Showing

PreviousNext property

$358

2 BR / 1 BA / Sleeps 4

1 Reviews

$358

Inquire

THE BOATHOUSE ON STONEWALL POND - CHIL RALD-138B

2 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Unique waterfront living in the heart of Chilmark. The Boathouse sits directly on the shores of Stonewall Pond, with sweeping water views of the Pond, Stonewall Beach and the Atlantic Ocean. You also have access to Stonewall Beach -- one of Chilmark's most prestigious private association beaches. The wraparound decks …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

spiritually reviving spot with mesmerising view

Left on Dec 27, 2013 for a stay in June 2013

we have stayed in this property 3 years running in both June and July. It's the most peaceful spot imaginable (no mobile phone signal) with unending wildlife activity ( we have seen young ospreys learning how to fish (hilarious); sea otters eating their dinner right by the deck; busybody geese families; horseshoe crabs;a seal; deer and even a Labrador on a paddle board).

We have been coming …

PreviousNext property

$500

3 BR / 3 BA / Sleeps 6

HILLSIDE HIDEAWAY ON BLUEBERRY RIDGE - CHIL VBAR-39MH - Chilmark vacation rentals
1 / 25

$500

Inquire

HILLSIDE HIDEAWAY ON BLUEBERRY RIDGE - CHIL VBAR-39MH

3 BR / 3 BA / Sleeps 6 | Quick view

Details

A quiet oasis tucked away on Blueberry Ridge, the Hillside Hideaway enjoys a tranquil country setting with rolling meadows, and thoughtfully designed outdoor landscaping with patios and outdoor living spaces set amid nicely manicured grounds and gardens. Inside, the house is designed to enjoy the serene setting as …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$358

3 BR / 2 BA / Sleeps 6

Chilmark Rental With Private Beach! (Chilmark-Rental-With-Private-Beach!-CH236) - Chilmark vacation rentals
1 / 16

$358

Inquire

Chilmark Rental With Private Beach! (Chilmark-Rental-With-Private-Beach!-CH236)

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Located on South Road near Able's Hill, this family oriented house comes with access to a private South Shore beach across Chilmark Pond. Have fun boating, kayaking or canoeing across the pond to the beach. A family room in the lower level provides space for the younger members of the family to romp and congregate …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$572

3 BR / 2 BA / Sleeps 6

DIETR - Menemsha Pond Waterfront, Mooring, Wifi, Central A/C - Chilmark vacation rentals
1 / 22

$572

Inquire

DIETR - Menemsha Pond Waterfront, Mooring, Wifi, Central A/C

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Steps from Menemsha Pond – look across the ever-changing surface of the water to Menemsha, the Creek, the Lobsterville dunes, Vineyard Sound and the Elizabeth Islands. Magnificent sunsets from the living room. This cathedral-ceiling Modernist masterpiece is constructed entirely of Western red cedar. Central air and …
  • Waterfront
  • Ocean or water views
  • Phone / Internet
  • A/C or climate control
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$358

4 BR / 3 BA / Sleeps 8

STRAA - Chilmark vacation rentals
1 / 25

$358

Inquire

STRAA

4 BR / 3 BA / Sleeps 8 | Quick view

Details

CHILMARK,Black Point Beach Heaven Sand Sun Surf and an immaculate house and guest quarters too................WOW This is not a fancy posh beach house. It is a wonderful relaxing, immaculate vacation destination for you and your family. You will find peace, ocean breezes, the sound of the surf, star filled skies, moon…
  • Phone / Internet
  • Deck
  • Grill
  • Linens Provided
  • Dishwasher
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$1,358

4 BR / 3 BA / Sleeps 8

1675 - Spectacular Home with Waterviews of Vineyard Sound and Elizabeth Islands - Chilmark vacation rentals
1 / 16

$1,358

Inquire

1675 - Spectacular Home with Waterviews of Vineyard Sound and Elizabeth Islands

4 BR / 3 BA / Sleeps 8 | Quick view

Details

Beautiful, custom 4-bedroom house in an exclusive neighborhood with private association beach and tennis court. Spacious, comfortable living and dining room with cathedral ceilings, open to kitchen and upstairs loft with office. TV/sitting room nook off dining room. Expansive deck with stunning north shore water views…
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

PreviousNext property

$286

4 BR / 5 BA / Sleeps 8

1 Reviews

$286

Inquire

653 - ATLANTIC OCEAN BREEZES,GLORIOUS VIEWS!

4 BR / 5 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

A boutique hotel experience in an unrivaled setting at the end of a one mile single lane road. Enjoy the sunrise from the ocean, sunset over the adjoining 13 acre Sheriff's Meadow Foundation conservation preserve. This home has a wonderful view toward Squibnocket Beach, a mile away, and the Squibnocket Peninsula, with…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

Details

Reviews

(1)

Fabulous stay

Left on Jun 16, 2014 for a stay in March 2014

We stayed at this gorgeous home with a large family group in March. Fortunately for us, the weather was ideal. We had a lovely stay - everything at the house was wonderful and everyone loved being at this home and on the Vineyard for a winter vacation. The house is spacious, comfortable and very beautiful. The property is private.

PreviousNext property

$1,143

4 BR / 3 BA / Sleeps 8

1 / 21

$1,143

Inquire

Spectacular Home with Private Pool & Tennis 116946

4 BR / 3 BA / Sleeps 8 | Quick view

Details

A spectacular Chilmark estate located on 6.9 acres complete with private pool and tennis courts. An updated master bedroom and bathroom will soothe you after a busy day at the beach. Comfortable furnishings paired with state-of-the-art appliances make this a truly magnificent vacation experience. Additional …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$1,472

5 BR / 5 BA / Sleeps 10

1 / 29

$1,472

Inquire

WINGR

5 BR / 5 BA / Sleeps 10 | Quick view

Details

Take me home country road....to the place I belong......Wingate Roost is home............and down a beautiful country road. Set among the hills of Squibnocket with views of the pond and the Atlantic this unpretentious home will envelope you in its understated elegance. Windows everywhere let the light and the hypnotic…
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Phone / Internet
  • Outdoor Dining Area
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$3,572

4 BR / 3 BA / Sleeps 10

1 / 11

$3,572

Inquire

Chilmark - 123611

4 BR / 3 BA / Sleeps 10 | Quick view

Details

N/A
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$571

3 BR / 2 BA / Sleeps 5

1 / 11

$571

Inquire

Fully booked for summer 2015

3 BR / 2 BA / Sleeps 5 | Quick view

Details

Light and bright with floor to ceiling sliding glass doors in every room. The views over the wetland to the pond are phenomenal. A truly magical spot to watch the glow of the Menemsha Sunset. A short walk to a private sandy beach for swimming, kayaking, or sunbathing. Recent improvements include new appliances, …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$572

4 BR / 0 BA / Sleeps 8

1 Reviews

$572

Inquire

#2021 Chilmark Waterfront w Dock

4 BR / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Chilmark waterfront rental home located on Quitsa Pond with views across Quitsa and Menemsha ponds out to the Elizabeth Islands. This martha's vineyard rental property offers dock, mooring along with access to small beach area just down the path on Clam Point Cove. Named appropriately, it is an ideal location for …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Chilling in Chilmark

Left on Sep 03, 2014 for a stay in August 2014

Our family thoroughly enjoyed our week at the Mayhew home in Chilmark. We rented kayaks for some boating right off the private pier, picked clams, swam off the docked and cooked out on the deck! Can't wait to go back next year.

PreviousNext property

$286

2 BR / 0 BA / Sleeps 4

1 / 8

$286

Inquire

#2084 - Lovely Chilmark Cottage for rent

2 BR / Sleeps 4 | Quick view

Details

Lovely Chilmark Cottage for rent. Situated with privacy in a wooded area not too far from beaches and Alley's General Store. Enjoy peaceful mornings and evenings on the private deck while heading to the beautiful South Shore on Lucy Vincent Beach during the sunny Vineyard days. Walk into this cottage and kick back and…
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$715

3 BR / 0 BA / Sleeps 6

1 / 17

$715

Inquire

#2069 Stunning Chilmark property in Abel's Hill

3 BR / Sleeps 6 | Quick view

Details

Stunning Chilmark property in Abel's Hill. Convenient location with great proximity to association beach and tennis, not far from Chilmark and West Tisbury town centers. Surrounded by open rolling hills with Japanese garden and fire pit, offering great privacy. Just steps to wonderful walking trails. Truly an …
  • Internet Access
  • A/C or climate control
  • Deck
  • Dishwasher
  • Microwave
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$286

2 BR / 1 BA / Sleeps 4

1 / 19

$286

Inquire

MEADOW HOUSE ON BLUEBERRY RIDGE - CHIL VBAR-39GH

2 BR / 1 BA / Sleeps 4 | Quick view

Details

Quietly tucked away in a pastoral setting on Blueberry Ridge, Meadow House features a modern interpretation of a sleek barn. The home is designed to enjoy the views of the surrounding secluded meadows both inside and out. The main living space features an open design floorplan with Living and Dining Areas accented by …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Patio
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$4,000

6 BR / 0 BA / Sleeps 13

1 / 30

$4,000

Inquire

#2080 Tranquil and extremely private setting in Chilmark

6 BR / Sleeps 13 | Quick view

Details

Chilmark retreat at its finest. This tranquil and extremely private setting is on the south side side of Martha's Vineyard within close proximity of the stunning Lucy Vincent Beach. This sprawling well designed six bedroom fully air conditioned ranch style home gives you plenty of indoor lounging and outdoor splendor…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$179

2 BR / 1 BA / Sleeps 4

1 / 13

$179

Inquire

FENNB - Menemsha, Waterview, Walk to beach

2 BR / 1 BA / Sleeps 4 | Quick view

Details

Amenities and Features include... Menemsha, Waterview, Walk to beach Additional amenities include: coffee maker, fans - portable, lobster pot, food processor, washer / dryer, cd player, outside shower - enclosed, vacuum, outdoor furniture, ironing board.
  • Ocean or water views
  • Phone / Internet
  • Deck
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$320

1 BR / 1 BA / Sleeps 4

2 Reviews

$320

Book

Chilmark Cottage

1 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

This small cottage on a hill, built in the 1950's, has been updated for comfort and style while maintaining the feel of the old-time Vineyard. One bedroom, one bathroom, a computer room, and a great room that includes kitchen, living, and dining area fit comfortably into 450 square feet. Many windows let in light, …
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Porch
  • Books
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(2)

up-island charm

Left on Mar 14, 2014 for a stay in August 2013

We love our stays here in the summer with our two kids. The cottage is cozy, but, with the studio and spacious, private yard, we are comfortable here with extended family. The beaches nearby are amazing, and having access to Lucy Vincent is essential for us. But, great as the beaches are, we often find ourselves laying around the yard all morning and enjoying the peaceful setting. Everyone …

PreviousNext property

$215

2 BR / 1 BA / Sleeps 4

1 / 23

$215

Inquire

THE POND HOUSE ON STONEWALL BEACH - CHIL JJAF-95GH

2 BR / 1 BA / Sleeps 4 | Quick view

Details

Luxurious beachfront living in Chilmark with sweeping water views of Stonewall Beach, Squibnocket Ridge, and Stonewall Pond. The Pond House sits directly on the intersection of Stonewall Beach and Pond, with water views throughout the house and across the large wraparound deck. Walls of windows and French doors frame …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Patio
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$329

4 BR / 2 BA / Sleeps 8

1 / 4

$329

Inquire

Secluded Chilmark (Secluded-Chilmark-CH208)

4 BR / 2 BA / Sleeps 8 | Quick view

Details

Secluded location on a cul de sac overlooking a private meadow with spreading oak trees. The traditional exterior welcomes you to our spacious contemporary. the main living area features a great room with fireplace which opens to a dining room and kitchen with an island eating bar. Off the great room is the main deck …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$736

5 BR / 4 BA / Sleeps 8

1 / 31

$736

Inquire

MICHA - Chilmark Hilltop Luxury Home, A/C, Wifi Internet

5 BR / 4 BA / Sleeps 8 | Quick view

Details

MVVR EXCLUSIVE: Spectacular 5 bedroom, 4.5 bath retreat. Lovely distant waterviews overlooking the South Shore. Hilltop setting with privacy and a five minute drive to Lucy Vincent Beach. This spacious custom home has been decorated by one of the island's premier professionals. A combination of contemporary …
  • Ocean or water views
  • Phone / Internet
  • A/C or climate control
  • Porch
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$425

4 BR / 3 BA / Sleeps 8

1 / 16

$425

Inquire

TEELK - Menemsha Village Cottage, Walk to Menemsha Beach, A/C, WiFi

4 BR / 3 BA / Sleeps 8 | Quick view

Details

Ferry Tickets available - Please Inquire Charming 4 bedroom, 3 bath traditional summer cottage. Enjoy this impeccably maintained summer home surrounded by a mature landscaped yard with lots of flowering shrubbery. A large deck offers privacy and a wonderful setting for those summer barbeques. A modern well equipped …
  • Phone / Internet
  • A/C or climate control
  • Deck
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$500

3 BR / 2 BA / Sleeps 8

1 / 35

$500

Inquire

HILL HOUSE ON STONEWALL POND - CHIL RALD-140

3 BR / 2 BA / Sleeps 8 | Quick view

Details

Hill House sits atop a bluff along the shores of Stonewall Pond with panoramic water views of the Pond and Stonewall Beach, as well as views over Quitsa Pond in the other direction. There is also access to Stonewall Beach, one of Chilmark's most prestigious private association beaches. Hill House is all about the view…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$1,029

4 BR / 3 BA / Sleeps 8

1 / 30

Details

Outstanding private rental home nestled on 7.2 private acres in the seaside community of Chilmark on the Island of Martha's Vineyard, features a key to Quansoo Beach, one of the most beautiful private association beaches on the island. Warmth, comfort and charm await you and your family in this air conditioned, 4500 …
  • Phone / Internet
  • A/C or climate control
  • Porch
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$500

5 BR / 3 BA / Sleeps 12

1 / 11

$500

Inquire

ENRIP - Privacy, Lovely Yard, Short Drive to Lucy Vincent Beach

5 BR / 3 BA / Sleeps 12 | Quick view

Details

Spacious, well furnished and equipped, comfortable home in quiet neighborhood on 3 acres. Two master bedrooms, one on each floor; pool table. Within walking distance (about 1 mile) to small North Shore beach (Great Rock Bite). Three mile drive to Lucy Vincent Beach. Amenities and Features include... Privacy, …
  • Internet Access
  • Deck
  • Grill
  • Dishwasher
  • Microwave
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$358

4 BR / 5 BA / Sleeps 8

1 / 36

Details

Featuring one of the most stunning water views and waterfront locations in Chilmark, The Beach House At Stonewall is just that. Stonewall Beach is directly at the property's edge. There is a private beach, and south-facing views of Stonewall Beach & Pond, Squibnocket Point, and on out to No Man's Land. Sitting atop a …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Patio
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$636

4 BR / 3 BA / Sleeps 8

1 / 18

Details

Panoramic South Shore ocean vista from this outstanding private rental home. Less than one mile to famous Lucy Vincent Beach. Owner also offers private beach rights to the south side via canoe or kayak (provided by owners.) Classic style and modern luxury combine to make this family retreat a very special rental. Part…
  • Private Beach
  • Ocean or water views
  • Phone / Internet
  • A/C or climate control
  • Porch
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$593

4 BR / 2 BA / Sleeps 10

1 / 14

$593

Inquire

BERWD - Waterview, Walk to Menemsha Beach

4 BR / 2 BA / Sleeps 10 | Quick view

Details

Sweeping water view over Vineyard Sound to the Elizabeth Islands. Freshly renovated Cape-style, three bedrooms, with sofa beds in den and sunroom, sleeps 8-10 people. Short walk to lovely Menemsha Village, and less than two miles to Lucy Vincent's Beach. Large, landscaped treed lot of 2.3 acres on a hill. New …
  • Ocean or water views
  • Internet Access
  • Deck
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$604

3 BR / 2 BA / Sleeps 6

1 / 26

$604

Inquire

LEWID - Menemsha Waterfront, Magnificent Views and Private Location, WiFi

3 BR / 2 BA / Sleeps 6 | Quick view

Details

This quintessential Chilmark home has been impeccably maintained and continuously updated. The dining and living areas open to a wrap around deck. Enjoy spectacular water views and sunsets from just about every room in the house. Stroll to the beach and Menemsha village where you will find the fish market, village …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Deck
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$900

5 BR / 4 BA / Sleeps 12

1 / 30

$900

Book

Striking 5BR/4BA Chilmark Contemporary with Views of the Sound

5 BR / 4 BA / Sleeps 12 | Quick view

Details

Come enjoy the secluded beauty of this award-winning, architect-designed home in Chimark on almost four acres of land. Relax on the two level deck or on the beach at Lucy Vincent, Squibnocket, or nearby Menemsha. The remarkable design makes great use of over 3500-square-foot space by joining the east and west houses …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

PreviousNext property

$400

5 BR / 4 BA / Sleeps 12

1 / 21

$400

Inquire

HAUCJ -

5 BR / 4 BA / Sleeps 12 | Quick view

Details

An award winning architectural design coupled with Vineyard charm and seclusion, this house has two wings allowing for multiple family co-existance. This vacation home is open, spacious and filled with light with a wrap-around deck for sun or shade. Amenities and Features include... Additional amenities include: …
  • Phone / Internet
  • Deck
  • Grill
  • Dishwasher
  • Microwave
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$736

1 BR / 2 BA / Sleeps 3

1 / 14

$736

Inquire

YEOM1 - Waterview, Walk to Private Association South Shore Beach

1 BR / 2 BA / Sleeps 3 | Quick view

Details

"The Little House" on the beach. Two minute stroll to South surf beach. Incredible views from sunrise to sunset. Private tennis courts shared with owners and other tenants. Access to Stonewall Pond for launching canoes and kayaks. This wonderful cottage is a one of a kind. A pet will be considered on a case by case …
  • Waterfront
  • Ocean or water views
  • Phone / Internet
  • Porch
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$286

4 BR / 2 BA / Sleeps 8

1 / 23

Details

Located on Flanders Lane, this house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Walk to watch sunsets in Menemsha or dine in one of the places to eat there or take in a day at the beach. Additional amenities include: beach chairs, dock/boat-slip, coffee maker, bakeware, …
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$343

3 BR / 2 BA / Sleeps 6

1 / 24

Details

Pristine modern summer cottage with distant views of Lucy Vincent Beach, privately nestled on historic Eddy Farm, hillside, off of South Rd. This light filled home with acres of privacy is the perfect retreat for those looking for a long term summer stay in Chilmark with Lucy Vincent Beach just a couple of minutes …
  • Ocean or water views
  • Phone / Internet
  • Deck
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$1,215

6 BR / 4 BA / Sleeps 10

1 / 23

$1,215

Inquire

BRESP - Waterview, Association Beach

6 BR / 4 BA / Sleeps 10 | Quick view

Details

Contemporary Home commands one of Martha's Vineyard's most spectacular views overlooking the Elizabeth Islands and Vineyard Sound. Breathtaking sunsets. Outdoor patios and deck and multiple living areas provide many options for family gatherings or quiet times. Amenities and Features include... Waterview, …
  • Private Beach
  • Ocean or water views
  • Phone / Internet
  • Deck
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$383

3 BR / 3 BA / Sleeps 6

1 / 18

$383

Inquire

ITALA - North Slope Custom Home, Large Wrap Around Deck, WiFi

3 BR / 3 BA / Sleeps 6 | Quick view

Details

Contemporary Post and Beam home, private location, bounded by large oaks and stone walls. Enjoy this impeccably maintained 3 bedroom, 3 bath home. Custom designed and featuring a chef's kitchen. The cathedral ceiling great room is open to the spacious dining and kitchen area. Custom features include exposed wood beams…
  • Internet Access
  • Deck
  • Grill
  • Dishwasher
  • Microwave
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$386

3 BR / 2 BA / Sleeps 6

1 / 20

Details

This bright and cheerful, wooded retreat is truly tranquil, yet just a little over a mile from West Tisbury village, with its General Store (Alley's), Farmer's Market, Artisan's Festivals and Flea Market. This home has been recently updated by its new owners. They have chosen the loveliest colors and simple, …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$429

4 BR / 3 BA / Sleeps 8

1 / 24

$429

Inquire

LENOM HOUSE AT STONEWALL POND - CHIL RALD-138A

4 BR / 3 BA / Sleeps 8 | Quick view

Details

Enjoy sweeping water views across Stonewall Pond and Beach, as well as access to the private ocean beach at prestigious Stonewall Beach. Lenom House is tucked away between Stonewall and Quitsa Ponds, with dramatic water views of both well known Chilmark Ponds, plus the south shore and Stonewall Beach. The open first …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$493

4 BR / 2 BA / Sleeps 8

1 / 15

$493

Inquire

Charming Chilmark Guest House (Charming-Chilmark-Guest-House-CH225)

4 BR / 2 BA / Sleeps 8 | Quick view

Details

Perched high above the surrounding terrain, this affordable Chilmark rental offers sweeping views of the ocean and upisland all the way to Aquinnah. See the sunsets from the deck. It is spacious with 4 bedrooms to accommodate family and friends. See Chilmark rental #CH224 for family reunions or larger parties. Great …
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$572

3 BR / 3 BA / Sleeps 8

1 / 20

Details

Fabulous Chilmark home offers two levels of living sapce. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half bath, a master suite with private bath with …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$454

4 BR / 2 BA / Sleeps 6

1 / 24

$454

Inquire

LEWDG - Waterfront, Waterview, Walk to Beach, Hi Speed Internet, WiFi

4 BR / 2 BA / Sleeps 6 | Quick view

Details

Casual immaculately clean in picturesque Menemsha, Chilmark waterfront. Beautiful views. A short stroll to the beach, fish market, boutiques, fishing, and shore dinners. Guest House - Main House on property nearby may be occupied by Tenants or Owner. Amenities and Features include... Waterfront, Waterview, Walk to…
  • Waterfront
  • Ocean or water views
  • Phone / Internet
  • Deck
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$279

3 BR / 2 BA / Sleeps 6

1 / 15

$279

Inquire

PERRG - A/C, WiFi

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Amenities and Features include... A/C, WiFi Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, cd player, landscaped, porch - screened, outside shower - enclosed, vacuum, outdoor furniture, ironing board.
  • Phone / Internet
  • A/C or climate control
  • Patio
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$2,000

5 BR / 6 BA / Sleeps 10

1 / 16

$2,000

Inquire

1522 - WATERFRONT VINEYARD CONTEMPORARY HOME LOCATED ON TISBURY GREAT POND

5 BR / 6 BA / Sleeps 10 | Quick view

Details

Vacation in Chilmark near the pristine shores of the Tisbury Great Pond in this brand new, custom contemporary built with only the best materials. Four-bedroom main house with a detached guest suite. Open living / dining/ kitchen area with cathedral ceilings and exposed beams overlooking a luxurious setting by the …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

PreviousNext property

$2,036

4 BR / 3 BA / Sleeps 8

1 / 22

$2,036

Inquire

1199 - Beautiful Main House and Barn with a Pool and views over a Pond

4 BR / 3 BA / Sleeps 8 | Quick view

Details

A complete complex in a beautiful, peaceful setting: main house and barn with built-in pool, hottub, private tennis court and pond. One can walk to a lovely North Shore beach. This complex is surrounded by roses and perennials. Also, beach stickers for Lucy Vincent and Squibnocket are provided. Large kitchen supplied …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

PreviousNext property

$643

4 BR / 3 BA / Sleeps 8

1 / 7

$643

Inquire

1505 - ENJOY OCEAN VIEWS FROM THIS CHILMARK HOME

4 BR / 3 BA / Sleeps 8 | Quick view

Details

Unique combination of 1940's camp-style home and new (2007) two-story addition. Beautiful Ocean views from all floors, two decks, two living rooms and wonderful prevailing SW breezes. Five minute walk to Ocean Beach adjacent to Lucy Vincent Beach. Access to private Able's Hill Association beach and 3 tennis courts. …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Patio
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

PreviousNext property

$643

4 BR / 2 BA / Sleeps 8

1 / 18

$643

Inquire

1470 - Relax in the Pool and Enjoy Beautiful Views from this Vineyard Home

4 BR / 2 BA / Sleeps 8 | Quick view

Details

A fascinating, lovely classic Eliot Noyes (architect) contemporary in a private setting with spectacular views off the water looking toward Lucy Vincent beach and East towards West Tisbury. There is a great room (with dining, and living room and kitchen) with decks on either side (4-10 feet off the ground with two …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

PreviousNext property

$2,215

5 BR / 4 BA / Sleeps 8

1 / 13

Details

Located in a tranquil setting overlooking Chilmark Pond off of South Road this is a magical summer vacation spot. Additional amenities include: coffee maker, lobster pot, food processor, cd player, wine glasses, crib, cassette, pillows, outside shower, blankets, ironing board.
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

PreviousNext property

$1,072

6 BR / 5 BA / Sleeps 10

1 / 21

$1,072

Inquire

229 - ARCHITECTURAL AWARD WINNING HOME WITH PANORAMIC VIEWS OF THE VINEYARD SOUND

6 BR / 5 BA / Sleeps 10 | Quick view

Details

Spacious, 10 room, architectual award-winning design home perched atop a hill w/panoramic view of Vineyard Sound and the Elizabeth Islands. The large deck has marvelous water views and the sunsets are spectacular! Its charming interior includes a Living Room with vaulted ceilings,fireplace and bar;large, fully …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

PreviousNext property

$686

3 BR / 3 BA / Sleeps 6

1 / 16

$686

Inquire

746 - THE ESSENCE OF THE ISLAND WIITH ASSOCIATION BEACH

3 BR / 3 BA / Sleeps 6 | Quick view

Details

Beautifully restored, maintained, and furnished, this 1740 Island farmhouse is situated on 80 private acres of glorious Chilmark hills overlooking Menemsha Pond and includes a small private association beach on Menemsha Pond to wend your way down to. A little bit of heaven on earth! Additional amenities include: …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

PreviousNext property

$486

4 BR / 3 BA / Sleeps 8

1 / 21

$486

Inquire

286 - CHARMING COUNTRY HOME IN CHILMARK

4 BR / 3 BA / Sleeps 8 | Quick view

Details

Tastefully furnished and decorated with antiques and art. This upscale Chilmark summer home is an original Yankee Barn located off South Road that has all the accoutrements for summer entertaining. The post and beam structure features a beautiful cathedral living room brightened by southern light; has sliders out to a…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Books
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask
1 234
page 1 of 4
Load more