"Over South", Family farm house in Chilmark

Top rated by guests
Morning light.
Kitchen/ dining room. Large table to accommodate all the family.
Dining
View of circular driveway.
Exterior
review stars
9.6Outstanding
(13 Ratings)
"We really enjoyed our stay in Chilmark. We’ve been coming to MV for 25 years and this house had everything we needed. Perfect location, amenities, and we loved the Monday to Monday rental to avoid the..."
Ryan J.
Don't miss out! Price and availability may change
9.6 / 10
Outstanding(13 Ratings)

House in Menemsha, MA

8 guests · 4 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

Situated on the quiet end of the Island, yet only a 20 minute drive from Vineyard Haven, this rustic, authentic Chilmark farm house boasts four bedrooms, two baths, and an outdoor shower. Two bedrooms downstairs,one Queen and one Twin and two upstairs, One twin and one single, a large kitchen/dining room, and spacious comfortable TV room with cable.
Large deck on two sides with BBQ. The house is approximately 1500 square feet and sits on a 1/2 acre plot with plenty of parking. Included in the rental are all the amenities of home, dishwasher, washer/dryer, BBQ. All linen needed including towels and beach towels. The house also has lots of board games, movies and books to help you relax on your vacation. The house rents from Monday to Monday, avoiding Cape weekend traffic and hopefully making car reservations easier to achieve.
The front and back yards are large enough to accommodate a boat trailer with a 360 degree drive.
The house is just off State Road, so no dirt roads to navigate. One mile south from Chilmark village and Chilmark Chocolates. Rental of house entitles tenant to purchase drive-on beach pass for Lucy Vincent and Squibnocket beaches. A beautiful 10 minute drive to Aquinnah Cliffs and lighthouse, Philbin and Lobsterville beaches.Serviced by the Vineyard Transport Authority you don't have to drive if you don't want to.
A 15 minute walk to Menemsha through the woods(on sand roads), this house is perfectly located for all your vacation needs.
Due to popular demand we are going to continue our Monday to Monday booking. This gives our guests a full weekend on the Vineyard and reduces the stress of Cape traffic. Also ferry travel is not as busy on Mondays.

Map of Menemsha, MA


Ratings and reviews

9.6 / 10
Outstanding(13 Ratings)
10 / 10Outstanding·Jul 2025
We really enjoyed our stay in Chilmark. We’ve been coming to MV for 25 years and this house had everything we needed. Perfect location, amenities, and we loved the Monday to Monday rental to avoid the busy Saturday check in/out. Lesley was a gracious host and very communicative. Thanks for a great stay, we’ll be back next year.
10 / 10Outstanding·Aug 2024
Location is awesome for up island and old school house was great for my family vacation!
10 / 10Outstanding·Jul 2024
It was a charming and comfortable home. We did not know this when we booked it but the caretaker lives in the smaller house next door. I would have normally been a little reticent about that set up but the properties are well separated for privacy and it was nice to have someone nearby to help with settling in and answer questions about the island. Also, it was a huge plus to not have to bring towels and linens. In our experience rentals don't typically supply them and it was a great convenience to not have to supply our own.
10 / 10Outstanding·Jul 2024
We absolutely loved our stay -- the location, house layout, deck, dirt road to Menemsha, overall vibe of house were all favorite highlights! We hope to return. :)

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at "Over South", Family farm house in Chilmark. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is "Over South", Family farm house in Chilmark pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"