Family-friendly holiday rentals in Charlestown

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.

Atlantic Street Guesthouse

In order to book you have to be 30 years of age! This is NOT A PARTY HOUSE! Spacious, beautiful walking distance to restaurants, parks, wharfs & beaches. Everyone's best kept secret! The neighborhood is quiet, a beautiful yard, patio, chairs & grill. Pet friendly $45-fee per night, per pet (max 2). Driveway parking. Respect neighbors & mandatory noise ordinance rules. 4 Capacity or Perfect for family 5 w/ children. Small gatherings of 7 is fine. No gatherings outside after 10pm

Relax or roam from our private spacious home

Bright and sunny newly renovated second and third floor of house built in late 1800s. Three blocks from Mystic Seaport, a short walk to downtown Mystic. Off street parking on the side of the house. House has plenty of space with two bedrooms plus a bonus room with a queen size futon. I Homey and comfortable to make you feel you can put your feet up and relax. User friendly. First floor is used as an office only on weekdays. Only 1/2 mile from Mystic Amtrak station, an easy walk.

Historic charm & modern luxury in downtown Mystic

We are long-time AirBNB guests who have tried to create the home we are always looking to book -- family friendly with modern amenities. Open floor plan on the main level, new heat and air con throughout the house, three bedrooms and family bathroom on the second floor. Art supplies, toys and children's books all ready for you as well as a pack n play and booster seat. Backyard oasis with pergola, walking distance to drawbridge. Pets considered on a case by case basis.

Aqua Vista

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

Sunset Hill Idyllic In-Law Suite 5 min from Beach

ONLY a $10 cleaning fee from us! Our spot is PERFECT for attending summer 2024 weddings, especially at Newport Vineyards! Avoid overpriced hotels and come get cozy at K & K's place. Enjoy walks on the BEST beaches (2nd & 3rd, avoiding red seaweed 1st beach). Find some peace and quiet amidst our serene setting, but just a stones throw from bustling Newport (avoid that congestion and the parking nightmare!)

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.

Charming Downtown Mystic Historic House

Enjoy Mystic in historic John Denison house. We are close to all Mystic has to offer. Great views, location, and impeccable cleanliness. Perfect for couples, solo adventurers, business travelers, and families. Guests required age 25 or older verified by Gov ID to book. Declared pet fee $150. Undeclared pets incur an automatic $500 charge. Please note: narrow stairs to the 2nd floor.