Search Holiday Homes in Chilmark

"This was an excellent stay at a beautiful property in Oak Bluffs! Rebecca was a great host who provided clear instructions and helped answer questions in a timely manner. Rooms were spacious, most tastefully decorated and we had everything that we needed. I definitely recommend staying here to have an unparalleled experience of the Vineyard."

"It was a great weekend spot. Had everything we needed, nicely decorated, and in a great and private location"

"Great stay!"

"Brenda and Derek were amazing hosts. They have a beautifully landscaped property with all the amenities needed for a relaxing family vacation. They are super responsive and take a lot of pride in giving their guests a top-notch experience. We will definitely consider staying at their properties again."

"Great trip and time on the lake. Highly recommend this property for families looking for ease and convenience."

"Nice and clean house, good location on the island, nice neighborhood "

"The most perfect spot! Our host and the neighbors were so nice and gave us great tips! Would definitely stay again"

"Quiet location"

"The home worked out well for our needs. They have a very nice fully fenced in yard which was very beneficial."

"House was neat architectural wise and family history of home ownership was very cool. However, listing noted there was a washer/dryer and there was not. House also noted that there was a fire pit and it was rusted through. Screen door handles were broken, windows need repair, and house has animals living in the downstairs bathroom wall. House needs updates to charge what was being charged a night. In addition, there was a Nor’easter that hit the island and we attempted to contact the host to let...