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  3. Chilmark

Hillside Oak

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

House in Chilmark, Massachusetts

Guests
8 Guests
Bedrooms
4 Bedrooms
Bathrooms
4 Bathrooms
Pets allowed
Pets allowed

Locally Owned & Operated

Martha's Vineyard

Martha's Vineyard

Casago Franchise Owner

Locally Owned & Operated
Rating4.27

What our guests are saying...

AI-generated from guest reviews for this property

Hillside Oak is a beautiful, unique, and spacious home that offers an excellent experience for gatherings and relaxing stays. The property is very comfortable, lovely, clean, and filled with light, with plenty of room indoors and out for guests to spread out. Its great location provides easy walking access to a private beach and nearby trails, adding to its peaceful appeal. Guests appreciated the beautiful beach views from the nearby shore and the quiet setting that makes the home feel like a perfect getaway. Hillside Oak also features a well appointed kitchen, a welcoming patio, a big lawn area, an outdoor shower, and thoughtful extras such as games, puzzles, and yoga mats.

Overview

Hillside Oak

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!

You must be 21 years or older to rent this property.

Amenities

Central AC
Central AC
Gas grill
Gas grill
Beach access
Beach access
Board games
Board games
Cable
Cable
Dishwasher
Dishwasher
Washer/dryer
Washer/dryer
DVD player
DVD player
Space heater
Space heater
Internet
Internet
Microwave
Microwave
Patio
Patio
Dog-friendly
Dog-friendly
Stove
Stove
TV
TV

Sleeping Arrangements

Bedroom 1

sleeps 2

Beds
1 queen bed

Bedroom 2

sleeps 2

Beds
1 queen bed

Bedroom 3

sleeps 2

Beds
1 double bed

Bedroom 4

sleeps 2

Beds
1 double bed

Location

Chilmark, Massachusetts, Home

(Exact address will be provided after booking)

Location

Rating

4.27
11 reviews
5 Star
64%
4 Star
9%
3 Star
18%
2 Star
9%
1 Star
0%
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Jane C2025-10-04

House is lovely, spacious and clean. Four couples stayed for a wedding. Plenty of room for all. Kitchen well appointed. Games, puzzles and yoga mats in closet. We loved sitting on the patio. Beach within walking distance. Overall an excellent experience -would definitely stay again.

faye W2025-09-01

The house is spacious, quiet and friendly. Well equipped kitchen. It is a short hike to a rocky beach with beautiful views. It is a bit isolated in off a long dirt road . It was all we wanted!

Dan D2025-07-20

We arrived to a house that hadn’t been cleaned, doors unlocked and dirty fridge. Costumer service was subpar and we had to spend a night at he hotel. By far the worse experience we’ve ever had in an AirBnb

Kathryn M2024-09-08

A beautiful home which reflects much love and care. It is spacious inside and out, with a big lawn area so it feels open and gets lots of light. Loved walking to the beach and the Land Bank Trail network. Perfect place for a big family gathering or celebration. Lots of space to spread out. New outdoor shower is great! We are long-time Vineyard renters and this home is quintessential Vineyard in all the good ways.

PHILIP S2024-07-09

Near private beach, foul tasting water like rust and ruins clothes in washing.

Judith H2023-09-03

The remote location was the perfect getaway for a family vacation that included our 93-year-old mother, siblings, 4 year old great granddaughter and our dog.

$850
avg / night
Rating4.27

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