Family-friendly vacation rentals in Aquinnah

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Top-rated family-friendly rentals in Aquinnah

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A bright sleeping area features a spacious white bed with decorative pillows and bedside lamps. A small kitchen area with light-colored cabinetry is visible in the background, complemented by a large window allowing natural light. A cozy seating area adds to the warmth of the space.

Guesthouse in Chilmark

4.98 out of 5 average rating, 247 reviews

Beautiful Guest House in Chilmark

This newly renovated guest house is located in a quiet and very private setting in Chilmark. The guest house is located above the garage adjacent to the main house with a private entrance. It has a queen size bed with two oversized chairs. There is a full bathroom and outdoor shower. A small kitchen features butcher block countertops, stainless steel sink, refrigerator and 2 burner electric stove and island. Air conditioning and heat. The space comes with a walk -on-pass to Lucy Vincent Beach.

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Guest favorite

Home in West Tisbury

4.96 out of 5 average rating, 123 reviews

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.

KitchenIndoor spacesWalkability

Top 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

4.98 out of 5 average rating, 51 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.

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Top guest favorite

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.

Guest suite in West Tisbury

4.95 out of 5 average rating, 188 reviews

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.

KitchenFamilyView

Top guest favorite

A historic home features classic New England architecture, with a peaked roof and wooden shingle siding. White trim outlines the windows and door, while a white picket fence surrounds the property. Lush greenery and colorful flowers enhance the welcoming exterior under a clear blue sky.

Home in Sandwich

5.0 out of 5 average rating, 247 reviews

Quintessential Waterfront Historic Cottage

Set in a historic district and on a quiet pond shore, create memories with family and friends that will last a lifetime. Enjoy quintessential New England views from every angle. Coffee, restaurants, shopping & a fresh spring water fountain within a short walk to village center and under a mile to the nearest beach. Spend time walking the local area, exploring Cape Cod and relaxing in an atmospheric setting. Each room has been curated in a timeless tone, with relaxation and comfort in mind.

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Top guest favorite

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.

Guesthouse in West Tisbury

4.98 out of 5 average rating, 124 reviews

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.

FamilyIndoor spacesLocation

Top guest favorite

The open living area features exposed wooden beams overhead and includes a spacious wooden dining table. Two lounge chairs, a round pouf, and a day bed are arranged for seating. Natural light filters in through large glass doors, leading to an outdoor area.

Guesthouse in Chilmark

4.99 out of 5 average rating, 116 reviews

4-Season Guest House on Historic Chilmark Estate

Beautiful private guest house in Chilmark on Martha's Vineyard. Secluded yet convenient. Drive on pass to spectacular Chilmark beaches! Newly renovated and gorgeous. Great location - 10 minute walk to Chilmark Store. Full kitchen, living area, kitchen island/dining table, queen bed, day bed (not for sleeping), fireplace/heater, private outdoor shower, deck and picnic table, full bath inside. Keurig machine. 2 friendly labs/3 chickens on premises. Easy bus access. Old-style MV charm.

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Guest favorite

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.

Home in Oak Bluffs

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.

Indoor spacesFamilyCleanliness

Top guest favorite

A charming two-story home is framed by vibrant greenery and colorful shrubs, with a paved pathway leading to the entrance. Solar panels adorn the roof, reflecting a commitment to sustainability. Lush grass and well-maintained landscaping create an inviting atmosphere.

Home in Falmouth

5.0 out of 5 average rating, 171 reviews

Private Pond-side Cape Cod Home

Charming 2 bedroom home located on Flax Pond. Enjoy a private sandy beach and dock. Swim, kayak, fish, boat (trolling motors only) and just relax. Enjoy the home’s spacious deck with comfortable seating for the whole family complete with chiminea for late night fires. 2 levels of lodging with central air. 2 full bathrooms, kitchen, dining room and great room. Minutes away from town beaches, bike path, golf, and shopping. Parking for approximately 4 cars.

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Top guest favorite

The image captures a panoramic view of the ocean, surrounded by lush greenery. The tranquil blue water extends to the horizon, with a distant lighthouse visible on a rocky coastline. A clear sky overhead enhances the natural beauty of the landscape.

Home in West Tisbury

4.96 out of 5 average rating, 109 reviews

Lambert's Cove Oceanview Beach Pass Trails nearby

Traditional salt box home set in the forested hills above Lambert's Cove. Short walk / drive to town beach. Perfect for family gatherings, home has 3 bedrooms , a loft for virtual work space or reading room, 1.5 baths plus the fully enclosed outdoor shower, fully stocked kitchen, a deck that has seating for relaxing and also an octagonal picnic table, as well as lots of yard space for children or pups to play. Beach towels along with4 beach chairs provided.

FamilyIndoor spacesView

Guest favorite

A charming farmhouse is set against a backdrop of autumn foliage, featuring vibrant trees and a cloudy sky. A garden with various plants and flowers is visible in the foreground, adding natural texture to the scene.

Loft in Westport

4.87 out of 5 average rating, 345 reviews

Brithaven Farm

Brithaven Farm is on 28 acres of fields, woods meadows and gardens. We are just 2 miles from East Beach and the Allen's Pond Wildlife Sanctuary. We are completely private from the road and reached by a long laneway through woods which opens up to fields and meadows The rental has 2 decks, one with a large awning with dining table and chairs to lounge and take in the view. There is an open plan living, dining kitchen area with french doors leading to the deck.

Indoor spacesFamilyQuiet

Guest favorite

The exterior of a charming multi-level home is showcased, featuring a spacious deck with seating and an umbrella. A stairway provides access to the upper level, surrounded by lush greenery. Large windows offer views of the wooded surroundings, creating a sense of integration with nature.

Home in Falmouth

4.97 out of 5 average rating, 167 reviews

Mid-Century Modern home 5 minute walk to beach

Perfect for a family or friend's getaway- relax and unwind in this unique home that feels like a treehouse. Hang out on the fully furnished decks, stargaze on the roof deck, or stroll to Wood Neck beach and explore the marsh. Close to Falmouth restaurants and shopping, Shining Sea Bikeway, and other Cape Cod attractions.

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