Kid-friendly holiday rentals in Chilmark

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Chilmark

Guests agree: These kid-friendly rentals are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Home in Tisbury

5 out of 5 average rating, 15 reviews

Family Friendly 5 BR, Walk to Town, Beach & Ferry!

Ideal rental for families and friends! Two fully equipped kitchens, two fully furnished outdoor spaces, oversized deck with grill, washer/dryer, sleeps 10 (2 King, 2 Queen, Full over Full bunk beds) 3 living spaces, 2 pack and plays, 2 full baths, outdoor shower, large yard, and central a/c in every room! No ferry ticket? No car? No problem! This home is located close enough to the Vineyard Haven ferry for a quick bike ride or comfortable walk. Walking distance to trails and beach!

Guest favourite

Home in Mashpee

4.92 out of 5 average rating, 38 reviews

Tranquil Cape getaway#2 with AC Kid & Pet friendly

Welcome to this peaceful Cape retreat! With its charming Cape style home and serene surroundings, this two-level residence offers a perfect getaway for relaxation and quality time with loved ones. Property Features: Four Cozy Bedrooms Outdoor Deck and Grill Complete Fenced-In Yard Swing Set Whether you're looking to relax indoors, enjoy outdoor activities, or spend quality time with family and friends, this idyllic haven offers all the necessary amenities for a memorable vacation.

Guest favourite

Home in Sandwich

5 out of 5 average rating, 21 reviews

The Cape Cottage-Fireplace*Kid Friendly*Pets OK

The Cape Cottage is a private, tranquil Cape Cod style cottage nestled near historic downtown Sandwich and just 6 minutes from the ocean. Newly renovated, this home is tastefully designed with a blend of coastal, farmhouse & contemporary design elements. We thoughtfully curated the home's details to evoke the comforts of home & give it unique charm that pays homage to Cape Cod's scenic beauty & quintessential New England. Check out our IG @thecapecodcottage for more pictures.

Superhost

Cottage in Barnstable

5 out of 5 average rating, 35 reviews

Charming Cottage, Walk to Beach, Whale Watch, Town

As seen on the pages of This Old House Magazine, The Cape Cod Times, & featured in a calendar of relaxing porches of Cape Cod, Sonny by the Sea is the perfect place to spend your vacation. Surrounded by all the beauty and charm of Cape Cod, but tucked into a quiet little neighborhood, there is so much to see and do that you could park your car and never use it again. Beautiful, super clean 2 bedroom, 1 full bath home with central air conditioning, wifi, linens, washer/dryer.

Guest favourite

Home in Hyannis

4.9 out of 5 average rating, 456 reviews

Beach House, Harbor View and Family Friendly.

Our house is a stones throw from the beach. The harbor, Hyannis, downtown, cafes, restaurants, anywhere from 5 star dining to family-friendly dining are all in walking distance. Several family friendly activities are very close. You’ll love our place because of the walk to the family friendly beach, the ambiance, the ocean view and the neighborhood feel. Our place is good for couples, solo adventurers, business travelers, fishermen, families (with kids) and large groups.

Guest favourite

Cottage in Hyannis

4.99 out of 5 average rating, 140 reviews

Beach Glass Cottage - Pond Front

Come stay at the Beach Glass Cottage! A pristine pond front, completely renovated and tastefully decorated, 3 bedroom, 2 bathroom cottage in the heart of Hyannis. Truly the perfect get-a-way for family and friends. The Beach Glass Cottage is tucked away from the action, but within walking distance to Main Street Hyannis, which features eclectic shops, restaurants, bars, ice cream with mini golf and the Cape Cod Melody Tent is a short walk from the cottage as well.

Superhost

Home in Hyannis

4.8 out of 5 average rating, 35 reviews

Family and Pet-friendly house on CapeCod

Your family and friends will love the place! No matter if this is your first time on Cape Cod or a yearly vacation. You will be close to everything when you stay in. Infant-friendly, child-friendly, kids-friendly, pet-friendly Most grocery stores (Trader Joe's, Whole Foods, BJ's, Stop&Shop, Shaws). Cape Cod mall with Target and Pharmacies less than 5 minutes away. Restaurants on Main st in 5 minutes drive or 20 minutes walk. Cragville beach is 10 minutes drive.

Guest favourite

Cottage in Hyannis Port

4.92 out of 5 average rating, 119 reviews

Beautifully Updated, Classic Cape in Hyannisport

NEWLY RENOVATED KITCHEN & LIVING ROOM Within 1/2 mile to the beach, historic Hyannisport, downtown Hyannis Main Street, restaurants, Melody Tent and nightlife. -New mattresses on beds. Private setting. Very quiet neighborhood. Includes Beach Parking Pass -($25 daily) for all Barnstable Beaches. Great for families & groups over the age of 25. * Sheets, towels, beach chairs, and much, much more * No parties, excessive noise , pets, or smoking permitted.

Superhost

Home in East Falmouth

4.81 out of 5 average rating, 27 reviews

Charming Cape Oasis in Ideal Location!

Welcome to the Cape! Vacation like a true New Englander in this charming, exclusive, newly-renovated ranch home. Nestled in a quiet community, this Pottery-Barn style oasis boasts plenty of space and charm in an unbeatable location. Enjoy a private, fenced-in back yard with spacious deck creating a peaceful hideaway to enjoy drinks, coffee, tea, and nature. Minutes from beaches, shops, restaurants, and ferry to Martha’s Vineyard!

Guest favourite

Home in Westport

4.85 out of 5 average rating, 104 reviews

Beach Home – Family Friendly - Solar Powered

1.5 mile to beautiful Horseneck beach. On 2 acres of woods & lawn. Large deck for grilling, outdoor shower, fire pit & large swing set. Spacious & bright layout with cathedral ceilings and hardwood floors . Family friendly private neighborhood. ABSOLUTELY NO PARTIES. IF YOU ARE LOOKING FOR A PLACE TO PARTY, PLEASE GO SOMEWHERE ELSE. WE WILL ASK GUESTS TO LEAVE IF THIS POLICY IS NOT FOLLOWED.

Guest favourite

Home in Falmouth

4.94 out of 5 average rating, 304 reviews

Absolutely Adorable 4 Bedroom Ranch

Property is very close to beach at lovely, freshwater Jenkins Pond. This nicely furnished rental has a fabulous lower level family/TV room with add'l sleeping area and a full bath. Outdoors there is a large yard with a large deck and outside shower during the summer season. Minimum 2-night stay, rates may vary depending on season, weekly and monthly rate available.

Superhost

Home in Centerville

4.86 out of 5 average rating, 7 reviews

Capecod pond and beach house

Relax with the whole family in this peaceful accommodation. 5 min Craigville beach and 5 min main st Hyannis There is also the option of swimming in the pond with a wonderful Kayak ride and adventure in a small forest that opens the way to the pond we have available 2 kayaks 3 adults bikes 2 kids bikes Ping pong table Cornhole enjoy and have fun