Entire home

History & Charm steps from Main Street and City Dock

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Welcome to the spacious Catch 22, located in the heart of downtown Annapolis on Fleet Street.
Enjoy the private back patio, located off the family room with a gas BBQ grill (not pictured).
The open plan of the main floor includes the kitchen, dining, living and family rooms.
The living room on the main level has a Queen sleeper sofa (linens included).
The Queen bed in the upstairs suite.

Reviews

10 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 9

Popular amenities

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

Explore the area

Map
Annapolis, MD
  • Annapolis City Dock
    ‪2 min walk‬
  • U.S. Naval Academy
    ‪11 min walk‬
  • Navy-Marine Corps Memorial Stadium
    ‪3 min drive‬
  • Annapolis, MD (ANP-Lee)
    ‪20 min drive‬

Rooms & beds

3 bedrooms (sleeps 9)

Family Room

1 Double Sofa Bed

Guest room 2

1 Queen Bed

Living Room

1 Double Sofa Bed

Queen Suite

1 Queen Bed

Twin Guest room

1 Single Bed

2 bathrooms, 1 half bathroom

Main Floor Powder Room

Toilet

Second Floor Hall

Bathtub or shower · Toilet

Second Floor Queen

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Separate dining area
Dining area

About this property

History & Charm steps from Main Street and City Dock

This charming 3-BR, 2.5-BA townhome is just a 1/2-block from the city dock and is a luxurious vacation getaway in the heart of the historic district of Annapolis. Built in 1881, this townhome has been completely renovated, with beautiful wood floors, an open floor plan and every modern convenience.

Entertain in the open kitchen that flows seamlessly into the dining room and living room and out to the private back patio. There are 3 bedrooms and 2 baths upstairs, with sleeping for 5 in the 2 Queen beds and 1 Twin. The en-suite Queen bedroom also has private balcony. On the main level is room to sleep up to 2 adults or 4 more kids on the family and living room's Queen sleeper sofas.

Take advantage of the rich culture, history, shopping and entertainment of Annapolis. The State Circle, the Annapolis Yacht Club and the Naval Academy are all within two blocks. Ego Alley and the historic William Paca, James Brice and Hammond-Harwood houses are a five-minute stroll. Park your car and experience all of downtown Annapolis within easy walking distance. Or just stay in and enjoy the three smart TVs, high-speed Wi-Fi and cable TV. Colonial charm. Rich history. Comfort and convenience.

SLEEPING ARRANGEMENTS 3 BR / 2.5 BA / Sleeps 7-9:
Queen Suite (sleeps 2):
- Second Floor
- Queen Bed
- En-suite full bath

Guest Bedroom (sleeps 2):
- Second Floor
- Queen Bed
- Full Bath in the Hall

Twin Guest room (sleeps 1):
- Twin Bed
- Full Bath in the Hall

Family Room (sleeps 1-2):
- Main floor
- Queen Sleeper Sofa
- Full Bath in the Hall upstairs or half bath on main floor

Living Room (sleeps 1-2):
- Main floor
- Queen Sleeper Sofa
- Full Bath in the Hall upstairs or half bath on main floor

HIGHLIGHTS:
- Private fenced-in back patio with gas grill (propane provided)
- Balcony off Queen suite
- Full gourmet kitchen
- Dining room table seats 8
- WiFi
- Multiple Flatscreen TV's
- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service
- Washer & dryer located inside the home
- No pets
- Keyless entry. Drive straight to your rental home and enter the door with an electronic lock code.

Property Distance to:
- U.S. Naval Academy – 2 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/no pets. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind.
Check-in time: 4:00 pm
Check-out time: 11:00 am

Property manager

iTrip Vacations Annapolis - Sean Degnan
Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
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 Annapolis, this holiday home is in the city centre. Annapolis Harbor and Ego Alley are worth checking out if an activity is on the agenda, while those looking for area attractions can visit French Soldiers Monument and Annapolis Maritime Museum. 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

  • Annapolis City Dock - 2 min walk - 0.2 km
  • William Paca House - 3 min walk - 0.3 km
  • Maryland State House - 4 min walk - 0.4 km
  • U.S. Naval Academy - 11 min walk - 0.9 km
  • Navy-Marine Corps Memorial Stadium - 3 min drive - 2.3 km

Getting around

  • Odenton Station - 22 min drive
  • Baltimore Washington International Airport (BWI) - 38 min drive

Restaurants

  • ‪The Choptank - ‬4 min walk
  • ‪Starbucks - ‬3 min walk
  • ‪O'Brien's Annapolis' Original Steakhouse - ‬2 min walk
  • ‪Chick & Ruth's Delly - ‬4 min walk
  • ‪Mc Garvey's Saloon - ‬2 min walk

Frequently asked questions

Is History & Charm steps from Main Street and City Dock pet-friendly?

No, only service animals are welcome at the property.

What time is check-in at History & Charm steps from Main Street and City Dock?

Check-in begins at 4:00 PM.

What time is check-out at History & Charm steps from Main Street and City Dock?

Checkout is at 11:00 AM.

Where is History & Charm steps from Main Street and City Dock located?

Located in Historic District, this holiday home is within a 15-minute walk of 14 Fleet Street and U.S. Naval Academy. 48 Fleet Street 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 16 out of 17 reviews
Rating 8 - Good. 1 out of 17 reviews
Rating 6 - Okay. 0 out of 17 reviews
Rating 4 - Poor. 0 out of 17 reviews
Rating 2 - Terrible. 0 out of 17 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Dianne F.

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

Family reunion

Location was excellent. Parking was challenging but possible. The front entrance could use a handrail. Uneven steps and nothing to grasp onto.
Stayed 7 nights in Nov 2024

10/10 Excellent

margaret g.

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

Mother/Daughter’s Hallmark Weekend

Property was clean and very well stocked. Location was really convenient for walking to town and shopping. Town beautifully decorated for Christmas! We had a great time, made some memories, and hope to be back.
Stayed 2 nights in Dec 2024

10/10 Excellent

Brian W.

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

Great Location!

Perfect location to DTA and USNA!
Stayed 4 nights in Oct 2024

10/10 Excellent

Katie J.

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

Boat Show Stay

Very clean, nice rental. My only complaint would be the number of people you can comfortably accommodate for the price, but the location is wonderfully convenient.
Stayed 6 nights in Oct 2024

10/10 Excellent

Hilary P.

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

Charming, Clean and Convenient!

Great location on a charming street, close to the boat show and super clean!
Stayed 6 nights in Sep 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Vivian S.

Catch 22 Excellent location

This house was perfect in location and layout. I would love to stay here again but, my mid is a Firstie and time in Annapolis is growing short. We loved the beds very cozy. The location cannot be beat.

10/10 Excellent

Blanche J.

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

Perfect for PPW

The short walk to USNA was perfect for spending time with our plebe during Parent's Weekend. Just a few steps to restaurants and shops in downtown Annapolis. The house was comfortable for 5 adults and 3 children/teens.
Stayed 5 nights in Aug 2024

10/10 Excellent

Steve K.

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

Annapolis

Beautiful well renovated historic Annapolis salt box a block away fro the heart of downtown. The house was perfect for our gang of 6 to visit Naval Academy, DC, family in Severna Park, and see the ocean at Rehoboth Beach.
Stayed 4 nights in Jun 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Corey B.

Great house

Very nice home, plenty of space and well furnished. Super convenient walking distance to many area shops and restaurants
Stayed 2 nights in May 2024

8/10 Good

Leslie M.

Liked: Check-in, communication, location

Great location

Cute space that is very walkable and right in the middle of everything USNA related. Loved sitting on the stoop and watching people go by. Hosts were very gracious and left a lovely welcoming basket for us for our graduating midshipmen and property managers were very responsive. I would say it doesn't comfortably fit as many folks as they say it does--we had two couples and two singles and our college-aged son that got the couch didn't sleep well. I'd say perfect for five or fewer. The house itself is very cute, though the front and back patio could use some love (dead plants, weeds). That said, it didn't make a huge difference as we were usually out and about.
Stayed 7 nights in May 2024

10/10 Excellent

Jonathan S.

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

Great stay

Went perfectly. Location was awesome. Good communication. No issues.
Stayed 2 nights in May 2024

10/10 Excellent

Helen S.

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

Incredible location to see Annapolis

This home is located a few yards from the city dock and the center of Annapolis. Easy walking exploring the history of the city. It is well appointed and very comfortable for a family gathering.
Stayed 4 nights in May 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

katie g.

Perfect location

I used to live in the historic district of Annapolis and remember this unique street very well. It’s quaint, full of character, and steps away from the lively market square with all of the dining, shopping, and entertainment. We were active over the 2-night stay, and we appreciated the VERY clean, quiet, and comfortable home when we needed a little downtime.
Stayed 2 nights in Dec 2023

10/10 Excellent

Denise M., Georgetown

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

Fantastic space, great location

This property has everything that my family of six needed. Lots of sleeping space, full kitchen, 2 1/2 baths and nice back patio. Walking distance to all things DTA and USNA. Super clean, not cluttered and very comfortable. We loved it! We will be back!
Stayed 4 nights in Sep 2023

10/10 Excellent

Lori A.

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

Perfect Location

Our family enjoyed staying on Fleet Street for 2/C Parents' Weekend. The property was immaculate and had everything you could need. It is centrally located to USNA and DTA. We will definitely book for future visits.
Stayed 3 nights in Sep 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Sheila

Ideal location

House was in the ideal location to walk to USNA-main gait/visitor center. Close to main st and Dock but quite. Parking garage is close and affordable.

10/10 Excellent

Laura G.

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

Wedding trip

We had a great stay. The house was in a great location. We were able to walk everywhere we needed to go. The house was comfortable and clean. It had more than enough room for our party of 7.
Stayed 2 nights in Jun 2023

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