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Chilmark House and Guest House

Bedrooms 4
Half Baths1
Space 222 m²
Property type house
Minimum Stay 7 nights


About the property


This two-house property is situated about 100 yards up a country lane off the South Road in Chilmark. Alley’s General Store is one mile to the east and Beetlebung Corner and The Chilmark Store are four miles to the west. You can continue out State Road to Squibnocket Beach, or head up to Menemsha to watch the sunset, perhaps while enjoying a freshly boiled lobster from Larsen’s. We’re about a mile from the farmer’s markets and crafts shows in West Tisbury.

The main house is about 40 years old and we renovated it in 2002. We built the Guest House in 2004. The wood paneling in both houses give a warm, inviting ambiance.

We ask that you supply your own bed linens and towels, but most everything else you need is supplied, including beach chairs, well-equipped kitchen, hair dryer, etc.

Please note there is a $200 per rental cleaning fee when renting main and guest houses together.

More Details

Jeremy Driesen
Member since: 2009
Speaks english
Response time
Within an hour
Response rate
Calendar last updated:
13 August, 2017

About Jeremy Driesen

We are Jennie and Jeremy Driesen and we live in Pelham, NY with two children, a black dog, and supposedly a cat, too. Jeremy is an events producer/drummer/photographer and Jennie is a model and actress. Jennie and Molly, our black dog, have appeared a number of times in the Black Dog catalog.

Jeremy Driesen purchased this house in 2002

Why Jeremy Driesen chose Martha's Vineyard

We stayed with friends in Chilmark and fell in love with Lucy Vincent Beach and the whole feel of Chilmark. While we were there, 8 Swans Way came on the market. It seemed a bit impulsive at the time, but we bought it. One of the best things we ever did. We have spent a number of full summers on the island and forgot to go home one September (we enrolled the kids in The Chilmark School and stayed for 14 months).

What makes this house unique

Note that it may be possible to rent only one of the two houses in months other than July and August. Please contact owners if you're interested. During July and August, we do only two-house rentals.

We love so many things in Chilmark and the Vineyard in general, including, in no particular order, Lucy Vincent Beach, Menemsha, The Chilmark Store, Chilmark Chocolates, The Chilmark School, The Chilmark Library, the MV Fair, The Ritz, Sharky's, Offshore Ale, biking, last-minute pot luck dinners with friends, etc etc etc.


Accommodation and facilities for this holiday house rental in Chilmark, Massachusetts

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 222 m²
House Rules:
  • Check-in: 3:00 PM / Check-out: 11:00 AM
  • Max. occupancy: 11
  • pets considered ...
  • children welcome ...
  • non smoking only
Location Type:
  • Rural ...
  • Away From It All
  • Sports & Activities
  • Broadband Access
  • Clothes Dryer ...
  • Fireplace
  • Hair Dryer
  • Heating
  • Internet ...
  • Living Room
  • Parking ...
  • Parking Off Street ...
  • Washing Machine ...
  • Wireless Internet ...
  • Wood Stove
  • Coffee Maker ...
  • Cooking Utensils ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Ice Maker
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster ...
  • Dining ...
  • Dining Area
  • seating for 6 people
  • 2 Bathrooms
  • 1 Half Bath
  • Guest House Full Bath - toilet , shower enclosure
    Main House Upstairs Bathroom - toilet , This bath is within a bedroom.
    Main House Downstairs Bath - toilet , shower enclosure
    Main House Outdoor Shower - outdoor shower
    Guest House Outdoor Shower - outdoor shower
  • 4 Bedrooms, Sleeps 11
  • Guest House Futon Sleeper Sofa - 1 sofa bed/futon , Good for a child or two.
    Main House Open Bedroom - 3 single bed , Upstairs, no door, open room, good for a few kids.
    Main House Downstairs Bedroom - 2 single bed
    Guest House Master Bedroom - 1 large double bed , Bedroom with full bath.
    Main House 2nd Floor Bedroom - 1 large double bed , Bedroom with half bath.
  • Our property tends to work well for extended families. Mom, dad, and the kids are in the main house. Grandma and grandpa are in the guest house, or it could be a second small family there.
  • Books ...
  • Satellite / Cable ...
  • Television ...
  • Toys ...
  • Deck / Patio ...
  • Lanai / Gazebo ...
  • Lawn / Garden
  • Outdoor Grill ...
  • churches
  • cinemas
  • festivals
  • health/beauty spa
  • library
  • live theatre
  • marina
  • museums
  • playground
  • recreation centre
  • restaurants
  • synagogues
Leisure Activities:
  • antique hunting
  • beachcombing
  • bird watching
  • boating
  • horse riding
  • miniature golf
  • paddle boating
  • photography
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness centre
  • groceries
  • hospital
  • laundrette - serviced
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • golf pass optional
  • hiking
  • jet skiing
  • kayaking
  • mountain biking
  • parasailing
  • pier fishing
  • racquetball
  • sailing
  • diving
  • snorkeling/diving
  • bay fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • wind-surfing


Wonderful! 4.9/5 -
(17 traveller reviews)

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Chilmark House and Guest House
average rating of 4.9411764 based on 17 reviews

Property was great! Exceeded expectations.

  • 4 of 5

House, cottage and property were perfect for our group. One family with 6yr and 6mth old stayed in cottage and other family with teens in main house. Loved the big outdoor shower with foliage and hummingbirds in the middle of the yard. Big dining table on deck was perfect for our large group. Good proximity to Lucy Vincent beach and Menemsha. Mid 70's and sunny everyday. One of our best Vineyard vacations ever!

  • Review Submitted: Aug 17, 2017
  • Date of Stay: Jul 2017
  • Source: VRBO, from HomeAway
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Away from it all, but close enough to see it all!

  • 5 of 5

Great tranquil property! Outdoor showers were awesome. Yard was big enough for the kids to play in. You feel completely secluded yet the road is only 100 yards away. It reminded me of my childhood. Book it if you can!

  • Review Submitted: Jul 23, 2017
  • Date of Stay: Jul 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thanks! Great to have you!
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Fantastic Visit

  • 5 of 5

Jeremy is a class act and his home is wonderful. My family and I truly enjoyed our stay at his lovely home. My entire family thanks you for your hospitality.


The Limbergers

  • Review Submitted: Jul 10, 2017
  • Date of Stay: Jun 2017
  • Source: VRBO, from HomeAway
Owner's Response: Many thanks for the kind words and delighted you had a good time!
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Excellent, Affordable Up Island Charmer

  • 5 of 5

We stayed here with our 11 year old daughters in July. The futon easily converted into a bed for the girls, and a set of double doors could be closed to separate the kitchen/dining room area where they slept from the back of the cabin, which offered some privacy. The girls enjoyed boogie boarding and swimming at Squibnocket Beach (limited accessibility at high tide, check the tide schedule for best times to go), and we took the MVTA bus to Lucy Vincent and used our walk-on passes there as well. The West Tisbury Farmers' Market, Alley's General Store, and the Chilmark General Store were all worth a stop and just a short drive away. Jeremy and Jenny were exceptionally welcoming and great guides for the up island area. Their guest cabin is a lovely place to stay in Chilmark.

  • Review Submitted: Aug 18, 2015
  • Date of Stay: Jul 2015
  • Source: VRBO, from HomeAway
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Great rental- would definitely stay again

  • 5 of 5

My husband, our toddler, and I stayed in the Chilmark cottage and very much enjoyed our time. The cottage is clean and comfortable, and the owners were very friendly and helpful throughout our booking process and stay. The outdoor shower and outdoor space, with a line to hang beach towels, were especially nice touches. The rental includes eligibility to buy a parking sticker for the local Squibnocket Beach. We loved swimming and watching surfers at this beach. It was a great stay and a wonderful week.

  • Review Submitted: Aug 5, 2015
  • Date of Stay: Jul 2015
  • Source: VRBO, from HomeAway
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Lovely Time in Chilmark

  • 5 of 5

My husband, son and I have stayed on the Vineyard many times and were so please with this rental. The property was lovely, secluded and impeccably clean. The owners were easy to communicate with and we wouldn't hesitate to stay here again.

  • Review Submitted: Jul 19, 2015
  • Date of Stay: Jul 2015
  • Source: HomeAway
Owner's Response: Thanks so much for the kind words! It was great to have you guys and we hope you'll come again!
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Car: recommended

THIS IS A NON-SMOKING RENTAL. Renter must provide all sheets, towels, and pillowcases.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee A$253.6
Damage Deposit A$380.4

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.