Experience Historic Annapolis — Stay in This Unique Dual-Suite Home with On-Site Parking

Annapolis, Maryland
$720 avg/night Minimum Stay 2 Nights
Bed 3

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Night 2 nights

Min Stay

Experience the Difference: Professionally Managed by iTrip Annapolis

Stay right in the heart of Historic Annapolis, just 2 blocks from Main Street. This 2-unit property offers the opportunity to stay together while each having your own apartment. The Historic building, once a grocery store and the residences of the store, is the perfect blend of convenience and comfort in the two well-appointed spaces, each with their own full kitchen, bedrooms and bathroom.

Main Sail on themain floor: 2 bedroom/1 bath, sleeps 6

The Jib on the 2nd floor: 1 bedroom/1 bath, sleeps 4



Property Highlights:

Central Location: Walk to all the attractions of Historic Annapolis, including Main Street, just 2 blocks away, and the U.S. Naval Academy, another 2 blocks away.



Sleeping Arrangements :

Main Sail, main floor (Sleeps 6)

King Bedroom: King Bed, Full-size Sleeper Sofa (linens provided)

TV

Queen Bedroom:Queen Bed

Shared Bathroom: Full bath in the hall with stand-up shower



The Jib, 2nd floor (sleeps 4)

King Bedroom: King Bed

Twin futon (plus 2 more Twin futons in the closet; linens provided)

Full Bathroom in the hall with combo bathub/shower



Additional Features:

Modern Amenities: High-speed internet and WiFi, two flat-screen TVs

Dining: Full kitchens with seating for 4-6 guests in each unit

Luxury Linens: Luxury bed and bath linens, complimentary toiletries Starter Kit, and boutique-level service

Convenience: 2 Full-size washer and dryers - one in the 1st floor unit, the 2nd in the main entrance of the 2nd unit

Easy Access: Keyless entry; Walk into the building's lower level then up to the 2nd floor where there will be a lockbox on the wall with the key to the unit.

Convenient Parking: Parking for one car on driveway behind home

Dog-Friendly - available after payment of $150 per dog is made prior to checkin



Property Distance to:

Main Street: 2 blocks

U.S. Naval Academy: 4 blocks

Washington, DC: 32 miles

Baltimore: 31 miles



Amenity & Supplies Starter Pack:

Included: A starter set of coffees, sweeteners, soap, shampoo, conditioner, lotion, hand sanitizer, paper towels, toilet paper, dish soap, sponge, and dishwashing liquid

Fresh Linens: All beds are made with freshly-laundered sheets, and towels are provided in the baths.



House Rules:

Age Requirement: At least one member of the party must be 25 years of age.

No Smoking

Respect: Be respectful of the house, contents, neighbors, and neighborhood. No parties.

Check-in/Check-out: Check-in time is 4:00 pm, and check-out time is 11:00 am.

Read More Expand
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms
  • GENERAL

    Recycling Unit Size: 1550 Sq Ft (144 Sq M) Uses Some LED Lighting
  • KITCHEN

    Coffee/tea Maker Dishwasher Ice Maker Microwave Oven Refrigerator Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Hair Dryer Shampoo
  • LANGS SPOKEN

    English
  • ENTERTAINMENT

    TV
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Games
  • LOCATION HIGHLIGHTS

    In The City Center
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Availability

Review Review

  • Christy B.

    Submitted Nov 16, 2025

    Stayed Nov 14, 2025

    Location location perfect house close to everything. If you want to be close to downtown this is the perfect place for you.

Your dates are Available!

Total

Includes taxes and fees
$720+
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