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Bedrooms 6
Half Baths1
Property type estate
Minimum Stay 3 - 7 nights


Half Baths
Minimum Stay
3 - 7 nights

About the property


Your compound spreads across the only hill on Chappaquiddick, Sampson’s Hill, the highest elevation in Edgartown, with a 180 degree view of Nantucket Island! Park where your family and guests can enjoy outdoor activities and gatherings with benefits of a full size heated pool, tennis, basketball, and volleyball courts and two Jacuzzis. There is an 8 person Jacuzzi on the porch of the home that has fantastic built in back massagers. Family Reunion? Look no further, memorialize your vacation on this compound of fun and beauty. Pick from 6 bedrooms and 4 ½ baths that comfortably sleep 16 people with air conditioning throughout the home. The home is referred to as an upside down home reserving the top floor as a shared living space that has picture windows that run the full length of the home, so that all guests can enjoy and see the 180 panoramic view of the ocean and see as far as Nantucket. The living room contains a 10 foot carving of a right whale, that was carved by a local artist, in the center of the living room as well as other art that you are not likely to see elsewhere. Brand new details abound, for gourmet kitchen. The top floor contains the living room and dining area that includes a central granite counter dining area that can accommodate all of the guests located off the gourmet Kitchen. The entertainment center located on the top floor includes a 60 inch TV along with a stereo system with speakers inside as well as outside on the porch.

The porch off the top floor runs the full length of the home and is accessible via doors leading from the dining and living room. You will be able to enjoy outdoor dining with the gas grille with three large dining areas located on the porch. The binocular view finder located on the porch will allow you to see Nantucket clearly and the activity on the waters between the Vineyard and Nantucket (i.e. the binocular view finder located on the porch is the same view finder that you will find on the Empire State Building and other scenic spots around the country.) The home brings together your family yet offers privacy. There are three floors to fill up if you wish to use the whole home, as you enter at the middle floor, there are four bedrooms and three full bathrooms. This floor has a screened in three season porch that runs the length of the home, each of the four bedrooms can access to the porch and view via a door in each of the bedrooms. The porch features classic wicker furniture as well as well as ceiling hung fans and swirling chairs hung from the ceiling. On this floor you also have access to the 8 person Jacuzzi with built in massages as well as outdoors showers.

The porch has a wet bar and small refrigerator as well as fuze ball, ping pong, and air hockey tables that the family can enjoy. The lower level of the home contains two bedrooms as well as a full bath and a common area with a refrigerator and sink. The bedrooms on this floor have direct access to the porches via the outside doors leading to the porches.

The home abuts a historical marker that is located on the top of Sampson’s hill that designates the spot that a semaphore once stood from 1801 to 1840 that relayed news from Nantucket to Chappaquiddick and up the coast ultimately reaching Boston with whaling news of the day, after the whaling days ended a church was established that stood on the spot until 1939. There are ancient ways that lead to the top of Sampson’s Hill that were used to access the semaphore and church that once stood there that traverse across the property. There is a trail system that connects the ancient ways throughout the island so you can access all of Chappaquiddick and its beaches via the ways that cross this property. There are bikes available so that you can bike to the beach and other locations utilizing the ancient ways that run through the property.

This property abuts 100’s of acres of conservation land and it is not unusual to see deer and other wildlife. The sky is illuminated at night by the stars and you can easily see the Nantucket light house shining at night from the porch. There is a conservation trail that leads from your property to the Chappaquiddick Community Center where adults and children have sailing, swimming, tennis, and snorkeling, movies, stories, lessons for children and adults. The summer brings ice cream socials, foreign film nights, musical events etc. which you can access by googling Chappy Community Center. You can participate in any of the activities that you might have an interest in during your time on the Island.

You can access downtown historic Edgartown by parking your car or biking to the parking lot located on Chappaquiddick at the “On Time Ferry” which takes you back and forth from Edgartown to Chappaquiddick. You can park your car or bike here and go by foot to Edgartown (without the hassle of parking in Edgartown) to enjoy nightlife, restaurants, shopping, ice cream parlors, moves and the parks that Edgartown center has to offer. You will be able to access the many beaches, ponds, and reservations that Chappy has to offer via walking, driving, or biking on the main paved road or on the ancient trails that lead to these destinations. This family home with all of its amenities and the Island of Chappaquiddick is an enchanted destination for your family. Did I mention ping pong, table fuse ball, swings...

There is a web page that provides more details on this home and the other two homes that occupy the top of Sampson's Hill being --The Country House and The Monet Home- --if interested in vacationing in more than one home or a different home that accommodation can be made. Please call Steve or Mary with any questions or to book your summer vacation at ---508-654-5413--or 508-6545401--I will look forward to speaking with you---Steve

More Details

Stephen Olsson or Mary Olsson
Member since: 2011
Speaks: english
Response time:
Within a few days
Response rate:
Calendar last updated:
August 21, 2016

About Stephen Olsson or Mary Olsson

I have been sailing to the Vineyard since the 1960's and living on the Island off and on since the 1970's. The beauty and diversity of the Island never ceases to amaze me as well as the place that the Island has played in the history of the country.

Stephen Olsson or Mary Olsson purchased this estate in 2011

Why Stephen Olsson or Mary Olsson chose Edgartown Area

I already own one property next door you can see it on VRBO at # 355429. Bought land on the island in 1974 and have been vacationing and spending time year round here with my family and friends for 40 years. As well, I have been renting to return vacationers and new renters, which keep the house full in the summer, so I bought and am fully renovating a second home next door to create an compound. both houses have great privacy.

What makes this estate unique

The home sits on the highest hill in Edgartown next to a Historical Monument placed there by the Dukes County Historical Society designating the location of where a semaphore stood since 1801 to the 1850's relaying whaling news from Nantucket to Chappaquiddick up the coast to Boston. The deck on the top floor of the home affords a 180 degree view of Nantucket and Nantucket Sound. The home provides all the comforts of an upscale home along with the amenities of having a tennis, basketball and volleyball court to play with family and friends--The property has a full size heated pool and a four person Jacuzzi next to the pool and pool house. The home has two porches---one porch is a three season screened in porch that has a 8 person Jacuzzi off the porch with the four bedrooms each having a door leading onto the porch where there is a wine cooler and refrigerator and reclining chairs and coaches. The upper porch runs the length of the home and there is an outside gas grille and a teak table that will accommodate up to 18 at the table for a feast. The home provides all the amenities one would look for when planning a vacation for family and friends!


4.7/5 -
(3 traveler reviews)

average rating of 4.6666665 based on 3 reviews

Perfect Retreat for Family and Friends

  • 5 of 5

What a great way to kick off the summer! We had 4 families total between two of the houses. There was plenty of space for everyone, dinner nightly on the spacious, private deck. We loved the pool, tennis/basketball court, and the kids found frogs in the pond. We bought a drive on beach pass and went out to Wasque which was quiet and beautiful as well. It was our first time on Chappy and loved the natural beauty and how peaceful it is, it was a true getaway. We hope to return!

  • Submitted: Jul 9, 2016
  • Stayed: Jun 2016
  • Source: HomeAway
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Wilmot, New Hampshire

Wonderful family vacation in Chappy home

  • 5 of 5

Our 3 generational-family, including 4 teenage boys, spent an incredible week

at this amazing compound in early August, 2015. The home is not easy to find

but, once there, proves well worth the effort. It is three floors with bunk rooms

for the kids on the lower level, 4 good sized bedrooms with 3 bathrooms on

the second level, and the living/dining/kitchen space on the top level. The

living area is large and comfortable and affords a wonderful view out across

the water toward Nantucket. The kitchen is well stocked with dishes and glassware which is always a treat when away from home. The property

includes a large swimming pool, hot tub, and tennis/basketball court, all of

which made this stay a real hit with our grandboys. In addition, we walked

the many trails, went to the Chappy beaches, and used the short drive to the

"On Time" ferry for excursions into Edgartown.

All in all, this was one of the top family vacations we have experienced and we all agreed that we would love to come back in the near future and enjoy it all over again. We used to bring our son and daughter to Martha's Vineyard when

they were high school/college age and they loved the opportunity to share this

wonderful island with their spouses and children. This home was a big part

of that positive experience and clearly the best that we have ever had on MVI.

  • Submitted: Nov 22, 2015
  • Stayed: Jul 2015
  • Source: HomeAway
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1 0

Lovely property on Chappy

  • 4 of 5

Terrific property up on a hill in Chappy. This house has everything you need for a great stay, particularly for a large family or multi-family group. We thought the web site accurately described the property and its many amenities including pool, tennis court, bikes, hot tubs, volleyball, etc. The upside down design of the house was great - nice views from the deck and lots of natural light in the kitchen and living room where you spend most of your time. We really enjoyed being on Chappy, but you need to know that it's a bit more isolated than being on the main island and can be a hassle going back and forth at certain times of day (so you need to plan ahead). We were there at the end of the summer and there were a few deferred maintenance type items but nothing out of the ordinary for a summer rental property.

  • Submitted: Nov 22, 2015
  • Stayed: Aug 2015
  • Source: HomeAway
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Nearest Airport
12 Miles
Martha's Vineyard
Nearest Ferry
1 Miles
Vineyard Haven & Oak Bluffs
Nearest Beach
1 Miles
East Beach
Car: not necessary



Rates & Availability

Enter dates for accurate pricing

Additional information about rental rates

Refundable damage deposit $1,500

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.
Calendar not updated in over 2 months and may not be available. Look for rentals with Request to Book or updated calendars.


Edgartown Estate Accommodation and Amenities

Property Type:
  • estate
  • Guests provide their own meals
Floor Area:
  • 4000 sq. ft.
Location Type:
  • Near The Ocean ...
  • Ocean View
  • Resort ...
  • Rural
  • Water View
  • Away From It All
  • Family
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning
  • Clothes Dryer
  • Covered Parking
  • Garage
  • Heating
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room ...
  • Mobile Phone
  • Parking ...
  • Parking Off Street
  • Telephone
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Catering Available
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Ice Maker
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Pantry Items
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 18 people
  • 4 Bathrooms
  • 1 Half Bath
  • Full 1 - toilet , combination tub/shower , Private bath for bedroom with king size bed
    Full 2 - toilet , shower , Private bath for bedroom with queen size bed
    Full 3 - toilet , combination tub/shower , Located on floor with 4 bedrooms.
    Full 4 - toilet , shower , Located on the lower floor with 2 bedrooms
    Half 1 - toilet , Located on top floor with kitchen, dinning and living room
    Bathroom 6 - outdoor shower , Used after returning from beach, before or after jacuzzi
  • 6 Bedrooms, Sleeps 16
  • Bedroom 1 - 2 king , With private full bath
    Bedroom 3 - 2 king
    Bedroom 4 - 2 queen
    Bedroom 5 - 5 queen , Queen size bunkbed-- sleeps 2 on each level & trundel for 5
    Bedroom 6 - 5 queen , Queen size bunkbed sleeps 2 on each level & trundel bed 5
    Bedroom 2 - 2 queen , with private full bath ---
  • The beds are all sealy postropedic mattresses---Also on the 3 season porch there is a coach that turns into a queen size bed
  • CD Player
  • DVD Player
  • Ping Pong Table
  • Satellite / Cable
  • Stereo
  • Television ...
  • VCR
  • Video Game Console
  • Video Games
  • Balcony
  • Deck / Patio
  • Lanai / Gazebo
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • Tennis ...
  • Wood Deck
  • Events Allowed
  • Long-term Renters Welcome
  • Minimum Age Limit for Renters
  • children welcome
  • non smoking only
  • pets considered ...
  • wheelchair accessible
Pool / Spa:
  • Heated Pool
  • Hot Tub
  • Private Pool
  • arboretum
  • autumn foliage
  • bay/sound
  • botanical garden
  • churches
  • cinemas
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • playground
  • pond
  • recreation center
  • restaurants
  • synagogues
  • zoo
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • horseback riding
  • horseshoes
  • luaus
  • miniature golf
  • outlet shopping
  • paddle boating
  • photography
  • scenic drives
  • shelling
  • shopping
  • shuffleboard
  • sight seeing
  • sledding
  • walking
  • whale watching
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • equestrian events
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • golf privileges optional
  • hiking
  • hunting
  • ice skating
  • jet skiing
  • kayaking
  • mountain biking
  • parasailing
  • pier fishing
  • racquetball
  • rafting
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • sound/bay fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing

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

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