Entire home

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

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Fridge, microwave, dishwasher, coffee/tea maker - 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free (Annapolis)
Experience the charm of Eastport at Third Time's the Charm, where a beautifully manicured backyard with a firepit and private deck invites relaxation. Enjoy luxury linens, stainless-steel appliances, and dedicated workspace within this comfortable home.

Reviews

9.4 out of 10
Exceptional

Entire home

3 bedrooms2 bathrooms1176 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space

Add dates for prices

About this property

Entire place

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

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

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • No onsite parking available

Kitchen

  • Coffee/tea maker
  • Dishwasher
  • Microwave
  • Refrigerator

Bedrooms

  • 3 bedrooms

Bathroom

  • 1.5 bathrooms
  • Hair dryer
  • Shampoo
  • Shower

Living spaces

  • Living room

Entertainment

  • TV

Outdoor areas

  • Barbecue grill
  • Firepit
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Service animals only (pets not allowed)

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: 1,176 square feet

Similar properties

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 not 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
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 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

Property is also known as

15336

About the area

Eastport, a neighborhood in Annapolis, is home to this vacation 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 Maryland Hall for Creative Arts are also worth visiting. Visit our Annapolis travel guide
View more Vacation homes in Annapolis
Map
Annapolis, MD

What's nearby

  • U.S. Naval Academy featuring military items, interior views and heritage architecture
    U.S. Naval Academy
    12 min walk - 1.1 km
  • Maryland State House
    Maryland State House
    17 min walk - 1.5 km
  • Annapolis Harbor
    2 min walk - 0.2 km
  • Annapolis Maritime Museum
    6 min walk - 0.6 km
  • Annapolis City Dock
    14 min walk - 1.2 km

Getting around

  • 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
  • Buddy's Crabs & Ribs
    16 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 is parking?

This property doesn't offer parking.

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?

Check-out is at 11:00 AM.

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

Located in Eastport, this vacation 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.

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

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 2 out of 3 reviews
Rating 8 - Good. 1 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

8.0

Cleanliness

10

Location

Reviews

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

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
This review is from a guest who booked and stayed through a partner site and can't be verified.

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.