Entire home

Striking 5BR/4BA Chilmark Contemporary with Views of the Sound

Holiday home in Chilmark with kitchen and balcony

Spacious, award winning house nestled in the hills of Chilmark

Spacious wrap around deck with all day sun and shade

Plenty of space for dining or lounging on this deck ! Good dogs always welcome!

Overview
Amenities
Policies
Location

Wonderful

5 bedrooms4 bathroomsSleeps 143500 sq ft

Popular amenities

Dryer
Pet-friendly
Parking available
Washer
Barbecue grill
Kitchen

Explore the area

Chilmark, MA

Place, The Yard
‪4 min drive‬
Place, Lucy Vincent Beach
‪10 min drive‬
Place, Menemsha Beach
‪10 min drive‬
Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
‪21 min drive‬

Rooms & beds

5 bedrooms (sleeps 14)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Queen Bed

Bedroom 5

1 Double Futon

Convertible bed(s)

2 Double Futons

4 bathrooms

Bathroom 1

Bathtub

Bathroom 2

Bathtub or shower

Bathroom 3

Bathtub · Shower only

Bathroom 4

Shower only

Spaces

Deck or patio

Kitchen

Balcony

Garden

Dining area

About this property

Striking 5BR/4BA Chilmark Contemporary with Views of the Sound

Come enjoy the secluded beauty of this award-winning, architect-designed home in Chimark on almost four acres of land. Relax on the two level deck or on the beach at Lucy Vincent, Squibnocket, or nearby Menemsha. The remarkable design makes great use of over 3500-square-foot space by joining the east and west houses with a guest room-den 'bridge.' The layout makes it perfect for extended family get togethers, weddings and other special occasions.

The west wing master bedroom has a king-sized bed with a private bath. Two second-floor bedrooms have queen-sized beds and share a bath with a striking, 14-foot-high, skylit, cathedral ceiling. The east wing has a king sized bedroom as well as a sleeping loft with two queen sized beds. The living rooms second level has two fold out full sized futons. The den offers a fold-out, sofa bed.

The two-level living area opens out onto the deck with distant views of Vineyard Sound and the Elizabeth Islands. The kitchen offers a Jenn-Aire cooktop and is fully stocked for groups up to 16. A huge, tiled, laundry room with washer and dryer is located on the lower level just steps from the outdoor shower.

There is plenty of storage in the lower level garage for bikes, kayaks and other toys as well as two cars.

Keywords: House

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Amenities

Kitchen

Washing machine

Dryer

Pet-friendly

Free WiFi

Air conditioning

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Similar properties

Chilmark Pond is a 10 minute walk from the house. The beach is across the pond.

Kitchen
Washer
Dryer
Pet-friendly

House Rules

Check in after 4:00 PM

Minimum age to rent: 30

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed: limit 2 total

Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:

Load and start the dishwasher

Strip any used beds and gather used towels

Remove personal items, remove leftover food and drinks and take out the rubbish

Turn off the lights, lock the doors and return the keys

Close all windows and sliding doors while A/C is running

Let us know if anything is not working or broken

Run towel through laundry and sheets too if there is time.

Failure to complete these may result in a negative review from the host.

Indoor fireplace MAY NOT be use

No smoking on the deck on the outside house

Please clean up after your pets. There is a scoop to use outside the main door if you do not have liter bags

Important information

You need to know

Extra-person charges may apply and vary depending on property policy

Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges

Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed

On-site parties or group events are strictly prohibited

Host has indicated that there is a carbon monoxide detector on the property

Host has indicated that there is a smoke detector on the property

Safety features at this property include a fire extinguisher and a deadlock

Property Registration Number C0086910620

About the area

Chilmark

Located in Chilmark, this holiday home is in a rural area. Tisbury Town Hall & Katharine Cornell Memorial Theater and Martha's Vineyard Preservation Trust Historic Buildings are local landmarks, and the area's natural beauty can be seen at Inkwell Beach and Middle Road Sanctuary. Fulling Mill Brook Preserve and Polly Hill Arboretum are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

View more Holiday homes in Chilmark

Chilmark, MA

What's nearby

The Yard - 4 min drive - 2.1 km
Lucy Vincent Beach - 10 min drive - 5.6 km
Menemsha Beach - 10 min drive - 6.4 km
Martha's Vineyard Museum - 21 min drive - 18.0 km
Inkwell Beach - 27 min drive - 23.6 km

Getting around

Vineyard Haven, MA (MVY-Martha's Vineyard) - 18 min drive

Restaurants

‪State Road - ‬9 min drive
‪Plane View - ‬18 min drive
‪Menemsha Galley - ‬9 min drive
‪Chilmark Tavern - ‬9 min drive
‪7aFoods - ‬11 min drive

Frequently asked questions

Is Striking 5BR/4BA Chilmark Contemporary with Views of the Sound pet-friendly?

Yes, this property allows pets (limit 2 total).

What time is check-in at Striking 5BR/4BA Chilmark Contemporary with Views of the Sound?

Check-in begins at 4:00 PM.

What time is check-out at Striking 5BR/4BA Chilmark Contemporary with Views of the Sound?

Checkout is at 10:00 AM.

Where is Striking 5BR/4BA Chilmark Contemporary with Views of the Sound located?

Situated in a rural location, this holiday home is within 3 miles (5 km) of Waskosim's Rock Reservation, The Yard and Middle Road Sanctuary. Fulling Mill Brook Preserve is 2.4 mi (3.9 km) away.

9.2

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

8.6/10

Cleanliness

9.6/10

Check-in

9.8/10

Communication

9.4/10

Location

9.6/10

Listing accuracy

10/10 Excellent

Christine B.

30 Jul, 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely property with everything you need. Very private, on a quiet road

Stayed 13 nights in Jul 2025

10/10 Excellent

Allison p.

5 Jul, 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place for a big group.

Loved all the beach chairs, coolers and toys avaliable to use during our stay.

Stayed 4 nights in Jul 2025

10/10 Excellent

Jorge V.

18 Sept, 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great House

The house was a great place to stay with the family.

Stayed 3 nights in Sep 2023

10/10 Excellent

Neil G.

4 Dec, 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet escape

Great house in beautiful setting. Plenty of space and amenities for our four families, eight adults and six kids.

Stayed 3 nights in Nov 2024

10/10 Excellent

Robin D.

24 Aug, 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place for family

Very spacious. The family enjoyed their stay.

Stayed 7 nights in Aug 2023

10/10 Excellent

Deborah W.

13 Sept, 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great vacation home for extended family

Some of the home is dated but it's in a very quiet location with lots of room. Our extended family really enjoyed our stay. The property owners were very responsive.

Stayed 7 nights in Aug 2024

8/10 Good

Yvonne P.

27 May, 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Time

This property offers lots of space for big family. The property was well kept. The house was very clean. I do have a few recommendation. The panty items needs to be looked at, lots of the items were expired for a few years, I did throw some of them away. The Oven needs to be replaced, We were baking and it was smoking. The Pots and pans and kitchen appliance needs to be upgraded. All in all that did not stop us from having fun and improvise. Love it and would rent it again.

Stayed 3 nights in May 2025

10/10 Excellent

Ethan D.

23 Jul, 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay!

Great house with plenty of room for our group of 10.

Stayed 7 nights in Jul 2023

8/10 Good

Caitlin M.

5 Nov, 2021

Liked: Check-in, communication, listing accuracy

Secluded stay for families

We had a great time in Chillmark. Came for a family wedding and there was plenty of space for everyone to have alone time and gather together as a family. The property could use some TLC but overall it was a great stay for us.

Stayed 4 nights in Oct 2021

10/10 Excellent

Ann Marie T.

7 Jul, 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great week in Chilmark to celebrate the 50 year anniversary of Jaws!

We had such a great stay at this house in Chilmark. The kitchen was incredibly well-stocked, which made it easy to cook and serve meals for our whole group. The rooms were spacious and comfortable, and we were pleasantly surprised after seeing earlier reviews that mentioned it might be outdated — we found it cozy and charming.The back deck was a highlight. It stretched the full length of the house and was enclosed with latticework, which gave us peace of mind with kids running around. We brought corn hole and set it up on one end, and there were two round tables with plenty of chairs on the upper part where we could all hang out and eat together.The house felt very private, tucked into the woods, but still just a short drive (about 3 miles) to Menemsha. It was an ideal place for a big family getaway — peaceful, comfortable, and really well set up for a group.We had family of all ages that came to celebrate the 50 year anniversary of the movie Jaws. We found staying in Chilmark was far away from the crowds that invaded the island but close enough if we wanted to participate. This house really is special and the property owners are awesome. Responded very fast when I reached out to them and very pleasant to speak too. I highly recommend this home.

Stayed 7 nights in Jun 2025

10/10 Excellent

Randa C.

28 May, 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful property

We all enjoyed our privacy in this beautiful large home. Everyone had their space and we all slept great on the very comfortable mattresses. The host is great, and he was very helpful, and answered all our questions. Thank you for a fine weekend.

Stayed 3 nights in May 2022

8/10 Good

Carrie D.

9 Dec, 2022

Liked: Check-in, communication, location, listing accuracy

Good rental

House definitely needs a deep clean and some deferred maintenance issues but other than that, good rental. Plenty of room for all the family and nice to have 2 master bedrooms. Privacy of lot is great.

Stayed 4 nights in Nov 2022

10/10 Excellent

Judith H.

21 Jul, 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Relaxation Retreat

It is an absolutely perfect home and location for relaxation. However, it was close to civilization when the need to socialize arose. Took advantage of family yoga with Yoga J @ Chilmark’s library with 5-yr old great niece. Also spent hours at Oak Bluffs library and park. Donavan’s @ Nancy’s was also a must. Beaches galore and long nights of Uno and Guestures made this a wonderful vacation. Home was spacious with lots of private space to read, workout or nap. Did a lot of napping. Highly recommend this home away from home.

Stayed 8 nights in Jul 2024

10/10 Excellent

Perla S.

8 Jun, 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

Laid Back weekend

While some things were a bit outdated the house in all was great especially for a large group. We didn't really use the backyard as we had to go around to get to it but we spent a lot of time on the back porch. James was very responsive when I messaged him about two things after arriving and so kind. Definitely need a car to get to and from but it was a great time.

Stayed 3 nights in May 2022

10/10 Excellent

Sean M.

25 Aug, 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Up Island Home for a large group

The house was well equipped and the kitchen well stocked. Plenty of sheets, towels and beach gear. Not having to bring all our beach stuff was a big plus. The house is sectioned off into two separate areas which was great for our group. We were 3 families of siblings and the parents and ranged in age from 17 to 82 and everyone was comfortable and happy. We were able to have the older folks, 82- 49 on one half of the house and the younger folks, 17- 23 on the other. At most we were 16 people for a night and between 12-14 the other nights and there were plenty of places to sleep. Everyone got a bed, pullout or futon that wanted one. James was very responsive to any issues we had, which were few. It’s a bit off the beaten path so you need a car. Being able to access one of the most beautiful beaches on the island in Lucy Vincent Beach makes staying in Chilmark and off the beaten path totally worth it. We would absolutely return to the house and can’t recommend it enough for large groups and families.

Stayed 8 nights in Aug 2022

10/10 Excellent

Carol E.

2 Oct, 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Staying here is a lot like having good friends who loan you their wonderful vacation home for a week. The kitchen is very well stocked, including a spice cabinet that has just about everything, along with other staples. In most rentals I’m rummaging around for something to put fruit in, but here there’s a nice bowl on the counter just waiting for our apples. There’s also a ‘junk drawer’ with all those little things like rubber bands, safety pins, pencils etc that you may suddenly need but didn’t think to bring. Communication was very good. The cleaners had neglected to put out soaps and shampoo and Jim showed up within an hour with supplies. John later wrote to make sure the house was clean and we got the bottle of wine. The house was very clean but no wine. He sent the cleaner over with one, just in time for us to get it chilled and take it to dinner at The Homeport. (Chilmark is a dry town.) The house has lots of room for a large group to spread out. We were in the east wing and joked that we made our steps. The large deck makes the most of the lovely wooded setting. The house is clean, comfortable, attractively furnished with nice touches and very welcoming. Be aware that the road there is a lengthy, winding, single dirt track but our loaded minivan had no trouble on it. An Uber initially missed the turn but was fine on the road. You need to set your gps before you leave the town as there is little to no signal. Once at the house you’re fine. Ready to kick back.

Stayed 3 nights in Sep 2025

8/10 Good

Nancy G.

14 Sept, 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

We really enjoyed our time in this great, pet friendly Chilmark location!

Stayed 14 nights in Aug 2025

8/10 Good

Stephen M.

11 Jul, 2025

Stayed 3 nights in Jun 2025

6/10 Okay

Tanya G.

30 Sept, 2021

Liked: Check-in, communication, location, listing accuracy

Disliked: Cleanliness

Annual Girls Getaway

Chilmark is beautiful and this was tucked privately down a long dirt road. There was ample space for the 7 of us with no problems accessing bathroom or getting some quiet time when needed. The owner was quick to respond to questions and was able to accommodate our requests. We arrived to a nice bottle of white wine. The down side to this property is the overall lack of cleanliness. Dirty floors, walls and a very overpowering smell of mildew and must throughout the home. The house is heavily shaded and although the seclusion is peaceful, the home remained damp our entire stay and the home is not equipped with adequate moisture control--especially after such a wet season. The one small dehumidifier in the basement had a note on it to empty it if full as the drainage system may not always work. We emptied it a few times but the unit is not anywhere big enough to handle the living space. Even the couch and rugs were damp like we were glamping. Linens appeared clean but the problem with having renters launder the towels is lack of oversight and my facecloth was covered in red markings (lipstick I hope)which did fade signficantly after I washed it myself. Affordable price for this area but it is time for that 12 hour deep clean, humidity control and fresh paint. Still enjoyed our time together and we hope the owners are able to address these concerns because then they would have a real gem!!

Stayed 3 nights in Sep 2021

2/10 Terrible

Judith F.

20 Sept, 2021

Disliked: Cleanliness, listing accuracy

Unfortunate

Dirty. Needs updating! Sheets not ready for use. Had to wash towels…clean bathrooms to use on arrival. Stove needs repair. Did not appreciate having to use a match to light burners. Owner sent cleaning crew next day took over 5 hours of cleaning….needs a deep cleaning! It is a lovely location with a lot of space….but cannot recommend at this time! Would appreciate a rebate on our stay!

Stayed 5 nights in Sep 2021

6/10 Okay

mark s.

13 Sept, 2021

Liked: Check-in, communication, listing accuracy

Almost heaven

Rental process was smooth, responsive. Nobody mentioned the lane thru the woods to the property was dirt, curvy with many holes, our minivan bottomed out several times. Perhaps the trench digging on the road was part of the problem? Bedrooms, living spaces were as advertised, back deck was great.

Stayed 5 nights in Sep 2021

10/10 Excellent

Marilyn B., brokline,Ma

7 Sept, 2021

Liked: Cleanliness, check-in, communication, location, listing accuracy

Title

Nice, secluded spot. House has lots of room. We were happy. Great owner, too.

Stayed 14 nights in Aug 2021

10/10 Excellent

Mel O.

26 Jul, 2021

Liked: Cleanliness, check-in, communication, location, listing accuracy

we loved it!!

This is a great casual house tucked away in the woods and set up beautifully for a large crowd.

Stayed 7 nights in Jul 2021

10/10 Excellent

Tracy P.

14 Jul, 2021

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect place for in-law or 2 families!

The house was amazing, and well divided to allow space and privacy for our numbers - my husband and me, our 4 adult daughters and their spouses/significant others, and an infant. There were still beds left. Note one wing has a king suite off a sitting area with a loft that had 2 queens - it worked for us, but would not for those not related, perhaps. Lots of living space which was well-used since we had a fairly rainy week. Well equipped kitchen, huge wrap around deck, and lovely wooded setting up-island. Owners were accessible if we had a question. Only sorry I didn't buy beach passes earlier in the season, but plenty of other beaches to go to. A great experience! Hope to go back soon.

Stayed 7 nights in Jul 2021

10/10 Excellent

Catherine R., United States

26 Jun, 2021

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best group house anywhere!

We’ve stayed in a lot of VRBOs over the years. This place was perfect for our post-COVID family reunion (3 families of 4) and the best equipped by far of any place we’ve ever stayed. Extremely well equipped kitchen, abundant beach chairs and boogie boards in good condition, plenty of fans and bedding, and beach and house towels galore. Very clean. Good combo of common areas and private spaces. We’d go back for our next reunion in a heartbeat. 100% recommend.

Stayed 7 nights in Jun 2021

About the host

Hosted by John Hauck

We are self-employed, dog owners and world travelers. Martha's Vineyard is perhaps one of the nicest places to relax in the world!
Great fishing too!

Why they chose this property

We have been visiting the Vineyard since the early 70's - always renting. Buying a place just made sense because we always wanted to come back. We were looking at another property for sale when we looked up the hill and saw this beautiful house with a deck running the entire length of the house. As it turned out, the realator showed us the place the next day! We were delighted!!!

What makes this property unique

Peace and quiet,,, star-filled heavens..... deer and wild turkeys......minutes from Menemsha and good fishing.... lounging on the deck with sun or shade all day long.