3 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
Spacious and comfortable beach cottage on 2 secluded acres in prime Aquinnah location, dripping with quintessential MV character and charm. Perched on a hill with 180 degree views of Vineyard Sound...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
*** We have transferrable car ferry reservations for guests who would like to book for summer 2026 . Just reach out to us. ***This charming, rustic cottage is located on Martha's Vineyard iconic...
Created Jul 20, 2026
2 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Petite Mid-century, renovated guest house is private with own driveway, yard, and easy walk to Menemsha Pond, harbor, public beach, Galley restaurant & ice cream, fish markets. Views of Pond,...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
You can enjoy the Menemsha Sunsets from your own private deck. This summer cottage was converted from an early fishing shack in the 1900s. It is a lovely, classic island cottage. It has views of...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Amazing Chilmark summer compound. On the Cliffs! 2 separate houses that can be rented together or separately. Privacy. Google Wequobsque Cliffs. Tennis court. Private beach. Prime Chilmark...
Created Jul 20, 2026
2 Br Cottage Vacation Rental In Chilmark, Massachusetts
Unwind in Chilmark at this wonderful cottage. With two bedroomsone queen bed and one twin bedguests find a nice spot to rest after a day of exploring. Airconditiong for hot summer days and heat for...
Created Jul 20, 2026
5 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Pond front cottage and attached Silo house, 4-5 bedrooms on large acreage fronting Menemsha Pond, big views of the long lawn and waterfront. Quiet private neighborhood in Chilmark . Private...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
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...
Created Jul 20, 2026
5 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
A storied property in Chilmark for almost 150 years, the hilltop Tower House combines current taste, comfort and elegance with its own special provenance -- as an authentic part of the Vineyard's...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
Beautiful Aquinnah Home: Ocean View, Walk to BeachOceanview Escape Near Lobsterville Beach | Dog Friendly + Spacious DecksFind your perfect Marthas Vineyard getaway at this charming Aquinnah...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
This rental is a 3 bedroom, 2 full bath house with a deck, where you can enjoy the fresh island air. A porch swing on the ground level provides another quiet spot to rest and relax. The living...
Created Jul 20, 2026
5 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Located just a 5 minute walk from Chilmark's famous North Tabor Farm, this charming house is a dream for families or groups. The house has 5 bedrooms, 4 with a queen bed plus one bedroom with both...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chilmark, Masachusetts, Massachusetts
Discover privacy and coastal charm at this exceptional 7.25-acre rental in Chilmark. Enjoy exclusive access to Quansoo Beach, one of Marthas Vineyards most beautiful private beaches. The 4,500 sq....
Created Jul 20, 2026
6 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Our family home is a 4-acre waterfront paradise with wonderful sunsets. The private location sits between a large wooded hill and a 200-acre private estate. The six-bedroom, 412-bath, two-kitchen...
Created Jul 20, 2026
2 Br Cottage Vacation Rental In Chilmark, Massachusetts
A wonderful two bedroom cottage nicknamed The Palace ,and it truly is one!on a private estate with private access to the Chilmark Pond barrier beach facing the Atlantic. newly renovated, updated,...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Simpler, secluded living, just 5 minutes walk through woods to a gorgeous private beach, where stairs lead down from a spectacular cliff-top view of the Island's entire south shore. This lovely...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Think resort-type elegance in a relaxed beach house vibe. 4BR, 3 bath, outdoor shower, 4-ft deep spa pool. Lots of light!Chilmark is the laid-back end of Martha's Vineyard. The house is near Lucy...
Created Jul 20, 2026
1 Br Cottage Vacation Rental In Chilmark, Massachusetts
Located in Menemsha Village. This quaint cottage is located a stones throw from the Menemsha Harbor. It is the smallest and most affordable of the three houses we rent, yet offers great views.The...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Welcome to 15 Old Farm Road, a private and beautifully designed Chilmark retreat set on over three acres of landscaped grounds. Surrounded by rolling lawns, mature plantings, a tranquil pond, and a...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Best view of sunset on island.Fully equipped modern house; air conditioning, large deck, barbecue, outdoor shower, linens, towels, beach chairs, kitchen with dishes, flat ware, cooking utensils,...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
Escape to this delightful summer haven just a short walk from Philbin Beach, Marthas Vineyard's most beautiful. The spectacular Aquinnah/Gay Head cliffs are a mere half mile up the road. The...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Everything you think of when you dream of Chilmark... pastural rolling 2+ acres with water views and stone walls. Ideal location less than 1.25 miles to all Chilmark beachs... St Lucy Vincent,...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Welcome to the barn! This beloved home started as a post and beam barn built in 1983. 10 years later it was expanded; on one side, an open gourmet kitchen is flanked by a fireside breakfast nook,...
Created Jul 20, 2026
4 Br Cottage Vacation Rental In Chilmark, Massachusetts
Our waterfront cottage on Chilmark Pond is a short boat ride to a stunning barrier beach on the Atlantic Ocean. There is access to Abel Hill Association tennis courts, miles of private beach for...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
Three Winds is a modern beach home in Aquinnah, Martha's Vineyard; The island's westernmost point. The house sits on windswept rolling terrain, overlooking the Vineyard Sound and the Elizabeth...
Created Jul 20, 2026
