Chilmark Casita - New Listing! Newly Renovated w/Central AC!
Chilmark Vacation Rental - ID 34169

As my wife and I sip on the last of the Chilmark Coffee Company coffee we brought back from our annual anniversary vacation on the Vineyard, we reminisce on how much we enjoyed our stay at Chilmark Casita and yearn to return in the coming years. Although we always enjoy the up island vibe found in Chilmark, all that Jo and Sam provide here has proven to be exactly what we seek for this special occasion.

As the name suggests, the house is small but it is perfect for a couple searching for the comfort and conveniences of home in a place that is unmatched for our desires. The kitchen and living space are very well appointed and the deck and private outdoor space rounded out a very relaxing stay. We especially appreciated the quality of everything provided from the higher level linens to the kitchenware which is seldom seen at a vacation rental.

Although we did find it difficult to do much more than go to Lucy Vincent Beach and hang at the house on most days, the location so close to West Tisbury, Aquinnah and Menemsha, made venturing out to the farmer's market and watching the sunset very convenient. It is also close to the main roads for journeys down island if you want to explore other parts of the Vineyard.

Thank you Jo and Sam for sharing your little slice of paradise with us!

We had such a wonderful week at La Casita! It was the perfect location, not too far from anywhere and so quiet. We spent our days exploring different trails, towns, and beaches and returned each evening to enjoy the wonderful deck. We always prioritize rentals with outdoor showers and this house has one of the nicest ones weve enjoyed. Jo was so helpful and responsive to all our questions. Highly recommend a stay at La Casita.

We had a nice vacation at Chilmark Casita. The spacious deck was a real treat on sunny days, and the flowers blooming were a bonus. Our mornings were spent drinking fresh ground coffee and watching the squirrels and chipmunks play. During the evening, we enjoyed the quiet solitude of the property. For us, an added bonus was the close proximity of the walking trials. The home was quiet, clean, and well stocked for a summer getaway. The host was very accommodating and thoughtful, and the welcoming gifts were very much appreciated.

Dear Jo and Sam,

We enjoyed our time at La Casita! You are wonderful hosts and provided all the amenities that make a perfect stay. We had hoped for a rural setting and location and La Casita delivered.
The deck offered time to relax and enjoy the sun, trees, flowers, and birds.

You truly thought everything that a renter would need and far beyond anything we have experienced throughout our 20+ years of renting on the Island and elsewhere. All the comforts of home were there for us. Also, we enjoyed the incredible the paintings. It appears someone in your family or you know is extremely talented!

We look forward to returning to La Casita!

Jennifer and John

My family and I enjoyed our time staying at La Casita - the home is well-appointed with everything you need, exceptionally clean, and welcoming. The deck is a wonderful spot for morning coffee, and the outdoor shower is just wonderful after a long day at the beach. Jo was a warm and responsive host and went out of her way to make us feel at home! We just loved our time there!

We had a wonderful stay at La Casita! The house is beautiful. Very welcoming and clean. The deck on the side is amazing! We enjoyed sitting outside and having our coffee in the morning and dinner in the evening. My daughter loved having the art shed as a space to draw. Jo was wonderful to work with and very responsive to any questions we had. Many memories made at La Casita!

On the outside, this Chilmark house is small, rustic and neatly nestled in a wooded lot on the road. You could easily miss it if not for the bright yellow roadside mailbox with "Casita" painted on it - the perfect landmark. Inside though, it is charming, modern, and well-appointed with every amenity you need for a very comfortable stay on the Vineyard. The large back deck is very private for dining or enjoying nature. We had a lovely week at the Casita, which is also nicely situated near the gorgeous up-island beaches and a quick ride to other island towns. Highly recommended!

Jo, Sam and Max were fantastic hosts. La Casita is located in close proximity to West Tis and Menemsha and all that Up Island has to offer (without being too far from Down Island conveniences). My dog and I enjoyed the comfortable and spacious cottage, beautiful deck and landscaping and a really great and well appointed kitchen. I had more space than I could enjoy! The amenities were as stated, the photos were accurate, and I wish I had more time! I've been renting on the Vineyard for 20 years and have stayed in all parts of the island and in many different types of homes. La Casita is clean, comfortable, charming yet modern, spacious and affordable. The hosts were easy to communicate with and Max made sure everything was ready and welcoming. I hope to be able to come back again! Thanks Jo, Sam and Max!

We enjoyed our stay at La Casita. Staying in Chilmark was new for us and it did not disappoint! This part of the island is beautiful and so is La Casita. We enjoyed visiting the local public beaches nearby, the farmers markets and hiking. The home offers much privacy and the deck is so inviting to sit and read (we took advantage of the variety of books available in the house) or enjoy your morning coffee. The inside of the house is very spacious and extremely clean. The beds are especially comfortable and having comfortable linens and blankets was a plus. The house is beautifully decorated with lovely lighting and artwork. The owners are very easy to work with and the caretaker Max was very responsive (we had an issue with not enough hot water for showering but this was immediately taken care of.) Having rented several houses over many years, La Casita is truly one of the best!

We thoroughly enjoyed our stay at La Casita. The home was clean and comfortable and had all the amenities of home. The outdoor shower was perfect after a long day out hiking, fishing, or playing pickleball. We spent a large part of our stay relaxing on the deck enjoying breakfast or dinner or just watching the squirrels and chipmunks going about their business.

Jo and Sam made sure to let us know they wanted our stay to be perfect and were only a phone call away with any questions or concerns.

We have just returned from our fourth stay at La Casita. Jo and Sam are responsive and friendly. The house is perfect for a couple (and sometimes their adult son!) looking for an up-island retreat. It is quiet but close enough to all of our favorite spots--Lucy Vincent Beach, Menemsha, and miles and miles of walking trails to make it easy to get around. Well-stocked, exceptionally clean and comfortable, we also love just sitting out on the spacious deck as we enjoy a leisurely breakfast and read. This is a special find and we will surely return again!

We thoroughly enjoyed our stay at La Casita. The location is great and within minutes to Cronigs, Chilmark General Store and Lucy Vincent Beach. The home is well appointed and there is an excellent cooking kitchen. The outdoor space is wonderful and peaceful. The owners were very responsive. We would definitely consider staying here again.

Curated with love and care, La Casita is a hidden gem with all new amenities, a wonderful outdoor shower, full air-conditioned, a fully stocked kitchen and best of all, conveniently located in Chilmark near the wondrous Lucy Vincent Beach. It has been my home away from home for two years and highly recommend staying there.

My family and I had a lovely and productive stay at La Casita. Some of us found it the perfect jumping off point to all the beauty and beaches Martha's Vineyard offers; others of us worked remotely at La Casita during the day. We all came together in the evening for dinner on the spacious balcony or to take a quick trip to Menemsha Beach to watch the sunset. For those of us "on the clock" La Casita is a great place to work -- reliable internet, lovely sunlight and nature views as the setting, and a separate "artists' studio" which worked well for having zoom meetings without being disturbed (or being disturbing). Clean, cozy, well decorated, home, perfect for a solo, a couple or a small family vacation. Both Jo, the owner, and Max, the caretaker were accessible, friendly, and always helpful.

Everything about the house is perfectly laid out. Very thoughtful clean and spanking new. The deck is divine for relaxing and the out door shower-perfect for after a long day at the beach. Very beachy decor and well situated near all the towns and beaches. Would definitely stay there again!

Nature abounds in this cozy oasis nestled in the woods. My month long stay at LaCasita was filled with walks on nature trails, days at the beach and great food from the Chilmark General Store.

The well apportioned house is filled with abundant natural light (making remote working super pleasant). The contemporary kitchen is fully outfitted for all your cooking adventures. And then there is the generous deck (completely private) with a modern outdoor shower. At night the deck lighting is pure magic, only to be matched by the fireflies in the yard at dusk.

The up island location is terrific, close to Lucy Vincent, Squibnocket and the Yoga Barn. My stay was made extra special by Sam and Jo. Thank you for being such wonderful hosts!

We just returned from a wonderful week in our favorite part of our favorite island. Our stay at La Casita couldn't have been better. It was the perfect place to call home for that special week. The cottage was spotless and cozy, close to beaches and so many of the conservation trails that we love to visit up island.

We had everything we needed to cook and relax at home in between our adventures. The owners could not have been more accommodating, even leaving us some yummy local treats to sample. We have been coming to the Vineyard for many years and now have another special spot to look forward to visiting again. Thank you so much, Jo!