Vacation Home Rentals By Owner In Chilmark, MA

Showing 45 Of 45 Vacation Rentals

$513.82

Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!

Chilmark, Massachusetts, United States

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. Below the house is our private, child-safe (no surf) beach on lake-like Menemsha Pond (3 minutes by car). Or enjoy key access to our 2nd private beach -- a spectacular site on the South Shore, offering both ocean surf and pond swimming (15 minutes by car). brLarge bay windows bring the 10-mile view right into the house.... or you can savor it first-hand from chairs on the quiet, sunny front porch. Upstairs: watch sailboat races on the inland ponds from two bright bedrooms (one king, one double twin/king), and spot rabbits or deer on the estate lawn from the upstairs study (daybed). Downstairs: the sofa pulls out to a bed in the living area (with adjacent handicap-access bathroom/shower room) to accommodate a wheelchair-bound guest. Efficient kitchen, washer/dryer, internet, cable TV, music, games and library promote easy relaxation at home! In fall and winter the house is a snuggery, with warm bedding, central heat.br[Please note: our small, historic but efficient staircase may prove a bit steep for the elderly, those with infirmities, or small pets].brbrMake your own memories in this historic property!: Lovey's Cottage guesthouse is part of the hilltop Tower House estate, an up-island landmark for its Queen Anne, yellow-painted main house with red roof, and ball-topped tower. The property has changed hands only once since beginning as a multi-acre farm in the early 1800's. It has been in our family for over 50 years now -- and is being cared for by a third generation for whom the estate property was their great summertime home.brbrBe private -- or part of your own larger group. Lovey's Cottage has its own parking and front entrance through a small walled garden that gives onto the beautiful view. Carefully designed to work as a completely independent and private residence, Lovey's can also be rented together with the Tower House* (which sleeps 10, in 5 bedrooms) -- an arrangement which works very well for weddings, or large groups of friends, or a family with varying needs and ages. Lovey's can be a wonderful solution for grandparents needing separate and quiet time, for in-laws valuing their personal space, or even for a young family with children's nap-time or early-bedtime requirements.brbrEnjoy the fall, or spring: Lovey's Cottage, with its central heat, is a wonderful spot to spend an off-season week, holiday, or get-away break. The rolling up-island landscape affords splendid open views, town beaches are accessible for long seaside walks, and island staffers at restaurants, attractions, and boutiques can take more time to welcome and converse with you than in their busier months. Many stores and services stay open into late fall, and re-open in early spring, so there's a 'buzz' to savor in these non-summer months!

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Exceptional(4)

$498.13

/ Nightly

Private Vacation Home

Quaint & Quiet Quitsa: 3-bedroom house with WiFi, AC in peaceful Chilmark

Chilmark, Massachusetts, United States

Make yourself at home in this brilliant 3-bedroom retreat. Nestled on Quitsa Pond, in walking distance of Squibnocket Beach, in the town of Chilmark, this gorgeous house is the perfect getaway for guests seeking relaxation and tranquility. Wake up and enjoy your morning coffee or tea on the deck overlooking the peaceful yard and pond. Walk to the water and fish or swim. This beautiful cape has been in our family for generations, but is updated to meet modern needs. With a king bed, bunk beds (twin top/full pullout futon below), and a queen bed, there's plenty of space for everyone to unwind. The two bathrooms offer one accessible shower and an upstairs bathtub/shower. The house features modern amenities like AC/heating, full size washer/dryer, a hair dryer, an iron, WiFi, streaming TV and a parlor grand piano . After a day of exploring, retreat to the cozy living room to play board games, watch a movie or just soak in the spectacular water-front view! Fall in love with Chilmark and enjoy all the magic it has to offer.

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Exceptional(17)

$367.85

/ Nightly

Private Vacation Home

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

Chilmark, Massachusetts, United States

Chilmark Guest HousebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrTucked 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 for beach-goers, as it sits within minutes of Menemsha (three miles), Lucy Vincent Beach (four miles), and Squibnocket Beach (five miles).brThe house enjoys a beautiful, natural setting, with thickets of woods surrounding the grassy lawn. On summer mornings, ride your bikes or walk less than two miles to the tranquil expanse of Great Rock Bight Preserve. Upon your return, linger outside on the deck and sip a steaming cup of coffee in a rocking chair. brbrIt's a joy to come home after a day at the beach, as you light the gas grill, set the outdoor table for a sunset dinner, and watch the kids release any lingering energy on the outdoor play structure. Back inside, lofty ceilings, exposed cross beams, and large panes of glass bring in an abundance of light and nature. As a result, you'll feel surrounded by the island's beauty as you cook in the kitchen, play board games at the table, and stream movies in the living room. brbrBoth bedrooms open to the deck, one of which is a charming children's room with bunks and a selection of toys and books. A private washer/dryer and complimentary WiFi are provided for your comfort and convenience as well.brbrThings to KnowbrbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.brParking notes: There is free parking available for 3 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

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Exceptional(9)

$1258.84

/ Nightly

Private Vacation Home

Private Hillside Home, Fully Equipped Kitchen, Dog-Friendly, A/C, W/D

Chilmark, Massachusetts, United States

Hillside OakbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNestled in the serene scrub oak forest of Chilmark, this stunning 4-bedroom home offers a perfect retreat for families and friends seeking a peaceful getaway on Martha's Vineyard. With an open floor plan and an abundance of windows, the contemporary design allows natural light to flood the space, creating a warm and inviting atmosphere. The home features two queen beds and two double beds, accommodating up to eight guests comfortably. Enjoy the convenience of a fully equipped kitchen, complete with a new stove and modern appliances, perfect for preparing meals together.brbrStep outside onto the expansive patio and take in the tranquil surroundings, or fire up the gas grill for a delightful barbecue under the stars. The property is dog-friendly, so you can bring your furry friends along to enjoy the lush outdoor space. A short 10-minute walk leads you to the private Brickyard beach, where you can relax and soak up the sun, while the nearby Menemsha Hills and Brickyard trail system offer miles of scenic hiking paths for outdoor enthusiasts.brbrLocated just a short drive from some of the island's most beautiful beaches, including Lucy Vincent Beach and the vibrant town of Oak Bluffs, this home is ideally situated for exploring all that Martha's Vineyard has to offer. With the Vineyard Haven ferry only 15 miles away, you can easily venture off the island for day trips or excursions. brbrWhether you're looking to unwind in nature, enjoy family game nights with the provided board games, or explore the local attractions, this Chilmark home is the perfect base for your island adventure. Book your stay today and experience the beauty and charm of Martha's Vineyard!brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 4 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

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Exceptional(24)

$769.65

/ Nightly

Private Vacation Home

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks

Chilmark, Massachusetts, United States

The Eliot NoyesbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrEnjoy the beauty of Martha's Vineyard in classic mid-century style at this four-bedroom Chilmark home! This is a unique and secluded architectural gem with a private swimming pool and deck, beautiful ocean views, and nearby access to some of the island's most sought after beaches.brbrBuilt in 1964 by the award-winning architect Eliot Noyes, of The Harvard Five, the residence was featured in Life Magazine. This iconic single-level home sits just five minutes from Menemsha beach. The property is wonderfully private, yet it's also only three minutes from Lucy Vincent Beach and three miles from the recently renovated Squibnocket Beach; both of which can be accessed by bringing the rental agreement to town hall at Beetlebung Corner for the permit.brbrWith exterior walls constructed almost entirely of floor-to-ceiling glass, this oceanview home is composed of three components closely connected by covered decks. It’s the perfect place for a family getaway, a stylish retreat, or a beach vacation with close friends.brbrStep inside the open living space to find an abundance of mid-century design, exposed wood ceilings, and plenty of seating for your guests. Admire the views of the ocean and the surrounding trees and garden as you choose a book from the shelves, sit down to play a board game, browse the WiFi, or curl up by the flatscreen cable TV.brbrWake up each morning with the help of the Nespresso machine in the kitchen, which also features open shelving and a dishwasher for your convenience. Flip pancakes and scrambled eggs with your kids and sit down as a family around the dining table for eight.brbrYou'll be only a short drive from Menemsha, Lucy Vincent, and Squibnocket Beaches, but you'll also have access to a gorgeous private swimming pool. Sunbathe on the deck with a cocktail in hand, play a game of cards at one of the patio tables, and then light the gas grill for an afternoon barbecue. brbrThe yard, enclosed by a beautiful stone wall, offers a wonderful space for picnicking, playing and relaxing, while the outdoor shower and private washer/dryer help keep the sand and grass outside.brbrWith four bedrooms (that are separate from the main living area) and two bathrooms, The Eliot Noyes will accommodate as many as eight guests. You'll find one king bedroom, one queen bedroom, and two bedrooms with a set of twin beds apiece - each of which opens onto a gorgeous, private deck space.brbrKnown for its tranquil atmosphere and scenic natural beauty, Chilmark is the perfect place to escape the hustle and bustle of everyday life. Spend your days basking in the sun on Menemsha Beach or pick up a pass to access the private stretches of sand at Lucy Vincent and Squibnocket Beaches. brbrYou'll also be just three miles from the Menemsha Hills Reservation, a 211-acre expanse that is ideal for hiking among wetlands, woodlands, and the island's second-highest peak.brbrCome and experience this stunning glimpse of island life. Book your getaway at the Eliot Noyes House on Martha’s Vineyard today!brbrParking notes: There is free parking available for 3 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

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Most popular vacation rentals in Chilmark

Exceptional(24)

$568.98

/ Nightly

Private vacation home

Peaceful Chilmark Farmhouse by Menemsha Beach

Chilmark, Massachusetts, United States

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Exceptional(24)

$805.84

/ Nightly

Private vacation home

Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches

Chilmark, Massachusetts, United States

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Exceptional(24)

$781.90

/ Nightly

Private vacation home

Pet-Friendly Historic Chilmark House

Chilmark, Massachusetts, United States

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Exceptional(24)

$745.52

/ Nightly

Cottage

Chilmark pond side cottage with beach access, sweeping views

Chilmark, Massachusetts, United States

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Exceptional(24)

$710.09

/ Nightly

Cottage

Bright and cozy menemsha cottage

Chilmark, Massachusetts, United States

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Exceptional(24)

$599.88

/ Nightly

Private vacation home

Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby

Chilmark, Massachusetts, United States

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Exceptional(24)

$596.33

/ Nightly

Private vacation home

Beautiful Chilmark beach house. Great screen porch. Fun house. Pet friendly.

Chilmark, Massachusetts, United States

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Exceptional(24)

$411.69

/ Nightly

Private vacation home

Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.

Chilmark, Massachusetts, United States

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Exceptional(24)

$417.79

/ Nightly

Cottage

Charming Rustic Cottage

Chilmark, Massachusetts, United States

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Exceptional(24)

$419.67

/ Nightly

Private vacation home

Tilton House - Menemsha Harborside

Chilmark, Massachusetts, United States

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Bath

Sleeps

Vacation Home Rentals By Owner In Chilmark, MA

$513.82

$498.13

$367.85

$1258.84

$769.65

Rent a place that suits your needs

Most popular vacation rentals in Chilmark

$568.98

$805.84

$781.90

$745.52

$710.09

$599.88

$596.33

$411.69

$417.79

$419.67

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