Entire home

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

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

A spacious living area with a large sofa set, a red armchair, a wooden coffee table, and a fireplace. A spiral staircase is visible in the background.
Property video
A garden with various potted plants and a green watering can.
A deck with outdoor furniture and a glass door leading to a covered area.
A narrow pathway leading to a row of wooden houses with a brick chimney visible in the background.

Reviews

9.4 out of 10
Exceptional

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Garage parking available
    Enjoy the convenience of garage parking - a rare offering in the area.

Popular amenities

  • Balcony
  • Toys
  • Barbecue
  • Air-conditioning
  • Pet-friendly
  • Refrigerator

Explore the area

View map
Chilmark, MA
  • Place, Waskosim's Rock Reservation
    ‪4 min drive‬
  • Place, The Yard
    ‪5 min drive‬
  • Place, Middle Road Sanctuary
    ‪5 min drive‬
  • Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪25 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

Add dates for prices

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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 Cape Cod Beaches. Fulling Mill Brook Preserve and Polly Hill Arboretum are also worth visiting. Discover the area's water adventures with snorkelling and waterskiing nearby, or enjoy the great outdoors with hiking and cycling.
View more Holiday homes in ChilmarkOpens in a new window
Map
Chilmark, MA

What's nearby

  • Waskosim's Rock Reservation - 4 min drive - 2.5 km
  • The Yard - 5 min drive - 2.9 km
  • Middle Road Sanctuary - 5 min drive - 2.9 km
  • Fulling Mill Brook Preserve - 8 min drive - 4.3 km
  • Menemsha Beach - 13 min drive - 9.5 km

Getting around

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

Restaurants

  • ‪Plane View - ‬18 min drive
  • ‪State Road - ‬9 min drive
  • ‪Chilmark Tavern - ‬9 min drive
  • ‪Menemsha Galley - ‬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).

How much does it cost to stay at Striking 5BR/4BA Chilmark Contemporary with Views of the Sound?

As of 2 Nov 2026, prices found for a 1-night stay for 2 adults at Striking 5BR/4BA Chilmark Contemporary with Views of the Sound on 4 Nov 2026 start from AU$3,720, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Striking 5BR/4BA Chilmark Contemporary with Views of the Sound?

On-site parking is available at the property.

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.

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 33 out of 45 reviews
Rating 8 - Good. 9 out of 45 reviews
Rating 6 - Okay. 2 out of 45 reviews
Rating 4 - Poor. 0 out of 45 reviews
Rating 2 - Terrible. 1 out of 45 reviews

8.8/10

Cleanliness

9.6/10

Check-in

9.8/10

Communication

9.2/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
We enjoyed our stay. Loved the kitchen sitting by the sliding door.
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Property was exactly as pictured and described. It was perfect for our group of ten. We appreciated the effort from the host in making our stay enjoyable.
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This home was perfect for our gathering of 5 families. Everyone had more than enough space and comfortable bedding. We enjoyed the large kitchen and common space to relax in the evenings. Definitely needed a car to get to the home but we were prepared and had enough room for the 4 cars we had. Loved that it was pet friendly!!
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very BIG, NICE house. Nobody has enough friends to fill all of the rooms and beds, and bedding offered. And there are more pans, pots, knives and utensils than you can count. No neighbor noise nearby, the air was so fresh all you smelled was fragrant plants and flowers. Was really nice to also be so close for once to Menemsha, we discovered Iggy’s Bakery there, and bought fresh seafood at Menemsha Seafood, a place usually too far to go to early in the day when we’re staying in Edgartown. Highly recommend this house. If dirt roads or being in the country freak you out, this may not be your spot, but we loved everything about it. Did I mention how much extra space it has? Stick the inlaws or annoying couple at the far end of the house.
Stayed 7 nights in Aug 2026
Verified review

8/10 Good

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
Verified review

10/10 Excellent

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
Response from VrboOwner on 19 July 2025
Great to hear and we hope that you will join us again!
Verified review

10/10 Excellent

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
Response from VrboOwner on 18 Dec 2023
Thank you so much for staying with us and your kind review. Hope to have you with us next season - John & Jim
Verified review

10/10 Excellent

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
Response from VrboOwner on 26 Aug 2023
Robin, Glad you enjoyed your stay. Hope to host you again.
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Response from VrboOwner on 18 Dec 2023
We appreciate your taking the time to share your experience with us. Hope to see yu back again next season. John & JIm
Verified review

10/10 Excellent

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
Response from VrboOwner on 21 June 2025
That is our specialty! Come back and see us again. thanks, john
Verified review

10/10 Excellent

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
Response from VrboOwner on 21 June 2025
We aim to please and are constantly changing things up as upgrades. Thanks, john
Verified review

8/10 Good

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
Response from VrboOwner on 19 July 2025
We hope that you will join us again. Thank you for taking the time to review us!
Verified review

10/10 Excellent

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
Response from VrboOwner on 19 July 2025
We hope that you will join us again sometime. Thanks for the review!
Verified review

8/10 Good

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

great family vacation

house and location are great, plenty of space. There was a heat wave and we each had three fans b/c no airconditioning. Kitchen utensils and dishes were plentiful, Could be a little cleaner but overall a great family house. We were 12 people and all comfortable
Stayed 8 nights in Jul 2020
Response from VrboOwner on 26 Aug 2023
Thanks for your review Fern. We have passed your comments on to the housekeeping service.
Verified review

10/10 Excellent

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

Wonderful spacious, secluded home

This property is perfect for a few families traveling together. It is spacious and well-equipped— there is nothing that this kitchen doesn’t have, including more spices than I have at home! The location is fabulous— near Lucy Vincent beach, Menemsha with amazing fresh fish markets and sunsets, Aquinnah for incredible views of the cliffs and the menemsha hills which is a hike not to missed. The owners are incredibly welcoming (they were so lovely to leave a bottle of chilled white wine) and responsive to any questions and needs. I would highly recommend!
Stayed 5 nights in Jul 2020
Response from VrboOwner on 26 Aug 2023
Thanks Rimi! We hope that you will stay with us again!
Verified review

10/10 Excellent

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
Response from VrboOwner on 21 June 2025
We are happy that you enjoyed our "magic" ! john
Verified review

10/10 Excellent

Photos don't do it justice!

Our group, seven adults and two children, stayed here for four nights for a wedding on the island. The house exceeded expectations! We had a couple with two little kids who essentially had their own apartment with a king sized bed, a TV room/living room, bathroom, and sleeping loft for the little ones. As everyone else has said, the long deck out back was great for quiet coffee in the morning, BBQ dinners, and afternoon drinks. There are two dining tables which seat 6-8, and plenty of bathrooms - essential for peace in the house. Even when it was raining, it was still light and bright. We would definitely stay here again!
Stayed 4 nights in Jun 2018
Response from VrboOwner on 26 Aug 2023
Valerie's group was great to host and it's always a pleasure to hear that a guest has enjoyed the peace and quiet that our place offers much as we do. We use VRBO/Homeaway ourselves to find places to stay when we travel so hopefully we've learned a bit along the way as to what makes a stay special. We'd love to host you again.
Verified review

10/10 Excellent

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
Response from VrboOwner on 19 July 2025
Thank you for taking the time to review us. The house was built in 1983, and we have done regular upgrades as needed - such as new water heating systems, propane range, new oven (July 2025) and appliances. We agree the deck is the best - sun and shade and room to play. Hope you will join us again sometime
Verified review

8/10 Good

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
Response from VrboOwner on 21 June 2025
Hi Yvonne, Thank you for taking the time to comment on your stay in our house. An oven was on order for over a month and could not be installed until June 13, 2025. The repairman did check our the old one and found all elements functioning properly. We could not get it to smoke.... Oven was replaced with double convection oven for you to use on your next visit. ":Pantry" is a collection of items guests have not used and left for next tenant. We will monitor in future. New cookware was purchased and much old stuff thrown out to make room for the new frying pans, pots and lids.. Glad you had fun!! john
Verified review

10/10 Excellent

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
Response from VrboOwner on 19 July 2025
You hit the nail on the head with your review of our summer house!! We hope that you will join us again! Thank you for taking the time to review us.
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property. Serene setting. Great communication and quickly resolved an issue. (My 83 year old mother was cold.). Couldn’t ask for a better place to stay. It easily accommodated all seven of us.
Stayed 4 nights in Jun 2026
Verified review

8/10 Good

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
Response from VrboOwner on 18 Dec 2023
Hi Carrie, We appreciate your letting us know your concerns. The house was well cleaned and painted this Spring. John & Jim
Verified review

10/10 Excellent

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
Response from VrboOwner on 18 Dec 2023
Thanks for the review Sean. Hope that you will join us again. john & jim
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