Family-friendly vacation rentals in Chilmark

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Chilmark

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

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Guest favorite

A vibrant green kayak glides over calm waters, with a person seated inside holding a paddle. In the background, a cottage displays large wall-to-wall windows reflecting the surrounding trees, providing a connection to nature.

Cottage in Sandwich

4.95 out of 5 average rating, 229 reviews

WOW VIEW! Waterfront w/ Private Beach, King Bed!

Wake up to magnificent panoramic views of a beautiful lake with waves lapping below your window! Search on YouTube for tour: "WOW View! Cape Cod Lakefront Cottage. Private Beach, King bed" Guests love this stylish and open cottage on the shore of a large recreation lake with its own private beach. Wall-to-wall floor-to-ceiling windows with a new modern kitchen, luxurious King gel/coil bed, office space, bathroom with curved shower, and much more! It's like being on your own luxury houseboat!

Guest favorite

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.

Guest suite in Oak Bluffs

4.95 out of 5 average rating, 364 reviews

Lovely 2 BR Oak Bluffs Apartment

This 100% private apartment is on the first floor of a shared house where owners and their son live upstairs. There are no shared spaces. You have a private entrance and parking. The living room, bedrooms, bathroom, and kitchenette are bright and clean. It is exactly 1 mile from Oak Bluffs Center, a half mile from The Cottages and Farm Neck Golf Course, and a block from Tradewinds walking trails. Across the street is the bike path, & the bus stop is on the corner for easy island transportation!

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

A kitchen area features a bar with three wooden stools, inviting casual dining. Hanging pots and pans are showcased above the counter, while a vase of red roses adds a touch of color. A brick wall complements the white cabinetry and appliances.

Apartment in Tisbury

4.93 out of 5 average rating, 125 reviews

Harbor view apartment, a quick walk from the ferry

This is a great one bedroom apartment on the second floor of a house. My place is close to the beach, public transport, the Steamship Authority ferry, Black Dog Tavern, Main Street Vineyard Haven, Stop & Shop grocery, and lots of great shopping. You’ll love the convenience! Walk to the apartment right off the ferry boat. Lots to do in walking distance, and onsite parking. The Martha's Vineyard Museum is a 5 minute walk, down the same street. My place is great for couples and solo adventurers.

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

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, 215 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 in addition to a private outdoor shower. A small kitchen features butcher block countertops, a stainless steel sink, refrigerator and electric stove. Central air conditioning + heat make it the perfect getaway for all seasons.

Guest favorite

The exterior of the cottage is shown, featuring a welcoming blue door and a well-maintained front yard with colorful flowers. The view includes a quiet street lined with trees and nearby houses, providing a glimpse of the neighborhood atmosphere.

Cottage in Fairhaven

4.84 out of 5 average rating, 223 reviews

Cottage by the Bay

Cottage in Fairhaven, perfect for a vacation for a small family, a romantic getaway or a home away from home if you are in the area for business. Enjoy all a vacation has to offer. During warmer weather, walk to the public beach and boat ramp - swim, sun, boat. Spend evenings by the outdoor fireplace. When it is cold out side, enjoy parks, museums, arts and cultural events, with evenings spent enjoying hot chocolate in front of the gas stove as the fire blazes providing a cozy warmth.

Top guest favorite

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

4.98 out of 5 average rating, 342 reviews

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.

Guest favorite

A coastal-themed painting is displayed near a bright blue door. The artwork features sandy shores and gentle waves, complemented by tall grasses, conveying a serene beach scene.

Apartment in Falmouth

4.95 out of 5 average rating, 171 reviews

Your Private Garden

**10% discount for 7 night stays - One bedroom 2nd floor apartment in my owner-occupied home- perfect for a couple - with a spacious eat-in kitchen, shower bathroom, generous living room and separate bedroom. Bright and airy-in a prime location-1/2 block from Main Street, a block from Falmouth Harbor, an easy walk to the beach...with off-street parking. Relax in the secluded area -your Private Garden. Longer bookings eligible for a discount. No smoking please, and no pets.

Top guest favorite

A spacious deck features two wooden Adirondack chairs facing a serene waterfront view of Vineyard Sound. Lush greenery surrounds the area, and the calm water reflects the soft hues of the sky, creating a peaceful outdoor setting.

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.

Top guest favorite

Aerial view showcases a peaceful coastal neighborhood, with homes set against a backdrop of the ocean. The green lawns and sandy shore create a harmonious landscape. Soft clouds drift above, and the water glistens under natural light, enhancing the serene coastal environment.

Apartment in Little Compton

4.96 out of 5 average rating, 320 reviews

Home by the Sea

Private entrance to the full 1st floor with an ocean view in quiet neighborhood. The apartment features a bedroom with full sized bed, private bathroom, private living room with dining area, gas fireplace, tv and couch. Washer/dryer, refrigerator, microwave, coffee maker, toaster and hot plate included are in the apartment. There also is an additional outdoor H/C shower, private patio and gas grill.

Top guest favorite

A charming cottage surrounded by lush gardens features a stone pathway leading to the entrance. Vibrant white hydrangeas and green foliage create a serene atmosphere. The inviting porch, framed by greenery, provides a glimpse of the comfortable outdoor space.

Cottage in Tisbury

4.98 out of 5 average rating, 203 reviews

Little Lobster - King size bed

Adorable new cottage, 10 minute walk to Vineyard Haven. Wonderful, cotton soft waffle robes. Garnet Hill linens and towels. Gas grill, full kitchen with all accessories. Beautiful landscaping. Lovely farmers porch with adirondack chairs and table. Very private. Off street parking. No dogs or any pets of any kind, . Please only 2 people. Children are people!