Send this page to a friend

Thank You

Your message has been sent.

You can send this page to up to five email addresses. Please separate each email address with a comma.

check navigate-up

Ken Winslow

Member since: 2004
Call Owner
Speaks: english

Waterfront Estate with Private Waterfront and Beach

20 Reviews
Sleeps19
Bedrooms 9
Bathrooms5
Half Baths1
Property type estate
Minimum Stay 2 - 7 nights

Overview

Cape Cod Estate Rental Photos and Description

9 bedrooms, 5 1/2 baths, sleeps 19,

Chosen by Cape Cod Life magazine as one of the Top Ten places to stay on Cape Cod, our waterfront estate has breathtaking views of over 180' of Pleasant Bay and 300' of your own PRIVATE waterfront. Plus you are directly on the water, not across the street or down the lane. Family owned, the estate has been a landmark on Pleasant Bay for 100 years. There are 3 acres of open lawn, 17 rms, 9 bedrms, 5 1/2 baths plus an enclosed outdoor shower with dressing room. All of the bedrooms plus the dining room and family room are air conditioned. The 2001 kitchen features a 48' Sub-zero refrigerator, Corian counters, plus the estate includes the former servants wing with a 2nd fully equipped kitchen. There is lots of room for everyone to spread out with three living rooms, game room with pool table and darts, private deck on the beach, and mooring for your boat.The estate is on one of the highest points on Pleasant Bay offering magnificent views. You walk down a bluff to the waterfront below. There is a large crescent shaped beach at low tide. This gets covered as the tide comes in and a deck is on the waterfront to enjoy at high tide. Guests often rent kayaks, paddle boards and other water craft to explore the bay and the local islands and beaches. Swimming is always wonderful in the warm water. Available by the week in summer and off-season weekends for vacations and important family gatherings. WIFI. By the week only from early June to late Sept. Weekends considered in April and May and October and November.The nine bedrooms are really nine bedrooms - not common rooms that become bedrooms at night with pull out sofas. There are no sofa beds, futons, trundle beds, bunk beds or cots. Everyone has a personal and private space. All of the bedrooms have twins beds or queens. The master bedroom has a king bed. Each bedroom sleeps two guests except for one extra large bedroom that has three twin beds. Beach, bed and bath linens included. No cleaning fee or taxes or hidden fees.

The fabulous estate.....: This very special property is a landmark to the area and owned by the same family since it was built on the shores of Pleasant Bay 100 years ago. It had been lovingly cared for and maintained and matches the grandeur of times past with modern amenities. It is an ideal environment for multi generational family members to vacation together - or old or new friends with lots of room to spread out, enjoy each others company, yet find privacy and peace.

Down the end of an old cape cod road, then down the end of a private seashell driveway, there are no streets, traffic, or even pedestrians nearby. Pleasant Bay is reached by a pathway down the bluff in front of the house and features a deck to sit on.The Bay has a gradual sandy bottom, warm water great for swimming, floating on rafts, paddle boarding, sailing, kayaking, and walking along the shore.

More Details
Suitability:
  • children welcome
  • non smoking only
  • suitable for elderly or infirm
  • wheelchair accessible
Ken Winslow (Owner)
Member since: 2004
Call Owner
Speaks: english

Reviews

5
based on 20 traveler reviews

Waterfront Estate with Private Waterfront and Beach
average rating of 5.0 based on 20 reviews
5

Unique, special and excellent wedding venue!!

  • 5 of 5

I take full credit for finding Gentle Heritage, Winslow Estate. Being an owner of a second property on Cape Cod, my daughter felt that her wedding should be on the Cape since we are on Cape as much as possible during the year. Besides the location and the property being so unique and gorgeous, especially when you have a day like we had weather-wise, the fact that the wedding party gets to stay there days before the wedding and after if they so choose is a bonus!! I truly believe that this allowed the wedding party to bond before the big day. It was also nice that we were the only wedding going on at the venue, unlike most places we looked at. We were constantly asked throughout the day, "how did you find this place" so we were thrilled with how everything turned out. So, from a wedding standpoint, it's a 10 in our opinion.

  • Submitted: Oct 29, 2015
  • Stayed: Sep 2015
  • Source: HomeAway
Did you find this review helpful?
1 0
5

A wonderful family holiday at Gentle Heritage

  • 5 of 5

In our family's week long stay at Gentle Heritage we were sixteen ranging from 92 to 18 and unanimous in our enjoyment of the house, its location, views, comfort and amenities. We have stayed in large vacation homes in about ten different countries but this house tops them all.

Loet V. Sheffield, MA

  • Submitted: Aug 6, 2015
  • Stayed: Jul 2015
  • Source: HomeAway
Did you find this review helpful?
1 0
South Shore, Boston, Massachusetts
5

The perfect spot for a group getaway or retreat!

  • 5 of 5

This was the second year that our group of nine adult women--all artists and/or writers--gathered for a long spring weekend at this gorgeous waterfront property. We knew from our first visit that the property is, if anything, even better than described: secluded yet not too remote, spotless, well-maintained, and spacious, with plenty of room to spread out. We each had our own charming bedroom for reading, writing, and napping; we also made full use of the shared spaces, such as the TWO fully stocked kitchens, the porches, the sunroom, and the living rooms, where we worked on projects, played games, or just hung out together. The owners are friendly, professional, and, above all, responsive. We expect to make this getaway an annual tradition at this venue, and some of us have already recommended it to friends and relatives. It's a real treasure.

  • Submitted: May 25, 2015
  • Stayed: Apr 2015
  • Source: HomeAway
Did you find this review helpful?
4 0
5

The Winslow Estate was the perfect venue !

  • 5 of 5

The Winslow Estate was the most magical venue to hold our daughter and son in law's wedding! The kind hosts were most accommodating with any of our needs! Our guests flew in from all over the world and everyone was so taken back by the beautiful setting! We will cherish our memories of this very special event in our lives!!!

Paul & Denise Graves

  • Submitted: Oct 25, 2014
  • Stayed: Oct 2014
  • Source: HomeAway
Did you find this review helpful?
6 0
Marshfield, MA
5

Spectcular Property

  • 5 of 5

Gentle Heritage is an absolutely spectacular property! The views from the bluff over-looking Pleasant Bay are gorgeous. Everything was very clean and well maintained. We were there for a family wedding (held elsewhere), so it was a perfect place for so many of us to gather for the weekend. Luckily, the weather was perfect and several people even enjoyed a dip in the water. The listing description was accurate and the owners were very helpful and accommodating. I highly recommend this property!

  • Submitted: Oct 22, 2014
  • Stayed: Oct 2014
  • Source: HomeAway
Did you find this review helpful?
1 0
5

Unforgettable Wedding Location!

  • 5 of 5

Although my fiancé and I are not from Cape Cod, we knew as soon as we got engaged that the Cape was the perfect destination for our wedding. Despite residing in Chicago we researched from afar and narrowed our selection to 10 different venues/locations to visit the following month. Although we saw some amazing places, we knew in our heart the winner would be the Winslow Estate and upon arriving for our tour and driving up the entrance way, our decision was instantly made even before we got out of the car. Our criteria was simple: we wanted our ceremony and reception at the same location, preferably outside, where our wedding party was also able to stay through the weekend and the Winslow Estate accommodated all the above.

To say the estate is beautiful is a complete understatement. The house itself, the yard, the views of Pleasant Bay are all breathtaking. Although I’ll admit the price was a bit of a surprise at first, we can say now it was 100% worth it. Once we decided that the Winslow Estate was right for us, the owners (Ken and Ginger) were incredibly helpful, responsive and supportive throughout the entire planning process; always available to answer questions via phone or e-mail or provide recommendations as needed. Given that we were planning a wedding from Chicago, this level of support was certainly needed! We were able to have ourselves and our entire wedding party sleep and stay at the estate leading up to the wedding. We had a smaller guest count (around 85) that all fit comfortably during both the ceremony on one side of the yard and then under a covered tent during the reception on the other side.

I’d recommend the Winslow Estate to anyone without hesitation whether for weddings, family reunions, etc. Our memories from our wedding day are priceless, largely due to the location we held it at.

Thank you Ken and Ginger for an amazing experience!

  • Submitted: Oct 6, 2014
  • Stayed: Sep 2014
  • Source: HomeAway
Did you find this review helpful?
2 0

Map

Nearest Airport
8 Miles
chatham
Nearest Barpub
5 Miles
Land Ho!
Nearest Ferry
10 Miles
to Nantucket
Nearest Golf
5 Miles
public - Captains in Brewster
Nearest Train
85 Miles
boston
Nearest Motorway
2 Miles
routes 28 and 39
Nearest Restaurant
5 Miles
many

The estate is in South Orleans equal distance between Chatham and Orleans. Chatham's beatiful Main Sreet is noted for its quaint Cape Cod feeling and variety of shops including restaurants, antiques, clothing, and surf shops. Pleasant Bay is excellent for swimming, sailing, fishing, wind surfing, kayaking, motor boating (your own or rent one) water skiing, or just walking the shoreline. The estate comes with a mooring and a skiff and oars.

Nauset Beach in Orleans has big waves for body surfing, boogie or skim boarding, surfboarding and surf casting for bluesfish and bass.

Skaket Beach in Orleans is noted for the warm salt water flats, sand bars, clamming, and is always a favorite for children. You can walk seemingly forever into Cape Cod Bay when the tide is out or just swim sand bar to sand bar when it is in.

Photos

Rates & Availability

Orleans Estate Rental Rates

Rental Basis:
per property
Owner accepts payment in:
USD
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
 
Spring
May 7 2016 - May 28 2016
3 night minimum stay
$1,600
$10,000
 
 
Late spring
May 29 2016 - Jun 18 2016
7 night minimum stay
$12,000
 
 
Early Summer
Jun 19 2016 - Jul 1 2016
7 night minimum stay
$15,000
 
 
Peak Summer
Jul 3 2016 - Aug 26 2016
7 night minimum stay
$16,000
 
 
Early fall
Aug 27 2016 - Sep 10 2016
7 night minimum stay
$15,000
 
 
late fall
Sep 11 2016 - Nov 30 2016
2 night minimum stay
$1,600
$10,000
 

Additional information about rental rates

$7000 - 16000 per week
Linens - bath towel sets as well as beach towels - and cleaning fees are included in weekly rental rate. there are no taxes, facilities fees, or hidden costs. Rental fees are for the stated occupancy of the house only. Group gatherings, family reunion, birthday parties, etc. constitute additional use of the property and there will be increased charges.

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.
Enter dates to see total
Send a Message
Available arrival
Available stay (no arrival)
Unavailable

Amenities

Cape Cod Estate Accommodation and Amenities

Property Type:
  • estate
Meals:
  • Guests provide their own meals
Location Type:
  • Beach
  • Waterfront
Theme:
  • Family
General:
  • Air Conditioning
  • Alarm Clock
  • Basic Soaps
  • Clothes Dryer
  • Filtered Water
  • Fireplace
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided
  • Local Activities Guide
  • Local Maps
  • Local Restaurant Guide
  • Paper Towels
  • Shampoo
  • Telephone
  • Toilet Paper
  • Washing Machine
  • Wireless Internet
Kitchen:
  • Blender
  • Coffee Maker
  • Cooking Utensils
  • Dishwasher
  • Freezer
  • Ice Maker
  • Lobster Pot
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Toaster
Dining:
  • Dining Area
Bathrooms:
  • 5 Bathrooms
  • 1 Half Bath
  • Bathroom - toilet , combination tub/shower
    Bathroom - toilet , combination tub/shower
    Bathroom - toilet , combination tub/shower
    Bathroom - toilet , shower
    Bathroom - toilet , shower
    Bathroom - toilet
    Bathroom 7 - outdoor shower , enclosed
  • There is a fully enclosed outdoor shower with hot and cold water plus a dressing room.
Bedrooms:
  • 9 Bedrooms, Sleeps 19
  • Bedroom - 1 king
    Bedroom - 1 queen
    Bedroom - 1 queen
    Bedroom - 1 queen
    Bedroom - 3 twin/ single
    Bedroom - 2 twin/ single
    Bedroom - 2 twin/ single
    Bedroom - 2 twin/ single
    Bedroom - 2 twin/ single
  • The nine bedrooms are really nine bedrooms - not common rooms that become bedrooms at night with pull out sofas. There are no sofa beds, futons, trundle beds, bunk beds or cots. Everyone has a personal and private space. All of the bedrooms have twins beds or queens. The master bedroom has a king bed. Each bedroom sleeps two guests except for one extra large one that has a set of three twin beds. Two wings of the house plus the two second floor bedrooms have central air. All bedrms have A/C as well as the dining room and family room. Please see our web site for a floor plan and room sizes.
Entertainment:
  • Audio Tape Player
  • Books
  • Books for Adults
  • Books for Kids
  • CD Player
  • DVD Player
  • Game Room
  • Games
  • Games for Kids
  • Music Library
  • Pool Table
  • Radio
  • Satellite / Cable
  • Stereo
  • Television
  • Toys
  • VCR
  • Video Games
  • Video Library
Outside:
  • Barbecue
  • Beach Chairs
  • Beach Towels
  • Binoculars
  • Large Cooler
  • Outdoor Grill
  • Outdoor Grill Gas
  • Patio
  • Small Cooler
  • Terrace
Suitability:
  • children welcome
  • non smoking only
  • suitable for elderly or infirm
  • wheelchair accessible
Attractions:
  • autumn foliage
  • bay/sound
  • churches
  • cinemas
  • forests
  • library
  • live theater
  • marina
  • museums
  • playground
  • pond
  • recreation center
  • restaurants
  • water parks
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • horseback riding
  • scenic drives
  • sight seeing
  • walking
  • whale watching
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • equestrian events
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • golf privileges optional
  • hiking
  • jet skiing
  • mountain biking
  • paragliding
  • pier fishing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • sound/bay fishing
  • surf fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing
Notes:
1 king, 3 queens, 11 twins, 5 1/2 bathrooms plus a fully enclosed outdoor shower with hot and cold water and a dressing room. Please see our web site for a floor plan with room sizes. All of the bedrooms have A/C and several of the common areas do as well.

Learn more about this vacation rental at the owner's website:

Partner Offers

Contact the Owner

Request to Book

This property requires that you message the owner to complete your booking request.
Enter dates to calculate a quote