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2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free

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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.
The spacious living room includes a Queen sleeper sofa.
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.

Reviews

9.8 out of 10
Exceptional
2 bedrooms1+ bathroomSleeps 6109.3 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Explore the area

View map
Annapolis, MD
  • Place, Annapolis Maritime Museum
    ‪6 min walk‬
  • Place, U.S. Naval Academy
    ‪12 min walk‬
  • Place, Annapolis City Dock
    ‪14 min walk‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪40 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Front Queen Bedroom

1 Queen Bed

Garden-facing Bedroom

1 Queen Bed

Living Room

1 Queen Sofa Bed

1 bathroom, 1 half bathroom

2nd Floor Full Bath

Toilet · Shower only

Main Floor Powder Room

Toilet

Spaces

Deck or patio
Kitchen
Number of living rooms

About this property

2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free

Experience the Difference: Professionally Managed by iTrip Annapolis

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

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
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

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 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. 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.
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Map
Annapolis, MD

What's nearby

  • Annapolis Harbor - 2 min walk - 0.2 km
  • Annapolis Maritime Museum - 6 min walk - 0.6 km
  • U.S. Naval Academy - 12 min walk - 1.1 km
  • Annapolis City Dock - 14 min walk - 1.2 km
  • Maryland State House - 17 min walk - 1.5 km

Getting around

  • Odenton Station - 24 min drive
  • Fort Meade, MD (FME-Tipton) - 36 min drive

Restaurants

  • ‪The Choptank - ‬15 min walk
  • ‪Carrol's Creek Cafe - ‬4 min walk
  • ‪Boatyard Bar & Grill - ‬3 min walk
  • ‪O'Brien's Oyster Bar & Seafood Tavern - ‬16 min walk
  • ‪Royal Farms - ‬6 min walk

Frequently asked questions

Is 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free pet-friendly?

No, only service animals are welcome at the property.

How much does it cost to stay at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?

As of 23 April 2026, prices found for a 1-night stay for 2 adults at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free on 11 August 2026 start from NZ$784, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?

On-site parking is available at the property.

What time is check-in at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?

Check-in begins at 4:00 PM.

What time is check-out at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?

Checkout is at 11:00 AM.

Where is 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free 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

9.8

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

9.0/10

Cleanliness

9.6/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

R L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home was very clean, in a great area and check-in/access was no issue at all. Would recommend.
Stayed 2 nights in Mar 2026
From a partner site

10/10 Excellent

Sara S.

Eastport Charm

We visited Annapolis for a long weekend and stayed at "Third times the charm" in Eastport. It was very spacious for our family of four. We loved the backyard and firepit. The location is perfect- close to our favorite restaurant Boatyard- and several playgrounds for the kids. Check-in/out instructions were straightforward.
Verified

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
Response from VrboOwner on 3 December 2024
Hi Tayla! Thank you for allowing us to host your stay & we are thrilled to know you enjoyed your time in the home! We welcome you back anytime, Melissa~iTripAnnapolis
Verified

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
Response from VrboOwner on 7 February 2025
Hi Jeannie- thank you for staying with us & we hope to be able to show you a 5 star stay in the future! Melissa~iTripAnnapolis
Verified

10/10 Excellent

Lynne P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and a clean, well-appointed house. Iconic Eastport neighborhood.
Stayed 2 nights in Apr 2026
Response from VrboOwner on 13 April 2026
Thanks, Lynne! So glad you enjoyed everything. We hope to host you again next time you’re in Annapolis. Sean, iTrip Annapolis
From a partner site

10/10 Excellent

Great Stay

Nice location for the boat show. We enjoyed the back deck. The interior was comfortable and the kitchen was fully equipped. The property was clean and the management had good communication. Thank you.

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
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