House vacation rentals in Chilmark

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Top-rated house rentals in Chilmark

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Guest favorite

A spacious living area showcases wooden flooring and high ceilings with exposed beams. Large windows fill the space with natural light, while a cozy sofa and a white coffee table invite relaxation. A kitchen area is visible in the background, providing a functional and open layout.

Home in Tisbury

4.94 out of 5 average rating, 133 reviews

Vineyard Haven Walk to Ferry

I love this neighborhood! It is quiet, peaceful, and only a short walk to either Tashmoo Beach or downtown Vineyard Haven and the ferry. The house has plenty of outdoor space with it's own wood fired pizza oven, fire pit, garden and decks. There are nice seating areas near the fire pit, on the lower deck and on the upper deck. Walk through the backyard, down a dirt road and be at the water in five minutes. Beach towels included! Plenty of sliding glass doors and LOTS of light. Vitamix included!

Guest favorite

A clear view of Vineyard Sound is visible through the surrounding trees, showcasing the serene blue waters extending to the horizon. The gentle outlines of land can be seen in the distance, framed by lush greenery and a tranquil atmosphere.

Home in West Tisbury

4.97 out of 5 average rating, 105 reviews

Lambert's Cove Retreat, Water view, Beach pass

Enjoy stunning views of Vineyard Sound from this cozy three bedroom two bath home in a quiet neighborhood just minutes from Lambert's Cove Beach. This upside down house has one bedroom on the main level along with a full bath and open kitchen, dining, and family room. The downstairs has another living space, two bedrooms, laundry room, and full bath. Enjoy family time in the open upstairs with water views, or retreat to the lower level living room for some separation, quiet time, or work space.

Guest favorite

An outdoor deck with a wooden dining table and matching chairs is shown, illuminated by a vibrant sunset. Lush greenery and the neighboring buildings can be seen in the background, creating a peaceful setting for dining al fresco.

Home in Chilmark

4.96 out of 5 average rating, 27 reviews

Fun, Authentic, Waterfront Cottage/air conditioned

This authentic beach cottage is centrally-located in the fishing village of Menemsha with stunning views of the sunset, the harbor, the beach and Menemsha Creek. Charter a fishing boat in the harbor across the street or spend the day on the beach just a few steps away. As you meander back to the house, pick up fresh fish to grill on the deck or pre-cooked lobsters and steamers. If you prefer to eat out, rinse off in the outdoor shower and take a walk around the corner to dinner with a view.

Guest favorite

A charming post and beam house is set back from a sandy driveway, surrounded by lush greenery and colorful flowers. Large windows on the upper level allow for natural light, providing a welcoming entrance to the home.

Home in West Tisbury

4.97 out of 5 average rating, 145 reviews

Secluded Up Island Cottage

Charming Martha's Vineyard post and beam house on two secluded acres with two bedrooms in West Tisbury. The master bedroom has a queen bed, the second bedroom has a full bed, the loft has a full size futon. It is peacefully tucked away at the end of a road with only three other houses on it. It has easy access to beaches, bike paths and walking trails. Enjoy some family time in the wooded backyard grilling or relaxing with an outdoor shower or napping in the hammock after a day at the beach.

Top guest favorite

The exterior of a charming house is shown, featuring a gray shingle facade and a welcoming covered porch. Lush greenery and ornamental shrubs frame the entrance, while a gravel driveway leads up to the front door, creating an inviting approach.

Home in Oak Bluffs

4.93 out of 5 average rating, 198 reviews

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, ENDS 9/1) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

Guest favorite

The exterior of the yurt showcases a circular wooden structure with large, rounded windows, complemented by a metal roof. A private yard features lush greenery, colorful flora, and outdoor seating arrangements, creating an inviting space for relaxation and outdoor activities.

Home in Oak Bluffs

4.91 out of 5 average rating, 254 reviews

Unique Luxury Yurt w/ Free kayaking

Step into this unique yurt house! As soon as you walk in, you'll be greeted with a one-of-a-kind experience, from the textured concrete floors to the large circular skylight. Every detail is carefully planned, and you'll have the opportunity to unwind in a spacious private yard. Spend your evenings stargazing, take advantage of complimentary paddling, participate in our scheduled chicken feedings, do yoga in the roomy loft, and revel in the splendor of your exclusive island yurt!

Top guest favorite

A cozy living area features a stone fireplace, with a muted flame providing a warm glow. Above, a flat-screen TV is mounted against white shiplap walls, complemented by exposed beams. A dark wood coffee table sits at the center, surrounded by comfortable seating and decorative accents.

Home in New Bedford

4.99 out of 5 average rating, 232 reviews

Historic Cobblestone Carriage House near Downtown

Enjoy a piece of history at this carriage house! Jonathan Bourne owned a mansion along with this home, and his son purchased a whaler, Lagoda, in 1841. The ship is currently displayed at the New Bedford Whaling Museum, which is walking distance; just four/five blocks of downtown New Bedford, where you can also enjoy shopping, great food, entertainment, and the ferry to either Martha’s Vineyard or Nantucket. New 2025 (MBTA) commuter train rail to Boston and more. Check it out!

Top guest favorite

The exterior of the charming cottage is surrounded by lush greenery and mature trees. A well-maintained path leads to the entrance, framed by a green hedge. The inviting façade features a sloping roof and bright windows, creating a serene rural atmosphere.

Home in Woods Hole

4.93 out of 5 average rating, 121 reviews

Juniper Point Cottage With Ocean View

Charming Cape Cod cottage on semi-private road with and ocean view of Vineyard Sound. Renovations completed in mid-July, 2020. Three BR, 2 private attached baths, 1 semi-private bath, fully equipped kitchen, patio with BBQ grill, gas fireplace, cable-TV, WiFi internet, large second-floor deck, a/c.. Close to Vineyard Ferry, bus station and town. Seasonal rent. Please complete a reservation request to determine the rent in effect for your requested dates.

Guest favorite

The front exterior of the house is shown surrounded by lush greenery, featuring a well-maintained lawn. A pathway leads to the entrance, and the porch offers seating. Two sun loungers are positioned on the grass, inviting relaxation in the open space.

Home in Oak Bluffs

4.92 out of 5 average rating, 118 reviews

** Vineyard Vacation Retreat ** with HOT TUB

Gated 2br house with lots of different places to lounge and relax. Drive through the 10’ granite gate onto the shell driveway. The house is filled with art from local artist Alan Whiting, Colin Rule, Kara Taylor and Scott McDowell. There is so much to do and explore. The adventure is just starting so make sure to pack up your swimmers, suntan lotion and get out the door. Kick back and relax, you're home.

Guest favorite

The open living space features comfortable leather seating, a coffee table, and decorative pillows. A ceiling fan provides airflow, while natural light enters through large windows. The kitchen and dining area are visible in the background, showcasing a well-equipped space with modern appliances.

Home in Teaticket

4.93 out of 5 average rating, 122 reviews

Cute Single Family Home in Nice Neighborhood

Hello! We have an adorable two-bedroom (bedrooms are very small), single-family home within walking distance to the beach. (Bristol Beach is 3/10 of a mile away, and Falmouth Heights Beach is 1/2 mile from the house). Perfect for a family of 4 or couples retreat. Please note that the bedrooms are very small and neither of them can accommodate any sort of portable crib, such as a Pack and Play.

Guest favorite

An enclosed front porch features multiple windows providing a view of the surrounding greenery. Two rocking chairs are positioned on a patterned rug, alongside a wooden table and lamp. Natural light fills the space, creating a bright and open atmosphere.

Home in West Tisbury

5 out of 5 average rating, 46 reviews

Idyllic renovated home across from Seth's Pond

Idyllic renovated farmhouse across from Seth's Pond and 0.6 miles from the infamous Lamberts Cove beach. Enjoy the views from the expansive enclosed front porch, play in the 2 acre yard and relax on the back patio with hardlined gas grill. Brand new kitchen, many recent renovations and a fully stocked home ensure a comfortable stay

Guest favorite

A rustic barn exterior is presented, featuring large wooden doors with diamond-shaped windows. The structure is surrounded by lush green foliage, with a sturdy tree partially framing the scene. The warm tones of the wood contrast with the natural surroundings.

Home in Oak Bluffs

4.95 out of 5 average rating, 464 reviews

Studio apt in newly built barn

Gorgeous private apartment in the upstairs of our new post & beam barn. The apartment has a private entrance and is situated above my husbands workshop. It is a studio (all one open space), with one queen bed and a full size pullout couch, there is a kitchenette and bathroom.