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

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2 bedrooms, iron/ironing board, free WiFi - 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free (Annapolis)
Point of interest - 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free (Annapolis)
Close to U.S. Naval Academy, 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free provides amenities such as laundry facilities. Guests can connect to free in-room WiFi.

Reviews

10 out of 10
Exceptional

Entire apartment

2 bedrooms1 bathroomSleeps 684 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning

Add dates for prices

About this property

Entire place

You'll have the entire apartment to yourself and will only share it with other guests in your party.

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.

Property amenities

Internet

  • Available in the apartment: Free WiFi

Kitchen

  • Coffee/tea maker
  • Dishwasher
  • Ice maker
  • Microwave
  • Refrigerator

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Sofa bed

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shampoo
  • Shower

Living spaces

  • Dining table
  • Living room

Entertainment

  • TV

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre

Things to do

  • Bicycle parking

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)

General

  • At least 80% lighting from LEDs
  • Bicycle parking
  • Energy-saving switches in guestrooms
  • Unit size: 900 square feet

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

Property is also known as

14857

About the area

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 Maryland Hall for Creative Arts are also worth visiting. Visit our Annapolis travel guide
View more Apartments in Annapolis
Map
Annapolis, MD

What's nearby

  • Maryland State House
    Maryland State House
    5 min walk - 0.4 km
  • William Paca House
    William Paca House
    6 min walk - 0.6 km
  • U.S. Naval Academy which includes heritage architecture, military items and interior views
    U.S. Naval Academy
    6 min walk - 0.6 km
  • Ego Alley
    Ego Alley
    6 min walk - 0.6 km
  • Annapolis City Dock
    5 min walk - 0.4 km

Getting around

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

Restaurants

  • Starbucks
    5 min walk
  • Rams Head Tavern
    7 min walk
  • O'Brien's Oyster Bar & Seafood Tavern
    5 min walk
  • Buddy's Crabs & Ribs
    6 min walk
  • Chick & Ruth's Delly
    3 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.

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 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.

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

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 11 out of 11 reviews
Rating 8 - Good. 0 out of 11 reviews
Rating 6 - Okay. 0 out of 11 reviews
Rating 4 - Poor. 0 out of 11 reviews
Rating 2 - Terrible. 0 out of 11 reviews

10

Cleanliness

10

Location

Reviews

10/10 Excellent

Nancy E.

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

Perfect location

Perfect location, very clean and comfortable, walked to everything, loved having the car nearby.
Stayed 2 nights in Apr 2025

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

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 is from a guest who booked and stayed through a partner site and can't be 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!
This review is from a guest who booked and stayed through a partner site and can't be 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

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

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

Margaret S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful, well appointed house in a great location.
Stayed 2 nights in Sep 2025
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Kyrsten W.

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!

10/10 Excellent

Sara G.

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

Perfect place for visiting Annapolis !

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!
Stayed 3 nights in Apr 2025
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Angus M.

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