3 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
Summary:Lobsterville LandingThe Space:With sweeping water views of the Vineyard Sound, Lobsterville Beach and the shores of Menemsha by day and unforgettable stargazing by night, youve hit the...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
Summary:Whistling Hill HouseThe Space:Named for the sea breezes that circle this charming and unique home, the Whistling Hill House is nestled alongside the Marthas Vineyard Land Trust, ensuring a...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
Happily isolated from the bustle of Oak Bluffs and Vineyard Haven, this tranquil residence a 15 minute walk from the cliffs of Aquinnah offers simple, unpretentious comforts of old Martha's...
Created Jul 20, 2026
3 Br Cottage Vacation Rental In Chilmark, Massachusetts
Classic Vineyard summer cottage with private waterfront access to cove on Menemsha Pond on 1.5+/- acres within a few minutes walk to town dock and beach. One level, 3 bedrooms, 2 lavs (one with...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Discover a truly unique retreat just off the main road, yet worlds away. Nestled on a tranquil 22-acre estate in Chilmark, moments from Menemsha, this property offers unparalleled relaxation and...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
This beach house is a ten minute walk from Philbin Beach, the town beach on the surf side of Aquinnah. It is an upside down house with the kitchen living room, and deck situated upstairs to take...
Created Jul 20, 2026
5 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
*NOTE* We Just opened the calendar for the month of August! These weeks will go quickly. This is a very rare opportunity so dont wait to inquire. This exquisite and secluded waterfront property on...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Beautiful, open modern house set in four acres overlooking Chilmark Pond with access to private beach by boat across the pond or by road. Large upstairs open living/dining kitchen area with...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
Tanager House - This spacious 4-bedroom home is nestled on 3 acres in scenic Aquinnah, offering privacy and tranquility. Bordering wooded landscape and wetlands it's just a short walk from the...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Comfortable home, providing wonderfully peaceful and refreshing quiet, set on a white oak wooded lot, with 2 fireplaces, newly renovated eat-in kitchen, powder room, laundry room, upper level AC,...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Location! Location! Location! Charming, and nestled away, this must see post and beam home is situated on the edge of the Keith Farm, which provides multiple sweeping pastoral views and occasional...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts
Our Marthas Vineyard property is a great vacation home to experience the beautiful island setting in the town of Aquinnah. This new 4 bedroom 3.5 bath home overlooks the Vineyard Sound with...
Created Jul 20, 2026
2 Br Cottage Vacation Rental In Chilmark, Massachusetts
The Little House was built in 1960 as a one room studio/cabin. Since then a gourmet kitchen wing has been added, as well as a detached bunkhouse. The main structure has an open floor plan with...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
A brand new listing! You are very welcome to this peaceful, quiet and private house in Menemsha village, just minutes from the public beach, harbor, restaurants, shops and galleries. The location...
Created Oct 12, 2025
1 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Your cozy retreat in Chilmark with 1 bedroom featuring 3 comfortable twin beds upstairs in the loft. This charming house offers essential amenities like a washing machine, AC, WiFi, half bath and...
Created Oct 5, 2025
2 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
This stylish place to stay is perfect for a family getaway. Ultra modern 2 Bedroom, 2 full baths, 2 half baths, outdoor shower. Kitchen with Carrera marble from Italy. Private gym. 4 Bedroom Guest...
Created Sep 21, 2025
2 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
This stylish place to stay is perfect for a romantic getaway. Ultra modern 2 Bedroom, 2 full baths, 2 half baths, outdoor shower. Kitchen with Carrera marble from Italy. Private gym. Private beach...
Created Sep 21, 2025
2 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
This stylish place to stay is perfect for a romantic getaway. Ultra modern 2 Bedroom, 2 full baths, 2 half baths, outdoor shower. Kitchen with Carrera marble from Italy. Private gym. Private beach...
Created Sep 21, 2025
5 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
This one of a kind property boasts 60 acres directly on the South Shore of Martha's Vineyard with direct access to over 1000 feet of private Atlantic Ocean. Quenames Farm is sometimes home to Grey...
Created Sep 21, 2025
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Chilmark is waiting for you at this 4-bedroom house. Step into this enchanting retreat with 1 king bed, 2 queen beds, and 2 twin beds. Enjoy 1000-feet of very private South Shore Beach + small pond...
Created Sep 21, 2025
3 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
1710 Farmhouse In ChilmarkConvenient North Road location - close to Menemsha Beach, Chilmark Store and picturesque hiking trails. Idyllic 9 acre private retreat seeks quality time with...
Created Jul 6, 2025
5 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
5 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
One of Chilmark's most stately and classic Captains House, THE BLUE BARQUE has been thoughtfully and fashionably edited and updated with every modern comfort in modern farmhouse style.The house is...
Created Jun 15, 2025
4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts
Lady Slipper HillOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This magical property is the perfect east...
Created Jun 15, 2025
6 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
