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All Newly-Designed Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis

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Welcome to First Mate! Park, drop your bags and head out to the lively Eastport neighborhood full of restaurants, pubs and the sailing lifestyle.
The combo living room and family room has a gas fireplace (with remote) and flatscreen TV.
The gourmet kitchen sits at the center of the home.
Wake up with water views from the 3rd floor King suite.
Enjoy your morning coffee from the front porch and watch the friendly neighbors go by.

Reviews

10 out of 10
Exceptional
3 bedrooms3+ bathroomsSleeps 12325.2 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Gym

Explore the area

View map
Annapolis, MD
  • Place, Annapolis Harbor
    ‪2 min walk‬
  • Place, Annapolis Maritime Museum
    ‪8 min walk‬
  • Place, U.S. Naval Academy
    ‪17 min walk‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪34 min drive‬

Rooms & beds

3 bedrooms (sleeps 12)

Family Bedroom

2 Queen Beds and 2 Single Beds

King Guest room

1 King Bed

King Suite

1 King Bed

Waterview Suite

1 King Bed

3 bathrooms, 1 half bathroom

Buddy Bath

Bathtub or shower · Toilet

Main Floor Powder Room

Toilet

Queen EnSuite

Bathtub or shower · Toilet

Waterview EnSuite

Bathtub · Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Number of living rooms

About this property

All Newly-Designed Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis

Experience the Difference: Professionally Managed by iTrip Annapolis

Welcome to your Eastport escape!



This newly decorated custom home has everything—Severn River views, a huge private yard, stylish interiors, and parking for 2–3 cars. Just a short mile’s walk to Downtown Annapolis, the Naval Academy, and Eastport’s best dining and shopping, you’ll be perfectly positioned for relaxation and adventure.



Main Features

Main Floor

Gourmet kitchen with high-end appliances

Open dining & family room with cozy gas fireplace

Walk out to deck, backyard with fire pit & gas grill



Second Floor

King suite with ensuite private bath + balcony



King Guest room with balcony

Family bedroom: 2 Queens + 2 Twin trundles

Shared buddy bath with double vanities, shower + soaking tub



Third Floor

Private King suite with spa-like en-suite (shower + tub, double vanities)

Balcony with sweeping Severn River views



Highlights

Gourmet kitchen + dining for 6–8

Extra dining nook (seats 4)

Huge outdoor lounge + dining space

Gas grill + wood-burning fire pit (BYO firewood)

Balconies off back bedrooms

Driveway parking for 2–4 cars + free street parking

High-speed WiFi + smart TVs

Luxury linens & toiletries

Washer/dryer

Keyless entry + mobile app instructions



Close to Everything

Downtown Annapolis – 0.9 mi

U.S. Naval Academy – 1 mi

Washington, DC – 33 mi

Baltimore – 33 mi



House Rules

No groups under 25 without adult present

No smoking, pets, parties, or events

Please respect the neighbors

Check-in: 4:00 PM

Check-out: 11:00 AM

Add dates for prices

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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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Annapolis

Eastport, a neighbourhood in Annapolis, is home to this holiday home. Annapolis Maritime Museum and French Soldiers Monument are local attractions and those in the mood for shopping can visit Annapolis City Dock and Bay Bridge Market Place Shopping Center. Helen Avalynne Tawes Garden and Maryland Hall for Creative Arts 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 - 8 min walk - 0.7 km
  • U.S. Naval Academy - 17 min walk - 1.5 km
  • Annapolis City Dock - 19 min walk - 1.6 km
  • Maryland State House - 3 min drive - 1.8 km

Getting around

  • Odenton Station - 25 min drive
  • Fort Meade, MD (FME-Tipton) - 36 min drive

Restaurants

  • ‪The Choptank - ‬17 min walk
  • ‪Carrol's Creek Cafe - ‬6 min walk
  • ‪Boatyard Bar & Grill - ‬5 min walk
  • ‪O'Brien's Oyster Bar & Seafood Tavern - ‬19 min walk
  • ‪Royal Farms - ‬10 min walk

Frequently asked questions

Is All Newly-Designed Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis pet-friendly?

No, only service animals are welcome at the property.

How much does it cost to stay at All Newly-Designed Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis?

As of 8 Apr 2026, prices found for a 1-night stay for 2 adults at All Newly-Designed Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis on 26 May 2026 start from AU$1,247, 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 All Newly-Designed Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis?

On-site parking is available at the property.

What time is check-in at All Newly-Designed Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis?

Check-in begins at 4:00 PM.

What time is check-out at All Newly-Designed Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis?

Checkout is at 11:00 AM.

Where is All Newly-Designed Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis located?

Located in Eastport, this holiday home is within a 5-minute walk of Annapolis Harbor and U.S. Naval Academy. Annapolis Maritime Museum and Spa Creek are also within 10 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 3 out of 3 reviews
Rating 8 - Good. 0 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

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Lyle B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Walking distance to restaurants
Stayed 2 nights in Oct 2025
Response from VrboOwner on 12 Nov 2025
Thanks, Lyle! We’re delighted to hear that First Mate's location was convenient for walking to restaurants. We hope you enjoyed exploring the local dining options and had a fantastic stay. We look forward to welcoming you back for another visit!
From a partner site

10/10 Excellent

Rich W.

Great Stay!

Nothing but great things to say about our stay at First Mate. From the initial experience with the team at iTrip to the property, A+. The location is terrific, not just for Eastport, but a simple walk to downtown Annapolis. The house was super clean, modern, parking for multiple cars, balconies overlooking the water, you name it! We wish we could have stayed longer to enjoy the full property (e.g. Firepit). We will certainly look to stay again, if it is ever available again!
Response from VrboOwner on 21 Oct 2025
Thanks, Rich! We’re thrilled to hear that First Mate impressed you with its terrific location, cleanliness, and modern amenities. It’s wonderful to know that you found the house perfect for your needs, with parking for multiple cars and balconies overlooking the water. We’re glad you had a great experience with our team at iTrip and that you enjoyed your stay in Eastport and downtown Annapolis. We hope to host you again next time you’re in town—hopefully, you’ll have more time to enjoy the firepit and everything else the property has to offer! Melissa~iTrip Annapolis
Verified

10/10 Excellent

Sheryl M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
House was very clean. On-site parking is a , as is the yard which includes a fire pit, grill, and outdoor seating!
Stayed 4 nights in Mar 2026

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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