Entire home

Available for CW 2025 2 blocks from Main St with parking - dog-friendly

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Welcome to the Main Sail, 2 blocks from Main Street shops and restaurants, and steps from City Dock and USNA.
Welcome to the cozy living space of the Main Sail - the 1st floor of this Historic 3-unit building.
The full kitchen is located off the family room and is ready for your weekend dinner plans!
At one point in history, a grocery store, known as “Mr. Jonnies Store”, was located on the 1st floor and his family lived above,
The King bedroom includes a 2nd TV and a Full sleeper sofa.

Reviews

10 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 6

Popular amenities

  • Dryer
  • Washer
  • Kitchen
  • Pet-friendly
  • Air conditioning
  • Free WiFi

Explore the area

Map
Annapolis, MD
  • Annapolis City Dock
    ‪7 min walk‬
  • U.S. Naval Academy
    ‪13 min walk‬
  • Navy-Marine Corps Memorial Stadium
    ‪3 min drive‬
  • Annapolis, MD (ANP-Lee)
    ‪19 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
Dining area

About this property

Available for CW 2025 2 blocks from Main St with parking - dog-friendly

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.

Property manager

iTrip Vacations Annapolis - Sean Degnan
Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Pet-friendly
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property

About the area

Annapolis

Located in Annapolis, this holiday home 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 Helen Avalynne Tawes Garden are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Annapolis, MD

What's nearby

  • Maryland State House - 6 min walk - 0.5 km
  • Annapolis City Dock - 7 min walk - 0.7 km
  • William Paca House - 8 min walk - 0.7 km
  • U.S. Naval Academy - 13 min walk - 1.1 km
  • Navy-Marine Corps Memorial Stadium - 3 min drive - 2.2 km

Getting around

  • Odenton Station - 22 min drive
  • Fort Meade, MD (FME-Tipton) - 35 min drive

Restaurants

  • ‪The Choptank - ‬7 min walk
  • ‪Starbucks - ‬5 min walk
  • ‪O'Brien's Annapolis' Original Steakhouse - ‬5 min walk
  • ‪Chick & Ruth's Delly - ‬3 min walk
  • ‪Mc Garvey's Saloon - ‬7 min walk

Frequently asked questions

Is Available for CW 2025 2 blocks from Main St with parking - dog-friendly pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Available for CW 2025 2 blocks from Main St with parking - dog-friendly?

Check-in begins at 4:00 PM.

What time is check-out at Available for CW 2025 2 blocks from Main St with parking - dog-friendly?

Checkout is at 11:00 AM.

Where is Available for CW 2025 2 blocks from Main St with parking - dog-friendly 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 6 out of 6 reviews
Rating 8 - Good. 0 out of 6 reviews
Rating 6 - Okay. 0 out of 6 reviews
Rating 4 - Poor. 0 out of 6 reviews
Rating 2 - Terrible. 0 out of 6 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Jason H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great space and location

We had an amazing time in Annapolis and the accommodations were perfect! Very central location that made everything walkable!
Stayed 2 nights in Dec 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Liz D.

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!

10/10 Excellent

Daniel N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Spot

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.
Stayed 3 nights in Sep 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Elaine and Rob K.

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!

10/10 Excellent

Trish L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location

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.
Stayed 2 nights in Dec 2024

10/10 Excellent

Mary M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent for Downtown Activities

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.
Stayed 2 nights in Oct 2024

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests