4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
This beautiful and special Chilmark home offers lovely and open interior spaces as well as several outside living spaces with large screened porch, expansive decking and huge yard with play-set and...
Created Jun 15, 2025
5 Br Cottage Vacation Rental In Chilmark, Massachusetts
Enter our vacation world up a 0.2 mile paved driveway through the woods to the private hilltop with only two other houses. Open the gate and delight at the expanse of ocean view from the deck over...
Created Jun 15, 2025
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
*PLEASE NOTE: THE PRICES YOU CURRENTLY SEE ON THE WEBSITE ARE THE PRICES FOR 7 NIGHTS OR MORE THAN 7 NIGHT STAYS. FOR ANY STAYS LESS THAN 7 NIGHTS, THE NIGHTLY PRICE WILL INCREASE. PLEASE SEND THE...
Created Jun 15, 2025
3 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
*PLEASE NOTE: THE PRICES YOU CURRENTLY SEE ON THE WEBSITE ARE THE PRICES FOR 7 NIGHTS OR MORE THAN 7 NIGHT STAYS. FOR ANY STAYS LESS THAN 7 NIGHTS, THE NIGHTLY PRICE WILL INCREASE. PLEASE SEND THE...
Created Jun 15, 2025
2 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
This property is available August 5-19, 2023. Located just off North Road in Chilmark, this Blueberry Ridge guest house features 2 bedrooms, one bath, air conditioning and passes to Chilmark's...
Created Jun 15, 2025
3 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Wayside CampOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Conveniently located in the center of Menemsha,...
Created Jun 15, 2025
2 Br Cottage Vacation Rental In Chilmark, Massachusetts
This secluded Chilmark cottage, beautifully landscaped, sits on a high point off of Meeting House Road with a sweeping view of the Atlantic ocean. The house is light-filled and airy, with...
Created Jun 15, 2025
6 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
About this spaceMake great summer memories in this charming and spacious farmhouse. Watch the sunset over the Vineyard Sound and enjoy dinner and drinks on the wraparound deck. The property...
Created Jun 15, 2025
5 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
This private Chilmark compound has breathtaking views out to the Atlantic Ocean and 1/3 mile of private beach in your backyard. It sits on 19+ acres on the Wequobsque Cliffs providing a secluded...
Created Jun 15, 2025
3 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
3 bedroom, 3 bath house on 11 acres in Chilmarkoutdoor grill, dining. large open spacelarge living room, dining room.smaller kitchen but very functional.no air conditioningoutdoor hot tubpeaceful...
Created Jun 8, 2025
2 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
This well-furnished and architecturally unique two-to-three bedroom house is located on 2.5 secluded acres in Aquinnah. The house has gorgeous 180 degree water views and the private beach is just a...
Created Jun 8, 2025
4 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
This beautiful three-story house is recently available for rentals again. With room to spread out for up to 10 guests, the property offers privacy on 2 acres of beetlebung groves and oak trees,...
Created Jun 8, 2025
3 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Two rental opportunities are being offered within this one listing:The Upper House & Studio ApartmentThe Lower House & Studio ApartmentThe Upper House, Lower House and Studio Apartment are part of...
Created Jun 8, 2025
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
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...
Created Jun 8, 2025
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
One of the most spectacular oceanfront rentals available on the exclusive Island of Marthas Vineyard. This unique residence is situated on the Chilmark bluff overlooking Lucy Vincent Beach and the...
Created Jun 8, 2025
2 Br Cottage Vacation Rental In Chilmark, Massachusetts
This newly renovated one bedroom guest house with open-style living is the perfect Chilmark get away for a couple with one or two young children. With cathedral ceilings, the first floor great room...
Created Jun 8, 2025
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Our home is off Middle Road in Chilmark. It features a chef's kitchen with convectionoven, screen porch, roof deck, outdoor shower, and office area. The first-floor separate bedroom area has...
Created Jun 8, 2025
4 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
This spectacular beach house with stunning water views is located 20 feet from the edge of a grassy cliff overlooking Vineyard Sound. It was designed by the visionary architect Andrew Geller and is...
Created Jun 8, 2025
5 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Tucked into the woods, this elegant house offers a panoramic view of the full sweep of the Vineyard Sound from Woods Hole to Cuttyhunk -- by day, sailboats and the Elizabeth Islands and beyond,...
Created Jun 8, 2025
3 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Welcome to this charming Waterview farmhouse in Chilmark Marthas Vineyard. This phenomenal property boasts 3 bedrooms - one with a king bed, one with a queen bed, and one with a twin bed full...
Created Jun 8, 2025
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
*PLEASE NOTE: THE PRICES YOU CURRENTLY SEE ON THE WEBSITE ARE THE PRICES FOR 7 NIGHTS OR MORE THAN 7 NIGHT STAYS. FOR ANY STAYS LESS THAN 7 NIGHTS, THE NIGHTLY PRICE WILL INCREASE. PLEASE SEND THE...
Created Jun 8, 2025
