Cozy Cottage by the Beach - Waterview
Minutes from Downtown Annapolis

This beautiful cozy little cottage is nestled in a delightful quiet private beach community. The Anchors (owners) are super friendly, attentive and quick to respond to you if you have any questions. Our family of 4 from Katy, Texas, stayed there for 1 week to celebrate our son’s commissioning week and graduation from the US Naval Academy and we thoroughly enjoyed our stay at their cottage. Grocery stores, restaurants, pharmacies, etc. are just minutes away. I highly recommend this beautiful cottage for any couple or small family that wishes to get away, unwind and enjoy the tranquility of a private beach community in beautiful Annapolis, Maryland.

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

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

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!

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 stayed at the Anchors last weekend. It was the perfect way to mark the end of a long year in quarantine and the first weekend of spring. The property was so clean and the location was super convenient. We had all the creature comforts: two nice-sized bedrooms, a water view, nice yard space out back where kids can play, three Smart TVs (we brought our Fire stick so our 3 & 5 year olds could watch their favorites drama-free). Oh, and the FLUFFIEST towels! The hosts, Winston and Carolyn, introduced themselves (they were great) and helped us get acquainted with the neighborhood. They also shared several restaurants recommendations. The property is just up the street from the community beach and playground and there's a second playground within a few minutes in the other direction. The best of Annapolis is just a stone's throw away. There's great local restaurants (check out Main & Market), a grocery store (if you want to do your own cooking in the well-stocked kitchen), CVS, etc., in the immediate vicinity. Downtown Annapolis is less than a 10 min drive, so you're close to the action if you want to be. But you can also have a great time hanging close to the Anchors and within the super-friendly Oyster Bay community. Overall, this property was excellent for our quick family getaway. (My 5 year old did NOT want to leave!) It'd also be great for couples or for people who want to change up their work-from-home scenery for a few days. Highly recommend!!

Clean

Cozy two bedroom, the development has a private beach quiet neighborhood… nice stay

Remarkable! To sum it up, my two young children and I had an unforgettable stay. Winston and Carolyn were truly the hosts of all hosts—there aren’t enough stars to give or words to describe how wonderful it was..

Perfect house in a perfect location! We drove from Long Island to visit friends in Severn on our way to NC. This house is perfectly situated on a quiet block across from a creek with beach access via a 5 min walk down the block. We met Winston and Carolyn and they were lovely! We look forward to staying at this house again the next time we visit our MD friends! Winston and Carolyn, thank you for making your home feel like our home! Especially with a 4 year old and 2.5 year old! See you soon :) —barely have pics because we were too busy having fun!!

My BFF and I very much enjoyed our four day stay at the anchors cozy cottage. The queen bed super soft and comfortable, was told the full size bed was a little firmer, but still just as good, cozy sheets, and bedding.Rain showerhead made the shower luxurious I felt very spoiled!TVs with streaming services in each room if you choose to use them.Excellent location you can see the water through the front of the house and it’s just a minute walk down the nice quiet road. Lots of people walking their dogs and bike riders.Private beach for the residence.The owners were very accommodating and answered any questions very quickly.I give this an A rating and would definitely stay again if back in the Annapolis area.

I would definitely recommend this cottage! I was very impressed with cleanliness of this home. The neighborhood is very quiet and friendly. We booked this home to attend my son’s graduation from the US Naval Academy. It was the perfect distance from the stadium. The beach was very relaxing and private. We hated to leave.

Fantastic location - was close enough to downtown Annapolis for easy access but also felt like a beach getaway being just a short the the community beach. Incredibly responsive hosts!

It was nice to get outside DTA and see another part of Annapolis. 15 minutes from DTA it was quiet and beautiful small cottage perfect for our family. The home was clean and designed well. We would stay again. Thank you!!!

Great property and great time in Oyster Harbour!

We have stayed in many VRBO properties around the country and The Anchors is by far the most pleasant experience we have ever had. The cottage is immaculately clean, thoughtfully fitted out, and in a safe, quiet neighborhood. The beds are comfortable and there is plenty of hot water-these are the most important things we look for in a rental property. The rainfall shower is a pleasant touch! The owners, Carolyn and Winston, are tremendously gracious and accommodating. They made us feel very much at home in this jewel of a cottage! The neighborhood is very quiet and relaxed- you can actually feel your blood pressure go down as you arrive in this laid back community! Cannot wait to return!

Clean, well stocked, nice furniture, quiet neighborhood, lots of amenities, good location. I would highly recommend this property. We stayed very comfortably for a week. Went in and out of DC without issue. Check in and out was easy. I'd stay here again.

The hosts were so attentive and friendly, the location is wonderful- close to downtown yet tucked away in a nice neighborhood away from everything! Perfect getaway, can’t wait to rent this home again in the future.

A great location for our weekend in Annapolis with our 6 year-old grandson. Having the beach and playground just down the street was perfect! Clean house. Great local host!