Entire home

Pet-Friendly Historic Chilmark House

Photo gallery for Pet-Friendly Historic Chilmark House

A wooden swing chair on a porch with a white picket fence and lush greenery in the background.
A cozy living room with a fireplace, a sofa, a coffee table, and a dining table. There are two windows with arched tops and a skylight above the fireplace.
A two-story house with a covered patio, outdoor seating, and a lawn.
A cozy living room with a fireplace, a sofa, and wooden furniture.
A well-maintained grassy area with trees and a stone wall in the background.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Patio
  • Toys
  • Barbecue grill
  • Air-conditioning
  • Pet-friendly
  • Refrigerator

Explore the area

View in a map
Chilmark, MA
  • Place, Chilmark Chocolates
    ‪13 min walk‬
  • Place, Chilmark Public Library
    ‪18 min walk‬
  • Place, Chilmark Town Hall
    ‪19 min walk‬
  • Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪23 min drive‬

Rooms & beds

4 bedrooms (sleeps 10)

Bedroom 2

2 Single Beds

Bedroom 3

1 Double Bed

Bedroom 4

1 Double Bed

Master Bedroom 1

1 Queen Bed

3 bathrooms

Bathroom 1

Toilet · Shower only · Jetted bathtub

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Outdoor play area
Garden
Dining area

Add dates for prices

Similar properties

Interior
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  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
9.6 out of 10, Exceptional, (23 reviews)
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About the area

Chilmark

Located in Chilmark, this holiday home is in a rural area and on a lake. Gay Head Lighthouse and Martha's Vineyard Preservation Trust Historic Buildings are local landmarks, and the area's natural beauty can be seen at Middle Road Sanctuary and Wades Field. Chilmark Chocolates and Fulling Mill Brook Preserve are also worth visiting. Water tubing and windsurfing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and hiking/biking trails nearby.
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Map
Chilmark, MA

What's nearby

  • Chilmark Chocolates - 13 min walk - 1.1 km
  • Chilmark Public Library - 18 min walk - 1.5 km
  • Chilmark Town Hall - 19 min walk - 1.6 km
  • Menemsha Beach - 8 min drive - 5.3 km
  • Inkwell Beach - 36 min drive - 31.0 km

Getting around

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

Restaurants

  • ‪State Road - ‬12 min drive
  • ‪7aFoods - ‬9 min drive
  • ‪Chilmark Tavern - ‬9 min walk
  • ‪Menemsha Galley - ‬5 min drive
  • ‪Home Port Restaurant - ‬4 min drive

Frequently asked questions

Is Pet-Friendly Historic Chilmark House pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Pet-Friendly Historic Chilmark House?

As of 8 Nov 2026, prices found for a 1-night stay for 2 adults at Pet-Friendly Historic Chilmark House on 10 Mar 2027 start from £4,484, 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 Pet-Friendly Historic Chilmark House?

On-site parking is available at the property.

What time is check-in at Pet-Friendly Historic Chilmark House?

Check-in begins at 4:00 PM.

What time is check-out at Pet-Friendly Historic Chilmark House?

Checkout is at 11:00 AM.

Where is Pet-Friendly Historic Chilmark House located?

Situated on a lake, this holiday home is within a 15-minute walk of Chilmark Chocolates, Chilmark Town Hall and Chilmark Public Library. Stonewall Beach and Edys Island are also within 2 miles (3 km).

Reviews

10

Exceptional

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

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

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

Our favorite place to stay on Martha’s Vineyard

Our family had a such a wonderful vacation at Four Winds! The house was spacious and clean, with comfortable beds and everything we needed for our stay. Andy was a fantastic host and gave us many great recommendations for things to do. We can’t wait to visit again!
Stayed 7 nights in Jun 2021
Verified review

10/10 Excellent

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

Very spacious house!

We were very pleased with the house! The bedrooms and living areas are much bigger than the pictures let you know. Great kitchen, and lots of spices to cook with. Fabulous deck area. The shed is full of fun toys for kids and adults. And the location is amazing!!!Some of the bed's mattresses are on the older side, I would bring a full size mattress topper next time. We would definitely stay there again!
Stayed 7 nights in Sep 2020
Verified review

10/10 Excellent

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

Comfortable home with excellent vacation

We throughly enjoyed our stay in this family home with a large yard. We were pleasantly surprised to find it even better than the pictures. It is dog friendly as well. What makes it very desirable is its location - on a quiet lane, biking distance from some of the best beaches on MV and walking distance from the center of Chilmark.
Stayed 7 nights in Jul 2020
Verified review

10/10 Excellent

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

Lovely, well appointed home on a gorgeous lawn in the heart of Chilmark.

We had a terrific time on this well-situated and well-equipped home. The family rooms were so pleasant and open! The kitchen had everything we needed, accommodated our 9-14 person dinners (including baking cookies) and was a breeze to work in. We loved the enormous lawn and even got to know the charming neighbors. A single minor problem was corrected almost instantaneously (an easy toilet repair). The owners are wonderful, helpful and attentive. Couldn't have asked for more.
Stayed 7 nights in Jun 2019
Verified review

10/10 Excellent

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

Ideal Chilmark home

Andy was helpful and communicative with everything we needed for our stay. The property offers an ideal home and beautiful yard with large patio/deck for enjoying the grounds. The two open family/dining rooms provided a nightly gathering place to play cards and complete puzzles. Great location for our week in Chilmark. Will return again!
Stayed 7 nights in Jun 2019
Verified review

10/10 Excellent

Great location!

Lovely, spacious and comfortable home midway between Squibnocket and Lucy Vincent beaches. The large yard was heavily used by our group and dog. Well equipped kitchen and an abundance of towels. The host, Andy, was helpful and friendly.
Stayed 7 nights in Jul 2018
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