Entire home

Holiday & Military Bowl Promo: 10% Off Stays through Jan 3, 2026

Holiday home with kitchen, 3-minute walk to U.S. Naval Academy

Photo gallery for Holiday & Military Bowl Promo: 10% Off Stays through Jan 3, 2026

Gather around the spacious family room that greets you inside the Cedar House on East.
The table is set and ready for you to host your family, friends or Naval Academy Midshipman.
The main floor full kitchen has been beautifully updated.
This sunny guest room is one of the two King Suites in the home.
The street view of this storied Historical Cedar Home.

Reviews

10 out of 10
Exceptional
3 bedrooms3+ bathroomsSleeps 8

Popular amenities

  • Barbecue grill
  • Washer
  • Dryer
  • Kitchen
  • Outdoor space
  • Free WiFi

Explore the area

View map
Annapolis, MD
  • Place, Annapolis City Dock
    ‪2 min walk‬
  • Place, U.S. Naval Academy
    ‪2 min walk‬
  • Place, Maryland State House
    ‪3 min walk‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪32 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

2nd Floor King Suite

1 King Bed

2nd Floor Queen

1 Queen Bed

Main Floor Family Room

1 Double Sofa Bed

Top Floor King Suite

1 King Bed

3 bathrooms, 1 half bathroom

2nd Floor Hall Full

Bathtub or shower · Toilet

2nd Floor Suite Full

Toilet · Shower only

3rd Floor Full

Bathtub or shower · Toilet

Main Floor Powder Room

Toilet

Spaces

Kitchen
Separate dining area
Garden
Dining area

About this property

Holiday & Military Bowl Promo: 10% Off Stays through Jan 3, 2026

Experience the Difference: Professionally Managed by iTrip Annapolis
Step into Annapolis history at this beautifully restored three-story cedar home. Built in the late 18th century, this property is recognized in the Historic District’s National Registry as one that “embodies the distinctive characteristics of a period.” Over the centuries, it has served as a shoemaker’s store, an inn, and the residence of an Italian immigrant who played in the U.S. Naval Academy band. Later converted into three apartments, the home was thoughtfully restored in the 1970s and newly-renovated into the elegant single-family dwelling it is today.

Main Level Living
Enter through the front door to a spacious family room, perfect for relaxing after a day of exploring downtown Annapolis. With a plush queen sleeper sofa and a large flatscreen TV, this room doubles as a cozy gathering space or extra sleeping option. Original wood floors run throughout, creating warmth and character. The Main level, and all 3 bedrooms, each have their own flatscreen TV.

The adjoining dining room features a restored built-in hutch and seating for six. The full kitchen is stocked with everything needed for preparing meals at home, while a convenient powder room completes the main floor. From the kitchen, step outside to the fenced-in backyard with Adirondack chairs and a propane grill—an intimate spot for morning coffee or evening cookouts. The home is located just a 2-minute walk to City Dock, Main Street, State Circle, and the Naval Academy entrance.

**Parking is not on premises!! A dedicated parking spot at nearby garage (15-minute walk from the house) is provided. Please contact us for details.

SLEEPING ARRANGEMENTS 3 BR / 3.5 BA / Sleeps 8:
Top Floor King Suite:
King Bed
Ensuite Full Bath with double vanity, shower/bathtub combo and walk-in closet

2nd Floor King Suite:
King Bed
Ensuite Full Bath with stand-up shower

2nd Floor Queen Guestroom
Queen Bed
Full Bath in the Hall with shower/bathtub combo

Main Level
Full Sleeper Sofa
Powder room on Main Floor and shared Full Bath in the Hall on the 2nd Floor

Amenities & Highlights
Private fenced yard with Adirondack seating and propane grill
Fully equipped kitchen
Dining table with seating for 6
WiFi & big screen TVs in every bedroom and the Family Room
Luxury linens & complimentary starter toiletries
Washer & dryer inside the home
Contactless check-in via coded front door entry
Non-smoking property

Property Distance to:
- U.S. Naval Academy – 2 blocks
- Washington, DC – 30 miles
- Baltimore - 25 miles
***************
*Amenity & Supplies starter pack, coffees and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid.
* All beds are ready made for you with freshly laundered sheets & towels.

House Rules
Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Please respect the neighbors and neighborhood.
Check-in time: 4:00 pm
Check-out time: 11:00 am

Blending centuries-old charm with modern amenities, this property offers the ideal downtown Annapolis getaway—whether you’re visiting for the Naval Academy, a weekend retreat, or a family celebration.

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 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

Located in Historic District, a neighbourhood in Annapolis, this holiday home is near theme parks. The area's natural beauty can be seen at Sandy Point State Park and Smithsonian Environmental Research Center, while The Colonial Players and Hammond-Harwood House are cultural highlights. Looking to enjoy an event or a game while in town? See what's happening at Alumni Hall or Navy-Marine Corps Memorial Stadium. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Annapolis, MD

What's nearby

  • William Paca House - 1 min walk - 0.0 km
  • Annapolis City Dock - 2 min walk - 0.2 km
  • U.S. Naval Academy - 2 min walk - 0.2 km
  • Maryland State House - 3 min walk - 0.3 km
  • St. John's College - 3 min walk - 0.3 km

Getting around

  • Odenton Station - 22 min drive
  • Fort Meade, MD (FME-Tipton) - 36 min drive

Restaurants

  • ‪The Choptank - ‬4 min walk
  • ‪Annapolis Market House - ‬3 min walk
  • ‪O'Brien's Oyster Bar & Seafood Tavern - ‬4 min walk
  • ‪Starbucks - ‬4 min walk
  • ‪Chick & Ruth's Delly - ‬4 min walk

Frequently asked questions

Is Holiday Promo: Get 10% Off Holiday Stays pet-friendly?

No, only service animals are welcome at the property.

What time is check-in at Holiday Promo: Get 10% Off Holiday Stays?

Check-in begins at 4:00 PM.

What time is check-out at Holiday Promo: Get 10% Off Holiday Stays?

Checkout is at 11:00 AM.

Where is Holiday Promo: Get 10% Off Holiday Stays located?

Located in Historic District, this holiday home is within a 5-minute walk of John Smith House and U.S. Naval Academy. William Paca House and The Colonial Players are just steps away.

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. 2 out of 2 reviews
Rating 8 - Good. 0 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

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Cheryl J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Comfy, clean, and great location to walk to everything.
Stayed 4 nights in Oct 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Amazing new spot in DTA!

Thank you for a wonderful stay this long weekend! Bedrooms were well appointed, and the home had plenty of space to relax and enjoy the beautiful weather! The welcome box included all the essentials for a good start to our stay- it’s all in the details! The location of this property is PERFECT for a Midshipman visit, Navy football game, or just strolling on Main Street!

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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