Experience Historic Annapolis — Stay in This Unique Dual-Suite Home with On-Site Parking
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.
Our prices include all fees. No hidden fees.
Add dates for prices
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Similar properties
Walk to Main Street, City Dock and USNA Gate 1 From Historic Catch 22 with Private Patio
Historic District
Walk to Main Street, City Dock and USNA Gate 1 From Historic Catch 22 with Private Patio
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
About the area
Annapolis
Located in Annapolis, this holiday home is in the city centre. The area's natural beauty can be seen at Jonas Green State Park and Sandy Point State Park, while Banneker Douglass Museum and ARTFX Gallery of Fine Crafts and Arts are cultural highlights. Looking to enjoy an event or a game while in town? See what's happening at Tose Family Tennis Center or Alumni Hall.
O'Brien's Oyster Bar & Seafood Tavern - 5 min walk
Annapolis Market House - 7 min walk
Frequently asked questions
Is Experience Historic Annapolis — Stay in This Unique Dual-Suite Home with On-Site Parking pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Experience Historic Annapolis — Stay in This Unique Dual-Suite Home with On-Site Parking?
As of 15 May 2026, prices found for a 1-night stay for 2 adults at Experience Historic Annapolis — Stay in This Unique Dual-Suite Home with On-Site Parking on 20 Aug 2026 start from £447, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Experience Historic Annapolis — Stay in This Unique Dual-Suite Home with On-Site Parking?
On-site parking is available at the property.
What time is check-in at Experience Historic Annapolis — Stay in This Unique Dual-Suite Home with On-Site Parking?
Check-in begins at 4:00 PM.
What time is check-out at Experience Historic Annapolis — Stay in This Unique Dual-Suite Home with On-Site Parking?
Checkout is at 11:00 AM.
Where is Experience Historic Annapolis — Stay in This Unique Dual-Suite Home with On-Site Parking located?
Located in Historic District, this holiday home is within a 15-minute walk of Spa Creek and U.S. Naval Academy. Maynard-Burgess House and Ellen O. Moyer Nature Park at Back Creek are just steps away.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Location location perfect house close to everything. If you want to be close to downtown this is the perfect place for you.
Christy B.
Response from VrboOwner on 23 Nov 2025
Thanks, Christy! We’re thrilled to hear that The Schooner provided the perfect location for your stay. It’s fantastic that you enjoyed being so close to downtown. We hope to welcome you back for another wonderful visit in the future!
Melissa~iTripAnnapolis
About the host
Hosted by iTrip Vacations Annapolis - Sean Degnan
Languages:
English
Premier Host
They consistently provide great experiences for their guests