House in Menemsha, MA
10 guests · 4 bedrooms · 4 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this house rental
Well located off beloved Middle Road, property embodies all of the natural beauty of Chilmark: old stone walls, perennial plantings & mature trees. Property abuts 100 acres of Sheriff's Meadow Conservation land. Main house has three bedrooms each w ensuite baths. A separate private guest cottage w a bedroom, full bath, covered porch, kitchenette & back deck with outdoor shower. Main and guest house have air conditioning. Guest house & little summer bunkhouse meant for summer use. Main house is winterized and available for year round use. Each bedroom and the dining room has it own split air conditioning unit. Upstairs 2 bedrooms each with king beds, downstairs bedroom has 2 twin beds. The guest house also has a split AC unit, but is not winterized. The guest house will not be available for use from October through May. The sweet little bunkhouse does not have air conditioning nor it is winterized.
Amenities at 3 Bedroom House with Guest Cottage on 3 Acres off Middle Road
Non-smoking
Pets allowed
Family friendly
Map of Menemsha, MA
Ratings and reviews
10 / 10Outstanding·Sep 2025
Beautiful place in a beautiful part of the island!
10 / 10Outstanding·May 2025
We recently spent five days at this fantastic property in the Chillmark area. We are frequent VRBO renters, and this house is in our top 3 for amazing stays. The layout of the first floor is very open, with soaring ceilings in the living room, a spacious dining table, and an excellent gourmet kitchen. The bedrooms were spacious, and all bathrooms resembled those at a high-end resort. The house sits on a private lot with great outdoor space, including a lawn to play, a large furnished deck, and a Weber gas grill. The location on the island is exceptional, with easy access to Edgartown, Vineyard Haven, and various beaches. Returning to the kitchen, this is one of the best-outfitted kitchens I have seen, with plenty of counter space and every kind of pot, pan, dish, or glass you might imagine. The host keeps a well-stocked pantry open for sharing with his guests. There is a wine fridge and two coffee makers (one regular drip and the other a Nespresso Vertuo machine - don’t forget to bring capsules if you want to use the Nespresso). The host was quick to respond and helpful in answering questions before and during our rental. Overall, it was a wonderful experience!
10 / 10Outstanding·Dec 2024
We rented this house to be close to our daughter’s in-laws. It was perfect; private, clean and spacious. The extra cottage was exactly what we needed for our family. We had a terrific week and would recommend this house to anyone looking to rent in Chilmark. Fantastic stay! Thank you
10 / 10Outstanding·Aug 2024
Our group of six loved staying here. Fantastic location and grounds, as well as luxurious bedrooms (two with en suite bathrooms). The kitchen was well stocked for cooking and was heavily used. We enjoyed the guest house as well because we needed four beds for our group and it was great (hint: use the dehumidifier). Sam was responsive and a great communicator. Highly recommend!
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Top rated by guests
10Outstanding
(13 Ratings)
"Beautiful place in a beautiful part of the island! "
Paul C.Don't miss out! Price and availability may change
