Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
32 min drive
Rooms & beds
2 bedrooms (sleeps 6)
King Bedroom
1 King Bed and 1 Double Sofa Bed
Queen Bedroom
1 Queen Bed
1 bathroom
Full Bath
Toilet · Shower only
Spaces
Kitchen
About this property
2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free
Experience the Difference: Professionally Managed by iTrip Annapolis
Still available for Commissioning Week 2025!
Stay right in the heart of Historic Annapolis, just 2 blocks from Main Street, and feel like you’re in a 2-bedroom, 1-bath hotel suite with all the comforts of home! Your family will be close to everything when you stay at this centrally-located first-floor apartment in a Historic 3-unit building, once a grocery store and the residences of the store owner. Enjoy the perfect blend of convenience and comfort in this well-appointed space. The 2nd floor has a 1 bedroom, 1 bath unit that sleeps 4, also available for rent. Inquire within.
Inquire about discounted extended stays!
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.
Comfortable Living: The King bedroom, located at the back of the apartment, features its own TV and a full-size sleeper sofa. The second bedroom has a cozy Queen bed, both of which share a full bathroom in the hall.
Open Floor Plan: The family room, with another flatscreen TV, and eat-in kitchen create a welcoming space to relax and dine, with seating for 4 at the table and 2 more at the breakfast bar.
Sleeping Arrangements (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
Additional Features:
Dining: Eat-in kitchen table seats 4 with 2 more at the bar
Modern Amenities: High-speed internet and WiFi, two flat-screen TVs
Luxury Linens: Luxury bed and bath linens, complimentary toiletries Starter Kit, and boutique-level service
Convenience: Full-size washer and dryer
Easy Access: Keyless entry; Walk into the building's lower level via the corner front door with an electronic lock code.
Convenient Parking: Parking for one car on driveway behind home
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
Dogs allowed with $150 per pet fee paid prior to checkin.
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.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning
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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 apartment is in the city centre. Maynard-Burgess House and Kunta Kinte Plaque & Alex Haley Memorial are local landmarks, and the area's natural beauty can be seen at Jonas Green State Park and Sandy Point State Park. French Soldiers Monument and Maryland Hall for Creative Arts are also worth visiting.
O'Brien's Oyster Bar & Seafood Tavern - 5 min walk
Chick & Ruth's Delly - 3 min walk
Annapolis Market House - 7 min walk
Frequently asked questions
Is 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?
As of 12 Apr 2026, prices found for a 1-night stay for 2 adults at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free on 18 June 2026 start from AU$589, 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 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?
On-site parking is available at the 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 apartment building 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.
Beautiful, well appointed house in a great location.
Margaret S.
Stayed 2 nights in Sep 2025
Response from VrboOwner on 30 Sept 2025
Thanks, Margaret! We’re thrilled to hear that Main Sail was beautiful and well-appointed for your stay. It’s wonderful to know that you found the location great. We would love to host you again next time you’re in town.
Melissa~iTrip Annapolis
We had an amazing time in Annapolis and the accommodations were perfect! Very central location that made everything walkable!
Jason H.
Stayed 2 nights in Dec 2024
Response from VrboOwner on 14 Jan 2025
Hi Jason! Thank you for being a great guest & we welcome you back anytime! Thank you for sharing your positive feedback, we sincerely appreciate knowing you enjoyed your time in the home, Melissa~iTripAnnapolis
From a partner site
10/10 Excellent
Kyrsten W.
29 June 2025
Wonderful stay!
We absolutely loved our stay at the Main Sail! The home was beautifully decorated, fresh and modern without a lot of fuss. The beds were comfy and the hardwood floors throughout are beautiful! We appreciated the starter pack of K-Cups for coffee in the morning while we waited for groceries to be delivered. We would absolutely stay here again!
Kyrsten W.
Response from VrboOwner on 4 July 2025
Thanks, Kyrsten! We're thrilled to hear that you loved your stay at Main Sail. It's wonderful that you appreciated the beautiful decor and comfy beds. We're glad the starter pack of K-Cups came in handy while you waited for your groceries. We would absolutely love to welcome you back for another stay in the future!
Melissa~iTrip Annapolis
This property is ideal location to DTA. The best part is its own parking spot. The house was very clean and comfortable. I would highly recommend staying at this property.
Daniel N.
Stayed 3 nights in Sep 2024
Response from VrboOwner on 10 Sept 2024
Hi Daniel! Thank you for allowing us to host your stay & we are thrilled to know you enjoyed your time in the home! We welcome you back anytime, Melissa~iTripAnnapolis
My family loved staying here! The house was perfectly located to walk to town and a bonus that it has a parking spot! The home was clean and comfortable with all the amenities we could need! It was very easy to walk our dog around the neighborhood and there is a convenient dog friendly park on the water a block over. The property owner is very responsive and we felt well taken care of! We will absolutely be staying here again!
Sara G.
Stayed 3 nights in Apr 2025
Response from VrboOwner on 3 May 2025
Hi Sara! Thank you for being a great guest & we welcome you back anytime! We're thrilled to hear that your family loved staying at Main Sail and appreciated its perfect location and amenities. It's wonderful to know that the home was comfortable for you and your dog, and that you enjoyed the nearby dog-friendly park. We're glad you felt well taken care of by the property owner. We look forward to your next stay with us! Melissa~iTripAnnapolis
From a partner site
10/10 Excellent
Angus M.
13 Oct 2025
Main Sail Stay, Oct 2025
Definitely a 5 star stay. Everything when over and above our expectations. Thanks for your help for making it that way. Angus
Angus M.
Response from VrboOwner on 16 Oct 2025
Thanks, Angus! We’re thrilled to hear that Main Sail impressed you and went over and above your expectations. It’s wonderful to know that our efforts contributed to your 5-star stay. We hope to host you again next time you’re in town!
Melissa~iTrip Annapolis
From a partner site
10/10 Excellent
Liz D.
1 Apr 2025
Week of R & R
I had to plan a trip to Annapolis on very short notice to be with my Midshipmen who was having surgery. Cathy was very helpful in finding us a place in DTA that would provide a comfortable and conveniently located property for my son to recuperate. We will definitely stay here again and recommended it to friends who are coming in a few weeks!
Liz D.
Response from VrboOwner on 5 Apr 2025
Thank you for allowing us to host your stay Elizabeth, we appreciate your kind feedback
& we hope to host you again, Melissa~iTripAnnapolis
From a partner site
10/10 Excellent
Elaine and Rob K.
31 Jan 2025
Comfortable extended stay
We stayed at Main Sail for two weeks this January. It was a perfect house for my husband, myself and our midshipman. Location is fantastic. Great shower/bathroom for a downtown Annapolis house. The kitchen was well stocked with basics. Gas stove is a plus. Beds were very comfortable. Also a cozy and relaxing living space to watch NFL playoff games and the dedicated parking spot is a huge bonus for DTA!
Elaine and Rob K.
Response from VrboOwner on 4 Feb 2025
Hi Elaine! Thank you for allowing us to host your stay & we are thrilled to know you enjoyed your time in the home! We welcome you back anytime, Melissa~iTripAnnapolis
My husband and I stayed at Main Sail this weekend as our home base for attending the Annapolis Boat Show. This home is meticulously clean, well appointed, nicely furnished with all linens, has off street parking and is within easy walking distance if the downtown city docks, restaurants, Naval Academy and historic homes. Check in was a breeze. A great breakfast/ lunch spot favored by locals is a 5 minute walk as is the downtown shopping district.Price for the rental was reasonable compared with the cost of a hotel for the weekend if the boat show. I highly recommend this home and would definitely stay here again.
Mary M.
Stayed 2 nights in Oct 2024
Response from VrboOwner on 11 Oct 2024
Hi Mary! Thank you for being a great guest & we welcome you back anytime! Thank you for sharing your positive feedback, we sincerely appreciate knowing you enjoyed your time in the home, Melissa~iTripAnnapolis
We stayed in Annapolis with our adult/ teen children for the weekend. We brought one car so the off street parking was helpful. It's a shared parking space with another homeowner so do not drive a XL SUV. The beds were comfortable and we needed to utilize the pull out couch as well. We can't say enough about how perfect the location was. Walks into town and to the naval academy were plenty! The shops decorated for the holiday season was such a highlight. I highly recommend this adorable flat.
Trish L.
Stayed 2 nights in Dec 2024
Response from VrboOwner on 24 Dec 2024
Thank you for staying with us, Trish & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
About the host
Hosted by iTrip Vacations Annapolis - Sean Degnan
Languages:
English
Premier Host
They consistently provide great experiences for their guests