Top 10% of guest reviews in this areaTop 10% of guest reviews in this area
Highlights
Family fun awaits
Top-rated for families.
Beach equipment
A rare find — beach equipment ready to go for your days by the sea.
Centrally-located
You're never far from where you need to be with this convenient location.
Discover nearby landmarks
Walk to Annapolis Landing Marina
2 bedrooms1 bathroomSleeps 6
Popular amenities
Private pool
Onsite parking available
Kitchen
Washing machine
Air-conditioning
Barbecue grill
Explore the area
Annapolis, MD
Annapolis Landing Marina
Place, Annapolis Landing Marina
3 min walk
Annapolis Sailing School
Place, Annapolis Sailing School
6 min walk
Sparrows Beach
Place, Sparrows Beach
15 min walk
Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
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.
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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
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Annapolis
Located in Annapolis, this holiday home is on the waterfront. Historical Society of Talbot County and Kunta Kinte Plaque & Alex Haley Memorial are local landmarks, and travellers looking to shop may want to visit Annapolis City Dock and Bay Bridge Market Place Shopping Center. 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 cycling.
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 31 Jul, 2026, prices found for a 1-night stay for 2 adults at Stunning Waterfront Cottage in the Sailing Capital of the World! on 4 Aug, 2026 start from S$1,510, 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 at Stunning Waterfront Cottage in the Sailing Capital of the World!?
On-site 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!?
Checkout is at 11:00 AM.
Where is Stunning Waterfront Cottage in the Sailing Capital of the World! located?
Situated on the waterfront, this holiday 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 miles (3 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
This was the perfect place to stay for our family of 5. We enjoyed time at the pool. The staff was very friendly. The sunsets from the house were beautiful. We had everything we needed cook and relax. The drive to downtown was short and scenic with lots of options for food and shopping.
Absolutely adorable cottage located near a marina with a waterfront deck. The house was spotless, nicely furnished, and very comfortable. We enjoyed our time there and hope to return. Everything about the place was wonderful. You will not be disappointed. Thank you!
This is a very nice place and location to stay!
Wonderful experience.
Dirk W.
Stayed 4 nights in Sep 2023
Verified
6/10 Okay
Laura M.
27 Jun, 2026
Liked: Cleanliness, location
Disliked: Check-in, communication
This is a beautiful location and the cottage is sweet, but the hosts seem disconnected from this property that is part of a large Marina Complex. We checked in on Sunday afternoon at the check in time and the housekeeping was only half done. The contact person listed for the weekend didn’t respond to me about this issue. On Monday the housekeeping team returned. None of the ceiling fans were operating according to the manual and I reported this right away and I was told maybe someone could look at it. They did not. There was also a musty smell especially in the main bedroom that felt very unpleasant. Kayaks and bikes were listed in the rental but there was no sign or mention of their whereabouts. I didn’t bother asking. This rental needs more care for the price that is being charged.
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.
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 !
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!
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!
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 !
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!!
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!
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.