Private Waterfront on Pleasant Bay
Orleans Vacation Rental - ID 19102

We rented out the Bay House alongside our rental of Winslow Estate so more of our friends could stay near us during the wedding. We all loved the Bay House so much and kept commenting on how it's the perfect beach house. It has beautiful views right on the water, it was clean, had plenty of space, and was just very cozy. Would definitely recommend considering this rental!

My son and daughter-in-law rented this Estate for a week for their wedding. I rented the smaller house on the grounds for 5 days. The whole wedding party stayed in the Estate house, and my immediate family stayed in the "guest house." What a memorable event. Being able to be on-site for multiple days for the big celebration made for such amazing memories. The views of the water, as well as the togetherness it allowed, truly were special. Since the event, I have received several phone calls from our guests who said this was one of the top 5 weddings they have ever attended. Everyone who was there agreed that this place was just magical.

Our family had such a nice time at the Bay House - a perfect location and it fit our family very well!! The sweeping views of Pleasant Bay are just spectacular and photos don't do it justice!! The house is really lovely and very comfortable. The owners were fantastic hosts providing lots of info on the property and special Cape experiences - and a welcome gift as well! We've rented various properties in and around Orleans since 1997 and this felt like the first time we were truly immersed in the beauty of the Cape and tucked away in a very unique and beautiful spot!!

Our family rented for 2 weeks including the July 4th holiday which is a great time to be on the Cape. It was especially fun to watch the amazing fireworks over Pleasant Bay right from our beach. During our stay our kids (ages 15-27) were all happy kayaking, paddling and playing games on the lawn. The deck was terrific with comfy furniture and a big table and bbq. We all had favorite spots inside and out to sit, read, nap and enjoy the view.

Grandma with mobility issues was with us. The large master and bathroom worked out well for her and she enjoyed fantastic views of the water right from the living room. Access to deck was easy.

The house itself was decorated so nicely. The two masters worked out great as well as having the 3 full bathrooms. The smaller twin bedrooms and bunk bedroom fit the kids (and a guest) perfectly. Beds were comfy with nice quilts/covers. So great to have the linens included - sheets, towels and beach towels. The kitchen was bright and spacious and we loved all the dishes, serving trays and glassware. TVs with Roku in LR and Master BRs were great. Did a puzzle on the DR table and played games on the coffee table in the LR. Some puzzles and games in closet and cabinet. Beach chairs etc in cellar and outdoor shower got regular use. Everything you would want for a Cape vacation in any kind of weather.

Will always remember the amazing breezes! We hope to return to the Bay House in the future!

Gentle Heritage is a magical place. It is a step back in time to a more simple, innocent, and gentle era. I had the privilege of celebrating my 60th birthday with my siblings, nieces and nephews over Memorial Day weekend 2024 on this property perched on a bluff overlooking Pleasant Bay, and we were all taken by the serene setting, stunning views, and old-world charm. It is a special place that captured us immediately and will stay with us for years to come. We had the added treat of seeing the full moon rising over the bay at night, casting a glow over the water that was every bit as stunning as a sunset over the ocean in Key West. The two living rooms were perfect for a large multi-generational family (the adults watched our sports in the main living room while the kids played video games in the second living room), and the pool table provided entertainment (and some friendly competition) for the entire family all weekend.

Ginger and Ken are fantastic hosts. They are warm, friendly, and knowledgeable about the property and the area (the estate has been in the family for over 100 years), and they gave us wonderful recommendations for an amazing lobster clam-bake dinner and BBQ dinner, both delivered to the property. That was no easy feat for a party of 25 people like ours, but the caterers pulled off both dinners without a hitch. The lobster clam bake from Backside Bakes Catering was a true Cape Cod experience. They set up a long table for 25 people on the great lawn, served us hors d'oeuvres of creamy New England clam chowder, large shrimp cocktail, and bacon-wrapped scallops, and then cooked 25 large lobsters for our family right there on the property. They served us from beginning to end, cleaning up and taking away the table, chairs and place settings at the end. It was a fully catered delicious meal for the ages.

Gentle Heritage as run by Ginger and Ken helped us make our dream weekend a reality, and the reality was better than we dreamed. We have rented some beautiful places over the years, from the west coast to the east, but never something of this scale and grandeur. Our entire family agrees that Gentle Heritage is a 5-star property!

We rented the Bay House as the parents of the groom. It was perfect to have our own space to come back to with all of the wedding prep happening at this Estate. The house had lots of room for two families and the bathroom in the bottom floor is beautiful. We found the house to be very well equipped and thoroughly enjoyed breakfast on the deck every morning.

For 2 years in a row, our family (2 grandparents, son with wife and 2 young teens, and son with wife and 2 toddlers) has enjoyed the privacy and beauty of this Pleasant Bay location. It boasts a large bayside lot with 2 master suites, 2 twin rooms, and a bunk room, with lots of room outside to play. The waterfront, while not an actual swimming beach, is pretty fascinating ... lots of crabs, and even what looked like conch. If you have paddle boards or kayaks, you will love this waterfront. The homeowners are a delight to deal with too. We all loved The Bay House and hope to return in future.

We had a wonderful stay on Pleasant Bay. Our two families rented for two weeks and everyone had ample space to hang out together or to find some quiet away from the group. The views are spectacular and the ocean breeze is so soothing! The kitchen has plenty of space and is well stocked to allow for making meals (which for 10 adults can be a challenge), but everything we needed was available to us. We played games in the dining room, and had a movie night in the living room by bringing a few extra chairs in. The upstairs master suite is very cozy. The downstairs is a bit dated, but the bathroom for that room is brand new and beautiful. Our teen kids shared the twin rooms - one room is a bunk bed. We were told that the bunk beds are very firm, but overall everyone slept fine. There is a ton of parking on the large shell covered driveway, which was very convenient with our teen/adult kids all having cars and having to come and go for jobs/internship, etc. As well has having friends come to meet us for the day.

We own a boat that we kept at a transient mooring in Ryder's Cove. My husband would go get the boat and cruise across the bay, anchor out in front, and our group would load up from there to head out to the bars. It was super convenient. The deck is such a great spot for dinner and drinks, and the picnic table by the beach was perfect for an evening cocktail by the shore.
We had a little corn hole tournament on the upper level area of the back yard. The images make it look a little flatter than it is, the whole thing slopes down toward the shoreline.

The owners are attentive and respond quickly if there us an issue. We had some trouble with the wifi and the owners were quick to help us resolve it. Even though it couldn't be fixed on the spot they did their best to get the repair moving while we were there and let us know when they would be coming by.

Like many of the cape homes we've rented over the years, this home has updated amenities, but is still "Capey." Meaning, it can feel damp at times (especially in the lower level), it has aspects that are aging, but are easy to repair/update. The owners clearly take pride in the home and do their very best to maintain it.

I wish I could rate this 4.5 stars. I'd take off a 1/2 star only because we all wished the beds were a bit more comfortable. It's the only reason I can't give it a 5 star rating. Nonetheless this home absolutely has everything you need for a wonderful family vacation! We had a great two weeks, even with several foggy and rainy days which was typical of the summer of 2023!

We had the opportunity to stay at the Bay House for our daughter's wedding which took place next door at Gentle Heritage. While she was there with her full wedding party in the days leading up to the wedding, we along with our new in-laws enjoyed this house with the 2 very comfortable and private master suites. The house was spotless, had a well stocked kitchen and was nicely furnished. The views are beautiful and early one morning we were lucky to see a couple of deer saunter by. It could not have been better!

If you are looking for the perfect place to have a family or friend getaway - this is the place. Our family of 10 enjoyed this home while attending a family wedding next door at the Winslow Estate! It is comfortable and has every thing needed for a large family vacation. The views are breathtaking and it is so restful on the deck! The owners are so wonderful to deal with and made the stay relaxing and easy too!

The Bay House was the perfect rental for the wedding weekend. Situated next door to the Winslow Estate made it extremely convenient. Each bedroom was well appointed, especially the two queen bedrooms with en-suite bathrooms. The living spaces are spacious and the patio has a stunning view.

Ginger and Ken are gracious hosts and very responsive.

Lovely, well kept property in an exquisite setting. The spacious yard and private beach were great for kids. The view from the spacious deck, and many of the rooms was very beautiful and the setting was peaceful, quiet, and secluded. The house was attractive, comfortable and well equipped. Hope to return.

We stayed for a week with our family of six adults and four children, and had plenty of space both in the bedrooms and in the living areas and large deck, with its spectacular view of Pleasant Bay. They lawn behind the house leading down to the bay and the bay itself got lot of use by the children and adults.

The house was clean and well supplied, and Ginger and Ken were very attentive to the couple of minor issues that arose. In addition, they went out of their way to find and mail us promptly some items we had left behind.

We stayed here with a couple of other families in May 2021. It is a beautiful location right on the bay. Honestly, you could spend all day on the back porch looking over the bay. With a slight breeze and some sunshine, the place is absolutely serene.

The home is well-kept and clean. Very much has the Cape Cod charm to it. Both floors have master bedrooms that look out to the bay, as well as spacious bathrooms. Perfect house for a couple of families looking to vacation together. My kids especially loved the bunk bed on the main floor.

We enjoyed our week at the Bay House so much. Every single thing a family could want in a beach vacation - it's here. A perfect location with stunning views, room for the children to play outdoors, our own beach for swimming and fishing, peace and quiet - and yet still only a 10 minute drive to the grocery store, restaurants, etc. The home is so thoughtfully appointed that even on a rainy afternoon, we were busy with card games, etc. There was plenty of room for our family of four and for a few friends who visited while we were here - a truly spacious, very lovely home in an idyllic setting.

My family and I spent one of our best weeks in Cape Cod at Bay House. The perfect weather helped but the property itself was just great. The house is designed for a great family getaway. Everything we needed was right there. Very comfortable and pleasant surroundings. Perfect for a large family or two families to share. You really didn't have to leave but if you did it was convenient to great beaches, restaurants, fishing and other area attractions. The homeowners could not have been easier or more helpful and pleasant to work with.

My husband and I rented Gentle Heritage for our wedding to house all of our immediate family and ourselves, but we wanted a place for our closest friends as well. The Bay House was PERFECT! It's beautiful, spacious, clean and right next door to Gentle Heritage so we could all have our own space but be close to each other at the same time. It was so perfect! The homeowners did a fantastic job of making us all feel at home and prepared for everything. Our friends absolutely loved it! I highly recommend renting this property, especially if you are renting Gentle Heritage as well. It is well worth it. (There was also another house owned by Ken and Ginger that was just as beautiful -- Dock of the Bay -- and only a few miles away that we would have rented had we needed it. They have the perfect package of homes to accommodate a fantastic celebration! Simply perfect and unforgettable for everyone.

Our family had a wonderful time at this beach house. The house itself is modernized and has an open design. We loved both grilling out on the deck and cooking in the kitchen. The living and dining rooms were well laid out and spacious for our family to talk, play games, or just relax and read. Having linen service for bedding, bath towels, and beach towels was great and made packing so easy!

We enjoyed the outdoor spaces everyday. The large backyard was great for the kids to run around and play games. They especially enjoyed being about to use the outdoor shower. The bay water beach was perfect for our younger swimmers since the water was calm and refreshing but not cold.

Working with the Winslows for the rental was a friendly and easy process. They gave us a lovely gift basket at check-in, with some fun food and items to help us get settled right away. I highly recommend this beach house.

We rented Gentle Heritage and its accompanying guest house for a once-in-a-generation reunion with a clan of 28 and had an exceptional time. The property exceeded expectations in all regards. Spacious, beautiful, very comfortable, in great shape, and with unparalleled views and setting. Owners were incredibly gracious and easy to work with. This has our highest possible recommendation!

We have rented this property for over ten years and stopped only because our family circumstances changed. Otherwise we would have gone on forever.
We loved our stay at this property. The house is beautifully sited in a quiet location with an incredible view of Pleasant Bay and with access to a small private beach.
The property is well maintained and suitable for large families. It would be impossible to find a more delightful location in Orleans.

My family and I (including 3 small children) stayed in this home in June 2009. What a great place! Very spacious and open. We loved that the adult quarters are well separated from the children's quarters and being on the bay was priceless. My kids really enjoyed walking the grounds and looking for seashells. Although our weather wasn't the greatest we really enjoyed our stay. The owners were extremely easy to work with and even went out of their way to return a treasured teddy bear to us that my son had left behind by accident. I would highly recommend this property.

Just returned from a long weekend stay here. This house is perfect! Cozy, yet spacious. Clean, well equipped, great view, quiet, peaceful. Room to spread out, yet plenty of space to be together. Hesitant to write a good review, because I want to be sure it's available for me to rent again! Thanks to the owners, who were wonderful to work with.