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

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 the main 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.