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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Cape Cod Family Reunion - 4 homes on 2 private waterfront acres!

Bedrooms 11
Half Baths1
Property type estate
Minimum Stay 1 - 7 nights


About the property

Waterfront, 175ft dock 11 Bedroom / 8 1/2 Baths with outdoor shower

The Captain Heman Smith House, built in 1862, is the Lovely Focal Property of the Captain's Estate located directly on Nauset Cove.

The Main House and accompanying houses offer Spectacular Views of Nauset Cove and beyond.

Located In-Town on the Eastham/Orleans line, the Compound is a very Pleasant Gathering Place for large groups of family and friends.

The four buildings which are all fully equipped, provide a variety of accommodation options: Five bedrooms and four bathrooms in the completely renovated Captain Heman Smith House, a three bedroom, one bath cape at the water's edge, a new 1 bedroom Carriage House with it's own kitchen and full bath, and finally, a newly constructed two bedroom, two and a half bath cape with a granite kitchen. All of these unique dwellings overlook the beautiful spacious lawn, Nauset Cove and Hopkin's Island!

The Captain Heman Smith Compound is rated as ''One of the Best Rental Properties on Cape Cod'

More Details

Property Manager
Property Manager
Member since: 2006
Speaks: english
Response time:
Within a few days
Response rate:
Calendar last updated:
March 19, 2018

About The Owner

I've have been vacationing on Cape Cod my entire life. I've always valued staying at a property that has it all - location, quality, beautiful views and comfortable accommodations. This is all so important when celebrating life with family and friends and creating memories that will last forever.

The Owner purchased this estate in 2006

Why The Owner chose Orleans

There are a number of large houses on Cape Cod. Our property features the most bedrooms in the Orleans/Eastham area of Cape Cod. Our guests love the fact they can all be together yet have their own space.

What makes this estate unique

What family, friends and travelers alike all rave about, is the fact that our property has 4 separate houses and living spaces. All 4 homes are in a "U" shape that flows out into the beautiful yard and patio overlooking the water.

Guestbook comments from the manager

The Captain's Compound was the ideal place for our family reunion! What a beautiful spot - sea life in the water, rabbits galore and awesome sunrises. Best of all, our extended family were all there and not on top of one another as you find in other large rentals. Having the 4 homes was a dream come true...thank you!
Jun 2010
  • 1 of 7


Orleans Estate Accommodation and Amenities

Property Type:
  • estate
  • Guests provide their own meals
  • Housekeeper Optional
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 23
  • Max. adults: 23
  • Min. age of primary renter: 25
  • Children welcome
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
  • *If a cancellation is needed and the property can be rebooked for the same time/rate there will not be a penalty.
Location Type:
  • Beach
  • Waterfront
  • Waterfront ...
  • Family
  • Air Conditioning
  • Alarm Clock
  • Broadband Access
  • Ceiling Fans
  • Clothes Dryer ...
  • Free Long Distance
  • Internet
  • Iron & Board
  • Linens Provided
  • Local Maps
  • Local Restaurant Guide
  • Parking
  • Parking Off Street
  • Parking for RV/Boat/Trailer
  • Telephone
  • Towels Provided
  • Washing Machine ...
  • Wireless Internet
  • Blender
  • Catering Available
  • Coffee Maker
  • Cooking Utensils
  • Dishwasher ...
  • Freezer
  • Grill
  • Kitchen ...
  • Lobster Pot
  • Microwave ...
  • Oven
  • Pantry Items
  • Refrigerator ...
  • Stove
  • Toaster
  • Dining Area
  • seating for 22 people
  • 7 Bathrooms
  • 1 Half Bath
  • Bathroom 1 - toilet , shower , jetted tub
    Bathroom 2 - toilet , combination tub/shower
    Bathroom 3 - toilet , tub
    Bathroom 4 - toilet , combination tub/shower
    Bathroom 5 - toilet , shower
    Bathroom 6 - toilet , shower
    Bathroom 7 - toilet , shower
    Bathroom 8 - toilet
    Bathroom 9 - outdoor shower , Great Outdoor Shower overlooking the Cove!
  • .
  • 11 Bedrooms, Sleeps 23
  • Bedroom 1 - 1 king
    Bedroom 2 - 1 queen
    Bedroom 3 - 1 queen
    Bedroom 4 - 1 queen
    Bedroom 5 - 1 queen
    Bedroom 6 - 1 queen
    Bedroom 7 - 1 queen
    Bedroom 8 - 1 double
    Bedroom 9 - 3 twin/ single
    Bedroom 10 - 2 twin/ single
    Bedroom 11 - 2 twin/ single
  • .
  • Books
  • CD Player
  • DVD Player ...
  • Radio
  • Satellite / Cable
  • Stereo ...
  • Television
  • VCR ...
  • Barbecue
  • Boat Dock
  • Deck / Patio ...
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • Patio
  • Unscreened Porch / Veranda
  • Walkway to Water
  • Wood Deck
  • 12 garden chairs
  • suitable for elderly or infirm
Pool / Spa:
  • jetted tub
  • bay/sound
  • churches
  • cinemas
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • playground
  • restaurants
  • winery tours
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • horseback riding
  • miniature golf
  • outlet shopping
  • paddle boating
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • walking
  • whale watching
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • massage therapist
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • golf privileges optional
  • hiking
  • kayaking
  • mountain biking
  • paragliding
  • pier fishing
  • racquetball
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • sound/bay fishing
  • surf fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • wind-surfing
The Captain's House and the accompanying Houses combine for Eleven Bedrooms ranging in size and feel. Each is unique in character and aesthetic appeal, with great attention paid to the design. There is 1 King Size Bed, 6 Queen Size Beds, 1 Full Size Bed, 7 Twin Size Beds, Nine Bathrooms and a half bathrooms, Nine Showers, Three Bath Tubs and a Granite Jacuzzi Tub in the Master Bedroom. There are 3 Gorgeous Custom Tiled Showers. The four kitchens are fully equipped with everything one needs to create meals of any size. There is also a gas grill for outdoor cooking complete with two extra large white picnic tables for those memorable backyard meals. There are also multiple televisions, DVD players, VCR's, two Full Stereos with built in speakers, wireless internet access, linens and bath towels and plenty of Adirondack chairs.


5/5 -
(3 traveler reviews)

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Cape Cod Family Reunion - 4 homes on 2 private waterfront acres!
average rating of 5.0 based on 10 reviews
West Hartford, CT

Our very best family vacation!

  • 5 of 5

This property is picture perfect! Our whole family enjoyed every minute we were there. The Compound is a really special place, we were all together and still had our own space. The layout of the houses was ideal for our family and extended family. When we arrived the houses were all spotless. The kids loved swimming and fishing from the dock as well collecting various shells. The 4 kitchens were a huge plus for our “theme dinners”. We loved the fact that Nauset Beach was so close by and the proximity to shopping and the local restaurants was a huge plus. The owners were great and really personable. They have done a fantastic job with this landmark property right down to every last detail. I would recommend this rental to any large group looking for the quintessential getaway on Cape Cod, while still having all the modern conveniences of home. This rental was worth every penny, we look forward to returning again next year and for years to come – well done!

  • Submitted: Jun 16, 2008
  • Stayed: September 2007
  • Source: HomeAway
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29 10
Westport, CT

I wish we could live there!

  • 5 of 5

Our family rented the Captain Heman Smith House last fall for accommodations during our daughters wedding. The property was perfect! The wedding was held at the Chatham Bars Inn and The Captain Heman Smith Estate gave our family the feeling of having our own compound on Cape Cod for the long weekend. Family members were able to pop in and out giving us the perfect laid back gathering place. We loved the property so much we’re taking the family back next summer for a week in August! If you are looking for the ultimate Cape Cod vacation be sure to book a week at this landmark property.

  • Submitted: Nov 23, 2008
  • Stayed: September 2008
  • Source: HomeAway
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10 5

Captain Heman Smith House-Perfect!

  • 5 of 5

What a lovely property! We filled the compound to capacity and had plenty of room. This was the location for our annual family summer vacation, a group of 20. The property was very clean and well maintained.

The compound is divided into 4 houses/cottages which gave everyone their "own space" and the grandparents a quiet place to hide with the 11 children running around. Although we didn't swim from the docks, the kids spent hours fishing and crabbing down there.

Sunrises were lovely and the yard gave us enough room for a lobster/clam bake and to set up the badminton tent.

Shopping is very close by (within walking distance) which made it very easy for anything we needed! Great ocean and bay beaches are also close by.

We have been doing our annual trip for 9 years and this property ranks at the top! I would recommend this property for any large group looking to have a fun and relaxing trip!

  • Submitted: Dec 19, 2007
  • Stayed: July 2007
  • Source: HomeAway
Owner's Response: Thank you very much for your review! It means so much to us every time we hear about the great experiences families like yours have at the Compound. We look forward every summer to making the property even that much better. Summer on Cape Cod together with family and friends is what life is all about – creating an experience filled with memories that will last a lifetime. All the best!
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39 9


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Car: recommended

Other Activities: Kayaking, Standup paddle boarding.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Refundable damage deposit $1,000

Need more space?
We have a house next door for additional guests - 'The Castaway House'
HomeAway listing #229602

Need less space?
We have a house on Wellfleet Harbor - 'Just Bluffing'
HomeAway listing #156441

We also have a great new property on the bayside in Eastham - 'Barquentine Court'
HomeAway listing #189142

Please contact us for more information.

Manager's Cancellation Policy

  • Canceled bookings will not receive a refund

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