Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled
Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Chilmark House and Guest House - AUGUST REDUCED PRICING!

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


About the property


The 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:
July 14, 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.

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.


Chilmark House Accommodation and Amenities

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
  • 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
    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 ...
  • Water Sports Gear ...
  • 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


Exceptional! 5/5 -
(15 traveler reviews)

Chilmark House and Guest House - AUGUST REDUCED PRICING!
average rating of 5.0 based on 15 reviews

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: Jul 10, 2017
  • Stayed: Jun 2017
  • Source: VRBO, from HomeAway
Owner's Response: Many thanks for the kind words and delighted you had a good time!
Did you find this review helpful?
0 0

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.

  • Submitted: Aug 18, 2015
  • Stayed: Jul 2015
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0

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.

  • Submitted: Aug 5, 2015
  • Stayed: Jul 2015
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0

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.

  • Submitted: Jul 19, 2015
  • Stayed: 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!
Did you find this review helpful?
0 0
Los Angeles, CA

Perfect Cabin Under the Trees

  • 5 of 5

We had friends staying in a house a mile down the road in Chilmark, and Swans Way was the perfect oasis for my husband and I to be close by, but have our own place. I can't imagine the indoor shower is ever used, since the outdoor shower is a little bit of heaven. Showering in a thunderstorm was a first and an absolute treat! The area was lovely, simple, and rustic, and the farm stand behind the General Store offers everything you need for local farm fresh meals to accompany fresh fish (Larsen's!) dinners. We are from California and this was our first trip to the Vineyard - it won't be our last. Absolutely relaxing and peaceful! Perfect for a couple, and the place is well equipped.

  • Submitted: Jul 7, 2015
  • Stayed: Jun 2015
  • Source: VRBO, from HomeAway
Owner's Response: It was great having you guys. Thanks for the kind words.
Did you find this review helpful?
0 0
Newton, MA

Perfect vacation

  • 5 of 5

Our family had the most wonderful week in Chilmark at this house. The outdoor shower was truly heaven! House is clean and charming, property is lovely and peaceful. We'll be back!

  • Submitted: Aug 11, 2014
  • Stayed: Aug 2014
  • Source: VRBO, from HomeAway
Owner's Response: Thanks for the nice review.
Did you find this review helpful?
0 0


Car: recommended

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


Rates & Availability

Chilmark House Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Jul 2 2017 - Jul 29 2017
Changeover Day: Sunday
7 night minimum stay
Jul 30 2017 - Sep 2 2017
Changeover Day: Sunday
7 night minimum stay
Sep 3 2017 - Oct 31 2017
Changeover Day: Sunday
7 night minimum stay

Additional information about rental rates

Cleaning fee $200
Refundable damage deposit $300

Owner's Cancellation Policy

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

You might like these similar properties