Pet-Friendly Historic Chilmark Cottage

Four Winds Barn is a very special place in a very special town. We loved it!

Great spot, great ownerMay the four winds blow you safely home

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.

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!

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!

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!

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.

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.

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.

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.