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Private Hillside Home, Fully Equipped Kitchen, Dog-Friendly, A/C, W/D

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A house with a covered patio, a wooden deck, and a stone border.
A house with a patio, outdoor seating, and a covered area.
An outdoor seating area with Adirondack chairs and a wooden table, surrounded by trees and a grassy lawn.
A spacious living room with a fireplace, wicker furniture, and a large window.
A cozy living room with a fireplace, wicker furniture, and large windows.

Reviews

9.6 out of 10
Exceptional

Highlights

  • Cozy up by the fire
    Unwind by the fireplace-a top-rated spot for cozy moments.
4 bedrooms4 bathroomsSleeps 8

Popular amenities

  • Pet-friendly
  • Kitchen
  • Washer
  • Air conditioning
  • Barbecue grill
  • Balcony

Explore the area

View in a map
Chilmark, MA
  • Place, Waskosim's Rock Reservation
    ‪3 min drive‬
  • Place, Menemsha Beach
    ‪7 min drive‬
  • Place, The Yard
    ‪7 min drive‬
  • Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪27 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Twin Beds

Bedroom 4

1 King Bed

4 bathrooms

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Bathtub · Toilet · Shower only

Bathroom 3

Bathtub · Toilet · Shower only

Bathroom 4

Bathtub · Toilet · Shower only

Spaces

Kitchen
Office
Balcony
Garden

About this property

Private Hillside Home, Fully Equipped Kitchen, Dog-Friendly, A/C, W/D

Summary:

Hillside Oak



The Space:

Nestled in the serene scrub oak forest of Chilmark, this stunning 4-bedroom home offers a perfect retreat for families and friends seeking a peaceful getaway on Martha's Vineyard. With an open floor plan and an abundance of windows, the contemporary design allows natural light to flood the space, creating a warm and inviting atmosphere. The home features two queen beds and two double beds, accommodating up to eight guests comfortably. Enjoy the convenience of a fully equipped kitchen, complete with a new stove and modern appliances, perfect for preparing meals together. Step outside onto the expansive patio and take in the tranquil surroundings, or fire up the gas grill for a delightful barbecue under the stars. The property is dog-friendly, so you can bring your furry friends along to enjoy the lush outdoor space. A short 10-minute walk leads you to the private Brickyard beach, where you can relax and soak up the sun, while the nearby Menemsha Hills and Brickyard trail system offer miles of scenic hiking paths for outdoor enthusiasts. Located just a short drive from some of the island's most beautiful beaches, including Lucy Vincent Beach and the vibrant town of Oak Bluffs, this home is ideally situated for exploring all that Martha's Vineyard has to offer. With the Vineyard Haven ferry only 15 miles away, you can easily venture off the island for day trips or excursions. Whether you're looking to unwind in nature, enjoy family game nights with the provided board games, or explore the local attractions, this Chilmark home is the perfect base for your island adventure. Book your stay today and experience the beauty and charm of Martha's Vineyard!
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property Registration Number C0281980620
Property # 5245563
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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

Chilmark

Located in Chilmark, this vacation home is in a rural area and near the beach. Woods Hole Ferry Terminal and Oak Bluffs Harbor are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Inkwell Beach and Oak Bluffs Town Beach. Fulling Mill Brook Preserve and Chilmark Chocolates are also worth visiting. Discover the area's water adventures with fishing nearby, or enjoy the great outdoors with horse riding.
Map
Chilmark, MA

What's nearby

  • Waskosim's Rock Reservation - 3 min drive - 2.5 km
  • Chilmark Town Hall - 7 min drive - 4.6 km
  • Menemsha Beach - 7 min drive - 5.3 km
  • The Yard - 7 min drive - 4.6 km
  • Lucy Vincent Beach - 9 min drive - 6.0 km

Getting around

  • Vineyard Haven, MA (MVY-Martha's Vineyard) - 19 min drive

Restaurants

  • ‪State Road - ‬11 min drive
  • ‪7aFoods - ‬13 min drive
  • ‪Fella's Take Out - ‬12 min drive
  • ‪North Tisbury Farm & Market - ‬11 min drive
  • ‪Menemsha Galley - ‬5 min drive

Frequently asked questions

Is Private Hillside Home, Fully Equipped Kitchen, Dog-Friendly, A/C, W/D pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Private Hillside Home, Fully Equipped Kitchen, Dog-Friendly, A/C, W/D?

As of Jul 3, 2026, prices found for a 1-night stay for 2 adults at Private Hillside Home, Fully Equipped Kitchen, Dog-Friendly, A/C, W/D on Jul 12, 2026 start from $1,013, 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.

What time is check-in at Private Hillside Home, Fully Equipped Kitchen, Dog-Friendly, A/C, W/D?

Check-in begins at 4:00 PM.

What time is check-out at Private Hillside Home, Fully Equipped Kitchen, Dog-Friendly, A/C, W/D?

Check-out is at 10:00 AM.

Where is Private Hillside Home, Fully Equipped Kitchen, Dog-Friendly, A/C, W/D located?

Situated by the sea, this vacation home is 1.2 mi (1.9 km) from Waskosim's Rock Reservation and within 3 mi (5 km) of Middle Road Sanctuary and The Yard. Edys Island and Menemsha Beach are also within 3 mi (5 km).

Reviews

9.6

Exceptional

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

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

From a partner site

10/10 Excellent

Chitrang P.

Beautiful Hill House

Our family loved the house and will plan to go back. The location is great too.
Verified

10/10 Excellent

Jessica M.

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

Relaxing escape to Chilmark

Down the long winding road, passing fields of deer and beautiful views of the ocean, we came upon a quiet, hidden gem perfect for family time and relaxation. We thoroughly enjoyed our stay.
Stayed 7 nights in Jul 2023
From a partner site

10/10 Excellent

Spencer S.

Great House

Loved everything about this house - great location and accommodating property owner.
Verified

10/10 Excellent

Robin E.

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

Work trip

The house was great
Stayed 13 nights in Sep 2024
From a partner site

10/10 Excellent

Liselot E.

Very comfortable house in quiet area

The house was very comfortable. The area is super quiet, private beach within walking distance (5-10 min walk). Would come back again!
From a partner site

10/10 Excellent

Sara S.

One of a Kind

Unique and spacious home with amazing property!
Verified

10/10 Excellent

Jane V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We spent 5 days with 3 other couples for a wedding. Beautiful, clean, spacious home. Very private. We loved sitting on the outdoor patio. All the comforts of home. Well appointed kitchen. A closet with games and puzzles - we even found yoga mats for our morning yoga outside. We would’ve loved to have a fire in the fireplace on the chilly nights but understand this might be a safety issue. An outdoor fire pit would’ve been perfect. Would definitely stay again!
Stayed 5 nights in Sep 2025
Verified

10/10 Excellent

Judith H.

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

Perfect Place for Relaxation

SUV a must.Quiet and remote location. Home is spacious but needs small repairs in upstairs bathrooms. Also, changing the water filter more frequently may lower the sense of iron from the water. Kitchen was equipped with all needed for a one week stay. Perfect place to reflect surrounded by beautiful hiking trails and close proximity to the beach - not for swimming but gazing at the ocean and hiking over beach stones.
Stayed 7 nights in Aug 2023
From a partner site

6/10 Okay

Gary P.

Good & Bad

If you are looking for seclusion this place has it. 1.3 miles down a rugged dirt road. You need a SUV to comfortably get there. Great hiking trails. Great open interior layout. Beds are comfortable. Home needs some TLC. Musty odor in the home was pervasive. No outdoor furniture to speak of.Patio chairs were rickety at best. We sat in our beach chairs. Picnic table was fine.
Response from VrboOwner on Jun 20, 2023
Hi Gary! Thank you for your review. We have passed on your comments to our local staff and homeowners so that we can address these issues that you mentioned. We apologize that they weren't taken care of prior to your arrival. We do hope that we have another chance in the future to host you!

About the host

Hosted by VueStay Vacations by Casago

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