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Historic Downtown Annapolis Gem Steps to USNA and Main St with Private Patio and Parking

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Welcome to the newly-decorated Historic Hideaway walking distance to USNA and Main Street.
Gather around one of the many multiple flat screen TVs in the home in the living room.
Soak up the sun on the fully-furnished private backyard patio.
Enjoy the dining room with the double-sided gas fireplace.
Head upstairs to the 3 bedrooms and 2 1/2 bathrooms.

Reviews

10 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 8

Popular amenities

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

Explore the area

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

Rooms & beds

3 bedrooms (sleeps 8)

Convertible Balcony Bedroom

1 Double Bed

Main Floor Den

1 Queen Sofa Bed

Master Suite

1 Queen Bed

Top Floor Queen

1 Queen Bed

2 bathrooms, 2 half bathrooms

2nd Floor En Suite

Toilet · Shower only

2nd Floor Hall

Bathtub or shower · Toilet

3rd Floor Powder Room

Toilet

Main Floor Powder Room

Toilet

Spaces

Deck or patio
Kitchen
Balcony
Number of living rooms

About this property

Historic Downtown Annapolis Gem Steps to USNA and Main St with Private Patio and Parking

Experience the Difference: Professionally Managed by iTrip Annapolis

Take a stroll along the brick-lined sidewalks of Prince George Street in the Historic District and to this fully-renovated late 1800s charmer with touches of historical elegance.



On the first level, relax in the large living room with a cozy double-sided gas brick fireplace that is open to the dining room. The upgraded kitchen with granite countertops and stainless steel appliances is fully-stocked for the gourmet chef. Cozy up in the back Den that doubles as a bedroom with a new pullout Queen sofa, a half-bath and a curtain to close for privacy.



Head upstairs to the 3 Queen bedrooms and 2.5 more baths. The en-suite Queen bedroom has a spa-like bathroom complete with a custom vanity and a relaxing steam shower. The second bedroom converts between a Full bed and a desk with great natural lighting and leads to the balcony that overlooks the St. Johns College front lawn and the beautiful USNA chapel. The third level has another private suite with a Queen bed a private powder room.



But what's really breathtaking is the backyard retreat: enjoy sitting around the fire pit on the Adirondak chairs, grilling and eating al fresco around the dining table for 6 or lounge on the cozy outdoor love seats and sofa. The location of this home is prime as you are within walking distance to everything Downtown Annapolis has to offer from entertainment, and beautiful water views, Naval Academy, St. Johns College, and the state capital building.



**Parking is not on premises!! A dedicated parking spot at nearby garage (10/15-minute walk) is provided. Please contact us for details.



SLEEPING ARRANGEMENTS 3 BR / 2 Full/2 Half Baths / Sleeps 8:

Master Bedroom with En-Suite Full Bath:

- Second Floor

- Queen Bed

- Custom spa shower walk-in shower with steam shower



Convertible Full Bedroom with Balcony:

- Second Floor

- Full bed that converts to a desk

- Private Balcony

- Full Bath in the Hall



3rd Floor Loft:

- Queen Bed

- Powder Room



Den/Bedroom

- Main floor

- Flatscreen TV

- Sofa Queen Bed

- Powder room

- Privacy curtain



HIGHLIGHTS:

- Spacious gourmet kitchen

- Gas fireplace

- Dining room table seats 6

- Eat-in kitchen seats 2

- Spacious outdoor living, dining and fire pit area.

- High-speed WiFi

- Weber BBQ propane Grill

- Big Screen Smart TVs

- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service

- Washer & dryer located inside the home

- One parking spot in off-site garage.

- Keyless entry. Drive straight to your rental home and enter the front door with an electronic lock code.



Property Distance to:

- U.S. Naval Academy – 3 blocks

- Washington, DC – 30 miles

- Baltimore - 25 miles



* Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going.

* 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 or pets. Please respect the neighbors and neighborhood. No parties or events of any kind.

Check-in time: 4:00 pm

Check-out time: 11:00 am

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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

Located in Annapolis, this holiday home is in the city centre. Chesapeake Bay and Jonas Green State Park reflect the area's natural beauty and area attractions include French Soldiers Monument and Helen Avalynne Tawes Garden. Looking to enjoy an event or a game while in town? See what's happening at Tose Family Tennis Center or Alumni Hall.
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Map
Annapolis, MD

What's nearby

  • Hammond-Harwood House - 2 min walk - 0.2 km
  • U.S. Naval Academy - 3 min walk - 0.3 km
  • William Paca House - 3 min walk - 0.3 km
  • Annapolis City Dock - 5 min walk - 0.4 km
  • Maryland State House - 5 min walk - 0.4 km

Getting around

  • Odenton Station - 21 min drive
  • Fort Meade, MD (FME-Tipton) - 25 min drive

Restaurants

  • ‪Starbucks - ‬6 min walk
  • ‪O'Brien's Oyster Bar & Seafood Tavern - ‬7 min walk
  • ‪Chick & Ruth's Delly - ‬5 min walk
  • ‪Annapolis Market House - ‬6 min walk
  • ‪Federal House - ‬6 min walk

Frequently asked questions

Is Historic Downtown Annapolis Gem Steps to USNA and Main St with Private Patio and Parking pet-friendly?

No, only service animals are welcome at the property.

How much does it cost to stay at Historic Downtown Annapolis Gem Steps to USNA and Main St with Private Patio and Parking?

As of 4 May, 2026, prices found for a 1-night stay for 2 adults at Historic Downtown Annapolis Gem Steps to USNA and Main St with Private Patio and Parking on 9 Aug, 2026 start from S$664, 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 Historic Downtown Annapolis Gem Steps to USNA and Main St with Private Patio and Parking?

On-site parking is available at the property.

What time is check-in at Historic Downtown Annapolis Gem Steps to USNA and Main St with Private Patio and Parking?

Check-in begins at 4:00 PM.

What time is check-out at Historic Downtown Annapolis Gem Steps to USNA and Main St with Private Patio and Parking?

Checkout is at 11:00 AM.

Where is Historic Downtown Annapolis Gem Steps to USNA and Main St with Private Patio and Parking located?

Located in Historic District, this holiday home is within a 5-minute walk of French Soldiers Monument and U.S. Naval Academy. St. John's College and Hammond-Harwood House 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. 24 out of 26 reviews
Rating 8 - Good. 2 out of 26 reviews
Rating 6 - Okay. 0 out of 26 reviews
Rating 4 - Poor. 0 out of 26 reviews
Rating 2 - Terrible. 0 out of 26 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Kirsten L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice family accommodations

Location and charm of this place was enjoyable, feel lucky to have found it!
Stayed 4 nights in Sep 2022
Verified

10/10 Excellent

Sierra M.

Liked: Cleanliness, check-in, communication, location

Great location

Great location if you want to be close downtown
Stayed 3 nights in Oct 2022
From a partner site

10/10 Excellent

Jessica C.

Great house!

Perfect house for your family! Great location, cozy, and comfortable. Would definitely stay here again!
From a partner site

10/10 Excellent

Jessica C.

Great house!

Perfect house for your family! Great location, cozy, and comfortable. Would definitely stay here again!
Verified

10/10 Excellent

Jamie E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent proximity to USNA!

Roomy. Great outdoor spaces. Perfect location
Stayed 3 nights in May 2023
Verified

10/10 Excellent

Dan V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Weekend House

The house was everything we expected and needed. We were super close to town. Everything was a 5 min walk so no Ubers needed. The host was extremely helpful and responsive during our stay with any questions we had about the place. Would highly recommend and would stay again!
Stayed 2 nights in Jul 2025
Verified

8/10 Good

Jennifer Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Safe and charming rental

The location of this rental is pretty ideal (very close to the Naval Academy), and we felt very safe here. I loved the historic charm and would definitely book this rental again. Highly recommend!
Stayed 2 nights in Jun 2024
From a partner site

10/10 Excellent

Michael R.

Wonderful Stay!

This is an absolutely beautiful home in a perfect location. Couldn’t ask for anything else. It had everything we needed and was managed extremely well by iTrip Annapolis. We will not forget this memorable trip celebrating my Dad’s 80th birthday and Father’s Day! Thanks
Verified

10/10 Excellent

Elizabeth M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

USNA

Great property! All the amenities and comforts of home. Great location to USNA and Main Street. Highly recommend and I am confident we will be back.
Stayed 5 nights in Jun 2024
Verified

10/10 Excellent

Susan C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Wedding Staycation

Family and friends easily relaxed in this wonderful home away from home. Cathy from Itrip quickly answered all of our questions and ensured we had a wonderful weekend. Loved the house!
Stayed 4 nights in Sep 2023
From a partner site

10/10 Excellent

Tobias G.

Perfect location for I Day

Our family greatly enjoyed staying at this home when visiting for I Day. The location can't be beat if you have come for a big event at USNA. The house is spacious, charming, and has everything you need, including great air conditioning when the weather is hot and muggy. We thoroughly enjoyed our stay and hope to stay again for future visits.
Stayed 3 nights in Jun 2023
Verified

10/10 Excellent

Dirk M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay!

This property is exactly as described and incredibly convenient to all nearby attractions. We'll be back for sure! -DM
Stayed 4 nights in Sep 2022
Verified

10/10 Excellent

Edward F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

As advertised

Great location. Very nice, clean home.
Stayed 2 nights in Dec 2022
Verified

10/10 Excellent

James F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful property, great location

as advertised. great attentiveness by Cathy (prop manager).
Stayed 4 nights in Jul 2022
Verified

10/10 Excellent

Molly P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Birthday Blast

We rented this beautiful place for a joint birthday weekend. The location is absolutely perfect for walking. Parking in a nearby garage was free over the weekend. The property is exactly as described and beyond charming!! We had a fabulous stay and will absolutely be back.
Stayed 2 nights in Jun 2024
Verified

10/10 Excellent

Michelle R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Downtown

We had the most wonderful couple of days enjoying the Annapolis parade and visiting friends. The TH was well equiped and decorated very stately. Good conversation areas. We parked in front tempirarily and at a neaby garage
Stayed 2 nights in Mar 2025
Verified

10/10 Excellent

Anna S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfection!!

This beautiful home is on a beautiful DTA street! Everything you could want; excellent communication, pristine home in the most convenient location in Annapolis.
Stayed 3 nights in Oct 2023
Verified

10/10 Excellent

ana c.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Thanksgiving with our"Mid"

Location, Location, Location. Couldn't be any closer to EVERYTHING. Property was well maintained, with all the amenities (as advertised). Would love to rent it again👍👍👍
Stayed 4 nights in Nov 2023
From a partner site

10/10 Excellent

Sheila A.

Lovely Historic District Rental

Been traveling for two weeks visiting grandchildren. This VRBO home in the Historic District of Annapolis has provided us the perfect respite from our travels. The home is beautifully appointed with thoughtful individually packaged toiletry sets in each bath; the decor is homey and welcoming. History, shopping, and restaurants are within two blocks. Will return on future visits to this area.
Stayed 3 nights in Jul 2023
Verified

10/10 Excellent

James V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect house for USNA Reunion Weekend

Cathy who hosts the house is very communicative and made the stay seamless. We had some issues with house appliances during our stay but she was on it right away when we let her know, all you can ask in that situation. House is well kept and clean. Outdoor space is great, we utilized the outdoor fire pit during our stay.
Stayed 3 nights in Oct 2022
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Visit to our Son

We traveled to meet up with our son and his girlfriend who recently relocated to Annapolis. We wanted a place large enough for all of us to stay together and experience the area. What a great spot! We loved the walkability of the house and the area had so much to do and see. We'll be back! Thank you.
Stayed 4 nights in Nov 2023
From a partner site

10/10 Excellent

rebecca c.

Beautifully appointed and Oh! SO convenient!

Historic Hideaway is only a block away from Old Fox, the most charming book store and cafe- our favorite destination in Down Town Annapolis. It's also only blocks away from... absolutely everything. We've been able to visit and host our Midshipman, hang out with friends, wine, dine, shop, visit DC, park conveniently just blocks away for quick jaunts. Simply ideal. The kitchen and living spaces are modern and beautifully furnished. The master bed sleeps like a dream. The top floor sleeping space is absolutely brilliant. We've been so happy and cozy here. Top marks.
From a partner site

10/10 Excellent

Jessica C.

Great house!

Perfect house for your family! Great location, cozy, and comfortable. Would definitely stay here again!
From a partner site

10/10 Excellent

Jessica C.

Great house!

Perfect house for your family! Great location, cozy, and comfortable. Would definitely stay here again!
Verified

8/10 Good

Nancy L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Oct 2024

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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