The Compliments Keep Coming!

An epic landscape bedecked by a unique jewel

  •  5 of 5 Stars

A superb venue; a persistent rain the first day couldn’t dampen the great fun experienced by 6 couples while staying for a get-away at this magnificent property. The charming accommodations, fine food, many nearby leisure pursuits and breathtaking vistas of the wild beauty of Cape Cod were only exceeded by the warmth & genuine hospitality of the Winslows.

  • Submitted: May 8, 2017
  • Stayed: May 2017
  • Matthew C.

To call it spectacular doesn’t even do it justice!

  •  5 of 5 Stars

I rented the Winslow Estate for my daughter’s wedding. Renting from Wednesday to Wednesday gave us all time to get settled in and time to relax after the fact. As I stated above to call the estate spectacular is truly an understatement. Everything was as promised. Ken & Ginger were great to deal with. I would strongly recommend this property to anyone. A little piece of heaven on Cape Cod!

  • Submitted: Oct 20, 2016
  • Stayed: Oct 2016
  • Robert K.

Perfect venue to have a personalized wedding

  •  5 of 5 Stars

If you’re looking for that special place to hold your wedding, look no further. Unlike a resort venue with packaged plans, at the Winslow Estate you can make your wedding your own. The owners, Ken and Ginger, are eager to help you pull the pieces together with suggestions and lists of auxiliary vendors. Don’t be deterred by the idea of an afternoon wedding. Nothing was more romantic than the tent coming alive for dinner and dancing after enjoying mid afternoon cocktails and fantastic views of Pleasant Bay in the bright sunshine. Not to mention the brilliant sunset enjoyed by all the guests! There was plenty of room for the entire wedding party and spouses to stay at the estate and they enjoyed their own post-wedding hang time together in a very relaxed, fun space. The Winslow Estate is the perfect wedding venue!

  • Submitted: Oct 18, 2016
  • Stayed: Sep 2016
  • Susan F.

Exquisite, Fascinating!!

  •  5 of 5 Stars

My husband and I have stayed there for my birthday. We had a fantastic time! The owners ken and ginger are awesome and were very accommodating to our needs. We had a great time. We are planning on coming back here again next summer.

  • Submitted: Aug 31, 2016
  • Stayed: Aug 2016
  • Farrah R.

Gorgeous Views on the Water for peace on The Cape

  •  5 of 5 Stars

Three generations of our family spent a lovely week at the Gentle Heritage in late August. The views are spectacular of the water and surrounding land, and has a nicely-manicured lawn on which to play games while surrounded by the beauty. We could walk down the hill to enjoy a little seating area just above a small beach to launch our kayak. The home is cool in its long extended layout which reminds us of its history, with 2 kitchens and a joined wing that has its own suite and glassed in porch, tv room and dining are. Favorite spots to hang out were in the billiard room, another large screened porch overlooking the water off the Master bedroom and the main living room with it’s high ceiling and architectural beams. We also enjoyed an outdoor dining patio and lounge chairs on the lawn to gaze at the stars. The property has a good number of bedrooms and bathrooms to be used by the 12 in our group. The owners also provided information for a local chef who prepared a glorious meal at the home for us…highly recommended. Definitely worth a stay for relaxation and a great spot on The Cape!

  • Submitted: Aug 31, 2016
  • Stayed: Aug 2016
  • Amy & Roger

Absolutely picturesque

  •  5 of 5 Stars

Whether you are looking for the ideal Cape Cod wedding venue or a private rental for a week-long vacation, this property is perfect. The setting (right next to the water on Pleasant Bay in Orleans) is stunning, beautiful, relaxing and, quite simply, breath-taking. We were blessed with 6 straight days of gorgeous sunshine and warm temperatures – making this the most memorable vacation of our lifetime. You will not be disappointed!

  • Submitted: Jul 27, 2016
  • Stayed: Jun 2016
  • Tobin S.

They Love Us!

“If you are looking for “The Perfect Wedding Site”…look no further……in a special little corner of the world called Cape Cod is a another special place overlooking Pleasant Bay in Orleans MA. We had our daughter’s wedding here at Gentle Heritage on a perfect autumn day in October 2008 and guests are STILL raving about it, months later, as the most beautiful wedding they have ever attended! They all loved roaming the house and the grounds.

The bride & groom married here as well – couldn’t ask for a more picturesque background than the sea for guests to enjoy during the ceremony!!! The estate housed the wedding party that all came from “off-Cape”. That helped make the special day even more special with loved ones all around and close by before, the day of & after the wedding! More guests rented the Winslow’s Bay House next door so it made it all the merrier! The accommodations of Gentle Heritage were wonderful – plenty of room for all with so many bedrooms and bathrooms – porch, dining room, living rooms and billiard room were ALL used and enjoyed!! The site itself sits with gentle pride overlooking a panoramic view of one of the quiet inlets of the Atlantic Ocean – Pleasant Bay. Guests at the wedding thought they were in Bermuda!

The owners, Ginger & Ken could not have been any more gracious and accommodating! I have been amazed that so many that live here on the Cape are not familiar with this estate as it still seems to be a bit of a “secret place”….all the better for planning a special wedding day!!! You will certainly awe and dazzle your guests with it all I promise! No hotel or wedding site can surpass all that can be offered here…as there are NO other weddings happening here the day of yours! Or the day before or after!!! The week flies by, but you are left with heartwarming memories of a glorious seven days! I live in the town next to Orleans and love that I can still drive by Pleasant Bay and look across it and up to that hill and smile remembering the wonderful wedding we had there!!! I bet it’s a perfect place for a family reunion as well!

My daughter Jenn’s hug and words said it all… “Thank you for the wedding of my dreams and the most perfect wedding ever!”
Thank you Ginger and Ken for a wonderful week and all the memories we will cherish forever! “


More Raves!

“We looked everywhere for a place on the Cape where we could have the kind of wedding we wanted – a beautiful setting, a place where friends and family could hang-out, the ability to have the kind of wedding we wanted (and not one planned by a resort/hotel/etc.). It was really difficult to find such a place since most private homes can’t handle large groups of people.

We feel incredibly lucky to have found the Winslow Estate and we had exactly the wedding we wanted here. We rented the space for the week and had our bridal party join us to hang out. We had a very small, low-key rehearsal on Friday night. And on Saturday we had a clam bake and played whiffle ball. I imagine this spot works just as well if you want a formal event, but for us it was the perfect place to have a laid-back, casual party at a gorgeous, comfortable location. I’m pretty sure there is no other place like it on the Cape.”



“Words cannot describe how wonderful this property is. We enjoyed an absolutely perfect week here with our family of 14 celebrating our parents’ 50th wedding anniversary. We ranged in ages from 3 to 80 and absolutely everyone loved this house.

The views of the water, from just about everywhere in the house or on the property, are breathtaking. The rooms are all spacious, bright, charminly decorated and extremely well mantained. There are plenty of places for people or groups (large or small) to escape to or gather in.

The grounds, with the large open lawn and the private beachfront where the children played for hours on end, are simply gorgeous.

Ken and Ginger are the perfect hosts—attentive, warm, welcoming and extremely helpful. They genuinely care about the house and anyone inhabiting it.

It is hard to imagine a better property on Cape Cod. We fell in love with this house and desperately hope to return some day soon.”