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Chilmark House and Guest House

Bedrooms 4
Half Baths1
Space 2,400 sq ft
Property type house
Minimum Stay 1 - 7 nights


About the property

Charming House with Included Guest House

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:
June 16, 2018

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 Chilmark

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 Amenities for this vacation house rental in Chilmark, Massachusetts

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 2400 sq ft
House Rules:
  • Check-in: 3:00 PM
  • /
  • Check-out: 11:00 AM
  • Max. occupancy: 11
  • Children welcome
  • Parties/events not allowed
  • Pets considered ...
  • 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
    Main House Upstairs Bathroom - toilet , This bath is within a bedroom.
    Main House Downstairs Bath - toilet , shower
    Main House Outdoor Shower - outdoor shower
    Guest House Outdoor Shower - outdoor shower
  • 4 Bedrooms, Sleeps 11
  • Guest House Futon Sleeper Sofa - 1 sleep sofa /futon , Good for a child or two.
    Main House Open Bedroom - 3 twin/ single , Upstairs, no door, open room, good for a few kids.
    Main House Downstairs Bedroom - 2 twin/ single
    Guest House Master Bedroom - 1 queen , Bedroom with full bath.
    Main House 2nd Floor Bedroom - 1 queen , 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 theater
  • marina
  • museums
  • playground
  • recreation center
  • restaurants
  • synagogues
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • horseback riding
  • miniature golf
  • paddle boating
  • photography
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • golf privileges optional
  • hiking
  • jet skiing
  • kayaking
  • mountain biking
  • parasailing
  • pier fishing
  • racquetball
  • sailing
  • scuba diving or snorkeling
  • snorkeling/diving
  • sound/bay fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • wind-surfing


Wonderful! 4.9/5 -
(20 traveler reviews)

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Chilmark House and Guest House
average rating of 4.9 based on 20 reviews

Relaxing and tranquil

  • 5 of 5

We loved our stay at the Chilmark house. The house met all of our needs and the owners were wonderful to work with. We fell in love with Chilmark and Lucy Vincent beach.

  • Submitted: 31-Aug-2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thanks, Sara! Hope you'll come stay at our place again!
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Perfect for Our Family

  • 5 of 5

Great location. Very Quiet area. The house and guest house were a good fit for our needs. We had our daughter's family (husband and grandson) and our mother (mother in law). They used the main house and we used the guest house. Very nice having a bath and a half bath in the main house and a full bath in the guest house. Gas grill was good to use to offset the high cost of eating out. Only issue (which was not a problem for our use) is to access the second floor's 2 bedrooms you need to climb a spiral staircase. This maybe a problem for small toddlers or people with limited mobility. For us we had a great time.

  • Submitted: 17-Sep-2017
  • Stayed: September 2017
  • Source: HomeAway
Owner's Response: Glad you enjoyed. Hope you'll stay with us again!
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Roomy rental

  • 4 of 5

Great yard, Quiet. room for outdoor games. Small house awesome Bigger than looks in pictures! Main house roomy. Nice showers outside

  • Submitted: 18-Aug-2017
  • Stayed: July 2017
  • Source: VRBO, from HomeAway
Owner's Response: Hope you'll come stay with us again!
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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!

  • Submitted: 17-Aug-2017
  • Stayed: July 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thanks for the kind words and we're delighted you had a great vacation. We'd be delighted to have you back next year.
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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!

  • Submitted: 23-Jul-2017
  • Stayed: July 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

  • Submitted: 10-Jul-2017
  • Stayed: June 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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Car: recommended

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


Rates & Availability

Rental Rates for this vacation house rental in Chilmark, Massachusetts

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Jun 3 2018 - Jun 23 2018
Changeover Day: Sunday
7 night minimum stay
Jun 24 2018 - Jul 28 2018
Changeover Day: Sunday
7 night minimum stay
Jul 29 2018 - Sep 3 2018
Changeover Day: Sunday
7 night minimum stay
Sep 4 2018 - Sep 29 2018
7 night minimum stay
Sep 30 2018 - Nov 1 2018
3 night minimum stay

Additional information about rental rates

Refundable Damage Deposit C$395.52
Cleaning fee C$263.68

Owner's Cancellation Policy

  • No refunds for cancellations made after payment is made
Contact Owner