Charming Waterfront Home with Commanding Views of Pleasant Bay
About this house rental
This 6-bedroom 3.5-bathroom home is the perfect setting for two families or multi-generation families vacationing together, as it has two master bedrooms—each with a private bath—located on opposite ends of the home. Additionally, 4 bedrooms are located on the second floor: 1 bedroom with a full bed and a single bed; one bedroom with three single beds, and two smaller bedrooms, each with a single bed. Besides the two master bathrooms, there is a half bath on the first floor and a bathroom with a tub on the second floor. All bedrooms in the house have front and center views of Pleasant Bay and beyond to the Atlantic. The kitchen is well equipped with a new dishwasher and plenty of glassware. The adjoining dining room can easily seat dinner for 10. The spacious patio is accessed through the dining room for al fresco dining and taking in the view. The laundry room is just off the kitchen, and the parking lot can accommodate any number of cars. The outdoor shower is one of life’s simple luxuries. Ours is especially amazing, as you can shower away the day's sand and salt spray in relative privacy with a view of the Bay. Wow! The living room is expansive, with plenty of seating for family game night. Guests at one end of the living room can engage in conversation over the breathtaking view, while others on the opposite side of the room can play a board game or work on a puzzle. One friendly word of caution to our taller guests—like many historic cottages, the ceilings are noticeably low in the kitchen, dining room, and living room (6 ft 4 with a 6 ft 2 center beam). The bedrooms, however, have vaulted ceilings, and of course, the patio has unlimited sky. The patio is the heart and soul of the property. With plenty of seating, a Weber grill, and a constantly changing seascape, the patio will call your name to sit in a comfortable chair, dine under the open sky, and become mesmerized by the beauty of the Bay. South Cottage is located on a shady bluff at the edge of 3.6-acres belonging to Pleasant Bay Community Boating (PBCB). The waterfront is directly in front of the house, and the deck has commanding views of the Bay and its various sailing activities. Enjoy your morning coffee and your evening meals on the rustic decks overlooking the Bay. Spend your day beach combing, exploring the Cape or sailing with PBCB. *Summer guests (June 15-Sept 6) can enjoy a Simply Sail experience with one of our instructors at no charge (weather permitting)! Please reserve Simply Sail in advance through our website. *Off-season guests (Fall, Winter, Spring) will find that South Cottage is the perfect location to take in the changing seasons. Plus, it is a centrally located launch pad for exploring the Cape. On this 3.6-acre property, we have a sister cottage, named Square Top, which can be viewed at vrbo.com # 781357. (South Cottage is 724608). Many prospective guests ask about the differences between the two cottages— *View and location: South Cottage sits high on a bluff and is located further away from the road, whereas Square Top sits very close to the water but is also closer to the road. *Building: South Cottage is a rambling long cottage with vaulted ceilings in all the bedrooms, but noticeably low ceilings in the dining room, kitchen and living room. Square Top is an airy cottage with higher ceilings in the living room, but lower ceilings in the bedrooms. *Both houses have central AC, heat and wifi. The fireplaces are decorative only, and cannot be used for fires--thanks!
Amenities
Air conditioner
Pets allowed
Kitchen / Kitchenette
Internet / Wifi
Parking
Laundry
Balcony / Patio
Dishwasher
TV
Family friendly
Map of Orleans, MA
House in Orleans, MA
Reasons to book
People love it hereGuests give this property a top rating
Great for pets
Includes essentialsPets allowed, Kitchen / Kitchenette, Air conditioner and more
$$$$
Reviews
4.8/5.0
Outstanding(37 Reviews)
5.0
Spacious and comfortable place, very clean. Highly recommended.
5.0
Enjoyed sitting on the patio with the lovely view of the Bay just as much as we enjoyed exploring this part if the Cape. Roomy, clean, and charming.
4.0
Had a great Girls Weekend. Huntley was so accommodating. Cottage had a lot of charm and lovely views.
5.0
We had a great stay. The cottage is well located for water and town access and to explore the Cape. Good communication.
5.0
We enjoyed our stay at the sailing community because it had great views, an authentic Cape vibe, a good location, and the opportunity to sail. It is a lovely cottage that sleeps a ton of people. The ceiling height is low if you're over 6 feet!
5.0
Lovely older home, plenty of room to spread out. Stunning views from the porch. Short drive to downtown Chatham, and to Nauset beach. Outdoor shower was lovely. Only downside was time of year for our booking as being part of the sail club a lot of activity in the parking lot with boats getting pulled. Room in the driveway for one car, and all others park below in the sail club parking lot. So a tad inconvenient as we were asked on more than 2 occasions to move our vehicles so boats and trailers could get pulled out, etc.
But overall very positive stay. Unfortunately, we didn’t get an opportunity to take advantage of our free sailing lesson as we filled our days up with all other activities. Would definitely recommend though for a large family. We had a total of nine adults.
5.0
Our group of 8 spent a week in the South Cottage in early July. There was plenty of space, the property was extremely clean and the location was within 10 min of everything we wanted to do. I highly recommend staying here.
5.0
This charming and quirking cottage has fantastic views and plenty of rooms that made for a great gathering place for my family during the Thanksgiving holiday. The kitchen is now officially Thanksgiving tested and the cottage surprisingly has a lot of dishes, pans, etc.. for what you need. The layout worked well with many family members to spread out and the location of the cottage is so close to everything including pizza, grocery stores and many beaches. The Boating Club does a great job in managing the property. It was a great find and great stay.
5.0
The house was perfect for our group of 10. Cozy and comfortable with an amazing view and great location. Huntley was a great host. Would definitely stay again!
5.0
A lovely well appointed cottage, with low ceilings as mentioned in the listing. We were there in the off season so it was quiet with lots of opportunity to sit outside and enjoy the beautiful view.
5.0
We had a great stay at South Cottage. Management is very responsive and welcoming; the house was clean and very nicely furnished with lots of comfortable spaces. Our 3 generations had plenty of space to spread out, as well as to hang out together. The weather was perfect, so we didn't need to explore the ample supply of games, puzzles and books. Lots of dishware, utensils, and pots and pans in the kitchen. We cooked many fish dinners! The bay is beautiful and calming. The "kids" (young adults) swam, went sailing and kayaking, and took advantage of area beaches. Great vacation - we didn't want to leave!
5.0
Loved it!
We had a great stay at South Cottage. Management is very responsive and welcoming; the house was clean and very nicely furnished with lots of comfortable spaces. Our 3 generations had plenty of space to spread out, as well as to hang out together. The weather was perfect, so we didn't need to explore the ample supply of games, puzzles and books. Lots of dishware, utensils, and pots and pans in the kitchen. We cooked many fish dinners! The bay is beautiful and calming. The "kids" (young adults) swam, went sailing and kayaking, and took advantage of area beaches. Great vacation - we didn't want to leave!
5.0
This house is located in a lovely area of Cape and has beautiful views. It is perfect for a large family.
5.0
Gorgeous Views
This house is located in a lovely area of Cape and has beautiful views. It is perfect for a large family.
5.0
This house was rustic, roomy and comfortable but the water views were the best part......the sunrises were spectacular and worth getting up early.
5.0
Beautiful Sunrises
This house was rustic, roomy and comfortable but the water views were the best part......the sunrises were spectacular and worth getting up early.
5.0
We love it! Waterfront facing East for incredible sunrises + access to kayaks/ Sailing classes of the PBCB + Layout of the house With 2 suites, ideal for 3 families with teens to live well together, The house retains the charm of its age with all amenities. A big thank you to Nathalie, Hentley, Laurie, Sam, Mike, Tom, staff of PBCB for their kindness and making that trip unforgettable. This is more than simply renting a house. I will cherish the memories of my kayaking this beautiful bay at the hours I wish. Thank you from all of us. We will return.
5.0
Waterfront position for fabulous sunrises!
We love it! Waterfront facing East for incredible sunrises + access to kayaks/ Sailing classes of the PBCB + Layout of the house With 2 suites, ideal for 3 families with teens to live well together, The house retains the charm of its age with all amenities. A big thank you to Nathalie, Hentley, Laurie, Sam, Mike, Tom, staff of PBCB for their kindness and making that trip unforgettable. This is more than simply renting a house. I will cherish the memories of my kayaking this beautiful bay at the hours I wish. Thank you from all of us. We will return.
5.0
Great house, beautiful view from the deck. Also the option to sail and kayak right at the property. We had a great time we hope to come back. Would love to buy the house.
5.0
Ample space for a family of 6 adults and a child; beautiful location with amazing views of Pleasant Bay; nice location and helpful staff. Thoroughly enjoyed our stay.
5.0
A pleasant stay on Pleasant Bay
Great house, beautiful view from the deck. Also the option to sail and kayak right at the property. We had a great time we hope to come back. Would love to buy the house.
5.0
Pleasant stay on Pleasant Bay
Ample space for a family of 6 adults and a child; beautiful location with amazing views of Pleasant Bay; nice location and helpful staff. Thoroughly enjoyed our stay.
4.0
Absolutely fantastic! Plenty of room for our family of 10. Beautiful mornings sitting on the patio watching the sunrise while enjoying a cup of coffee. What a way to start the day! The house was spotless. Well stocked kitchen and charming bedrooms. Great location. We would definitely stay here again!
4.0
Love the view!
Absolutely fantastic! Plenty of room for our family of 10. Beautiful mornings sitting on the patio watching the sunrise while enjoying a cup of coffee. What a way to start the day! The house was spotless. Well stocked kitchen and charming bedrooms. Great location. We would definitely stay here again!
4.0
Anyone contemplating a stay at the South Cottage is in for a treat if you are bringing multiple generations or family elements together. The structure is old and has been added to over time. We slept eight comfortably. The two suites with private bathrooms made it easy to give multiple generations just what they needed. One suite required no navigating of stairs, while the other had only a few. The upstairs provided a common bathroom for another couple's bedroom and three bedrooms to house children of various ages. The family room was spacious and well lite; the kitchen is unfortunately cramped but manageable. The space our family enjoyed the most was the patio overlooking the bay. Most of our meals were eaten there, especially breakfasts. The dining room comfortably seated our eight and could have accommodated a few more. There were a few issues because they have had a problem with a cleaner, but when brought to the management's attention, there was a sincere effort to compensate for the shortcomings. We are looking forward to a return visit when the family gathers again.
5.0
Spectacular view and spacious accommodations at this charming Old Cape Cod cottage.
South Cottage feels like an old family summer house welcoming you back to another delightful vacation at the Cape, lovingly furnished and decorated in authentic old Cape style.
Here's what we especially appreciated:
Very comfortable seating on the deck for our whole family group of 12 to enjoy looking out over Pleasant Bay with nearby activities of the sailing school, outer beach in the distance, fragrance of pine and sweet grass. Stairs to the water’s edge.
Long dining room table by a big window with space for us all.
Plenty of room for everyone to gather in the charming and commodious living room with a corner for puzzle making, and tables and seating for playing games and reading.
Ample space for our group ages 12 to 81 years in the six comfortable bedrooms each with a window looking out at the Bay.
The friendly folks at Pleasant Bay Community Sailing helped us put together both sailing and kayaking adventures that were a highlight of the experience.
The property manager was always ready to assist with any questions or needs.
4.0
Great Week for Family
Anyone contemplating a stay at the South Cottage is in for a treat if you are bringing multiple generations or family elements together. The structure is old and has been added to over time. We slept eight comfortably. The two suites with private bathrooms made it easy to give multiple generations just what they needed. One suite required no navigating of stairs, while the other had only a few. The upstairs provided a common bathroom for another couple's bedroom and three bedrooms to house children of various ages. The family room was spacious and well lite; the kitchen is unfortunately cramped but manageable. The space our family enjoyed the most was the patio overlooking the bay. Most of our meals were eaten there, especially breakfasts. The dining room comfortably seated our eight and could have accommodated a few more. There were a few issues because they have had a problem with a cleaner, but when brought to the management's attention, there was a sincere effort to compensate for the shortcomings. We are looking forward to a return visit when the family gathers again.
5.0
gorgeous location, rambling, comfortable house with character
Well appointed house and kitchen, except for lack of sharp knives!
Comfortable beds, incredible view of the bay and beautiful, bobbing boats...a house that amply accommodates all 8 people very happily.
We all want to come back. Huntley was always helpful, Natalie always prompt with her replies. A solid success for our mini reunion.
5.0
Amazing Cottage and Cape Experience
South Cottage is a beautiful and charming rustic cape cottage. The cottage handled two families of four with ease and the outdoor deck/view of the bay is truly off the charts. Top 5 outdoor shower too! The house is well appointed - everything you need is there for cooking, entertaining. We are definitely coming back...
5.0
Beautiful view, floor plan of home perfect for our multi families.
Sailing on the bay was a huge hit!
5.0
Great location on Pleasant Bay
A wonderful place to vacation, especially if you have a large group. Plenty of room for everyone. The outdoor shower is the best, and what an incredible view from the shower.
5.0
great location and house!
we loved our stay here. very roomy, enough beds for everyone and view over the water was wonderful. close to the golf courses. looking forward to staying here next year!
5.0
Beautiful view
Would have been nice to have the beds made but otherwise everything was spectacular
5.0
Quintesential Cape Cod
Just returned home today from our family vacation at South Cottage. Had three generations of family traveling together, ages 5 to 81, so we had many needs to please. If you are looking for a true Cape cottage, that feels like a family retreat you have been going to for decades, then South Cottage is for you. The five year old described the cottage as the "house of maze" as there is plenty of room for everyone and the cottage sprawls out along the bluff it is situated on. The furnishings are worn and cozy, the dishes mismatched (but plentiful) and the bedrooms are roomy and welcoming. We enjoyed happy hour on the deck and having leisurely family dinners at the large dining room table overlooking the bay. We spent hours on the private beach and along the breakwater at low tide looking for shells and crab carcasses for our crab zoo. We saw seals from the deck and a huge owl on our front door railing. We played cards, did crafts and relaxed as a family. Between fans and the central air, the inside of the cottage was cool despite the warm sticky weather. The outdoor shower is an experience even my 80 year old mother enjoyed. There is nothing quite like feeling the breeze and looking at the bay while you're showering. They have fixed the issues with the Wi-Fi and TV that one reviewer mentioned. We had no issues with connectivity. The location is great, so easy to get everywhere. We were a little worried that the house would be too close to 28 or that we would be annoyed with the traffic from the sailing school, but neither were an issue. We couldn't even hear the road. We did take advantage of the kayaks and took a sail one day. We did not take advantage of the sailing lessons, but had fun watching the kids set off each day. In summary, we had a great time and would love to come back to South Cottage in the future.
5.0
Wonderful, quiet, roomy, quaint and with a patio for gorgeous sunsets!
Gorgeous old house filled with character with multiple bedrooms and bathrooms, all of which are lovely.
Very private with lovely hosts who checked in on us to make sure all was well, and then let us do our own thing.
Fantastic open common room with an amazing view.
Patio has lots of tables and chairs and a clear view of the bay for watching sunrise and sunset.
Fully equipped kitchen : we cooked each night for 8 adults and one child, no shortage of cookery or crockery.
Great beaches and biking are minutes away.
Charlie, Huntley and Abby will hook you up with kayaks (use anytime 9-4) or sailing lessons which we enjoyed thoroughly.
Our lab group had an amazing, relaxing and restorative time and we will be back next year!
Thanks to the PBCC crowd for a delightful time.
5.0
Best family vacation!
Thoroughly enjoyed or three generation family vacation here. The kids learned how to sail and we all got out in the kayaks. The staff at PBCC was very helpful and accommodating. The house had plenty of room for all of us and the kitchen was well stocked. The living room was perfect for game night for us and morning coffee on the deck was spectacular. The family has voted and next years vacation will hopefully be here as well!
3.0
Nice view, but of all our renting expr this was most mediocre based on expectations not being met.
Pros
-Great view
-Semi attentive hosts
-Lots of rooms in the house
-Good location to see all of the Cape.
-they house is very well stocked with dishes, cooking pots, etc.
Cons
-Don't rent this place if your over 6 foot tall. The whole house has ceilings that are very low. I had to spend the entire week ducked down just to move around
- we were promised sailing lessons with our rental but when we inquired about it they said they went doing it yet. We were there the last week in May and they said we were out of season. Didn't say anything about that when we rented.
-They told us the grill had broken nobs, but the problem was that the lighter was broken. They had no stick lighter in the house to get it lit.
-they tv is a 15 inch tube tv. That couldn't be moved out of a corner behind a door. For this kind of rent price buy a TV you can actually see and pay for more than the local channels on cable
- Wi-Fi really only works in the Living room
- probably not a great rental if there are more than 2 sets of adults. Only 2 queen beds.
-no yard for younger kids to play around in.
-they pictures make it look like there is stairs down to the water, but the stairs go have way to the water and stop. There is not even a landing at the bottom to sit at.
Rent the Square Top cottage if you want to stay there. Much nicer, is right at the beach.
4.0
Beautiful home on Pleasant Bay
Beautiful view and lots of elbow room. Saw foxes, seals, and eagles(?)!! Next door community sailing was very welcoming and great base to explore Cape. Would go back, although house itself is showing its age a bit, but patio is best part!
5.0
Lovely cottage on the water.
We loved the property and the location on Pleasant Bay. Nice people and lots of fun sailing and kayaking.
5.0
Can't wait to go back
We had a wonderful time in this very comfortable rustic home. We awoke to a beautiful sunrise and sat on the deck to watch the sunset. We walked along the beach and took Some amazing pictures. We are already planning to come back to next year.
FAQs
How much does this house cost compared to others in Orleans?
The average price for a rental in Orleans is $372 per night. This rental is $527 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Charming Waterfront Home with Commanding Views of Pleasant Bay. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.
Is Charming Waterfront Home with Commanding Views of Pleasant Bay pet friendly?
Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.
What amenities are available at Charming Waterfront Home with Commanding Views of Pleasant Bay?
We found 10 amenities for this rental. This includes air conditioner, pets allowed, kitchen / kitchenette, internet / wifi, and parking.
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