Pet-Friendly Historic Chilmark Cottage

Photo gallery for Pet-Friendly Historic Chilmark Cottage

A wooden dining room with a round table and six chairs.
A well-maintained grassy area with a stone bench and a stone wall.
A house with a stone facade, a large window, and a sign that reads "WINDS".
A wooden interior with a round table, chairs, a sofa, and a staircase.
A cozy cabin interior with a wooden floor, a sofa, a dining table with chairs, a TV, and framed pictures on the walls.

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Patio
  • Barbecue grill
  • Pet-friendly
  • Refrigerator
  • Washing machine
  • Internet

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

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

Add dates for prices

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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/biking trails and cycling.
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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
  • ‪Chilmark Tavern - ‬9 min walk
  • ‪Menemsha Galley - ‬5 min drive
  • ‪7aFoods - ‬9 min drive
  • ‪Home Port Restaurant - ‬4 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 1 Nov 2026, prices found for a 1-night stay for 2 adults at Pet-Friendly Historic Chilmark Cottage on 9 Jul 2027 start from £2,877, 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.
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Rating 10 - Excellent. 11 out of 13 reviews
Rating 8 - Good. 1 out of 13 reviews
Rating 6 - Okay. 1 out of 13 reviews
Rating 4 - Poor. 0 out of 13 reviews
Rating 2 - Terrible. 0 out of 13 reviews

9.2/10

Cleanliness

10/10

Check-in

9.6/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

8/10 Good

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay, just as described!
Stayed 14 nights in Jul 2026
Response from VrboOwner on 4 Aug 2026
So glad you enjoyed your stay. Hope to see you next year if it fits in with your travel plans.
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

6/10 Okay

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
Verified review

10/10 Excellent

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!
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