Prime Location! Modern Comfort 1 Block to Gate 1 w/ Parking & Walkability

Annapolis, Maryland
$1090 avg/night Minimum Stay 2 Nights
Bed 3

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 12

Max Sleeps

Night 2 nights

Min Stay

Experience the Difference: Professionally Managed by iTrip Annapolis

Welcome to Modern Elegance in Historic Annapolis

Step into this fully-renovated 1900s home, where modern sophistication meets timeless charm. Lovingly restored, this home offers parking for two cars (or one SUV)—a rare luxury in the heart of downtown Annapolis. Owned by four Naval Academy graduates—three U.S. Marines and one Navy nuclear surface warfare officer—this property stands as a tribute to the enduring bond they forged as members of the Academy's 14th Company and their decade of service to our nation. You’ll feel their legacy of camaraderie and commitment the moment you arrive.



Nestled on one of Annapolis's most picturesque streets, the home is just a block from the Naval Academy's main entrance. The inviting front porch is the perfect perch to soak in the vibrant energy of historic downtown Annapolis, creating a seamless connection between the home and the community’s storied past.



The interior boasts an elegant Great Room with a custom entertainment bar, open dining area, and Naval Academy-inspired decor that sets the tone for your stay. The gourmet kitchen is a chef’s dream, with seating at the breakfast bar for casual gatherings. With spacious accommodations for up to 11 guests, including a stunning top-floor suite, the home caters to families and groups seeking both comfort and style.



Whether visiting for a Naval Academy event, the boat show, or simply to explore Greater Annapolis, this home puts you steps away from local attractions, restaurants, and shops. From relaxing mornings on the front porch to evenings exploring the waterfront, your stay promises to be unforgettable.



Sleeping Arrangements: 4 BR / 2 BA / Sleeps 11

Main Bedroom 1 (2nd Floor): Queen Bed

Main Bedroom 2 (2nd Floor): Queen Bed

Guest Bedroom (2nd Floor): Two Twin Beds

3rd Floor Suite: Open sleeping/living space with 5 Twin Beds



Highlights

Front Porch: New furniture for lounging and enjoying the lively neighborhood views

Custom Bar: Seats 4-5 for entertaining

Gourmet Kitchen: Fully equipped with seating for 4 at the breakfast counter

Dining Area: Accommodates 6-8 guests

Modern Amenities: WiFi, smart TVs, luxury linens, and a boutique-level starter kit

Convenience: Keyless entry, laundry facilities

Parking: Space for 2 cars or 1 SUV

Important Notes

Guests must be 25+ years of age or accompanied by an adult.

No smoking, pets, parties, or events are allowed.

The steep staircase may not suit guests with mobility issues; please inquire if needed.



Distance to Nearby Attractions

U.S. Naval Academy: 1 block

Washington, D.C.: 30 miles

Baltimore: 25 miles



Amenities & Services

Start your stay worry-free with our complimentary starter pack, including coffee, toiletries, and household essentials. All beds come pre-made with freshly laundered linens, ready to welcome you home.



This home promises the perfect blend of history, luxury, and convenience, making it an ideal retreat for your Annapolis adventure.

Read More Expand
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided
  • GENERAL

    Energy-saving Switches Recycling Unit Size: 2196 Sq Ft (204 Sq M) Uses Some LED Lighting
  • KITCHEN

    Blender Cookware/dishes/utensils Dishwasher Electric Kettle Ice Maker Microwave Oven Refrigerator Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Patio
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Hair Dryer Shampoo Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • ENTERTAINMENT

    Smart TV
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Games
  • LOCATION HIGHLIGHTS

    In The City Center
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 12

Map Map

School District Availability

Review Review

  • Melissa S.

    Submitted Feb 18, 2026

    Stayed Feb 13, 2026

    The house was adorable, clean and super comfortable! We loved having onsite parking for 2 cars. The location to downtown Annapolis was amazing.

  • Krista K.

    Submitted Nov 30, 2025

    Stayed Nov 25, 2025

    Perfect location for a Thanksgiving holiday with the whole family!

  • Paula O.

    Submitted Nov 16, 2025

    Stayed Nov 13, 2025

    Awesome location to walk everywhere! It’s a great set up for watching games and having family fun!

  • Cindy H.

    Submitted Oct 7, 2025

    Stayed Oct 2, 2025

    Third time to stay here. We are always pleased.

  • Joseph W.

    Submitted Sep 22, 2025

    Stayed Sep 19, 2025

    Great stay, everything was easy, great communication. Really no outdoor hangout space though, which was one of the features we wanted and pics and description led us to think there was one. Also no grill, the app had a grill section but there was no grill. Other than that it was fantastic.

  • mike j.

    Submitted Aug 18, 2025

    Stayed Aug 16, 2025

    We stayed here in Annapolis to be near family for my Father's burial monday in Arlington National Cemetery. 50 plus family members here from around the country. Very emotional and meaningful trip. Our stay at Anchor at Annapolis Inn was outstanding. Accomodations were great and location across from Naval Academy and 2 blocks from downtown was outstanding. We would stay here again in a heartbeat. Great Experience.

  • Chris and Amy H.

    Submitted Jul 24, 2025

    Stayed Jul 18, 2025

    The best part of this place was the location. Directly located outside Gate 1. We do not recommend staying here in the summer. The AC does not work well in this house. The house was extremely uncomfortable. Not one of our guests slept the four days we were there. The air conditioning would not go below 76. Not only was the air conditioning not sufficiently cooling, but it also was either changed remotely or set to a schedule that would unexpectedly turn the cooling off. To pay for that much for a house in Annapolis in July and not have a properly functioning HVAC system is unacceptable. The cleanliness of the property was unsatisfactory. The wall and air vents haven’t been cleaned in a long time. You could see the layer of dirt. The property was supposed to have a keruig, which we eventually found in the laundry room and needed to be cleaned thoroughly before use.Before leaving a review we brought up our issues with the owner but they were not willing to do anything for us because we didn’t complain to them over the weekend.

  • Brian S.

    Submitted Jun 29, 2025

    Stayed Jun 24, 2025

    Perfect location in DTA. Nice to have parking in back of property. We were able to walk to everything. We were in town for our son’s Naval Academy Induction Day. Gate 1 of USNA is an easy 5 minute walk. Property is great if you have a group. Wide open sitting area in Bar/TV room. Property manager was very attentive and quick to respond. Would highly recommend, and we will likely look to stay here on future visits.

  • Submitted Apr 27, 2025

    Stayed Apr 25, 2025

    Great location to the academy and shopping

  • Michael C.

    Submitted Apr 7, 2025

    Stayed Mar 19, 2025

    This home is in a spectacular location in a spectacular town and truly is a great place to host family and friends. Our friend group (8 college classmates just over 60 years old) gathered for our traditional opening weekend of March Madness. The home has an AWESOME bar and great room where we could all gather to watch all the basketball games (something we have done for the past 40 years). And when we weren't watching basketball, we toured the Naval Academy, the local sites, the Annapolis Yacht Club - all within walking distance. So - what needs to be upgraded?1. Most folks won't go to Annapolis to watch television, but we did, and the television in the great room was not working - and the tech manager couldn't figure it out. We gerry-rigged it but the technology needs to be upgraded so that it is more easily useable. (The online guide was lacking.). And the TV in the kitchen wasn't working.2. It would be great if the house had a grill!! Again, we made do (by borrowing the neighbor's grill) but a simple grill would really enhance the experience.3. Paper products. We had two rolls of toilet paper - for 8 guys over 5 days (4 nights) - and one roll of paper towels. Hoping that this was an oversight and not a purposeful practice.Again, these are issues that can easily be addressed and corrected. Otherwise, it was a FABULOUS experience - many thanks for hosting us!!

  • Brian D.

    Submitted Mar 17, 2025

    Stayed Mar 6, 2025

    Location was great for our needs House met all our needs and was very clean and very welcoming

  • Jimmy C.

    Submitted Dec 29, 2024

    Stayed Dec 27, 2024

    Fantastic property, amenities and most if all location, location, location!

  • George C.

    Submitted Dec 25, 2024

    Stayed Dec 12, 2024

    This was the perfect place for my group to stay while visiting for the Army Navy weekend. We had 6 adults and 2 teens and the location within walking distance of both downtown and the Yard were ideal for everyone to sightsee. The house was clean and well maintained, and the first floor (living room/bar/kitchen) made a great place for the group to gather and cook meals. I’d definitely recommend this him and stay here again.

  • Michael S.

    Submitted May 28, 2024

    Stayed Dec 31, 1969

    Stayed here for a week and strongly recommend without reservation. Location is great to get on the yard and to be in DTA. Place was very clean, well represented per the listing and communication was appropriate. Sleeps 11 very comfortably, everything worked and my family was very happy!

Your dates are Available!

Total

Includes taxes and fees
$1,090+
View details