Very Charming, Roomy Three Bedroom Home
Off Middle Road, Chilmark Vacation Rental - ID 15956

This Up-island retreat on 5 acres has everything your family requires for a magical stay. You can access Lucy Vincent Beach via a quick canoe ride across the pond from their other Chilmark home a few mins away. They are minutes from Chilmark General Store/Chilmark Tavern and a short drive to Menemsha and Squibnocket Beach. My daughter took over the downstairs area which is a fully furnished apartment. Grill or read on the back deck, while watching deer in your stone-walled meadow. The owners are great to work with and communicate well as I have rented from them before at another of their properties. If it gets too quiet, Edgartown and West Tisbury are only a short drive away.

We had the good fortune to stay here in summer 2025. It was even better than advertised, clean, spacious, beautiful views, and a great location. The owners were very responsive and great to work with. We're looking forward to coming back!

We had a fantastic week at John and Caroline's home. It is comfortable but casual. It had everything we needed and more. The grounds are lovely. The beach access via canoe worked out great and we enjoyed paddling all 3 sections of the pond.

Homeowners John and Caroline are two of the most decent and honest people you'll ever meet. They're throwbacks to the good old days, when people treated each other fairly.

Our family of five enjoyed a lovely week at this house in late August. The location is special: the home is flanked by Fulling Mill Brook preserve, which has beautiful trails that connect to other Landbank properties, and the back deck looks over a gorgeous meadow marked by old stone walls; at sunset we would sit outside and watch a family of deer quietly graze nearby.

The house is very well designed and impeccably cleaned and maintained. The beds were comfortable and even the downstairs bedroom, which can be musty in many Vineyard houses, was kept perfectly dry with a dehumidifier. The owners were always available to answer questions and help out if needed. It was also fun to paddle over to Lucy Vincent Beach in the owners' canoe or kayak, and not have to worry about getting a spot in the beach parking lot.

We'd be delighted to vacation here again.

2021
Perfect vacation rental ! House had everything we needed for family of 6 adults . Homeowners thought of everything and checked in to make sure we were enjoying our time and had what we needed . Location was private and peaceful yet close enough to beach and other amenities . Highly recommend this home for your visit to the Vineyard . We are looking forward retuning next year !

It's been a couple of years but my daughters still talk about our stay on Martha's Vineyard at this home. The house was great but the short drive to the canoe that crosses a small pond to Lucy Vincent Beach was even better.

Edgartown during the 4th of July was fantastic. My husband and I had a blast recognizing scenes where Jaws was filmed.

We will be back one of these days!

I have to tell you this is the most thoughtful rental we've ever stayed at on island. I'm usually running out for various things but John and Caroline thought of everything. We truly appreciate the quiet setting too. Nothing but birds and the breeze! Can't wait to return with my family to this more than comfortable home next year.

My family had a wonderful stay at this house. It was comfortable, equipped with everything we could possibly need, and is located in a beautiful, peaceful setting. The owners were incredibly helpful and responsive before and during our visit. Our kids loved taking the canoe out on the pond to see the sheep and run around on Lucy Vincent. I highly recommend this lovely, homey house.

There is a feeling to this place that pictures can't convey, and it's one of being far from the madding crowd. The deck looks out on a large meadow and many times, we could hear the ocean roaring in the distance. Nature feels dominant here with trails winding through the beautiful woods of the Fulling Mill Book Preserve. Beware the ticks, especially with dogs, but that is true everywhere in the NE now. You hardly every hear car traffic, something I really appreciate, as you enter down a small, winding dirt road to get to the driveway of the house. For beach access, you can drive a short distance and hop in a canoe provided by the owners that will launch you across a small tidal pond to the vast Atlantic and to Lucy Vincent Beach, which has restricted public access. This little trip feels more like a fun adventure than a hassle because what you see as you cross is beautiful in every direction.

As for the inside, it feels like you are house-sitting for a friend as the owners have stocked it with most everything you'd have at home, and they have chosen quality dishes, furniture, decorations, sheets, etc. It feels homey and cared for. The owners were great, kind, and very responsive, and I wish I could return right about NOW.

This property is beautiful and vast. There were often deer and rabbits in the yard which my three year old loved. Sadly the interior was fairly uncomfortable. Both of the beds on the main floor had such terrible mattresses that we had to buy a pad for one which we left (you're welcome!). The furniture in the living room is basically wicker and very uncomfortable. Admittedly, I am 7 months pregnant so comfort is high on my list of priorities. I also understand this is a rental and we have stayed in many on the island but even so this one feels like it may need a little interior updating (new mattresses, new kitchen items, etc...).

The owners are very responsive and helpful. However, when we arrived one of the screens on the french doors leading out to the deck was ripped open and remained that way for the entire 2 weeks of our stay. This was unfortunate since the house gets a little warm (no AC) and having those doors open really allows for a breeze to come through.

Overall, this is a beautiful spot and offers all the charms of the island and Chilmark but we likely won't stay there again.

This was our second year staying at the house and we have nothing but good things to say. If you want a quiet, well-equipped up island rental close to Menemsha, Lucy Vincent Beach and Squibnocket, this is the place. The back deck, overlooking fields and woodland, is wonderful for a read, a glass of wine, or both! We hope to return.

I stayed at this beautiful home with my family over the July 4th holiday week. We all felt so lucky to be hidden and sheltered from the craziness of this holiday time. The home is very private, yet close to the beaches, shops, walking trails, etc. We had 3 generations of family together to celebrate a very special reunion, and I would not have chosen any other place to be. Everyone felt very comfortable and at ease. Plenty of room for the relaxing grandparents all the way to the energetic preschoolers. The owners really opened up their "home" for us (and made us feel like locals). I can't wait to return!

I live in New York full time, and my trip to Martha's Vineyard, staying in this charming home was like oxygen for my soul and mind. From the outdoor hammock; to the porch overlooking the garden; and the heavenly, just heavenly, outdoor shower, this home is about as peaceful and relaxing as it can get. It's incredibly private and serene, you will hear only the sounds of nature from the moment you wake up to the moment you close your eyes at night. I remember a special evening, sitting on the porch watching all the fireflies light up the garden - it was just magical. There are great trails to explore and hike through, which is especially marvelous if you have a dog! I absolutely loved my stay there and can't wait to return. The home is kept in wonderful condition - it has a slightly rustic feel to it; imagine beautiful wooden floorboards and furniture. The property is your quintessential Martha's Vineyard escape! The owners are just the nicest folks you'll ever meet too!

We love staying in this incredibly charming and spacious home. It’s located within a beautiful nature preserve that is perfect for long walks, bike rides, or simply sitting outside on the large outside deck and enjoying the views. We have stayed at the home on several occasions, and always find it extremely clean and well-equipped to suit the needs of our entire family. We look forward to returning for many more years to come. If you would like to speak to me personally about our experiences, feel free to call me at 941-400-4828.