Entire home

Book for CW 2025 Steps from marinas and restaurants at Eastport Third Time's the Charm

Photo gallery for Book for CW 2025 Steps from marinas and restaurants at Eastport Third Time's the Charm

Welcome to Third Time's the Charm, located in Eastport on Third Street, just steps from restaurants and marinas.
Enjoy family time in the private backyard.
View of the breakfast bar in the kitchen with seating for 4.
There are 2 Queen bedrooms in the home on the 2nd floor with a full bath in the hall.
The spacious living room includes a Queen sleeper sofa.

Reviews

9.0 out of 10
Wonderful
2 bedrooms1+ bathroomSleeps 6

Popular amenities

  • Dryer
  • Washer
  • Kitchen
  • Barbecue grill
  • Outdoor space
  • Air conditioning

Explore the area

Map
Annapolis, MD
  • Annapolis City Dock
    ‪16 min walk‬
  • U.S. Naval Academy
    ‪19 min walk‬
  • Navy-Marine Corps Memorial Stadium
    ‪4 min drive‬
  • Annapolis, MD (ANP-Lee)
    ‪20 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Front Queen Bedroom

1 Queen Bed

Garden-facing Bedroom

1 Queen Bed

Living Room

1 Double Sofa Bed

1 bathroom, 1 half bathroom

2nd Floor Full Bath

Toilet · Shower only

Main Floor Powder Room

Toilet

Spaces

Deck or patio
Kitchen
Separate dining area
Garden
Dining area

About this property

Book for CW 2025 Steps from marinas and restaurants at Eastport Third Time's the Charm

Still available for Commissioning Week 2025!

Eastport's Third Time's the Charm – Steps from Marinas, Dining, and Historic Annapolis
This beautiful home is located in Eastport, just across the Spa Bridge from Historic Annapolis. Enjoy the convenience of walking to marinas, yacht clubs, restaurants, shops, and the new Eastport Brewpub. Take a stroll along the waterfront or use the water taxi to explore the harbor.

Interior Features:
Living Room: Relax in the comfortable living room with hardwood floors and a flat-screen TV.
Kitchen & Dining: The recently renovated open kitchen features a breakfast bar, adjacent dining area, and sliding glass doors leading to a large deck.
Outdoor Space: Enjoy the manicured backyard, complete with a private deck, patio, firepit, and cornhole set.

Bedrooms:
Two Queen Bedrooms, each Sleeps 2, on the second floor with luxury bedding, sharing the full bath.
Additional Sleeping Arrangements: Queen sleeper sofa in Living room

Highlights:
Private fenced backyard, patio deck and covered front porch
Firepit with Adirondack chairs and cornhole
Gas grill (propane included)
Stainless-steel appliances including beverage fridge
WiFi, big-screen TV, and luxury linens
Dedicated work space
Starter pack of toiletries, cleaning supplies, and essentials
Washer & dryer

U.S. Naval Academy: 1.5 miles
Washington, D.C.: 30 miles
Baltimore: 25 miles

House Rules:
No smoking, parties, pets or events
Must be 25+ to book
Check-in: 4:00 pm | Check-out: 11:00 am

Property manager

iTrip Vacations Annapolis - Sean Degnan
Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Free WiFi
Air conditioning
Outdoor space

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House Rules

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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed, service animals permitted
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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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property

About the area

Annapolis

Eastport, a neighbourhood in Annapolis, is home to this holiday home. The area's natural beauty can be seen at Jonas Green State Park and Sandy Point State Park, while Annapolis Maritime Museum and The Colonial Players are cultural highlights. French Soldiers Monument and Helen Avalynne Tawes Garden are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Annapolis, MD

What's nearby

  • Annapolis Maritime Museum - 7 min walk - 0.6 km
  • Annapolis City Dock - 16 min walk - 1.4 km
  • U.S. Naval Academy - 19 min walk - 1.6 km
  • William Paca House - 19 min walk - 1.7 km
  • Navy-Marine Corps Memorial Stadium - 4 min drive - 3.7 km

Getting around

  • Odenton Station - 25 min drive
  • Fort Meade, MD (FME-Tipton) - 35 min drive

Restaurants

  • ‪The Choptank - ‬15 min walk
  • ‪O'Brien's Annapolis' Original Steakhouse - ‬17 min walk
  • ‪Mc Garvey's Saloon - ‬17 min walk
  • ‪Chipotle Mexican Grill - ‬16 min walk
  • ‪Boatyard Bar & Grill - ‬3 min walk

Frequently asked questions

Is Book for CW 2025 Steps from marinas and restaurants at Eastport Third Time's the Charm pet-friendly?

No, only service animals are welcome at the property.

Where is Book for CW 2025 Steps from marinas and restaurants at Eastport Third Time's the Charm located?

Located in Eastport, this holiday home is within 1 mi (2 km) of Annapolis Harbor and U.S. Naval Academy. Annapolis Maritime Museum and Spa Creek are also within 10 minutes.

Reviews

9.0

Wonderful

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. 1 out of 2 reviews
Rating 8 - Good. 1 out of 2 reviews
Rating 6 - Okay. 0 out of 2 reviews
Rating 4 - Poor. 0 out of 2 reviews
Rating 2 - Terrible. 0 out of 2 reviews

8.0/10

Cleanliness

9.0/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

8/10 Good

Jeannie M.

Liked: Check-in, communication, location, listing accuracy

Eastport Property

There was trash in upstairs bathroom and insects flying about in living room that we were able to kill with rolled up paper towels.
Stayed 3 nights in Dec 2024

10/10 Excellent

Talya M.

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

great stay

really cute space, great area walking distance to main st in annapolis
Stayed 2 nights in Nov 2024

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests