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.