Family-friendly holiday rentals in Suffolk County

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).

Extraordinary 1-Bedroom Apartment in South Boston!

Cozy, comfortable, centrally-located one-bedroom unit in Southie. Unbeatable location, steps from Carson Beach, L Street Bathouse, BCEC, Sail Boston, World Cup 2026! This property presents endless possibilities for creating your perfect getaway! Convenient private entrance ensures hassle-free coming and going. Whether commuting to work, enjoying a concert/game/event/the vibrant local scene, or simply indulging in the beach and parks nearby, you are sure to enjoy it at this very special home!

Lakeside apartment, patio, hot tub, outside shower

Private apartment, has lock box access, includes bedroom, living room, kitchen & bathroom. Private from public, patio and hot tub overlooks lake and conservation land. No stairs. Sofa converts to a comfortable queen or twin beds Kitchen is stocked with dishes, pots and pans for 4, coffee and water Hot tub always 104 degrees Kayak, sail boats & swimming available. Portable fire pit. $25 pet fee, 1 pet only under 50 #'s. Tesla EV charging Covid 19 CDC cleaning and disinfecting procedures.

Ocean view studio with hot tub & access to Boston

All the amenities needed in a clean, spacious and modern apartment tucked away in a peaceful coastal town close to Boston. Studio with stunning ocean views, large private deck, hot tub, separate entrance, fast internet, granite kitchen, comfy couches, Breville Barista, bbq, and Sealy queen bed. Space is private with quiet residents in adjoining units. Off street parking. 2 sets of stairs to private entry, shared entrance by request. Use of hot tub at no additional cost. Short walk to beaches.

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.

2BR Spacious Yacht - Heat & AC- On Freedom Trail

Escape the hustle and bustle of the city and unwind aboard Carpe Diem II, a yacht with 2 comfy queen staterooms for up to 4 adults. Each stateroom has a private bathroom and shower. Unwind on the aft deck with meals and cocktails as the boats sail by on the harbor, or warm up or cool off inside with central A/C and heat. Located in Charlestown Navy Yard, steps to Freedom Trail, North End, and Downtown. Book now and enjoy the unique charm of living on the water in this historic neighborhood.

Bright Family Oasis Near Boston w/ Parking

Bright, plant-filled oasis in a quiet Medford neighborhood just minutes from Boston, with easy access to transit and free parking. Guests return again and again for the spotless cleanliness, curated art, and true “home away from home” feel. Enjoy a fully equipped chef’s kitchen and private backyard. Perfect for exploring the city, then relaxing in a peaceful, beautifully designed space. Or working from home. Conveniently located for day trips to Salem, Cambridge and downtown Boston.

Pleasant Place 2

This stylish place to stay is perfect for a single person or couple. It is a very beautiful space in a lovely 2 family, owner occupied home. Winthrop is a beautiful oceanside residential community situated at the entrance of the most beautiful harbors in New England. Winthrop offers small town suburban living, within minutes to Boston. We have public transportation to downtown Boston in about 20 minutes, Logan Airport in 15 minutes. We also have a Ferry Service to Boston.

Sensory Serenity: Parking/Netflix/Wi-Fi/Frag-Free

Stay in our elegant Boho-Modern Home Only 15min from Boston's Major Attractions. ✔Queen Beds+Organic bedding, cleaned w/ natural cleaners for your BEST rest w/o combatting toxins/fragrances ✔Ideal for Families and Staycations ✔Inviting Dinning and Large Kitchen ✔Fast WIFI+Netflix ✔Off-Street Parking ✔Self check-ins with secure keypad ✔Laundry Everything you need is provided - Just pack up your clothes and enjoy your stay with us! Book today to reserve our luxury home!

Now availJamaica Plain & Arboretum 20min toBoston

Bright and sunny 2-bedroom retreat with a fully equipped kitchen, spacious bath with rain shower and tub, and TVs in each room. Enjoy fresh coffee daily with espresso maker, milk steamer, and grinder provided. Including a blender..A selection of teas .WiFi and off-street parking included. Private, peaceful, and filled with natural light—perfect for relaxing mornings and cozy evenings!

Entire Beach-Town Cottage, Barn Charm, near Boston

A nicely renovated, old barn, fully furnished, where contemporary style meets barn-charm. Located in a quiet neighborhood with private yard and only minutes to the beach. Parking on premises. The ideal location for a short getaway with family or friends or to unwind after a long day at work. Only 25' from downtown Boston and other North Shore towns with restaurants and bars.

Spacious and Luxurious House

Welcome to our stunning Airbnb! Our stylish and modern ranch style home is the perfect place for your next vacation or business trip. Located in a quiet and safe neighborhood, our home is perfect for couples, families, or a group of friends. It features 3 bedrooms and bathroom and can comfortably accommodate 6 guests