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2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free

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Located in Annapolis' Historic District, this charming home on Fleet Street is just steps from the waterfront. Enter the sunny family room with Semper Fi pageantry and head to the gourmet kitchen with sleek granite countertops. Unwind in the private fenced patio or explore nearby attractions like City Dock and shops.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms3 bathroomsSleeps 4950 sq ft

Popular amenities

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

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free

Laundry facilities and barbecues are available at this smoke-free holiday home. The holiday home has 2 bedrooms and offers free WiFi and a patio. Guests will find a kitchen with a fridge, an oven, a stovetop and a microwave.
Air-conditioned accommodation at this holiday home offers coffee/tea makers and a hairdryer. Rooms open to patios. Kitchens offer fridges, stovetops, microwaves and kitchenware and utensils.

Bathrooms include baths or showers. Guests can surf the web using complimentary wireless Internet access.

Property amenities

Internet

  • Available in the house: Free WiFi

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • TV

Outdoor areas

  • Barbecue grill
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)

General

  • Unit size: 950 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

30 Fleet Street Annapolis
8361
30 Fleet Street Private vacation home
30 Fleet Street Private vacation home Annapolis

About the area

Located in Annapolis, this holiday home is in the city centre. The Colonial Players and Maryland Federation of Art are cultural highlights, and some of the area's attractions include French Soldiers Monument and Annapolis Maritime Museum. Maryland Hall for Creative Arts and Helen Avalynne Tawes Garden are also worth visiting. Visit our Annapolis travel guide
View more Holiday homes in Annapolis
Map
Annapolis, MD

What's nearby

  • William Paca House
    William Paca House
    2 min walk - 0.2 km
  • Maryland State House
    Maryland State House
    2 min walk - 0.2 km
  • U.S. Naval Academy featuring military items, heritage architecture and interior views
    U.S. Naval Academy
    3 min walk - 0.3 km
  • Hammond-Harwood House
    Hammond-Harwood House
    5 min walk - 0.4 km
  • Annapolis City Dock
    2 min walk - 0.2 km

Getting around

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

Restaurants

  • The Choptank
    4 min walk
  • Starbucks
    2 min walk
  • O'Brien's Oyster Bar & Seafood Tavern
    2 min walk
  • Buddy's Crabs & Ribs
    2 min walk
  • Annapolis Market House
    2 min walk

Frequently asked questions

Is 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free pet-friendly?

No, pets are not allowed at this property.

What time is check-in at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?

Check-in begins at 4:00 PM.

What time is check-out at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?

Checkout is at 11:00 AM.

Where is 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free 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.

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2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 11 out of 11 reviews
Rating 8 - Good. 0 out of 11 reviews
Rating 6 - Okay. 0 out of 11 reviews
Rating 4 - Poor. 0 out of 11 reviews
Rating 2 - Terrible. 0 out of 11 reviews

10

Cleanliness

10

Location

Reviews

10/10 Excellent

Jenny H.

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

Great location

Great accommodations close to the Annapolis Boat Show! Walking distance to all events, restaurants and shopping! Perfect for 2 couples!
Stayed 3 nights in Oct 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Melissa B.

Fabulous on Fleet Street

This is a wonderful, fully equipped house close to everything in DTA. There was plenty of room, and it was extremely clean. Will definitely stay here again!

10/10 Excellent

Courtney T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a beautiful, well-decorated home in an unbeatable location—just steps from the City Dock, USNA, and Main Street. The house was very comfortable, and everyone raved about the beds and pillows! The management team was a pleasure to work with—super easy to reach by text and always quick to respond.Parking in downtown Annapolis can be tricky, but we were always able to find street parking nearby without too much trouble. I would absolutely stay here again and recommend it to friends and family—unless, of course, they’re planning to visit the same weekend we are… in that case, I’d definitely not recommend it!
Stayed 4 nights in Oct 2025

10/10 Excellent

Mike D.

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

Location location and comfortable

What a great little place to stay. The location is in the heart everything but off on a side street. So cozy and comfortable with everything updated. The decor is another awesome feature to this home. We will be back again and hope that this home is available.
Stayed 2 nights in Oct 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

john and h.

Commissioning Week

We had the absolute best week. We've stayed in Kevin's place before and love the location and home. We got in late Saturday and had a question, iTrip responded immediately. We had a small issue with AC as it was probably the first warmer days so far, and it was corrected immediately. The Fleet Street location, owners, and iTrip Annapolis were all fabulous! We've stayed all over the area for past 10 years but it is my favorite place by far❤️

10/10 Excellent

Hayden P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had an amazing stay here! Responsive host, amazing location, beautiful home.
Stayed 2 nights in Sep 2025

10/10 Excellent

Nancy B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
LOVED the location, close to all of downtown Annapolis and the house was a perfect size for the 4 of us.
Stayed 3 nights in Jul 2025

10/10 Excellent

Verified traveller

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

Great spot in the middle of everything

A perfect place to stay for a weekend in Annapolis…walking distance to everything, and the house is really comfortable and nicely appointed. Would stay here again for sure!
Stayed 2 nights in Jun 2025

10/10 Excellent

Ryan T.

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

Great place and location

Would definitely stay again. The parking garage recommended does not open until 6pm to the public on weekends.
Stayed 2 nights in Dec 2024

10/10 Excellent

Amy B., Roswell

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

Amazing!

This property was absolutely beautiful, extremely clean and it was perfect for our girls trip! So close to everything, we would highly recommend it if you come to Annapolis, perfect if you have a kid at the Naval Academy!
Stayed 3 nights in Oct 2022

10/10 Excellent

Kari H.

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

First timer

The property was nice and very clean. Easy walk to the Academy.
Stayed 3 nights in Jun 2024