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Pet-Friendly Historic Chilmark Cottage

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The modernized historic Four Winds barn
Living room
Dining area and kitchen
Living room
Dining area

Reviews

9.6 out of 10
Exceptional
3 bedrooms1 bathroomSleeps 5800 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi
  • Outdoor space

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

3 bedrooms (sleeps 5)

Bedroom 1

1 Double Bed

Bedroom 2

1 Single Bed

Bedroom 3

2 Single Beds

1 bathroom

Bathroom 1

Toilet · Shower only · Outdoor shower

Spaces

Deck or patio
Outdoor shower
Kitchen
Outdoor play area
Garden
Dining area

About this property

Pet-Friendly Historic Chilmark Cottage

Renovated historic barn (1870). Lofts converted to open bedrooms, private main bedroom, roomy living room/dining/kitchen area. Private deck. Large yard with stone walls and historic picket fence (shared with main house). Located between Lucy Vincent and Squibnocket beaches, 2 miles from Menemsha Harbor & Village and spectacular sunsets. A short stroll to Chilmark town center, Chilmark Store, Library, and Community Center.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Outdoor space

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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. Big yard, mostly fenced/walled in
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Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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 not indicated whether there is a smoke detector on the property
Property Registration Number C0742098816

About the area

Chilmark

Located in Chilmark, this cottage is in a rural area. Island Cove Miniature Golf and Island Cove Adventures are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Chilmark Chocolates and Fulling Mill Brook Preserve. The Grey Barn and Farm and Polly Hill Arboretum are also worth visiting. Discover the area's water adventures with windsurfing and sailing nearby, or enjoy the great outdoors with hiking and cycling.
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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 Town Beach - 27 min drive - 31.4 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 Cottage pet-friendly?

Yes, pets are allowed at this property.

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

As of 6 Mar 2026, prices found for a 1-night stay for 2 adults at Pet-Friendly Historic Chilmark Cottage on 6 Jul 2026 start from £322, 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 Cottage?

On-site parking is available at the property.

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

Check-in begins at 4:00 PM.

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

Checkout is at 11:00 AM.

Where is Pet-Friendly Historic Chilmark Cottage located?

Situated in a rural location, this cottage 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

9.6

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. 10 out of 12 reviews
Rating 8 - Good. 1 out of 12 reviews
Rating 6 - Okay. 1 out of 12 reviews
Rating 4 - Poor. 0 out of 12 reviews
Rating 2 - Terrible. 0 out of 12 reviews

9.2/10

Cleanliness

9.8/10

Check-in

9.4/10

Communication

10/10

Location

9.4/10

Listing accuracy

Reviews

10/10 Excellent

Jan F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Four Winds Barn is a very special place in a very special town. We loved it!
Stayed 7 nights in Sep 2025

10/10 Excellent

Tim D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great spot, great ownerMay the four winds blow you safely home
Stayed 7 nights in Aug 2025

8/10 Good

Michael Forden W.

Charming and rustic

Listing depicts the rental well, and the owners were very responsive. The yard is wonderful for dogs--we had three, and the neighboring renter in the bigger house added hers to the mix. Would definitely stay here again.
Stayed 7 nights in Jun 2018

10/10 Excellent

Mary R.

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

Idyllic vacation

Had a wonderful stay at this charming island barn. It is not fancy but was clean and had everything we needed. Beautiful yard for our dog to play in and close to Menemsha where we kept our boat. Owner was very responsive. Highly recommend.
Stayed 14 nights in Sep 2021

10/10 Excellent

Kim N.

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

Perfect getaway at the Barn

Our family is familiar with the Vineyard, particularly Chilmark, which is very special to us—my husband and I got married there and we try to return once a year when we can. Staying at the Barn gave us some precious, relaxing family time before the craziness of school resumed, and we are so grateful for discovering the Barn. It definitely had happy vibes and we loved reading about the history of Andy's family's connection to the house and this part of the island. Andy's communication was clear, prompt and super informative. All of his suggestions were spot-on (we had some great paddles at Nashaquitsa Pond and loved our walk at Fulling Mill Brook!). It's so close to Chilmark General Store for any basics and great coffee and pastries, and we lucked out with weather and got to enjoy Lucy Vincent [beach] every day. The Barn is even nicer than it looks in the photos...and while it is simple, we found that every time we needed something, it was there! From extra blankets to cooking oil, kitchen appliances and utensils, and all the beach gear (chairs, boogie boards, etc) we were well supplied. It was great to have access to the kayaks, too! The gas grill and picnic table on the private back deck made for some nice family meals. We also enjoyed the Farmer's Market and Artisans' Fair at the Ag Hall. The Barn's outdoor shower under the Japanese maple is a dream. Our teens had fun sleeping in the lofts and lots of windows and fans made the temperature very pleasant. We look forward to returning and thank Andy and his family for their hospitality!
Stayed 4 nights in Sep 2021

10/10 Excellent

elizabeth a.

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

rustic and relaxing

Wonderful location, and pet friendly. The barn was well appointed and had everything we needed. The owner was lovely and very responsive from the moment we booked the rental. The bed linens in the lofted bedroom areas are much nicer than the images on the listing. There is a storage area between the two properties with plenty of beach chairs, boogie boards, sand toys etc. We enjoyed our stay very much, thank you!
Stayed 7 nights in Aug 2021

10/10 Excellent

Kathy S.

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

Highly recommend!

We stayed at the barn for three weeks with our two 20-somethings who were with us bc their colleges went remote. We had a wonderful stay. We were worried we would be crowded but the barn is set up such that we had room to spread out. Lovely setting and the house was clean and had everything we needed. Chilmark is so beautiful and we rarely left town. Beautiful beaches are a bike ride/short drive away, good back roads for walking, and we rode our bikes to Menemsha for fish almost every day. The owner was great to work with and had lots of information about the area. The house next door had guests two of the three weeks but it was not an issue at all. You will enjoy your stay at the Barn!
Stayed 21 nights in Aug 2020

10/10 Excellent

Beth Ann K.

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

Lovely, little renovated barn

A wonderful little getaway in a country setting. Large yard to play games and hang out. Amazing beaches within two miles. Easy drive to other towns. Quaint town market within a mile. We thoroughly enjoyed our stay.
Stayed 7 nights in Jul 2020

10/10 Excellent

Charles M.

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

Nice property, but make sure the washer machine works.

This is a good property to stay in Chilmark. However, we did have an issue with the washer machine. We put in a large load of sheets and towels that we couldn't wash due to the washer machine not working properly. We contacted both members of the property that was listed, but no one answered our call so we left a voicemail and no one reached out to us afterwards. Due to the issue with the washer machine and no one available to respond to our voicemail we couldn't wash all of our linens that were used. Otherwise me and my family enjoyed our stay at this property.
Stayed 7 nights in Sep 2019

10/10 Excellent

Anne M.

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

Chilling in Chilmark

We had a wonderful stay in Chilmark. Andy & Deb were prompt responding and very easy going. The “barn” property was on point with the VRBO description, was very clean, had everything you need. Thanks Andy & Deb for sharing your special place with us on MV.
Stayed 7 nights in Aug 2019

6/10 Okay

Kim S., Wilson, Wyomng

Liked: Check-in, communication, location

Born from a barn

We were the first renters of the year so think we encountered challenges, the hot water heater wasn't on or working and the washer did not work until we fixed it. I'd suggest providing extra sheets for all the beds so that they can be changed while sheets are washing before check out. I'd also suggest cleaning out cabinets so that there's room for groceries, the supplies are more than adequate. I'm not sure why anyone would need 50 spoons or 8 banana split dishes. We were told the driveway was a loop but while renters were in the big house we were unable to take advantage of that due to their many cars. We carefully backed into a slot.
Stayed 7 nights in Jun 2019

10/10 Excellent

PABLO M., HASTINGS ON HUDSON

Great little house

The house was perfect for our family of 4. The kids loved the outdoor shower, as well as the extensive backyard. I really liked the deck and BBQ. The property was very comfortable, and was stocked with absolutely everything we needed. We remarked several times about how well supplied and comfortable the house is. Lastly, the owner is responsive and very nice. We highly recommend you staying here!

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 and barn. Wonderful yard great for kids and dogs. And it is conveniently located for most Chilmark activities (the best side of the island).

What makes this property unique

One of the few truly pet-friendly houses in Chilmark.

Languages:

English
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