Kid-friendly vacation rentals in Chilmark

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Top-rated kid-friendly rentals in Chilmark

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

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Guest favorite

Home in Sandwich

5 out of 5 average rating, 18 reviews

The Cape Cottage-Close To It All!

The Cape Cottage is a private, tranquil Cape Cod style cottage nestled in a sought-after neighborhood just 6 minutes from the ocean. Newly renovated & optimally located near historic downtown Sandwich, this home is tastefully designed with a blend of coastal, farmhouse, & contemporary industrial design elements. We have thoughtfully curated the home's details to evoke the comforts of home & give it a unique charm that pays homage to Cape Cod's scenic beauty & quintessential New England.

Superhost

Cottage in Fairhaven

4.83 out of 5 average rating, 210 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.

Guest favorite

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 favorite

Home in Mashpee

4.94 out of 5 average rating, 34 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.

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 favorite

Home in Hyannis

4.9 out of 5 average rating, 454 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 favorite

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 Falmouth

4.9 out of 5 average rating, 63 reviews

Gorgeous! beach home steps from beach and downtown

Welcome to our wonderful vacation home- a 5 min walk to town and an 8 minute walk to Surf Drive beach- which has amenities including restrooms, showers, food stand which has healthy options, and a calm stretch of water perfect for little ones. Our spacious home features large gathering areas but is plenty large to find privacy. The huge yard is perfect for lazy summer evenings spent home and features a swingset and all of the yard toys your family could want!

Guest favorite

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.

Guest favorite

Cottage in West Yarmouth

4.83 out of 5 average rating, 234 reviews

Charming Cottage near Beach and Ferry.

2022 renovation (floors, bathroom, cabinets) The cottage is only 150 yards from a sandy residential beach. Good for couples, families (with kids), and furry friends (pets). Enjoy a great outdoor shower, grill and deck, wifi, central AC/heat, cable TV, linens, washer/dryer. Additional Beach gear. No host interaction required. Great place to work remotely. Private yard and picnic table with lots of takeout options nearby.

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 favorite

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.