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Waterfront with Magnificent Views, Swim from your Private Dock, + 3 kayaks

Bedrooms 5
Half Baths2
Property type house
Minimum Stay 2 - 7 nights


About the property

5 bedrooms, 2 full and 2 - 1/2 baths, enclosed outdoor shower, sleeps 10

Striking water views from every room! Swim off the private dock. Bring your motor boat, sailboat, or raft to this waterfront home with private dock with over 100' salt water frontage off Pleasant Bay. Or, use the 3 kayaks provided to explore the numerous local waterways, ponds and conservation owned islands. Sunny, very private one acre just one mile from Orleans Center, tennis, & ball field, 2 miles form Nauset Beach.

The architect designed house is wonderfully bright and airy. There are large Anderson sliders out to the deck that features several sitting and eating areas to enjoy the gorgeous water views. There are 4 separate 'pods' connected by the exterior deck and overhangs. The central one houses the combination living room and dining room, as well as the new kitchen and appliances being installed in the winter of 2017. The master bedroom en suite is also in the center pod. The guest house pod has a water front bedroom with a queen bed and a bedroom with a set of twin beds that can combined. These two bedrooms share a common bathroom. Each bedroom has its own entry. The last two pods each have built in twin beds and 1/2 baths. Although this is not a large house, it offers much in the way of privacy. The five bedrooms are really five bedrooms - not common rooms that become bedrooms. There are no sofa beds, futons, trundle beds, bunk beds or cots. Everyone has a personal and private space.

Boating on 'the river' is a wonderful experience. See the beautiful cape cod homes from the water. Explore all the waterways, ponds and islands. Make your way down the channel to Chatham and watch the fish unload at the fish pier. Getting out to the open ocean can be tricky. Talk to a local or be sure to bring a chart for the 'Chatham cut''.

Wireless internet. Beach, bed and bath linens included. No cleaning fee or taxes or hidden fees.Completely air conditioned. Washer, drier and all the amenities. Everyone enjoys the fully enclosed outdoor shower. See our web site for more on the Dock of the Bay.

More Details

Ken Winslow
Member since: 2004
Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
May 10, 2017


Orleans House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
House Rules:
  • Max. occupancy: 10
  • children welcome
Location Type:
  • Beach
  • Waterfront
  • Family
  • Sports & Activities
  • Activities Guide
  • Air Conditioning ...
  • Alarm Clock
  • Basic Soaps
  • Ceiling Fans
  • Clothes Dryer
  • Fireplace
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Laundry Soap
  • Local Maps
  • Local Restaurant Guide
  • Paper Towels
  • Parking
  • Parking Off Street
  • Telephone
  • Toilet Paper
  • Washing Machine
  • Wireless Internet
  • 4 Ring Stove
  • Blender
  • Coffee Grinder
  • Coffee Maker
  • Cooking Utensils
  • Dishwasher
  • Ice Maker
  • Lobster Pot
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Toaster
  • Dining Area
  • 2 Bathrooms
  • 2 Half Baths
  • Bathroom - toilet , combination tub/shower
    Bathroom - toilet , shower
    Bathroom - toilet
    Bathroom - toilet
    Bathroom - outdoor shower , enclosed
  • One bathroom is a full bath with tub and shower combination. One bathroom has a shower. Two bathrooms are 1/2 baths. Everyone enjoys the enclosed outdoor shower the most!
  • 5 Bedrooms, Sleeps 10
  • Bedroom - 1 queen
    Bedroom - 1 queen
    Bedroom - 2 twin/ single
    Bedroom - 2 twin/ single
    Bedroom - 2 twin/ single
  • All bedrooms are really bedrooms - not common rooms that have pull out sofas for sleeping. All beds are really beds - not sofa beds, trundles, futons, bunk beds, or cots. Enjoy your peace and privacy in your own bedroom.
  • Books
  • Books for Adults
  • Books for Kids
  • CD Player
  • DVD Player
  • Games
  • Games for Kids
  • Radio
  • Satellite / Cable
  • Stereo
  • Toys
  • VCR
  • Video Library
  • Barbecue
  • Beach Chairs
  • Binoculars
  • Boat
  • Boat Dock
  • Deck / Patio ...
  • Kayak / Canoe ...
  • Large Cooler
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • Small Cooler
  • Wood Deck
  • 18 garden chairs
  • 10 beach chairs
  • suitable for elderly or infirm
  • wheelchair accessible
  • autumn foliage
  • bay/sound
  • cinemas
  • festivals
  • forests
  • library
  • live theater
  • marina
  • museums
  • playground
  • restaurants
  • winery tours
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • paddle boating
  • scenic drives
  • sight seeing
  • walking
  • whale watching
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • golf privileges optional
  • jet skiing
  • mountain biking
  • pier fishing
  • rafting
  • sailing
  • snorkeling
  • sound/bay fishing
  • surf fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing
The entire house was air conditioned in 2014. 2 queen beds, 6 twins beds allow for much privacy in 4 connected buildings.. 3 kayaks provided to explore the bay, one is a double and the other two are single kayaks, enclosed outside 'after-swim' shower.


Exceptional! 5/5 -
(12 traveler reviews)

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Waterfront with Magnificent Views, Swim from your Private Dock, + 3 kayaks
average rating of 5.0 based on 12 reviews

Wonderful spot

  • 5 of 5

What a wonderful location watching the boats go by all day. There is a spacious deck where we all could gather together outside for meals and another deck section set up as an outdoor living room. The area is very quiet and peace, yet not far from the center of Orleans and the local beaches. Although in truth we were so happy here, just floating on rafts off the dock, that we hardly left. The property is well kept and we, a group of artist women, all enjoyed having our own individual 'pods' for privacy. A great time was had by all and we are planning a return trip.

  • Submitted: Aug 2, 2016
  • Stayed: Jun 2016
  • Source: HomeAway
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Idyllic Cape Cod setting

  • 5 of 5

We had a wonderful week at this property enjoying the beautiful water views. It's a perfect spot for boating, kayaking & bird watching.

The spacious layout afforded all of us privacy. The house was clean and well maintained while the owners were most accommodating. We'll be back!

Thank you again, Ken & Ginger.


  • Submitted: Aug 2, 2016
  • Stayed: May 2016
  • Source: HomeAway
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A place to come back to!

  • 5 of 5

What a great place! It's like having your own little compound. The water views are beautiful. If you brought a boat or rented one you could dock it there. The place is very private, not only in and of itself but each of the buildings offers its own privacy. All you hear in the morning is the birds. Around the buildings and connecting them are expansive decks. The design of the house is unique and interesting. Internet connection is fast. Lots of cable channels. Close to town and restaurants, and close to Nauset. We'll be back!!

  • Submitted: Jun 10, 2016
  • Stayed: May 2016
  • Source: HomeAway
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What you want to wake up to every morning!!!

  • 5 of 5

This home is beautiful. Has everything you need! Privacy, beautiful water views, full kitchen, multiple baths, great deck you could spend hours watching boats go by, dock to swim off or kayak off of. The house has an amazing layout with the main structure having a master bedroom, kitchen, bath and open tv room/seating area. There are then 3 other bedroom areas off the very large deck where each has their very own separate areas for privacy to break away from your entire group staying at the house yet you all can meet up in the main room or deck to hang out with the entire family or friends. One of the coolest water front homes I have seen. The kids thought the setup was very cool and so did the adults. Great place for families big or small that love being right on the water. Hope to get back there in the future!


Kim and Ted and the boys

  • Submitted: Nov 2, 2015
  • Stayed: Oct 2015
  • Source: HomeAway
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Magical time

  • 5 of 5

This house was one of the best places we have ever rented. (And we have been renting on the Cape for over 25 years.) The view is fantastic. The house has four "pods" - each with bedrooms and bathrooms, affording privacy and coziness. The main pod has the kitchen and great room - a wonderful place to gather for dinner. The owners were very attentive and warm. Truly a magical place - we would strongly recommend it for a memorable stay!

  • Submitted: Sep 27, 2015
  • Stayed: Sep 2015
  • Source: HomeAway
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2 0
Stow, MA

Winslow Estates private house rental

  • 5 of 5

A spectacular setting at the water's edge, plenty of privacy, and a wonderfully unique and flexible floor plan for multiple families. We had attended a wedding reception that afternoon at the Winslow Estates, and were the guests of the groom's family that night. This was a perfect way to end the day, and not have make the two hours drive back up to Massachusetts. It would also be a terrific house to rent by the week with several couples.

  • Submitted: Aug 10, 2015
  • Stayed: May 2015
  • Source: HomeAway
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Nearest Airport
8 Miles
Chatham Airport
Nearest Barpub
2 Miles
Land Ho!
Nearest Ferry
15 Miles
Ferry to Nantucket
Nearest Golf
5 Miles
Nearest Train
100 Miles
Nearest Motorway
5 Miles
Route 6
Nearest Restaurant
2 Miles
Land Ho!

The Pleasant Bay River connects beautiful Meetinghouse Pond to all the activities on Pleasant Bay. Watch the boats go by for a day of swimming, sailing, fishing, wind surfing, kayaking, motor boating (your own or rent one) water skiing, or just walking the shoreline. Or, do all of this right in front of your house!

Five minutes away is Nauset Beach, great for body surfing, boogie or skim board, and surfing. Skaket Beach is also five mintues away at Cape Cod Bay. Known for its warm water flats, sand bars, little children love it.

Walk along the waterfront to a dirt road that leads to East Orleans Center. Come back with coffee and donuts for breakfast, luncheon sandwiches, pizza, or go after dinner for ice cream.

About five minutes away is one of the entrances to the Cape Rail Trail. Rent a bike or bring your own and ride for miles - almost to Provincetown. It is a very special way to spend the day for all ages.

Orleans Center is only a few minutes away. It offers great restaurants, fun shopping, and stores to meet all your needs.

Chatham is about 15 minutes away with one of the prettiest Main Streets anywhere. Choose a restaurant for your lunch or dinner, do some antique shopping, find a souvenir you'll love.


Rates & Availability

Taxes and fees are additional
This calendar has not been updated in over 2 months and the availability shown may not be accurate.

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.

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