4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Chilmark waterfront rental home with a dock located on Quitsa Pond with views across Quitsa and Menemsha ponds out to the Elizabeth Islands. This Martha's Vineyard rental property offers dock,...
Created Jul 20, 2026
5 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Lovely house at the top of Abel's Hill with access to private Abels' Hill Beach a half mile away. The house is wonderful for families with 5 bedrooms, three and half baths, two outdoor showers,...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
This spacious home sits on a picturesque two-acre property, just a short walk from Lobsterville Beach. The gourmet kitchen opens to an adjoining lounge for easy gathering. A separate living room is...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Mid-Century modern glass house, in Menemsha, on Marthas Vineyard. Designed by a Frank Lloyd Wright apprentice, this all glass house, embodies the integration of nature and architecture, with simple...
Created Jul 20, 2026
5 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Chilmark is quiet, laid back and much less congested than down-island counterparts. If you want to spread out and relax, this is an excellent part of the Island to visit. Alley's General Store and...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Menemsha, Massachusetts
The Grapevine is located on a private road in Menemsha, It was completely rebuilt not to long ago. originally it was a shack purchased from the government in 1950 and dragged on a flatbed truck....
Created Jul 20, 2026
5 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Welcome to this spacious and inviting Chilmark retreat set on three private acres in the desirable Prospect Hill community. With five bedrooms and five full bathrooms, this home is ideal for large...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
A recently renovated country home located in the Vineyard's most idyllic town of Chilmark, close to the West Tisbury line.2025 Season only: I have transferable ferry tickets for July 20th-July 27th...
Created Jul 20, 2026
5 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
Private setting on 5 acres, wonderful for family retreats, weddings. Natural fabrics and wood floors, can have cook and massages. Sleeps 12-14. Balconies and views of the ocean on all the upstairs...
Created Jul 20, 2026
2 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Summary:Chilmark Guest HouseThe Space:Tucked away in a private glen on three secluded acres, this light-filled home in Chilmark is Martha's Vineyard at its most peaceful. It's the perfect escape...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
As featured in the Summer 2023 issue of Vineyard Style Magazine, this fabulous beach house is ideally located in the highlands area of Aquinnah known as Pilots Landing and has lovely water views of...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Private 8 acre estate with new hot tub and tennis court. Enjoy your walks through 56 acres of preservation land and the Tiasquam river.The house is filled with art from local artist Colin Rule,...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
Stunning contemporary 4 bedroom Menemsha pondfront , beachfront home with a pool and extensive views over lawn, sand dunes and pond. Perched 90 feet above Menemsha Pond on a breezy elevation, the...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
Bring the kids and dogs for a fun relaxing stay in the secluded Aquinnah end of Martha's Vineyard. Our home is rustic and decorated in a shabby-chic style with many antiques mixed with Pottery...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Wonderful screen porch overlooking gorgeous setting. Right off South Road, a few minutes to fishing village of Menemsha and Lucy Vincent beach. Short walk to Landbank at Chilmark pond and paddle...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Relax at this retreat in the woods when you are not spending time on Lucy Vincent Beach or enjoying the sunset down the road in Menemsha. Surrounded by stone walls and walking paths over 20 acres...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
A hidden gem tucked in the woods of the desirable Tea Lane neighborhood. A freshly painted interior, brand new second floor carpeting, conservation grade Birch flooring on the main floor, modern...
Created Jul 20, 2026
2 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Superb fields-to-ocean-to-islands views from this charming guesthouse, on a historic Chilmark property. You'll enjoy a wealth of beach options. Squibnocket beach is only 5-minutes away by car....
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Beautiful, open holiday cottage that offers a secluded and affordable base for a wonderful Martha's Vineyard holiday. Designed by a leading island archiitect, this pagoda-like building features a...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
Unwind at this beautiful custom built home. Located in one of Martha's Vineyard's most peaceful and scenic areas, its just a few minutes walk to the beach. The house has hardwood floors throughout,...
Created Jul 20, 2026
2 Br Cottage Vacation Rental In Chilmark, Massachusetts
Unwind Up Island at this summer cottage, nestled in the woods and a short walk to Chilmark Pond. A canoe or kayak are just 5 minutes down the walking path to take you on a paddle ride to a...
Created Jul 20, 2026
3 Br Cottage Vacation Rental In Chilmark, Massachusetts
Everyday is a beach day! A magical beach retreat cottage at the water's edge, nicknamed Gadget. Wades Cove at Chilmark Pond. has immediate, private access to the barrier beach on the Atlantic. just...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
A unique opportunity to spend your vacation in peaceful Abels Hill in Chilmark. This lovely cottage is located in the highly sought-after Abels Hill neighborhood - a peaceful enclave with coveted...
Created Jul 20, 2026
5 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Gracefully situated atop the hills of Spring Point in Chilmark, our 4 BR (sleeps 8-10) home features panoramic water views sweeping from the Gay Head light house to the Elizabeth Islands. This...
Created Jul 20, 2026
5 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Designed by a student of the famous architect Walter Gropius, our house was built in 1949. The house is open and light, with floor to ceiling windows and sliding glass doors, a fireplace with a...
Created Jul 20, 2026
