We stayed for 4 days and loved it. The cottage was tastefully done and immaculate! A short 5 walk to a private beach was a wonderful bonus. The beds were very comfortable and our hosts Winston and Carolyn were so accommodating. We would definitely go back!

Wonderful

Excellent, had everything imaginable for my visit away from home, fabulous outdoor space, short distance to important events, no traffic, walk to beach. Very quiet and relaxing on a busy holiday weekend. Try it, you will love it. Sign up before i take your dates! I will return!

We loved the community/neighborhood. It was perfect for walks and the beach area was excellent and very well kept. The house was perfect; everything you needed and then some. We felt very comfortable and enjoyed the stay! Would definitely book this property again.

Immaculate little place, loved the neighborhood, quiet diverse with homeowners, family rentals, young people old people ethnicity diverse. The beach for the little community on Chesapeake Bay is small but nice , gated, is open until midnight had plenty of room for family parties, has a small play ground and volleyball owners were in touch but not intrusive, can’t find a single thing to complain about.

Winston and Carolyn are extremely nice and thoughtful hosts. The space feels larger than it is with two comfortable bedrooms a nice living area and kitchen. They had the bedrooms, kitchen, and bathrooms extremely well stocked and were very easy to communicate with. We loved Annapolis but it was wonderful to be away from Downtown in a very quiet and extremely friendly neighborhood. We will be back no doubt. Thank you so much Winston and Carolyn!

Great location, clean and cozy.

Nicely equipped, very comfortable and lovely location.

The property was quaint and nicely appointed. Comfortable and clean. Hosts were wonderful!

I rented this house almost 2 years ago for my mid’s commission week. The Winston couple are the best host of Annapolis I have met in the past 4 years. The house is spotless and has everything we need. We held a postgraduation party and Winston couple helped us to turn it to successful party. What a pleasant stay!! I believe that Winston couple become our friends and we definitely will come back in the future.

Quiet neighborhood, beautiful home

We loved staying here! Everything is updated. Kitchen tools very high quality. Appreciated all the extras found in the pantry. Bed super comfy. Nice pillows. Backyard is lovely. Street is quaint and quiet. Quiet beach is a 5 minute walk away. We enjoyed hiking in Quiet Waters Park and Thomas Point Park also. Friendly neighbors and friendly owners who live next door!

Oyster Harbor is a wonderful home to stay when in Annapolis. The cottage has everything you need to feel comfortable, make a meal, walk the lovely neighborhood and have easy access to DTA. We are lucky to have found this gem and are sure to return.

The Host was accommodating and easy to deal with on every way. The property easily accommodated 2 couples and literally is just a few steps from the local beach in a quaint and quiet neighborhood. Also an easy 5-10 minute drive to all local events and experiences around downtown Annapolis and the Naval Academy.

From the moment you communicate with Winston and Carolyn, you know you are in good hands. The house was spotless, the towels plentiful and plush, the bed linens comfortable and the space was warmly and beautifully decorated with an eye for comfort and practicality. The kitchen had everything for heating or preparing a meal. The setting of the adorable house was great as well within a friendly neighborhood and with slight water views and a beach and dock down the street. We had family staying there but it would be comfortable for two couples or a couple with children. Well priced, well placed, and well taken care of! The hosts were very quick to respond to questions and even left us a basket of snacks! They are kind and warm hearted people and it shows in their rental. I would definitely rent here again!

This cottage was every bit as cute as represented. I can’t say enough about this place as everything was perfect. Super clean. Well appointed. Comfortable. And what wonderful hosts. They went the extra mile to be sure I had everything I needed. I hope to stay here again!

Wonderful cottage in quiet neighborhood, nice and clean and well stocked with towels and kitchen gear. Love the community beach. Hosts are good at communicating.

Enough space for us; very close to the water and also super clean and well kept. Would definitely return.

We had a wonderfully relaxing long weekend at this comfortable little home. Beautiful sunrise at the private beach. Quiet evenings. All within a short drive to downtown Annapolis. Check out Quiet Waters Park while you are here. Winston and Carolyn are gracious and responsive hosts. We’ll be back!

We just love The Anchors, so much that my partner and I want to keep it to ourselves;) This was our third visit and we brought our friends along for a night who loved it, too. The neighborhood is perfectly serene but getting into the city is super easy. It's really nice to have both options. The community is very friendly, too. Everyone waves on walks and bike rides. Come and enjoy your stay here!

The Anchors is a wonderful place in every way. The house is beautifully furnished, spotless, has every amenities you could every need and is in one of the best locations in Annapolis. The house is located in a quiet neighborhood surrounded by water Yet a short distance from downtown. The owners are incredibly hospitable and had great communication. Definitely a wonderful place to stay!

Our getaway to Oyster Harbor was wonderful. Winston and Carolyn were amazing host. They answered all my questions immediately. The cottage was cozy, clean, and beautifully decorated. I plan to return again in the future. Thank you Winston and Carolyn!

The house was very clean and modern. The hosts were great. The beach is really just down the block. The beach is small, quiet, and clean. The neighborhood was very friendly and walkable. The one disadvantage of this location was that it is a bit of a ride from downtown Annapolis (about 15 minutes).

This is our third time staying here for a week in the summer, and we always love it. The house is welcoming and clean. Winston and Carolyn are right next door and available if you ever need them, but we never have! The house is completely stocked with anything you’ll need. We love how close it is to the neighborhood beach. The neighborhood has plenty of quiet streets to walk and enjoy the bay views. The house is also only a quick drive to downtown, shopping centers, and countless restaurants. This is the perfect spot to do it all. We will definitely be back again next year!

Great little house. Perfect our anniversary weekend.

We had such a great girls weekend! The hosts were so kind and responsive to all our needs. Quick walk to a private beach and the neighborhood was so friendly! House was perfectly clean and welcoming .

This was perfect for a weekend getaway. The mattress was exceptionally comfortable and I slept like a rock.

We had a great stay at the Anchors! The cottage was extremely clean and comfortable. The kitchen was better appointed than previous VRBOs at which we’ve stayed. Winston and Carolyn were welcoming and available. We especially enjoyed the beach, which is a short walk down the road, and playing the available games in the evening. We definitely recommend this place!

This house was perfect for a long weekend in Annapolis. It was quiet, clean and a quick car ride to downtown. I would highly recommend to anyone!

The cottage was wonderful - clean, quiet, and just great. Fit all of our needs. Winston and Carolyn were absolutely fantastic and I look forward to staying again on my next trip to Annapolis. I highly recommend this great place in such a quiet, charming, and safe neighborhood.

We had a great stay. Cute, clean, and great location. Everything was awesome! Hosts are wonderful!

The cottage is charming, stayed there with my 2 sons, age 11 and 17. Charming neighborhood with a private beach access, playground for kids. Winston and Carolyn are lovely, helpful, wish I’d had more time to get to know them! Short 10 min drive to Annapolis. The sunrise there over the water is beautiful. Highly recommend, their place had everything you might need. I could have stayed forever!