Stunning Waterfront Cottage in the Sailing Capital of the World!

Annapolis, Maryland
$555 avg/night
Minimum Stay 2 Nights
Bed 2

Bed

Bath 1

Bath

Home Private Vacation Home

Property Type

Sleep 6

Max Sleeps

Night 2 nights

Min Stay

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.

Read More Expand
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Beach Towels
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 750 Sq Ft (70 Sq M)
  • KITCHEN

    Cookware/dishes/utensils Dishwasher Microwave Oven Paper Towels Refrigerator Spices Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Recommended Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Barbecue Grill Garden Patio
  • POOL/SPA

    Private Pool Shared/communal Pool
  • BATHROOMS

    1 Bathroom Hair Dryer Shower Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Bicycle On Site Birdwatching Nearby Boat On Site Casino Nearby Cycling Nearby Ecotours Nearby Fitness Center Fitness Facilities Nearby Horse Riding Nearby Kayak On Site Marina Nearby Sailing Nearby Swimming Nearby Winery Tours Nearby
  • ENTERTAINMENT

    Books Games Table Tennis Smart TV With Cable/satellite Service
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Travel Crib
  • LOCATION HIGHLIGHTS

    Near A Hospital Near Outlet Shopping Near The Bay On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Hardwood Flooring In Public Areas If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Availability

Review Review

  • David T.

    Submitted Jun 8, 2026

    Stayed Jun 4, 2026

    Really nice house right on the water The pool was close and nice bonus! Really fun to take the water taxi into town!

  • Christine H.

    Submitted May 25, 2026

    Stayed May 21, 2026

    Cottage is lovely!Gave a four rating due to key lock box is tricky to open, WIFI login information was not up to date in welcome information nor in cottage handbook and water taxi information was not clear.Host had to update through messaging.Wish we were able to use more of the Marina facilities but it rained the entire weekend.The Black Market cafe was the best for grabbing coffee and pastries.

  • Mindy F.

    Submitted May 11, 2026

    Stayed May 8, 2026

    We had the best time. The space was perfect for our family of four (including a 9 month old baby). The deck was spacious and the view was breathtaking. The kitchen was spacious, bathroom was spacious and clean, bedrooms were great for our needs. We walked to the market, used the kayaks, strolled around the docks and used the playground. We hope to be back very soon.

  • KG O.

    Submitted May 10, 2026

    Stayed Apr 24, 2026

    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!

  • Dyuti D.

    Submitted Nov 16, 2025

    Stayed Nov 13, 2025

    This cottage was the perfect place to stay for our Annapolis weekend!

  • Lindsey G.

    Submitted Oct 15, 2025

    Stayed Oct 9, 2025

    Everything was great!!!!

  • Sam G.

    Submitted Oct 10, 2025

    Stayed Oct 4, 2025

    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.

  • Shearerie W.

    Submitted Oct 3, 2025

    Stayed Sep 26, 2025

    We loved the place and the water taxi experience!

  • Marianne B.

    Submitted Sep 17, 2025

    Stayed Sep 11, 2025

    Wonderful experience. Stephanie, our host was amazing. See below sunset

  • Cherie M.

    Submitted Aug 24, 2025

    Stayed Aug 21, 2025

    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!

  • Grace R.

    Submitted Aug 21, 2025

    Stayed Aug 17, 2025

    Great stay and so happy to find a family-friendly spot with prime location. Amenities on site were excellent.

  • Stephanie G.

    Submitted Aug 15, 2025

    Stayed Aug 6, 2025

    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.

  • Kirsten M.

    Submitted Jul 26, 2025

    Stayed Jul 19, 2025

    We enjoyed our stay and the location was great for traveling to Baltimore, DC, St. Michael’s, Ocean City and Assateague Island. We also enjoyed some of the amenities at the marina, including the kayaks, bikes, and especially the pool. The staff at the marina were very friendly.With that said, the communication/directions for accessing the amenities was not clearly communicated through messaging or once we arrived. We easily found the pool pass, but without the help of the people at the marina we never would have found the kayaks, life vests, bikes, or trail. While the house was clean, it doesn’t seem that it was “recently” remodeled. The walls need repainted in many rooms, the arm chairs need cleaned, the main entrance appeared to have some water damage previously, and the wood floors showed wear, especially at doorways. The washer also had mold in the detergent/softener drawer. We also had some difficulty with the refrigerator cooling down once we filled it with the food we had brought. Eventually it was able to cool down, but not before taking things out to try and get the temperature down. While none of this affected our overall stay, the cottage was slightly misleading in terms of new renovations. It definitely was updated, but pricey for the week we stayed. Again, overall we enjoyed our stay and the location worked out great for our needs.

  • Diana C.

    Submitted Jul 16, 2025

    Stayed Jul 6, 2025

    Beautiful cottage in a perfect location. Scott and his team are wonderful. We highly recommend this property!

  • Christina M.

    Submitted Jun 27, 2025

    Stayed Jun 24, 2025

    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

  • Kelly C.

    Submitted Jun 22, 2025

    Stayed Jun 19, 2025

    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 !

  • Jennifer B.

    Submitted Jun 8, 2025

    Stayed May 21, 2025

    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!!

  • Stacy B.

    Submitted May 20, 2025

    Stayed May 1, 2025

    It was just as pictured. Incredibly cute. The closeness to the water/ boats is a huge plus to us! We enjoyed the bakery. We also loved the town and how easy it was to navigate. We used the water taxis or Ubered. Uber was hit or miss - 2 drivers said they couldn’t find us that their gps was taking them into the water….but others found us just fine. We preferred the water taxis anyway. We plan to book again when we’re back in Annapolis - maybe around Christmas time.

  • Kathy T.

    Submitted May 8, 2025

    Stayed May 5, 2025

    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 !

  • Deanne R.

    Submitted May 2, 2025

    Stayed Apr 18, 2025

    Very relaxing. Loved the porch. Spent time outside enjoying the beautify scenery.

  • Beth B.

    Submitted Apr 6, 2025

    Stayed Apr 4, 2025

    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!

  • Melinda A.

    Submitted Mar 23, 2025

    Stayed Mar 14, 2025

    Enjoyable. Nice property. Very clean with updated features. If you enjoy being on the water and marina life, great place to stay.

  • Xavier F.

    Submitted Jan 26, 2025

    Stayed Jan 9, 2025

    Clean, cute, comfortable and well-equipped little cottage bumped up against Port Annapolis Marina. Beautiful views of all the boats and the marine traffic.

  • Catie B.

    Submitted Jan 1, 2025

    Stayed Dec 25, 2024

    I’m becoming a regular here because it is so lovely and cozy! Very convenient to my parents house down the road as well. Five stars again and again.

  • Catie B.

    Submitted Dec 10, 2024

    Stayed Nov 15, 2024

    Very well appointed with everything you might need. Lovely location and view of the boats/water/marina. There is a walkable bakery with a playground attached. Perfect for families who need to feed toddlers first thing. A cozy delight. We will be renting again .

  • Martha D.

    Submitted Nov 1, 2024

    Stayed Oct 25, 2024

    The cottage was lovely & views of the harbor were spectacular.

  • Mike C.

    Submitted Oct 21, 2024

    Stayed Oct 15, 2024

    Very cozy home sitting in the middle of the Annapolis boat harbor. The scene was so beautiful watch tall sailboats guide in and out of the harbor. Very close to all downtown Annapolis has to offer yet far enough away from the tourists to provide a peaceful and calm oasis. Did I mention the bakery, OMG! Just a few steps from the house is a small bakery that has the most delicious morning treats, both sweet and savory. They also prepare breakfast meals and delicious sandwiches to enjoy there or take on a picnic. Don't miss it if you stay here.

  • Brandi W.

    Submitted Oct 15, 2024

    Stayed Oct 11, 2024

    My husband and I have no regrets about staying here during our wedding weekend! We were super impressed with the coziness and cleanliness of the property. Our favorite part was getting to hear the wind whistling through the boats. It brought a sense of calmness during our special weekend.

  • Bethany D.

    Submitted Oct 11, 2024

    Stayed Oct 9, 2024

    The house was just as advertised. It was just perfect for a quick getaway and the perfect location to enjoy all things in Annapolis. Water taxi was a great way to get to downtown. Quiet and relaxing. Would love to go back!

  • Samantha G.

    Submitted Oct 2, 2024

    Stayed Sep 27, 2024

    My family and I stayed at the cottage over the weekend, and had a great time! We loved the deck and ease of walking to get coffee in the mornings. It is located away from the bustle of town, but not a far drive at all, which made it a great mix. My kids are already asking to go back!

  • Pete S.

    Submitted Sep 19, 2024

    Stayed Sep 13, 2024

    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!

Your dates are Available!

Total

Includes taxes and fees
$579+
View details