Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly
Cottage in Orleans, MA
8 guests · 4 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Includes essentialsPets allowed, Kitchen or Kitchenette, Air conditioner and more
About this cottage rental
This updated 4-bedroom 2-bathroom home has the best view on Pleasant Bay, hands down. The open floor plan is ideal for large family gatherings, and conversations blend easily through two large sliders that open onto an expansive deck overlooking the Bay. This nautical-style "Old Cape Cod" cottage sleeps 8. Two waterfront bedrooms—one with a king bed and one with a queen bed—have commanding views of Pleasant Bay. A third bedroom on the second floor sleeps two in twin beds. A fourth bedroom on the first floor has a queen bed with an adjacent first floor bathroom.
Built in 1941, Square Top commands center stage near the Northern end of an historic 3.6-acre estate, and the water’s edge is literally a stone’s throw away. Enjoy your morning coffee and your evening meals on the rustic decks overlooking the Bay. Spend your vacation beach combing, exploring the Cape and learning to sail with Pleasant Bay Community Boating (PBCB) located on this expansive property.
*Summer guests (June 1-Sept 6) can enjoy a five individual sails on a Sunfish sailboat and unlimited kayak uses during your stay.
*This sweet cottage--named "Square Top"--has central AC, heat and wifi. The fireplace is decorative only, and cannot be used for fires--thanks!
Built in 1941, Square Top commands center stage near the Northern end of an historic 3.6-acre estate, and the water’s edge is literally a stone’s throw away. Enjoy your morning coffee and your evening meals on the rustic decks overlooking the Bay. Spend your vacation beach combing, exploring the Cape and learning to sail with Pleasant Bay Community Boating (PBCB) located on this expansive property.
*Summer guests (June 1-Sept 6) can enjoy a five individual sails on a Sunfish sailboat and unlimited kayak uses during your stay.
*This sweet cottage--named "Square Top"--has central AC, heat and wifi. The fireplace is decorative only, and cannot be used for fires--thanks!
Amenities
Air conditioner
Pets allowed
Kitchen or Kitchenette
Internet / Wifi
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Family friendly
Map of Orleans, MA
$$$$
Ratings and reviews
10.0 / 10.0
We had an amazing time, view and host.
8.0 / 10.0
The house was clean, pleasant, needs updating. Kitchen is older gally style. Your parking is in a short walk, but you can drop off in front of house. Property is part of community sailing camp. Beautiful view. We were given a sailing lesson which was great! Also can use kayaks a
10.0 / 10.0
Location is great. The view of the bay and the sailing club is amazing . The beach is modest at best ,
The house was comfortable and clean and the manager very helpful. The house is old fashioned but the living space and the porch is right on the bay and great. The breeze from the bay was delightful.
10.0 / 10.0
We stayed here for our wedding week and I couldn't have asked for a better place. Great spot to hang out and steps to the beach. Everything was perfect. thank you!
10.0 / 10.0
The cottage is adorable and had everything our family needed for a wonderful stay. The staff of Pleasant Bay Community Boating (our hosts) could not have been more helpful. The views are just beautiful.
10.0 / 10.0
We had an absolutely amazing week at this house. We were able to enjoy some sailing, fishing, kayaking, an amazing sunset. The views from each of the bedrooms are amazing. Property is also closely located to Orleans beaches that are amazing as well.
10.0 / 10.0
Close to a lot of great spots and loved being on the water. House was perfect for our group. We’ll be back for sure!
10.0 / 10.0
We had a wonderful, relaxing time- mostly on the big wrap-around deck overlooking the beautiful bay. The cottage was immaculate and we were even able to check in early! We were also very fortunate to have stayed when the majority of the time there were no events, otherwise the dock would have been very busy and we wouldn't have been able to park close to the cottage. The only real downside was finding that the refrigerator outlet didn't work- but we made do with an extension cord. Thank you very much for such an enjoyable stay!!
8.0 / 10.0
This property was clean, airy and filled with light. The view of the Bay from the back of the house and deck was absolutely lovely. The house was complete in serving any kitchen, bathroom and living need we had for amenities. The central air conditioning was such relief given the unusual season of high humidity and little breeze from seaside locations. We found the property manager quick to respond to any queries we had and repairs that presented themselves. The only down side was parking off site which was an inconvenience since the Pleasant Bay Boating community used the parking in front of the cottage for parking or drop-off. Traffic and boat launch noise was at times aggravating. Overall, it did not put a dent in our overall enjoyment of this property.
10.0 / 10.0
We had a great time at Square Top. It was so fun being right in the middle of all the action of the community boating program. Thanks!
10.0 / 10.0
This comfortable cottage with stunning views was a perfect springboard to beautiful beaches, restaurants and more. We hope to return!
10.0 / 10.0
The location with water access is unbeatable and conveniently located to downtown Orleans and Chatham (<10 min drive) if do decide want to leave the property. We also took a quick drive up to Wellfleet to explore. We would start our mornings bright and early down at the essentially private beach, our dog loved swimming and the shallow water allowed us to take our daughter swimming, paddle boarding and kayaking. A few other highlights:
8.0 / 10.0
Pretty view! Really appreciated the quick response time and accommodating spirit of property manager.
4.0 / 10.0
This property is centrally located on the Cape making it convenient to visit all areas of interest. Additionally, it’s location facing Pleasant Bay is absolutely breathtaking.
There are kayaks and life vests, which we did not take advantage of, however the steps to the beach area were a bit treacherous. There is also a grill which we also did not use.
But… renters beware. The photos belie the actual premises. This house has incredible potential, but sadly it’s been very neglected. Many of the areas are in dire need of updating. While my party of 4 were mostly comfortable in our bedrooms, there was nothing inviting about our rooms. Linens were aged and clearly overused.
The kitchen was old fashioned, which we found charming on-line, was very run down all around.
Three bathrooms were advertised, but there are only two and the one on the first floor has only a prefab stall shower.
All of the fixtures in the bathroom were very outdated and many were rusted.
Electrical outlets and lighting was questionable, as well as the plumbing.
We enjoyed the back deck but it was also in need of a good cleaning and repairs in some places. The patio furniture was old, rusty and worn. The house could have been cleaner.
Mismatched chairs and linens. A plethora of mismatched floor rugs, bent screen doors, lighting fixtures with pull chains that were missing strings, no outlet in the upstairs bathroom, blinds without operating cords, no bathroom amenities whatsoever other than tp.
Additionally, the entrance to the house is up a concrete flight of stairs over a rickety flagstone path. We would not consider this wheelchair accessible.
In short, the house reminds one of a shore house that college
students might rent for summer vacation. It is very run down.
Parking, while “on property” is at least 200 feet away and information regarding checking in was confusing at best.
While there were visitor pamphlets in the dining area, more local info would have been welcomed.
There is good Wi-Fi and tv service. Water was hot and pressure in the showers was good. The a/c seems to be acceptable also.
We contacted the property manager with our concerns and to his credit we were refunded one nights stay and given a bottle of wine for our trouble. That was very nice, but it did not go far enough to entice us to return.
We enjoyed our Cape stay, but we’re disappointed in what we felt were misrepresentations. We won’t be coming back..
8.0 / 10.0
All the big stuff about this house is great -- superb setting, light and airy rooms, good beds, hot shower, responsive manager. But the experience was diminished a bit by unnecessary small staff - nonfunctional and misshapen shades in the front bedrooms, moldy shower mats, broken chair in the side yard, light pulls that were frayed or too short. Once these are fixed, it will be 110% perfect!
10.0 / 10.0
We had a lovely stay
10.0 / 10.0
Great views
I stayed with 7 family members in this cute and clean cottage. The views of the bay are amazing and we loved the sounds of the water and boats. We were able to use some kayaks from the property. The kitchen was good for quick meals. The parking in a separate lot was not a problem since we could still do drop offs and pick ups right outside.
10.0 / 10.0
Cozy beachside home
My friends and I stayed at this property for a wedding nearby. We enjoyed the porch overlooking the water and access to the dock. The home provided all the necessary amenities for the weekend. A great stay!
10.0 / 10.0
Windows on the view
Open and airy with lovely, restful decor. Views of the bay everywhere. Bathrooms and kitchen a bit old-fashioned, but perfectly adequate. BYB
10.0 / 10.0
Loved it!
Sunrise was amazing!!! Property was quaint and homey. I will be back! Great way to unwind!
10.0 / 10.0
Fantastic direct waterfront home!
My wife and I stayed for four days with our one-year-old daughter in tow. We had a wonderful experience. Communication with the owner and property manager were efficient and very friendly. The home, itself was clean, well appointed and had all of the necessary creature comforts for our needs, including mini split AC. The view from the deck, living room and north side bedrooms is absolutely spectacular. Our primary attraction to this property was the small, private beach area for the kiddo. It turned out to be perfect for her during low tide and allowed us to enjoy the beach within monitor range while she napped. It was also fun watching the sailboats and seals. The beach/ water is accessed by stairs, which were perfectly accessible, but the steep grade to the water obviously necessitates close watch of small children. All of this was fairly and accurately portrayed in the listing. Probably due to our oversight; we didn't realize that the parking area is a short walk through a trail, from the house. Not problematic, minimally inconvenient, and would certainly not affect our decision to stay here again. There is a driveway that permits easy unloading/ loading / pickup/ drop-off. All things considered, this place was perfect for our little vacation and we are likely to rent again!
10.0 / 10.0
Great stay at Pleasant Bay
We enjoyed our second stay at this property. The house was clean and well prepared, and the view from the deck is spectacular. The property manager was very helpful and responsive.
10.0 / 10.0
Lovely Time in the Cape!
You absolutely cannot beat the view from this deck anywhere in the Cape! We all loved watching the sailboats work their way around Pleasant Bay, very relaxing. The house itself was more than accommodating and property manager easy to work with. The only strike I'll give is parking. The walk was a little difficult back and forth to the main lot for many in our group. Would absolutely not hold me back from renting again, but worth mentioning to those who have some issues getting around. A wonderful week spent, thanks all.
10.0 / 10.0
Great house with great views
Perfect views of the bay and the beach was just a quick walk down the stairs. We had everything we need to have a great family vacation. We are also grateful to Huntley (the property manager) who was friendly and very helpful during our stay to provide extra toilet paper, come out at night to address noise from the water pipes and help us store our kayaks while we got our SUV fixed. Would definitely rent again!
10.0 / 10.0
Fantastic even ion a Rainy Weekend
Really great team of property managers. Beautiful clean place. Wish I could have taken advantage of Community Boating which comes with the place but weather didn’t permit! Place is exactly as described except for it should be clear that you can’t use the fireplace. Highly recommend. We had six people stay very comfortably. Kitchen only fit two people cooking but it was no problem for us. Just loved the place. Will return👍
10.0 / 10.0
Amazing location
The best view in cape cod hands down
10.0 / 10.0
Great stay
One of our favorite rentals ever. The view is even better in person. House is very comfortable. Private beach area and access to kayaks. Good AC. Great location for exploring different beaches and towns. Yes it is on a busy street but really was not a factor In terms of noise and there are great places to walk and hike within 10 minute drive. Kitchen is small but has everything you need. Huntley and Natalie were responsive to our needs and questions. Would definitely like to come back.
8.0 / 10.0
Cape Cod CoVID Style July 2020
The Square Top House on Pleasant Bay was absolutely perfect for a family getaway. With beautiful views of Pleasant Bay, our own little beach, access to boating, it was just what we needed. Huntley is a wonderful Property Manager. So kind and attentive. We are definitely coming back!
8.0 / 10.0
Comfortable house in a beautiful spot
Everything went smoothly and everyone was easy to deal with. For our needs the location was not ideal because you can't safely walk or bike from the house except out to the dock. The traffic on Route 28 is too fast.
10.0 / 10.0
Fantastic Location on Pleasant Bay
This is a wonderful house right on Pleasant Bay. It is very comfortable, clean, and convenient. Being part of PBCB is a tremendous benefit for anyone interested in sailing and/or kayaking. Beautiful dock. Great swimming. The staff is friendly and accommodating.
8.0 / 10.0
Enjoyed being on Pleasant Bay
We loved our two week stay, especially our granddaughter who took sailing lessons for a week. The view is spectacular. Our only reservation was the closenest to the road. It was not safe to walk along or bike on. We enjoyed the cottage and the property manager was very helpful with things that needed attention, like a sliding door and chairs that needed to be glued.
The sunrises and fog on the water made everything worthwhile.
10.0 / 10.0
Nice Cape experience and georgous views.
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.
10.0 / 10.0
Adorable little cottage on Pleasant Bay!!!
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!!!
10.0 / 10.0
loved it!
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.
10.0 / 10.0
Fantastic view, comfortable house
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....
6.0 / 10.0
Great deck to hang out on!
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!
10.0 / 10.0
The view is spectacular from quaint Square Top cottage
It's all about the view. There are huge windows and sliding doors leading to a wrap-around deck, that all face Pleasant Bay. I knew the sunrises would be beautiful, and we are early risers so we loved the view from the east-facing large bedroom on the 2nd floor. What surprised me was that sunsets were gorgeous too. A second upstairs bedroom also faces the bay. The other 2 bedrooms (one upstairs and one downstairs) face the road and also overlook a cranberry bog. There is a fair amount of road traffic noise, but when you are in the rooms facing the water you don't notice it. We were there off-season so we didn't have access to the sailboats. However, we did use their kayaks and life preservers, which were in great shape. I had a few small complaints when I first arrived but by the end of the week they all dissipated because of the spectacular views, which is why I am giving this 5 stars. I want to add a few points for people who are looking for a "luxury" type vacation rental. There is only one shower downstairs which is a small plastic shower stall. The upstairs bathroom is big and has a bathtub but not a shower. To reach the washer and dryer, you have to go outside and down some stairs to a basement and the machines are old. The screens leading to the decks had many rips and tears. This is run by a not-for-profit and we were dealing with 3 or 4 different people...all of whom were very nice but sometimes messages got crossed. To end on a positive note, the kitchen is very well equipped and we would definitely return. I think a family with kids interested in sailing would love this place in the summertime.
10.0 / 10.0
Disconnect and reconnect
This cottage will provide you the quintessential, old-fashioned Cape Cod vacation on Pleasant Bay. Not just a view of the Bay - you look down onto the bay from the deck!
This simple, rustic cottage is just what you need to disconnect from the rest of the world and reconnect with your family and friends. There is no TV, no Internet, and no frills, and that's what makes it perfect! Everything you need is here - comfortable beds, well-supplied kitchen, grill, outdoor shower, comfortable couches in a roomy open living area that leads through large sliding doors out to an extensive porch overlooking a stunning view over Pleasant Bay, small sandy beach for swimming or boating just steps away. Wake with the sunrise over the Bay at 6:00, relax with a book and coffee on the deck, play all day, do puzzles and play board games after dinner. It's like you're back in the 1950's! It's the way Cape Cod vacations are supposed to be. Just lovely.
10.0 / 10.0
A Slice of Heaven
Last summer our family had the pleasure of vacationing at Square Top. Our week was a special experience that exceeded our expectations and left us feeling renewed, refreshed and bonded with one another. Our three boys range in age from 6-14. PBCB campus is a boys' vacation dream come true. Each day they took to the crystal blue waters of Pleasant Bay sailing, kayaking, swimming and exploring. My husband and I thoroughly enjoyed beginning each day with coffee on the expansive deck overlooking the sunrise on then bay. We grilled out most nights and ended each evening transitioning from sunset to starry night. The experience brought me back to my own childhood summers on the Cape. It was a gift to share the magic of simple pleasures with our boys - clamming on the shore, puzzles and games on the table, steaming lobsters, sailing in the sea - a slice of heaven! I highly recommend Square Top to anyone looking to escape life's chaos. Whether you quench a good book on the deck or a more adventurous sail, you'll love every minute of it. The house is fully equipped and comfortably furnished. The setting is quiet and magical. The views are unparalleled!
FAQs
How much does this cottage cost compared to others in Orleans?
The average price for a rental in Orleans is $403 per night. This rental is $518 above the average.
Is parking included with this cottage?
Yes, parking is listed as an amenity at Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly. For more information, we encourage you to contact the property about where to park.
Is there a pool at this cottage?
We didn’t find pool listed as an amenity for this cottage. It may be worth double checking if a pool is important for your stay.
Is Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly pet friendly?
Yes! This cottage is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.
What amenities are available at Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly?
We found 10 amenities for this rental. This includes air conditioner, pets allowed, kitchen or kitchenette, internet / wifi, and parking.
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Looking for a memorable stay in Orleans? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.
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Newly Renovated Waterfront Beach House near Rock Harbor: 038-OA
House
in Orleans10 guests · 5 bedrooms · 4 baths
Pets allowed · Kitchen or Kitchenette · Air conditioner
Discover the beauty of Orleans with a stay at Newly Renovated Waterfront Beach House near Rock Harbor: 038-OA, a top rated House with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
New to VacationRenter
Cove's Edge
House
in Eastham10 guests · 4 bedrooms · 4 baths
Pets allowed · Air conditioner · Internet / Wifi
House in Orleans, for $839 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
$$$$
Sunny, Charming, Farmhouse - Kid Friendly
House
in Orleans8 guests · 3 bedrooms · 4 baths
Garden · Pets allowed · Kitchen or Kitchenette
Indulge in a peaceful retreat at Sunny, Charming, Farmhouse - Kid Friendly, our elegant House in Orleans. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
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