Secluded Cozy Cottage in Historic Downtown

Photo gallery for Secluded Cozy Cottage in Historic Downtown

A building with a black metal gate, a brick pathway, and greenery.
Property video
A kitchen with white cabinets, a granite countertop, and two black bar stools.
A living room with a sectional sofa, a dining table with chairs, a kitchen area, and a large clock on the wall.
A two-story white building with dark shutters, a wooden door, and a small porch with a white railing.

Reviews

9.6 out of 10
Exceptional

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Garage parking available
    Enjoy the convenience of garage parking - a rare offering in the area.
  • 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 or patio
  • Kitchenette
  • Dog-friendly
  • Street parking available
  • Barbecue
  • Air-conditioning

Explore the area

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

Rooms & beds

2 bedrooms (sleeps 8)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Office 1

1 Double Bed and 1 Single Bed

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Kitchenette
Garden
Dining area

Add dates for prices

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About the area

Annapolis

Historic District, a neighbourhood in Annapolis, is home to this cottage. Annapolis City Dock and Bay Bridge Market Place Shopping Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Chesapeake Bay and Jonas Green State Park. French Soldiers Monument and Annapolis Maritime Museum are also worth visiting.
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Map
Annapolis, MD

What's nearby

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

Getting around

  • Odenton Station - 23 min drive
  • Fort Meade, MD (FME-Tipton) - 35 min drive

Restaurants

  • ‪The Choptank - ‬4 min walk
  • ‪Starbucks - ‬1 min walk
  • ‪The Red Bean - ‬4 min walk
  • ‪Iron Rooster - ‬2 min walk
  • ‪McGarvey's Saloon & Oyster Bar - ‬2 min walk

Frequently asked questions

Is Secluded Cozy Cottage in Historic Downtown pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much is parking at Secluded Cozy Cottage in Historic Downtown?

There is free parking nearby.

What time is check-in at Secluded Cozy Cottage in Historic Downtown?

Check-in begins at 2:00 PM.

What time is check-out at Secluded Cozy Cottage in Historic Downtown?

Checkout is at 11:00 AM.

Where is Secluded Cozy Cottage in Historic Downtown located?

Located in Historic District, this cottage is steps away from 14 Fleet Street and Annapolis City Dock. 48 Fleet Street and 97, 99 and 101 East Street are just steps away.

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 20 out of 24 reviews
Rating 8 - Good. 2 out of 24 reviews
Rating 6 - Okay. 2 out of 24 reviews
Rating 4 - Poor. 0 out of 24 reviews
Rating 2 - Terrible. 0 out of 24 reviews

9.8/10

Cleanliness

10/10

Check-in

9.6/10

Communication

10/10

Location

9.4/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great time! The location is unbeatable
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The cottage was perfectly located in the heart of Annapolis. It has many eclectic decorations throughout out it. We enjoyed our stay.
Stayed 1 night in Jun 2026
Response from Management on 28 October 2026
Thanks for sharing your experience, Bridget. Glad you enjoyed your cottage stay in DTA. You’re always welcome back. Hope ur enjoying the cooler temps. All the best. Jennifer ☺️
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host was amazing, the house was perfect and well equipped, and the location was amazing!!!
Stayed 3 nights in Feb 2026
Response from VrboOwner on 12 March 2026
Tim, Thank you for the kind words & thoughtful review. For reasons VRBO can't seem to explain, I wasn't provided a host review option. I do apologize - hopefully other hosts will read this response so they know how absolutely wonderful you and your beautiful family were to host. You're the epitome of wonderful guests & overall good humans. Having the opportunity to engage with lovely people like yourselves is why I love hosting. THANK YOU! Fingers crossed your son is accepted into the USNA. I look forward to becoming your Annapolis home away from home. Until the next time - stay healthy, happy & in good trouble 😉Jenn
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely place. Very comfortable for our family
Stayed 1 night in Mar 2026
Response from VrboOwner on 12 June 2026
Thx for providing a review Robert. Glad you enjoyed your stay and Lynder’s cozy cottage. It was a pleasure hosting ur family. Hope to see you again. Jenn & Fletch
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
House was super cute and cozy. Beds were comfortable. Great location.
Stayed 1 night in Feb 2026
Response from VrboOwner on 12 June 2026
Thank you for the review, Tanya, Glad you enjoyed your stay. ☺️ Hope you’ll visit again soon
Verified review

10/10 Excellent

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

Adorable cottage

We had a very lovely stay . This is an excellent location .
Stayed 1 night in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This cottage is a hidden gem. Beautiful decor, perfect for our family of 4 & right in the center of all the main attractions. Jennifer was an amazing host!
Stayed 1 night in Nov 2025
Response from VrboOwner on 12 June 2026
Awww, Thx for the lovely review, Linda. It’s was a joy hosting your family. Happy you enjoyed the cottage and downtown historic annapolis. Please visit again ☺️
Verified review

10/10 Excellent

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

Wonderful location and the sweetest little cottage!

Perfect little cottage for 4 adults and an infant. Loved its location!
Stayed 1 night in Nov 2024
Response from VrboOwner on 20 April 2025
Thanks for your review Peggy. Glad you enjoyed your stay. You’re welcome back anytime. Jenn
Verified review

10/10 Excellent

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

Weekend stay

What an amazing place, very comfortable and walking distance from all Annapolis has to offer
Stayed 1 night in Jun 2024
Response from VrboOwner on 11 July 2024
Wade, Thanks for being a great guest. Glad you enjoyed your stay. ❤️ Look forward to your return. Enjoy your summer. Jennifer 😊
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
House is cute with lots of knick-knacks. Fantastic location in downtown Annapolis.Good fast internet and 5 bars coverage with T-Mobile. Heat and A/C worked well. Beds were comfortable. Very hot water. Nice spacious kitchen. Fairly well-stocked. Keurig coffee maker and lots of ice packs!The front door lock can be odd to use: you'll get instructions but know that you only have to touch the center of the circle where each number is, not the specific number (we managed to get ourselves locked out by trying to touch the exact number and had to text Jennifer to learn how to reset it).This house is not great for someone with impaired mobility or who is not very sure-footed. There is an immediate step down at the front door threshold, and a step up at the threshold to each bedroom, plus several throw rugs. These, plus narrow walkways due to having lots of furniture and seating (a plus for many renters) were troublesome for my 88-year-old husband. He stumbled and nearly fell several times.
Stayed 10 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely, secluded cottage close to downtown Annapolis. Host was very accommodating and communicated lots of great info. Looking forward to coming back when we can stay longer.
Stayed 1 night in Sep 2025
Response from VrboOwner on 25 November 2025
Glad u enjoyed ur stay. Look forward to ur next visit
Verified review

10/10 Excellent

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

Cute Cottage

Very Annapolis!
Stayed 2 nights in Jul 2025
Response from VrboOwner on 24 July 2025
Thanks for your review Shannon. Glad you enjoyed my cottage and your time in Historic Downtown Annapolis‼️🥳
Verified review

10/10 Excellent

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

Great Stay

We stayed at this gem with family for a auSNA event. The cottage was clean, well appointed and a perfect location. Jennifer was responsive and helpful throughout. We loved our stay!
Stayed 2 nights in Nov 2024
Verified review

10/10 Excellent

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

Midshipman Visit

Perfect location for family visit at USNA! House was super clean and cozy with easy access to all downtown and academy events.
Stayed 1 night in Feb 2025
Response from VrboOwner on 11 March 2025
Enjoyed hosting your family. Thanks for the review. You’re welcome anytime
Verified review

10/10 Excellent

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

Perfect Annapolis Get Away

We had a great time. Easy walk to everything. House was perfect and clean. The whole process was easy.
Stayed 1 night in Jul 2024
Response from VrboOwner on 23 July 2024
Thanks for taking wonderful care of my home & sharing your experience Chris. Happy to have you back. 😊
Verified review

10/10 Excellent

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

Great location!

Such a wonderful experience staying in this poperty for a couple of days. Walking distance to everything. Jennifer was a pleasure and very responsive. May make this an annual visit! Loved Annapolis!
Stayed 2 nights in Dec 2024
Verified review

10/10 Excellent

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

Great location

This little cottage was in an extremely convenient location. All needs within walking distance. Parking wasn’t bad - quick walk from garage. Overall would consider again!!
Stayed 1 night in Nov 2024
Verified review

10/10 Excellent

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

Annapolis walking visit

We brought a friend from Arizona to experience Annapolis. The location of this property is perfect. We were able to walk to the Naval Academy and tour it. We also walked to all the great stores, restaurants and bars. The weather was perfect. The cottage was the perfect size and super cute and comfortable.
Stayed 1 night in Jun 2025
Verified review

10/10 Excellent

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

Great location in Annapolis!

Just left this wonderful guest house in Annapolis. The home was extremely comfortable and cozy for the four adults in our group. Jennifer was incredibly helpful with the area, things to do, and local advice. Once the car was conveniently parked in a deck right around the corner, we didn't need it again. Delightful town, host, and stay!
Stayed 1 night in Dec 2024
Verified review

6/10 Okay

Liked: Check-in, location
Disliked: Listing accuracy

Cottage in Downtown Annapolis

The property was located in a great spot with easy walkable distances to downtown and the Naval Academy. There was a known issue with the bathroom that was not fixed nor where we given a heads up re: the situation.
Stayed 2 nights in Jun 2025
Verified review

6/10 Okay

Liked: Cleanliness, check-in, location
Disliked: Communication, listing accuracy

Inaccurate listing but good otherwise

The listing states that there is an office with a double bed and a twin bed. The owner took eight hours to get back to me when I asked about it when we entered. Unfortunately, there is no Office. She told me that the couch can sleep two people. It is not a pullout couch. She meant the actual couch was for adults to sleep on. And, there’s a daybed in the middle of the living room that she’s calling an office. If you only have four people and a small child, this house is great. It’s cute, has a nice patio, and is in a great location.
Stayed 1 night in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous location in the heart of Annapolis. We had a wonderful stay!
Stayed 1 night in Jun 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
We were only there for one night, but the cottage is so centrally located it cannot be beat! Beds are comfortable, kitchen is well stocked (although we didn't cook). Host was very communicative and provided lots of extra information for the area (restaurant recommendations, etc.).
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Stayed 1 night in Aug 2025
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