Entire home

Historic Annapolis Hideaway Steps to USNA and Main St w Private Patio & Parking

Photo gallery for Historic Annapolis Hideaway Steps to USNA and Main St w Private Patio & Parking

A dining area with a round wooden table, chairs, a brick fireplace, and a staircase with a white railing.
A dining area with a round wooden table, six wooden chairs with striped cushions, a chandelier, a brick wall, a staircase, and a kitchen in the background.
A garden pathway lined with colorful tulips and a wooden fence.
A cozy living room with a brick fireplace, a wooden bench, and a wall of black and white kitchen utensils.
A historic ship docked at a harbor with a prominent white building with a dome in the background.

Reviews

10 out of 10
Exceptional

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Firepit available
    One of the few properties with a dedicated outdoor firepit.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Maryland State House

Popular amenities

  • Balcony
  • Barbecue
  • Free Wi-Fi
  • Air-conditioning
  • Kitchen
  • Garage parking available

Explore the area

View map
Annapolis, MD
  • Place, U.S. Naval Academy
    ‪3 min walk‬
  • Place, Maryland State House
    ‪5 min walk‬
  • Place, Annapolis City Dock
    ‪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

Add dates for prices

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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

  • St. John's College - 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
  • Maryland State House - 5 min walk - 0.4 km
  • Annapolis City Dock - 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
  • ‪The Red Bean - ‬6 min walk
  • ‪Iron Rooster - ‬6 min walk
  • ‪McGarvey's Saloon & Oyster Bar - ‬6 min walk
  • ‪Middleton Tavern - ‬6 min walk

Frequently asked questions

Is Historic Annapolis Hideaway Steps to USNA and Main St w Private Patio & Parking pet-friendly?

No, only service animals are welcome at the property.

How much does it cost to stay at Historic Annapolis Hideaway Steps to USNA and Main St w Private Patio & Parking?

As of 29 October 2026, prices found for a 1-night stay for 2 adults at Historic Annapolis Hideaway Steps to USNA and Main St w Private Patio & Parking on 10 May 2027 start from NZ$3,681, 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 Annapolis Hideaway Steps to USNA and Main St w Private Patio & Parking?

On-site parking is available at the property.

What time is check-in at Historic Annapolis Hideaway Steps to USNA and Main St w Private Patio & Parking?

Check-in begins at 4:00 PM.

What time is check-out at Historic Annapolis Hideaway Steps to USNA and Main St w Private Patio & Parking?

Checkout is at 11:00 AM.

Where is Historic Annapolis Hideaway Steps to USNA and Main St w Private Patio & 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 26 out of 28 reviews
Rating 8 - Good. 2 out of 28 reviews
Rating 6 - Okay. 0 out of 28 reviews
Rating 4 - Poor. 0 out of 28 reviews
Rating 2 - Terrible. 0 out of 28 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location for access to the Naval Academy and downtown Annapolis.
Stayed 3 nights in Aug 2026
Response from VrboOwner on 21 September 2026
Thanks, Nathan. We hope to host you again soon
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The historic Hideaway is a perfect home in the heart of Annapolis. My four girlfriends and I had a fabulous time. Although the weather did not cooperate, we had a perfect home to gather and feel most comfortable. Thank you for providing such a beautiful space!
Stayed 2 nights in Sep 2026
Response from VrboOwner on 28 September 2026
Thanks, Valerie. We hope to host you again soon!
Verified review

10/10 Excellent

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
Response from VrboOwner on 19 July 2023
Thanks, Kirsten. Come back and stay with us again next time you're in Annapolis! Sean
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Clean, and lovely back yard
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location

Great location

Great location if you want to be close downtown
Stayed 3 nights in Oct 2022
Response from VrboOwner on 19 July 2023
Thank you Sierra, we are glad you enjoyed your stay at Historic Hideaway. - Cathy
From a partner site

10/10 Excellent

Great house!

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

10/10 Excellent

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

Excellent proximity to USNA!

Roomy. Great outdoor spaces. Perfect location
Stayed 3 nights in May 2023
Response from VrboOwner on 19 July 2023
Thank you for your kind review of Historic Hideaway! We hope to have the opportunity to host you again. Safe Travels! -Tiffany
Verified review

8/10 Good

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
Response from VrboOwner on 22 June 2024
Hi Jennifer! Thank you for staying with us & I do apologize that you did not feel your stay was a 5 star stay. We strive to provide a 5 star experience for our guests. We hope to have an opportunity to host you again in the future!
Verified review

10/10 Excellent

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
Response from VrboOwner on 2 October 2023
Susan thank you for the kind review of Historic Hideaway. Please come back and stay with us again. Safe Travels! -Tiffany
From a partner site

10/10 Excellent

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
Response from VrboOwner on 19 July 2023
Tobias we are so happy to hear you enjoyed your stay at Historic Hideaway. Thank you for the kind review. We hope to have the opportunity to host you again. Safe Travels! -Tiffany
Verified review

10/10 Excellent

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
Response from VrboOwner on 13 July 2024
Hi Elizabeth! I am so happy you enjoyed your stay with us & we welcome you back anytime! Melissa~iTripAnnapolis
Verified review

10/10 Excellent

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
Response from VrboOwner on 19 July 2023
Thank you so very much for the wonderful review of Historic Hideaway! We look forward to hosting you again soon! - Cathy
Verified review

10/10 Excellent

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

As advertised

Great location. Very nice, clean home.
Stayed 2 nights in Dec 2022
Response from VrboOwner on 25 October 2023
Thank you Edward. Please come back and stay with us again. Safe Travels! -Tiffany
Verified review

10/10 Excellent

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
Response from VrboOwner on 18 July 2025
Thanks, Dan! We're thrilled to hear that Historic Hideaway was everything you expected and needed. It's great that you enjoyed the convenient location and found our host helpful and responsive. We would love to welcome you back for another fantastic stay in the future! Melissa~iTrip Annapolis
Verified review

10/10 Excellent

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
Response from VrboOwner on 19 July 2023
Thank you James! We are very happy you enjoyed your stay at Historic Hideaway and we hope you will come back and stay again! - Cathy
From a partner site

10/10 Excellent

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
Response from VrboOwner on 20 June 2025
Thanks, Michael! We’re thrilled to hear you enjoyed your stay at Historic Hideaway and found it to be the perfect location for celebrating your Dad’s 80th birthday and Father’s Day. We’re glad to know that the home had everything you needed and that our management met your expectations. We’d love to host you and your family again anytime you’re back in Annapolis! Melissa~iTrip Annapolis
Verified review

10/10 Excellent

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
Response from VrboOwner on 6 July 2024
Thank you for staying with us Molly & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
Verified review

10/10 Excellent

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
Response from VrboOwner on 24 October 2023
Thank you Anna for the kind review of Historic Hideaway. We would love the opportunity to host you again. Safe Travels! -Tiffany
Verified review

10/10 Excellent

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
Response from VrboOwner on 28 November 2023
Thanks, Ana! We look forward to hosting you again next time you’re in Annapolis. Sean, iTrip Annapolis
Verified review

10/10 Excellent

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
Response from VrboOwner on 18 March 2025
Thank you for staying with us, Michelle & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
From a partner site

10/10 Excellent

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
Response from VrboOwner on 3 August 2023
Thank you Sheila for the kind review of Historic Hideaway. We are so happy to hear you enjoyed your stay. Please come back and stay with us again. Safe Travels! -Tiffany
Verified review

10/10 Excellent

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
Response from VrboOwner on 19 July 2023
Thank you so much for staying with us at Historic Hideaway and for your kind words James! We hope to host you again anytime! - Cathy
Verified review

10/10 Excellent

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
Response from VrboOwner on 24 November 2023
Thanks, Heather! We look forward to hosting you again! Sean
From a partner site

10/10 Excellent

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.
Response from VrboOwner on 23 February 2025
Hi Rebecca! Thank you for being a great guest & we welcome you back anytime! We sincerely appreciate knowing you enjoyed your time in the home, Melissa~iTripAnnapolis
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home with lots of charm! Great location to walk to the academy and DTA!
Stayed 3 nights in Sep 2026
Response from VrboOwner on 9 September 2026
Thanks, Liz. We look forward to hosting you again soon.
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