Family-friendly holiday rentals in Dukes County

Guest suite in Oak Bluffs

A spacious living room is highlighted by a large grey sectional couch adorned with various throw pillows. A wooden coffee table sits in front, featuring storage compartments. Two abstract paintings in calming blues are displayed above the couch, while soft lighting illuminates the area.

Lovely 2 BR Oak Bluffs Apartment

*To returning guests: Airbnb has restructured their fees; so while our nightly price may look higher at first glance, it is our same pricing overall This private apartment is on the 1st floor of a family home with a personal entrance & parking; owners and their son live upstairs. There are no shared spaces. It is a mile from Oak Bluffs Center, a half mile from the Cottages and Farm Neck Golf Course, and across the street is a bike path. The bus stop is on the corner for easy island wide travel!

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4.95 out of 5 average rating, 434 reviews

4.95 out of 5 average rating, 103 reviews

The exterior of the barn features wooden double doors that provide access to the interior. A stone wall runs along the garden, accompanied by seating areas consisting of a picnic table and two chairs. Lush greenery surrounds the property, enhancing the secluded feel.

Guesthouse in Chilmark

Beautifully Renovated 1800s Chilmark Barn

Beautiful 2-story private barn in Chilmark on Martha's Vineyard. Secluded yet convenient. Perfect for a couple or a couple with older children (space not good for those with mobility issues). Downstairs living area, dining area, fridge, toaster, coffee maker, half bath -- shower is outside in the private garden. Loft-style sleeping area upstairs (2 private sections). 2 friendly labs and 5 chickens on premises. Walk to Chilmark Store, easy bus access. Walk-on pass to town beaches, no car pass

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4.96 out of 5 average rating, 123 reviews

Home in West Tisbury

Lambert's Cove, 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.

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Guest suite in West Tisbury

A spacious guest suite is illuminated by natural light from multiple skylights. The room includes a comfortable queen size bed with crisp linens, a sitting area with a light-colored couch, and a coffee table. Wood flooring adds warmth to the inviting atmosphere.

The Loft Guest Suite. Private. Newly Renovated.

This beautiful guest suite is a 5 minute walk to the village of West Tisbury on Martha’s Vineyard and has a private entrance on the 2nd floor of our newly renovated modern barn house. Surrounded by trees, beside a large meadow, this large 400 square foot suite has vaulted wood ceilings and skylights. Enjoy the outdoor shower and new outdoor sitting area. The location is centrally located, a short walk to a village, providing amenities. Ask about our other guest suites if you are with others.

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4.95 out of 5 average rating, 184 reviews

Guesthouse in West Tisbury

An open studio layout is showcased, featuring a spacious bed with a metal frame. A cozy seating area is arranged with patterned cushions and a wooden coffee table. Natural light pours in through multiple windows, illuminating the warm wood flooring and inviting ambiance.

Vineyard Meadow Artist Studio

This lovely artist's studio is just steps from miles of trails. Walk to the beach or meander through the woods of Long Point Wildlife Refuge, experiencing the serenity of this still untouched corner of Martha's Vineyard. This studio includes a bathroom with a shower, a washer/dryer and a kitchenette. It is the perfect spot for a lone artist, a couple or a family to enjoy Martha's Vineyard any time of year. This property shares the driveway and parking with Vineyard Meadows Writer's Cottage.

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4.98 out of 5 average rating, 123 reviews

A charming cottage is framed by a lush garden with vibrant flowers. The front porch features two rocking chairs, inviting relaxation. Soft lighting emanates from inside, through the gothic-style windows, under a welcoming blue roof surrounded by greenery.

4.92 out of 5 average rating, 212 reviews

impeccable cottage STEPS to downtown OB & beach!

Unique opportunity to stay in an impeccable cottage in Downtown Oak Bluffs. With a front porch with rocking chairs, a back deck & grill, & an outdoor shower, and A/C! - this is the ideal oasis for your Vineyard Vacation. Turn right and find yourself steps from restaurants & shops on Circuit ave. Turn left and walk 5 mins to beautiful beaches. Everything you want out of vacation at your fingertips. Relax, and truly experience the Vineyard the way it was meant to be, at the @WeePackemInn

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4.97 out of 5 average rating, 355 reviews

A cozy outdoor seating area is arranged with several white lounge chairs on a gravel surface. A brick fireplace is positioned near the house, accompanied by potted plants and a view of the deck area adorned with covered furniture in the background.

Cottage in Tisbury

Martha's Vineyard Getaway Cottage

Contemporary cottage on quiet, private, wooded lot. Pristine, bright & comfortably furnished. Open living area, hardwood floors, vaulted ceilings, indoor/outdoor fireplaces, well appointed kitchen, washer/dryer, cable/internet/phone with unlimited national calling, SmartTV with Netflix and additional internet streaming services. Walk or bike to beaches and trails, 5 minute drive from downtown shops and restaurants. Property abuts West Chop Woods with lovely, quiet walking trails.

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An open living area features a light-colored sofa adorned with blue and white cushions. A flat-screen TV is mounted above a white brick fireplace. Large windows provide natural light, and a dining area with a table and chairs is visible in the background.

4.96 out of 5 average rating, 135 reviews

**Vineyard Vacation Retreat** -3 BR

Just a stone's throw from Oak Bluffs and it's beaches, this chic 3 bedroom home provides comfort and privacy. The large bedrooms and open concept kitchen/dining/living area accommodate up to 6 people comfortably. A place for you to put your feet up, kick away your worries, and enjoy some rest and relaxation. 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.

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A spacious two-story home is set against a backdrop of lush greenery. The exterior features a covered front porch with seating and a well-maintained lawn, complemented by colorful flower beds along the walkway. Large windows invite natural light into the inviting space.

4.93 out of 5 average rating, 113 reviews

Vineyard Social-Spacious 5BR Home in Oak Bluffs

Experience comfort and style in this newly completed 5-bedroom home just 1 mile from downtown OB. The home features fantastic outdoor spaces, including a large front Farmers Porch and an oversized Patio with a gas grill. Enjoy all the desired amenities, including an outdoor shower, an open kitchen layout, and a 75" Smart TV. Both walkable and bikeable to Oak Bluffs Center and Harbor you can easily explore the town's lively shops, restaurants, and local attractions.

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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.

4.93 out of 5 average rating, 322 reviews

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

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Guest suite in Oak Bluffs

Quiet Hide Away

Lovely efficiency suite with private entrance in a quiet neighborhood. Private space located over attached garage. Plenty of space for two guests. Comfortably appointed with queen bed, dining set, living area with tv and full bath. Enjoy a coffee or cocktail on the private deck. Toaster oven, refrigerator and coffee maker will start your day right before heading to nearby beaches, golf courses or shopping.

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4.98 out of 5 average rating, 206 reviews