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

Guest suite in Oak Bluffs

4.94 out of 5 average rating, 308 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!

Jan 4 – 11

R1,905 ZAR per night

Guest favorite

Home in West Tisbury

4.98 out of 5 average rating, 123 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.

Jan 10 – 17

R4,738 ZAR per night

Guest favorite

Home in Oak Bluffs

4.93 out of 5 average rating, 169 reviews

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and the outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, 6/21) 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!

Apr 18 – 25

R12,304 ZAR per night

Guest favorite

Guesthouse in Chilmark

4.98 out of 5 average rating, 198 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.

Feb 27 – Mar 6

R6,684 ZAR per night

Guest favorite

Cottage in Falmouth

4.93 out of 5 average rating, 136 reviews

“Cozy Cottage” on Great Bay

Due to the coronavirus, we’re taking extra care to disinfect frequently touched surfaces between reservations.” Our Cozy waterfront cottage is located 120ft from great bay. Our closest beach is 2.5 miles and we are 4 miles from the center of town. Equipped with gas heat and Central A/C. We also have a gas fired fireplace to keep you cozy. Outside shower for days at the beach.We have one single kayak, two double Kayaks, a rowboat and a canoe for a scenic view of Great Bay. Quiet spot.

Mar 8 – 15

R3,437 ZAR per night

Guest favorite

Apartment in Tisbury

4.92 out of 5 average rating, 102 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, the 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! The new Martha's Vineyard Museum is a five minute walk, down the same street. My place is great for couples and solo adventurers.

Oct 14 – 21

R4,007 ZAR per night

Guest favorite

Home in Middleborough

4.94 out of 5 average rating, 296 reviews

Private retreat setting on 4 acres 1

Gatherings, parties, events, reunions, etc. with 8 or more total sleepers /non sleepers MUST be discussed prior to booking. A 5 minutes from Rte. 495, secluded, 2 bedroom 1200 sq.ft. apartment. Amenities include -- in-ground pool, horseshoe pits, tennis/basketball court, fully lit for night time use. Central air, full bath, eat in kitchen, Juliet balcony, private drive & entrances, 2 HD flat screen TV"s, Netflix, On Demand WIFI. Very comfortable for two or a couple with children.

Apr 26 – May 3

R1,863 ZAR per night

Guest favorite

Cottage in Sandwich

4.95 out of 5 average rating, 161 reviews

Waterfront Lake Cottage, Private Beach, Wow View!

Wake up to a magnificent view of a beautiful lake with waves lapping gently below your window! Guests love this stylish and open designed home dramatically located on the shores of a large, recreational lake. It's like being on your own luxury houseboat! Enjoy the wall-to-wall windows with a panoramic view, a beautiful new modern kitchen, your own private beach, a new luxurious King hybrid gel/coil bed, private office space, large bathroom with curved shower, and much more!

Oct 12 – 19

R6,938 ZAR per night

Guest favorite

Apartment in Falmouth

4.96 out of 5 average rating, 151 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.

Oct 16 – 23

R2,695 ZAR per night

Guest favorite

Apartment in Barnstable

4.99 out of 5 average rating, 231 reviews

Your dog will love it here and you will too.

If you love to travel with your dog (dogs), like I do, then this is the perfect place for you and your dog. We have a large fenced in yard for your dog to play in and for you to relax in with your dog. We have a one bedroom apartment with a full kitchen, bath, living room and dining area When you book would you PLEASE let me know whether or not you will be traveling with a dog and if you are what breed of dog will you be bringing. Thanks!

Jan 1 – 8

R2,423 ZAR per night

Guest favorite

Cottage in Tisbury

4.96 out of 5 average rating, 217 reviews

Not Your Great Aunt's Island Cottage

In town, 1930's winterized cottage, lovingly updated by architect-owner. • Stylish informal decor, open floor plan, outdoor terrace • 2 blocks to Main Street/harbor/ferry/town beach/movie theater/playhouse • Central Air / Daikin Emura Zoned A/C • Close to bike rentals, restaurants, shops, spa, library, mini-golf, etc. • Large yard with wood/gas grills, bocce, corn hole, beach chairs, fire pit • Outdoor shower • 3BR + sleeping loft

Dec 8 – 15

R6,966 ZAR per night

Superhost

Home in Edgartown

4.87 out of 5 average rating, 141 reviews

Martha's Vineyard Vacation Home

My place is close to the Bike Path, Edgartown, South Beach, Katama General Store, Katama Farm, Edgartown Lighthouse, great views. Take the bike path either direction for all of the island's attractions. You’ll love my place because of the Renovated Kitchen, Renovated Bathrooms, Comfortable Furniture, Convenience to Everything, Outdoor Shower, Deck. My place is good for couples, solo adventurers, and families (with kids).

Oct 21 – 28

R7,628 ZAR per night