away from home for travelers. As hosts, we share this ethos wholeheartedly. Our goal is to create a space where guests feel not only comfortable but also a sense of belonging. From the carefully curated decor to the thoughtful amenities, we strive to make our property a haven for those seeking refuge from the demands of daily life.

Why they chose this property

Explore Eastport's unique character by taking a leisurely stroll along the waterfront, where sailboats sway in the gentle breeze. Indulge in the culinary scene with a variety of seafood restaurants, local pubs, and charming cafes, each offering a taste of the Chesapeake Bay's bounty.

For history buffs, the historic district of Annapolis is a short walk away, showcasing colonial architecture, museums, and the iconic Naval Academy. Don't miss the opportunity to take a boat tour or catch a water taxi to experience the city from a different perspective.

What makes this property unique

Step into our thoughtfully decorated space that seamlessly combines contemporary amenities with coastal-inspired decor. The cozy living area invites you to unwind after a day of exploration, complete with plush furnishings and maritime accents. The fully equipped kitchen beckons culinary enthusiasts to whip up a delicious meal using local ingredients or simply enjoy a morning coffee in the private backyard.

The bedrooms boast comfortable beds dressed in crisp linens, ensuring a restful night's sleep. Immerse yourself in the coastal ambiance of the tastefully decorated space.

Just a short walk to Boatyard Bar & Grill, Forward Brewing, O'Learys Seafood, Lewnes Steakhouse, Chart House, Ruth's Chris, Annapolis Canoe and Kayak Rentals, Annapolis Pirate Adventures, and more!
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