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Stunning Waterfront Cottage in the Sailing Capital of the World!

Photo gallery for Stunning Waterfront Cottage in the Sailing Capital of the World!

Living Room
Side View of Cottage
Back yard looking up to deck
Exterior
Main Entrance into Mud Room

Reviews

10 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 6750 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Gym

Explore the area

View in a map
Annapolis, MD
  • Place, Annapolis Landing Marina
    ‪3 min walk‬
  • Place, Annapolis Sailing School
    ‪6 min walk‬
  • Place, Sparrows Beach
    ‪17 min walk‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪53 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

The Captain's Room

1 King Bed

The First Mate's Room

1 Double Bed

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Garden
Dining area

About this property

Stunning Waterfront Cottage in the Sailing Capital of the World!

Experience an exceptional waterfront setting in the Sailing Capital of the World. This upgraded 2‑bedroom, 1‑bath cottage sleeps 4–6 guests and offers a thoughtful blend of charm and modern comfort.
The open floor plan features hardwood floors, custom cabinetry, and granite countertops. The fully equipped kitchen includes new appliances—stove, microwave, side‑by‑side refrigerator, dishwasher, and coffee maker—and comes stocked with all essential cookware, dishes, and utensils.
The marble‑tiled bathroom includes a spacious shower, vanity, and all the necessities for a comfortable stay. The living room offers a sleeper sofa, two plush chairs, and a large flat‑screen TV with cable. A bright dining area with seating for four provides an ideal spot for morning coffee or an intimate meal.
Double French doors open onto a deck with seating overlooking Back Creek and the expansive backyard. Guests are welcome to relax with waterfront views or enjoy the provided kayaks.
Conveniently located just minutes from Historic Downtown Annapolis, the property offers easy access to the Chesapeake Bay. Grocery stores, pharmacies, liquor stores, and excellent restaurants are all within two miles.
As part of the marina community, guests enjoy access to seasonal pool use, a fitness center, Wi‑Fi, bicycles, and a water taxi stop just steps from the cottage. Black Market Bakers is also nearby and highly recommended for breakfast, lunch, or a sweet treat.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Air conditioning
Gym

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House Rules

Check in after 3:00 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

No 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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock

About the neighborhood

Annapolis

Located in Annapolis, this vacation home is on the waterfront. Historical Society of Talbot County and Kunta Kinte Plaque & Alex Haley Memorial are local landmarks, and travelers looking to shop may want to visit Bay Bridge Market Place Shopping Center and Annapolis City Dock. Wild Bird Center and Annapolis Maritime Museum are also worth visiting. Discover the area's water adventures with sailing and fishing nearby, or enjoy the great outdoors with ecotours and horse riding.
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Map
Annapolis, MD

What's nearby

  • Annapolis Landing Marina - 3 min walk - 0.3 km
  • Annapolis Sailing School - 6 min walk - 0.6 km
  • Sparrows Beach - 17 min walk - 1.5 km
  • U.S. Naval Academy - 20 min drive - 7.6 km
  • Annapolis City Dock - 21 min drive - 8.3 km

Getting around

  • Odenton Station - 27 min drive
  • Fort Meade, MD (FME-Tipton) - 30 min drive

Restaurants

  • ‪The Choptank - ‬9 min drive
  • ‪Carrol's Creek Cafe - ‬9 min drive
  • ‪Sammy's Italian Pizza Kitchen - ‬7 min drive
  • ‪Boatyard Bar & Grill - ‬9 min drive
  • ‪O'Brien's Oyster Bar & Seafood Tavern - ‬10 min drive

Frequently asked questions

Does Stunning Waterfront Cottage in the Sailing Capital of the World! have a pool?

Yes, this property has a pool.

How much does it cost to stay at Stunning Waterfront Cottage in the Sailing Capital of the World!?

As of Apr 21, 2026, prices found for a 1-night stay for 2 adults at Stunning Waterfront Cottage in the Sailing Capital of the World! on May 8, 2026 start from $394, 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.

Is Stunning Waterfront Cottage in the Sailing Capital of the World! pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Stunning Waterfront Cottage in the Sailing Capital of the World!?

Check-in begins at 3:00 PM.

What time is check-out at Stunning Waterfront Cottage in the Sailing Capital of the World!?

Check-out is at 11:00 AM.

Where is Stunning Waterfront Cottage in the Sailing Capital of the World! located?

Situated on the waterfront, this vacation home is within a 5-minute walk of Annapolis Landing Marina and Annapolis Sailing School. Sparrows Beach and Bay Bridge Market Place Shopping Center are also within 2 mi (3 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 210 out of 220 reviews
Rating 8 - Good. 10 out of 220 reviews
Rating 6 - Okay. 0 out of 220 reviews
Rating 4 - Poor. 0 out of 220 reviews
Rating 2 - Terrible. 0 out of 220 reviews

10/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Dyuti D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This cottage was the perfect place to stay for our Annapolis weekend!
Stayed 3 nights in Nov 2025
Verified

10/10 Excellent

Shearerie W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved the place and the water taxi experience!
Stayed 2 nights in Sep 2025
Verified

10/10 Excellent

Grace R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay and so happy to find a family-friendly spot with prime location. Amenities on site were excellent.
Stayed 4 nights in Aug 2025
Verified

10/10 Excellent

Lindsey G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was great!!!!
Stayed 3 nights in Oct 2025
Verified

10/10 Excellent

Stephanie G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was perfect for USNA parent's weekend. The location on the marina was peaceful and beautiful. The amenities were great. Would definitely come back.
Stayed 5 nights in Aug 2025
Verified

10/10 Excellent

Diana C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful cottage in a perfect location. Scott and his team are wonderful. We highly recommend this property!
Stayed 5 nights in Jul 2025
Verified

10/10 Excellent

Marianne B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful experience. Stephanie, our host was amazing. See below sunset
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

Cherie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a cute, clean cozy quaint cottage & area to stay in!!!! We loved we were out of downtown Annapolis to enjoy some quiet relaxing time but a quick water taxi or uber ride away to venture into town! It’s was a great get away after dropping our son off in DC for college. We can’t wait to come back! Thank you for sharing your cottage with us!
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Dirk W.

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

Wonderful Stay

This is a very nice place and location to stay! Wonderful experience.
Stayed 4 nights in Sep 2023
Verified

10/10 Excellent

Sam G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
One needs a car here as the stores and restaurants are not in the immediate area.That would be the only negative that I would mention. The kitchen was more than adequate, and we enjoyed our meals there.Wish we could have stayed longer than 3 days, and I would not hesitate to recommend this beautiful cottage.
Stayed 3 nights in Oct 2025
Verified

10/10 Excellent

Kathy T.

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

Great stay!

Our family had a great time!Wonderful location. Owner was very responsive and friendly. We did a quick 3-day visit and enjoyed every minute. Easy access to great restaurants and the attractions in Annapolis. Highly recommended !
Stayed 2 nights in May 2025
Verified

10/10 Excellent

Kelly C.

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

Perfect Long Weekend

This was our second time staying at the captains cottage, and it was perfect for our needs - our 3 year old loved the playground and pool nearby and it was very conveniently located to the wedding venue we were in town for. Can’t wait to come back next year !
Stayed 3 nights in Jun 2025
Verified

10/10 Excellent

Jennifer B.

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

Great stay!!

Loved our stay at the unbelievably cute house in a stunning setting. Perfect for families needing more space than a hotel with a full kitchen and living room. Beautifully renovated and decorated. Very convenient to downtown Annapolis and the Naval Academy. Highly recommend!!! Thank you!!
Stayed 3 nights in May 2025
Verified

10/10 Excellent

Beth B.

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

Thank you!

We had a wonderful stay in your cute cottage! It was the perfect place to stay while visiting our son and exploring Annapolis. Highly recommend!
Stayed 2 nights in Apr 2025
Verified

10/10 Excellent

Teresa G.

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

Wonderful stay

This house had everything we need and was a delightful retreat in the midst of a crazy wedding weekend. We would love to stay again next time we are in town!
Stayed 3 nights in Sep 2023
Verified

10/10 Excellent

Martha D.

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

Beautiful Views

The cottage was lovely & views of the harbor were spectacular.
Stayed 4 nights in Oct 2024
Verified

10/10 Excellent

Robert S.

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

Favorite Annapolis Stay

We love the cottage!!!
Stayed 3 nights in Sep 2019
Verified

10/10 Excellent

Xavier F.

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

Great waterfront cottage

Clean, cute, comfortable and well-equipped little cottage bumped up against Port Annapolis Marina. Beautiful views of all the boats and the marine traffic.
Stayed 3 nights in Jan 2025
Verified

10/10 Excellent

Pam B.

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

Beautiful Location

Wonderful home during our USNA 2/C parent's weekend!
Stayed 4 nights in Sep 2024
Verified

10/10 Excellent

Christina M.

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

Lovely little cottage

The cottage was conveniently located, clean, comfy and super cute. I highly recommend renting this cabin if you are planning to rent a boat and explore Annapolis by water. It was also easy to get to downtown and the Academy by car. We loved walking to the pool and the coffee shop/bakery. The beds were comfy and the cabin was very clean. I’m
Stayed 3 nights in Jun 2025
Verified

10/10 Excellent

Deanne R.

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

Visiting my midshipmen!

Very relaxing. Loved the porch. Spent time outside enjoying the beautify scenery.
Our friend showed up several times over our visit!
Stayed 3 nights in Apr 2025
Verified

10/10 Excellent

Pete S.

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

Stunning Marina Views and Perfect Annapolis Location!

We had an amazing stay! The view of the water and marina was incredible, and we loved eating crabs out on the deck while watching the boats come and go. The location was perfect—just a short and easy bike ride to the Annapolis city dock area. Would definitely stay here again!
Stayed 3 nights in Sep 2024
Verified

10/10 Excellent

Melinda A.

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

Waterfront Captains Cottage

Enjoyable. Nice property. Very clean with updated features. If you enjoy being on the water and marina life, great place to stay.
Stayed 3 nights in Mar 2025
Verified

10/10 Excellent

Verified traveler

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

Great spot right on the water!

Beautiful views, clean cottage, equipped with everything you need
Stayed 2 nights in Oct 2023
Verified

10/10 Excellent

Annie C.

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

Perfect Cottage

This was the perfect place for our family’s jumping off point for our visits to DC and Annapolis. Great amenities for a relaxing night after exploring all day.
Stayed 3 nights in Jun 2023

About the host

Hosted by Scott Tinkler

Host profile image

Languages:

English
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