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Find peaceful homes for rent in Chilmark, a tranquil area of Martha’s Vineyard. Enjoy the serenity and beauty of this island gem.

Chilmark Vacation Rentals Martha's Vineyard

Homes for Rent in Chilmark, Martha’s Vineyard | MV Seacoast

Master Bedroom

Bedroom 2

Bedroom 3

Bedroom 4

Bedroom 5

Welcome to the gentle breezes of Ocean Pines in Katama.  This 2866 sq. ft. contemporary home and privately sited on 1 acre offers easy summer living near South Beach and a few minutes from the village of Edgartown.  There are two ensuite master bedrooms. The media room has a  plasma TV.  This room can double as a 5th bedroom with its daybed & trundle that can combine into a king size bed. The basement game room has ping pong table.  The private association tennis courts are nestled in the woods next door.  Smooth paved roads and safe bike paths provide easy access to South Beach and Edgartown Village. Multiple AC splits provide cool air throughout the house.

10 Old Dunham Corner Way

READY FOR 2025 BOOKINGS!
Beautifully crafted post & beam home nestled in a pastoral setting. To reach this three-bedroom air-conditioned oasis you drive past grazing Alpacas before turning right at the strawberry field. You enter thru the farmer's porch into an open floor plan. Three skylights in the family room provide natural sunlight. The dining area accommodates seating for eight. The kitchen includes all new appliances. The two bedrooms on the main floor each have large windows to take advantage of the island breezes and a set of French doors that lead to outdoor decks. The second-floor bedroom has an en-suite powder room and a private deck that provides a great spot for star gazing. Recent improvements to this charming house include a large screened porch off the great room, a completely remodeled master bathroom, updated to 3.5 bathrooms,  a new TV room and another primary bedroom en suite with a walk-in closet.

26 Bridle Path Road

Beautiful little 2 bedroom home in a quiet neighborhood.  It is brightly decorated and nicely furnished with an open living area porches & new appliances.  Impeccably maintained cottage used to be in the Campground before moving to the edge of East Chop.

12 Chickawaukee Street

Reverse contemporary designed with pleasing architectural angles to catch an ocean glimpse or open fields of conservation land. Cathedral living room open kitchen/dining plan with sliders to the large wrap-around deck. Perfect vacation home just a five minute walk to beautiful South Beach!  For 2019 many improvements - new kitchen counters cabinets & sink new 2nd floor shower and LR couch.

7-A Katama Farm South

READY FOR 2025 BOOKINGS.

Beautiful new contemporary in Dodgers Hole.  Open living-dining-kitchen Great Room with vaulted ceilings and beach stone fireplace.  Gourmet kitchen granite counter tops. 2 flat screen TV's.  Two master bedroom suites on the 2nd floor. A large deck and landscaped yard are perfect for outdoor entertaining or relaxing after a sunny day at the beach.
Property offers central AC

7 Sparrow Lane

This is a large single house with 2 levels 4 bedrooms on 2nd level master bedroom with separate full bath  front porch with lounging chairs full deck with table chairs and gas grill off dining room through sliding doors.  Good-size yard and walk-to-town make for a terrific family accommodation.  The finished basement has high ceilings and a media space perfect for the kids to hang out! The basement has a full bath with a shower and washer/dryer. The studio suite above the attached garage is very convenient for in-laws and guests.  It contains a Queen bed TV kitchenette full bath with shower private deck & grill.  Doors between the units can be locked for privacy.  There is an outdoor shower for use to remove sand.

80 Midland Avenue

Ready for 2025 bookings.

Historic Cape reverse set up, with living area, kitchen and powder room on the upper level with spectacular ocean views and the remaining living space on the lower level, consisting of an additional family room with a fireplace and double sofa bed, four bedrooms and two bathrooms. Upstairs the kitchen is fully equipped to create any meal. The living areas include dining as well as a tv and of course the panoramic ocean view. This private beachfront home is set back on one acre of lush lawn and landscaping. Be sure to meander to the beach which overlooks the sound depicting a clear view of the steamship authority ferry and various fishermen. You are minutes from the village of Oak Bluffs and an East Chop stroll.

BR1 King en suite with shower stall, 1st floor
BR2 Queen, 1st floor
BR3 Double, 1st floor
BR4 (2)Twin beds, 1st floor
Hall bath with tub/shower, 1st floor
Double sofa bed, 1st floor sitting room
Half bath, 2nd floor

10 Temahigan Ave

READY TO BOOK FOR 2025 SEASON!!
This very comfortable property will be one the family or friends want to return to year after year.  A clean well kept rental with two outdoor showers and a large deck on the front taking in plenty of sun! 4 Bedrooms with one being a large room on the 2nd floor that has King at one end,  4 twins at other end and Queen sleeper in the middle.  On the first floor  1 queen size bedroom. Primary ensuite bedroom with king size bad.  Living room  open to the Kitchen with an island and dining area make this a great social house for get togethers and barbecues !
Studio above garage - queen size bed plus a futon.
Property is located in the very popular area of Windsor Drive.  Close to the bike path. Across VH/Edg Rd is Felix Neck Sanctuary,  lovely walking neighborhoods of Majors and Hidden Coves connecting to Sengy Pond looking out to State Beach. Well worth the price!

1 Essex Court EDG

Rustic cottage with the original Sweet Water Farm silo right on Katama Bay Fantastic sunsets walk to South Beach clamming swimming boating at your doorstep.  Very comfortable. One of the best locations on Chappy. Carefree summer living. Small but adequate for 2 couples or small family.  There is a wood stove for chilly nights.  Walk to the Atlantic Ocean along the Bay.  A summer you will never forget.

108 Bayview Ave.

READY FOR 2024 BOOKINGS! A modest 3 bedroom ranch is tucked into a fabulous location! Just a short distance from the boat landing on Katama Bay and one half-mile from South Beach. In the recent renovation brings new paint updated kitchen, bathrooms and flooring. This property has a great back yard and an outdoor deck to BBQ and an outdoor shower. This is a wonderful location to walk or jog in the morning/evening. Pack a picnic rent Kayaks and launch at the landing and paddle to the South Shore for the day! And on your way back you can go clamming for your dinner! (Town of Edgartown sells the clamming license). Close to South Beach and close to the bike path and VTA bus to ride into Edgartown.  Also close to The Dunes South Beach Restaurant. A great location for a wonderful vacation!

11 Town Lot Road

This luxury enclave, complete with 4 bedrooms and 3.5 bathrooms, is located in a private community that is centrally located and comprised of upscale properties. The simply elegant home is a brand new construction that is nestled in a woodland setting with quaint views of a golden meadow and a beautiful pond. The stunning property connects to miles of walking/hiking trails and a bike path to Farm Neck Golf Club, in addition to 3 down island towns and beaches. With carefully crafted architecture, this house is full of character and integrity. The contemporary design offers upstairs and downstairs master bedroom suites as well as a first and second floor family-style living rooms complete with plasma screen TVs. At the top of the winding staircase is the hallway that wraps around to observe the open entry hall below. Two additional bedrooms are located upstairs with a bath and the kitchen has gorgeous cabinetry with high end appliances. There is wide oak flooring throughout and gleaming marble tile detail in the bathrooms. Other highlights include french doors that open to a large deck off of the living and dining room, complete with a table that sits 8 people, a lounge couch, and chairs. Additionally, there is a stone patio off of the first floor master bedroom, a stone fireplace anchors the living room, and a large and spacious backyard borders the back of the home.

24 Paddock Lane

READY FOR 2025 BOOKINGS

Welcome to the Falu House, a European-inspired A-Frame cottage in walking distance to the Lagoon and close to the Oak Bluffs town center!

This cozy home boasts two bedrooms and bathrooms, a perfect getaway for a memorable family vacation. The cottage has recently been renovated to create a comfortable, laid back vacation retreat. The open-concept living area is ideal for relaxing after a day of exploring the island, while a fully equipped kitchen invites you to whip up delicious meals for family and friends. The free-standing gas stove provides warmth and coziness during cooler nights. And with new air-conditioning in the living and bedroom spaces, you will stay comfortable during those warm summer days. 

Outside you will find a spacious deck overlooking the wooded surroundings--the perfect spot to savor your morning coffee. Use the charcoal BBQ grill to entertain legendary summer gatherings, or enjoy a glass wine by the fire pit on the newly added garden patio. A spacious outdoor shower completes your Vineyard experience! 

Both bedrooms offer comfortable queen-sized beds with premium cotton sheets. The property provides linens and towels and is pet- and infant-friendly (we offer a travel crib, high chair, and baby bath upon request). We also provide beach gear, including beach towels, a cooler, beach chairs, and a beach umbrella. 

The property is a five-minute walk to Lagoon pond where you can launch your kayak or paddle board and enjoy the sunset. The MV Sail Camp is also in walking-distance. Oak Bluffs Town Center is a 20-minute walk or 4-minute drive. The neighborhood is peaceful and quiet while close to all amenities as well as the ferry terminals in Vineyard Haven and Oak Bluffs.

Conveniently located in Oak Bluffs this house is a perfect home base for your Martha's Vineyard adventure.

Property provides linens and towels and is pet friendly.

86 Washington Ave

Welcome to Your Vacation Retreat on Renear Street.

Escape to this charming 4-bedroom, 2-bathroom home that comes with a car! (see details below), offering a perfect getaway for families, couples, or a gathering of friends. With space to comfortably sleep up to 8 guests, this property is ideal for making lasting memories.

Property Features:

4 Bedrooms: Two spacious bedrooms on the second floor each feature king-sized beds and a cozy sitting area. On the first floor, you'll find two queen-sized bedrooms—one with a built-in office space, perfect for those needing to work remotely.
2 Full Bathrooms: Modern and well-appointed, designed for comfort and convenience.

Open Concept Living: The fully-equipped kitchen features stainless steel appliances, including a microwave and dishwasher, and seamlessly flows into the living room. A chaise sectional sofa is perfect for movie nights, while bar stools invite conversation around the kitchen area.

Outdoor Space: Relax and unwind in the beautifully landscaped yard, offering privacy and tranquility. Enjoy morning coffee on the wrap-around deck with rocking chairs and a bistro table. In the evening, gather around the smokeless fire pit, sink into the two-person hammock, or enjoy a chair swing. The lawn also features a corn-hole setup for some friendly competition.

Outdoor Shower: After a day at the beach, rinse off in the convenient outdoor shower, or use the provided beach chairs, sun umbrella, and towels to make the most of your beach days.

Parking & Location: The property offers 2 parking spaces with additional street parking available in this quiet residential neighborhood. The Vineyard Haven Ferry is just a 5-minute drive away. Take a scenic walk along Lagoon Pond Road to reach Vineyard Haven, where you'll find a variety of restaurants, shopping, a movie theater, and the Martha’s Vineyard Museum steps away. Nearby beaches include Owen Park and Eastville, and you’re only 3 minutes by bike to the Edgartown-Vineyard Haven bike path.

Policies: No smoking, no pets.

Renting a car? Our house has a 2025 all-electric, all-wheel drive Toyota SUV available for rent on the Turo app. Rental rates on Turo are much lower than customary rental rates on the island, and there are no ferry car fees or ferry booking challenges in bringing a car to the island during the summer! This car offer is subject to availability. Go to Turo.com for more details and search for "Toyota bZ4X 2025" or try copying and pasting the following link to get to the car for rental: https://turo.com/us/en/suv-rental/united-states/tisbury-ma/toyota/bz4x/3125674?endDate=06%2F20%2F2025&endTime=10%3A00&searchId=wHUL2OcN&searchRegion=MA&startDate=06%2F17%2F2025&startTime=10%3A00.

This Vineyard Haven home is truly a retreat—perfect for relaxation and adventure alike. Book your stay today and experience the best of Martha’s Vineyard! This property features a year-round tenant in a studio apartment on the lowest level of the home, which has its private entry, indoor and outdoor space, and no shared space with the renting guests. With the Martha’s Vineyard housing shortage, providing housing for a year-rounder is a considerable value to the community.

3 Sisters Renear Retreat, w Car

This house has a 2025 all-electric, all-wheel drive Toyota SUV available for rent on the Turo app. Rental rates on Turo are much lower than customary rental rates. The car offer is subject to availability. Go to Turo.com for more details and to rent.

Chilmark Vacation Rentals Martha's Vineyard

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