Family-friendly holiday rentals in Suffolk County

Coastal Cottage Home

Come have fun at The Coastal Cottage. This newly updated home is only a minute walk to your private beach and is the main floor of the home. Enter into the comfortable living room, with coastal boho vibes and a large sectional couch. One bedroom has a Queen bed, the other has a full and twin bunk bed and a crib. Enjoy the large kitchen with large dining table, breakfast nook and massive granite island. Enjoy grilling, the outdoor shower, or hang in the courtyard to relax with family and friends.

The Day-Burrill-Wadsworth-La Voix House

The Day-Burrill-Wadsworth-La Voix House is located in Winthrop, MA in the North Shore of Boston. Super close to Logan Airport for your traveling needs. A Level 2 EV Charger is available! This renovated 3 Bedroom penthouse apartment features a private roof deck, off-street parking, sunroom, and free in-unit laundry! A safe, spacious, and serene space. A historic building, it was one of the first handful of homes in Winthrop... built in 1860 (but since converted to two apartments and renovated).

Newly remodeled home with ocean views!

Spacious home newly remodeled with all high end touches. This house has views of the Boston skyline and harbor Islands. Each bedroom and floor has it's own split system air conditioning for maximum comfort. Preferred neighborhood of North Weymouth which is 10 miles from Boston. This house provides a convenient location for you and your family to explore the city with all the comforts of home. Full laundry facilities are on the same floor with the bedrooms. 2 decks to relax and enjoy the views.

Hospitality · Location · Beach

Truly Oceanfront! Spacious Family Petfriendly Home

Truly ocean-front! Don’t be fooled by Winthrop listings of side-street homes. This is an entire 1st floor unit with a private entrance. In an owner-hosted, classic triple-decker home with normal family/town sounds. Pro-cleaned and pet-friendly. Adjacent to Boston by car, ferry/transit. Family time with everything you need. Enjoy our rocky beach or walk a few blocks north to the sandy, lifeguarded stretch. Cafés and restaurants are walkable, and groceries deliver. Quiet hrs: 10pm-7am for all.

3BR Immaculate and Sunny Home Near the Beach!

This lovely private, upper duplex is perfect for couples and small families. Great location - 7 houses back from 4-mile long, Nantasket beach; 2 blocks from a quaint shopping area; less than 5 miles to the train or ferry (30-min ferry ride to downtown Boston). Beautifully decorated with nautical decor, a fully equipped kitchen and open living space for gathering together. Beach supplies provided. Absolutely no smoking/animals/drugs/parties. Max: 4 guests. Proudly hosting for over 10 years.

Hospitality

Beautiful 3BR Home by the Water - Family Friendly

Welcome to our newly renovated 3-bed, 2-bath single-family home nestled in a serene and welcoming neighborhood in North Weymouth: • Walk to Wessagusset Beach and George Lane Beach • Just a 2-mile drive to Hingham Shipyard's dining, shops, and commuter boat to Boston • 11 miles from Downtown Boston • 3 miles from commuter rail or subway stations (bus #220, a 2-minute walk, takes you to Quincy Center or Hingham Shipyard) Ideal for families or groups seeking relaxation and easy city access.

The Landing at Cohasset Harbor

Welcome to "The Landing," our tranquil barn retreat, nestled in Cohasset Harbor. This space offers the perfect setting to unwind. We have two queen beds, one in a loft and one in the main area, and a full bath with a clawfoot tub and shower. The barn sits behind our main house on the edge of a marsh and a river that leads into the ocean. Enjoy being directly across from Cohasset Harbor and just a 7 minute walk up the street to lovely downtown Cohasset with its shops, restaurants and bars.

Hospitality · Location

Sunny 3 bedroom on beach

Welcome to our beautiful 3 bedroom apartment on the beach! Enjoy stunning ocean views and easy access to Winthrop Beach, only 2 minutes away. Accommodations for up to 8 guests, making it perfect for families or groups of friends. Located on the 2nd floor of a historic building, this home offers a bright and airy living area with plenty of natural light and a cozy seating area, perfect for relaxing after a long day at the beach. The dining area, kitchen and private deck with ocean views.

Rock Steady - Panoramic Ocean Front Home

Just north of Boston, our home is a mid century ranch we renovated in 2019. The Airbnb is a spacious ground floor living space surrounded by a private cove that is truly breathtaking. 1000 square feet of sunlit comfort. Enjoy the sound of the waves, stunning sunrises and a landscaped back patio that abuts our cliff. In the summer take advantage of the town beach down the street. During the winter relax in front the fireplace. Top it all off with hi-speed Wi-fi – it's a perfect getaway.

Entire Beach-Town Cottage, Barn Charm, near Boston

A nicely renovated, old barn, where contemporary style meets barn-charm. Located in a quiet neighborhood with private yard and only minutes to the beach. The ideal location for a short getaway with family or friends. Only 25' from downtown Boston and other North Shore towns with restaurants and bars. For pricing transparency: AirBnb now includes cleaning and all service fees and taxes in the total. Hosts nightly fees are 20-25% lower (bc cleaning is included)! 15% of fees go to Airbnb!

4br SouthBoston free parkg nrBeach, 6 min>BCEC

Bring the whole family or team -- you'll love our quiet, safe, beachside neighborhood. Our location on the South Boston peninsula means more peace and less traffic, yet a short scenic walk up K Street brings you to great restaurants. <5min walk to a great grocery store, the legendary L St Tavern and L St Bathhouse. <1.5 mi to Convention Center & Seaport. 3 BRs w queen beds and 1 sm BR w bunks, large kitchen, liv & dining rooms, & bonus sunroom w/desk. Call us today -- we'd

Winthrop Hideaway | Near Airport, Beaches & Boston

Escape to Get to the Point Boston, a cozy private studio in charming Winthrop just minutes from Logan Airport and downtown Boston. Enjoy free off-street parking, high-speed WiFi, premium linens, a Nespresso coffee station, complimentary snacks, and no cleaning fee. Walk to beaches, parks, restaurants, and stunning Boston skyline sunsets. Perfect for couples, business travelers, airline crews, and weekend explorers seeking comfort, convenience, and value.