Kid-friendly holiday rentals in Chilmark

4.8 out of 5 average rating, 56 reviews

Home in Dennis Port

Walk to Sea St. beach & restaurants - Cape Cod 👙⛱

Discover the perfect beach retreat in this fully updated 4-bed, 2-bath home in Dennis Port. It features a stunning kitchen, hardwood floors & modern bathrooms. Stay comfortable with central AC, new windows & recessed lighting . Enjoy the convenience of in-home laundry and spacious living areas. With multiple beaches and restaurants nearby, this house is perfectly situated. Plus, it's freshly painted inside for a welcoming feel. Book now and experience the best of modern beach living in Cape Cod!

5 out of 5 average rating, 15 reviews

Home in Tisbury

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!

5 out of 5 average rating, 22 reviews

Home in Sandwich

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 and antique design elements. We thoughtfully curated the home's details to evoke the comforts of home and give it unique charm that pays homage to Cape Cod's scenic beauty and quintessential New England. Check out our IG @thecapecodcottage for more pictures.

5 out of 5 average rating, 35 reviews

Cottage in Barnstable

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.

4.9 out of 5 average rating, 458 reviews

Home in Hyannis

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.

4.99 out of 5 average rating, 141 reviews

Cottage in Hyannis

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.

4.92 out of 5 average rating, 119 reviews

Cottage in Hyannis Port

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.

4.81 out of 5 average rating, 27 reviews

Home in East Falmouth

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!

4.85 out of 5 average rating, 104 reviews

Home in Westport

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.

4.94 out of 5 average rating, 305 reviews

Home in Falmouth

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.

4.86 out of 5 average rating, 7 reviews

Home in Centerville

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