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Pet-Friendly Historic Chilmark House

Photo gallery for Pet-Friendly Historic Chilmark House

House and back deck
Kitchen, dining, and part of living room
Living room
Porch with double sleeper couch
Den with desk

Reviews

10 out of 10
Exceptional
4 bedrooms3 bathroomsSleeps 102500 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View in a map
Chilmark, MA
  • Place, Chilmark Chocolates
    ‪11 min walk‬
  • Place, Chilmark Public Library
    ‪16 min walk‬
  • Place, Chilmark Town Hall
    ‪18 min walk‬
  • Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪17 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

About this property

Pet-Friendly Historic Chilmark House

Renovated historic house (1870). Large living room/dining area. 4 bedrooms sleep 8 plus sofa sleepers. 3 full bathrooms. Located between Lucy Vincent and Squibnocket beaches, 2 miles from Menemsha Harbor & Village and spectacular sunsets. A short stroll to Chilmark Center, Chilmark Store, Library, Community Center, Tennis & Basketball Courts, Chilmark Chocolates Store & Town Hall. 3 Kayaks available. Property contains historic stone walls, metal & granite sculptures and original hitching posts. The house includes a large secluded deck and sprawling private yard with hammock and swings, plenty of room to play and run. The yard is shared by people who rent our barn.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Check out before 11:00 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
Pets welcome, especially friendly dogs.
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Smoking

Smoking is not permitted

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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Property Registration Number C0742098816

We should mention

This property does not have any lifts
A car is required for transport to and from this property

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 hiking/biking trails and cycling nearby.
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Map
Chilmark, MA

What's nearby

  • Chilmark Chocolates - 11 min walk - 1.0 km
  • Chilmark Public Library - 16 min walk - 1.4 km
  • Chilmark Town Hall - 18 min walk - 1.5 km
  • Oak Bluffs Harbor - 26 min drive - 30.0 km
  • Inkwell Beach - 27 min drive - 31.7 km

Getting around

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

Restaurants

  • ‪State Road - ‬12 min drive
  • ‪Menemsha Galley - ‬5 min drive
  • ‪Chilmark Tavern - ‬9 min walk
  • ‪Home Port Restaurant - ‬4 min drive
  • ‪7aFoods - ‬9 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 21 Mar, 2026, prices found for a 1-night stay for 2 adults at Pet-Friendly Historic Chilmark House on 31 Aug, 2026 start from S$897, 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.
Learn moreOpens in a new window
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

10/10 Excellent

Melanie B.

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

10/10 Excellent

Karen H.

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

10/10 Excellent

Joanne A.

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

10/10 Excellent

Karen G.

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

10/10 Excellent

Jason G.

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

10/10 Excellent

Rachel B.

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

About the host

Hosted by Andy Freed

Host profile image
Professor at Purdue University

Why they chose this property

We expanded and renovated original 1870 house. Enjoyed the design challenges, development of the house, land, and converted the barn into a modern and warm guest cottage. It is conveniently located for most Chilmark Activities.



Location is convenient to all Chilmark activities.

What makes this property unique

Provides privacy, a unique caring community, a great location. A place for children to play, pets to run, bikes to ride, and kayaks for paddling on the ponds.

Languages:

English
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