Nautical Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly

I rented this cottage very late in the season. I was booking a fun 'weekend' getaway for my girlfriends. The owner let me book for 3 days (instead of the normal one week stay) because we were so close to the date. The view is absolutely spectactular!!! Overlooking Pleasant Bay and watching little white sailboats sail on by!!! We spent many hours on the deck...even in misty/foggy weather!!! The cottage is adorable with a large great room - including family room sitting area and kitchen. The kitchen is a little small but we never ate in so it did not matter. All we needed was to chill our wine and have hors d'oeuvres. The rooms are very nautical and very 'cape coddy' feeling. Just the ticket!! It says that it sleeps 8 and it does if you have couples. There are three bedrooms with king/queen size beds and one bedroom with two twins. So, if you have three couples in the three beds (that's six ) and two kids in the two twins - you are great! But, we had five adult women and it worked out PERFECTLY!!!! Everyone got their own room except for the twin bed people. But, they did not care! The house is right down the street from many fantastic restaurants and Chatham downtown (one way) and Orleans downtown (the other way). We went to Nauset Beach - which has massive waves!!!! Lots of seals in the water - and sharks - if you dare! We were on the beach when the lifeguard pulled out everyone from the water because he witnessed a shark grab a seal!!! Exciting! Anyway, this property has responsive staff and very nice groundkeepers (who we met). It is part of the Pleasant Bay Community Boating sailing school. I would highly recommend the Square Top house for a wonderful Cape Cod getaway!!!

Many thanks to Natalie for her efforts in accommodating our last minute reservation. The staff at Pleasant Bay Community Boating also bent over backwards for any request we had. I was hoping for a nice Cape experience for my family and we got it. The cottage is a good central location to explore the Cape. We were able to visit both Provinceton and Hyannis Port. We’re not boaters but we so enjoyed watching the sailboats criss cross the bay in the gentle breeze. I even watched a seal feed on a large school of fish while standing on the dock at daybreak, he literally swam right under me-priceless. I would very much recommend. The front of the home is right on a somewhat busy road and the living quarters are “rustic” but the views, boating vibe and courteousness of Natalie and Huntley made it a great memory for my family.

Great location, great setting. Excellent space to all be together for meals and to hang out. Stunning view. Excellent access to sailboats and small beach. We really liked having our own beach in our "backyard". The kids AND the grownups loved all of it.

The house is quite lovely and efficient. The wrap-around porch overlooking the bay is an incredibly stunning place to be, and the living/dining area just inside the house, which has the same view, is almost as nice. When I looked at the website, I thought the least appealing place was the kitchen, but the kitchen is in fact well-equipped and functional. Just bring some dish towels, and, perhaps, more towels generally. My guests and I were at the Cape for a wedding, so we did not take advantage of all the house offers, including an outside grill and opportunities for boating. Perhaps another time....

We were a bit shocked as we entered Square Top the first day. The steep and narrow stairs to the upstairs bedrooms, very small kitchen with an older stove, and a laundry room that had not been used in years. But, once we went outside and realized how much we loved the deck and outdoor shower, we settled in. The 2 bedrooms facing the water were very comfortable and thank goodness for the large bathroom and airconditioning upstairs. My niece had the bedroom facing the busy road but used one of the many fans to drown out the noise. We had planned on cooking fresh fish on the grill that was provided but it wasn't working properly, even after the property manager came to try and fix it. We had a lovely sail and enjoyed all the action provided by the neighboring sailing club. Best of all, the weather was perfect!