Historic Downtown Annapolis w/ Rooftop Deck

20 Fleet Street, Annapolis, Maryland • .3 mi from USNA

Featured
Townhouse 6 Guests 2 Bedrooms 1.5 Bathrooms 6-night min

Pricing & Availability

Year Nightly Rate 6-Night Total 15% NONREFUNDABLE Deposit Status Action
2027 $1,100 $6,600 $990 Booked Unavailable
2028 $1,150 $6,900 $1,035 Booked Unavailable
2029 $1,200 $7,200 $1,080 Booked Unavailable
2027
Nightly Rate $1,100
6-Night Total $6,600
15% NONREFUNDABLE Deposit $990
Booked
Unavailable
2028
Nightly Rate $1,150
6-Night Total $6,900
15% NONREFUNDABLE Deposit $1,035
Booked
Unavailable
2029
Nightly Rate $1,200
6-Night Total $7,200
15% NONREFUNDABLE Deposit $1,080
Booked
Unavailable

About This Property

This 2-bed, 1.5-bath townhome mixes modern renovations with 1900 classic charm. It's been lovingly decorated to accommodate 6 guests. You'll love the proximity to downtown Annapolis - simply walk one-half block to Main Street circle and Annapolis City Dock. You'll truly be in the middle of everything in this beautiful historic home!

Why guests love staying at 20 Fleet Street:

☼ Historic row home right in the heart of downtown Annapolis with tons of natural light and upgraded features, ideal for families, romantic getaways, or a group of friends visiting historic Annapolis, USNA, and other tourist sites
☼ Centrally located in downtown Annapolis, on historic Fleet Street, just 1/2 block from the action
☼ Two bedrooms: Primary: king bed; Guest: 2 twin beds
☼ The full bathroom is on the second level with both bedrooms and has a tub-shower combo; there is a half-bath on the main living area
☼ Kitchen with all major appliances, a drip coffee maker, kitchen supplies and tools and more
☼ Comfortable living room for watching movies and playing games, with a sliding glass door out to a private outdoor space
☼ Two outdoor spaces - one at the ground level is fully fenced with outdoor dining and a gas grill; the other is a fenced rooftop with outdoor dining
☼ Smart TV in the living room
☼ Fresh linens, towels, toiletries & essentials provided
☼ Professionally cleaned before each visit

​Look no further than this historic rowhome in downtown Annapolis!

Please note that there is no parking on Fleet Street. Guests are encouraged to park in nearby public parking garages.

We’ll follow up with a short online registration once you book. It’s fast, simple, and helps us prepare for your visit. Guests will be asked to pay a small damage waiver OR refundable deposit.

20 Fleet Street is managed by a small, female-owned business. We're committed to making sure all of our guests feel welcome and have the best trip ever. Book your trip with confidence that not only will this property be amazing, but the service and attention you get will be, too.

Amenities

Wi-Fi
Deck/Patio
Grill
Big-Screen TV
Washer/Dryer
A/C
Smart Lock

Have Questions About This Property?

Directions to USNA

Search

July 2026

  • M
  • T
  • W
  • T
  • F
  • S
  • S
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9
  • 10
  • 11
  • 12
  • 13
  • 14
  • 15
  • 16
  • 17
  • 18
  • 19
  • 20
  • 21
  • 22
  • 23
  • 24
  • 25
  • 26
  • 27
  • 28
  • 29
  • 30
  • 31

August 2026

  • M
  • T
  • W
  • T
  • F
  • S
  • S
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9
  • 10
  • 11
  • 12
  • 13
  • 14
  • 15
  • 16
  • 17
  • 18
  • 19
  • 20
  • 21
  • 22
  • 23
  • 24
  • 25
  • 26
  • 27
  • 28
  • 29
  • 30
  • 31
0 Adults
Size
Amenities