Family-friendly holiday rentals in Stoneham

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Top-rated family-friendly rentals in Stoneham

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite

Apartment in Woburn

4.94 out of 5 average rating, 249 reviews

Comfy-Spacious-private 1BR conveniently located

This stylish, private place is perfect for a couple, small family or groups of 4. Just minutes from Boston or the North Shore. Travel by car, Uber, or local train to enjoy Boston excursions, Salem witches, Cape Ann antiquing, sand beaches, fall leaf peeping, skiing, historical sights, sporting events, graduations, and retail therapy at nearby malls, outlets, or ionic Newbury St. A multitude of local and city restaurants and breweries provide an array options for your pleasure. YMCA next door!

Indoor spacesFamilyParks

Guest favourite

A well-equipped kitchen presents stainless steel appliances and an island with seating for four. Natural light floods the space through large windows, creating a bright and inviting atmosphere. The adjacent sunroom is visible through an open entryway, enhancing the home’s spacious feel.

Home in Wakefield

4.95 out of 5 average rating, 303 reviews

Home w/Yard+Parking & <15 Miles to Boston & Salem

Large kitchen (w/s.s. appliances & all the amenities), sun room, dining room, flat screen smart TVs in the living room & finished basement, high speed wi-fi (1gig) & laundry. Lots of windows make it bright. French doors open to a 16x16 deck leading to large fenced in yard. House is good for couples, business travelers, families, friends and pets. Close to downtown, train is a 5 minute walk away, highways, Lake Quannapowitt, Breakheart, 9 miles to Encore Casino & <15 miles to Boston & Salem.

KitchenFamilyPets

Top Guest favourite

The bedroom features a spacious bed with decorative pillows and a quilt. A bedside lamp and wooden furniture complement the room. Natural light enters through two small windows, and an art piece depicting Boston adorns the wall.

Apartment in Stoneham

4.99 out of 5 average rating, 128 reviews

Cozy Basement Apartment-Stoneham

This is a private in-law apartment in the basement of the home. Full Kitchen/living room combination, full bath and 1 bedroom with private entrance. Close to Routes 93 and 128 and 95. 15-45 minute drive to Boston depending on the traffic and time of day. Convenient to grocery stores and shopping plaza, casino. We live in the main house above the apartment. There is potential for a little overhead noise. Please read the whole listing and house rules. Must be 21 to request this listing!

Indoor spacesFamilyLocation

Top Guest favourite

A dining area presents a round table set for four with elegant dishware and glassware. The nearby living room features a cozy sofa, a coffee table, and large windows allowing natural light to fill the space. The walls are painted in calming grey tones.

Home in Melrose

4.98 out of 5 average rating, 121 reviews

Family-Friendly, Private Near Boston & Salem MA

Enjoy the entire private 2nd-floor apartment of this home, built in 1910. This home has updated amenities while keeping the charm of the original design. This 1,200-square-foot living space features a beautiful, private second-floor porch to enjoy the outdoors. This home is located within walking distance to a quaint downtown full of great restaurants and shops. This location is great for people looking to visit Boston, Foxborough, Salem, Encore Casino, TD Garden, and all of New England.

FamilyIndoor spacesAccuracy

Guest favourite

A modern kitchenette is featured with stainless steel appliances, including an oven and refrigerator. A spacious gray sectional sofa is positioned on a geometric patterned area rug. Bright windows allow natural light to illuminate the room, complemented by decorative mirrors and a potted plant.

Apartment in Woburn

4.88 out of 5 average rating, 149 reviews

Newly Finished Guest Haven in Woburn

Welcome to our newly finished in-law lower level suite in Woburn! This private 1-king bed bedroom, 1-bath retreat features a cozy living room, a well-equipped kitchenette with a private entrance. Located on a quiet dead-end street, it’s just 5 minutes from Woburn Center, 15 minutes from Encore Boston Harbor, and a 20-minute drive to downtown Boston. Perfect for business travelers or couples, enjoy a peaceful stay with easy access to dining, shopping, and entertainment. Book your stay today!

Indoor spacesFamilyBathroom

Top Guest favourite

A cozy living area is presented, featuring a modern black sofa and two soft pink ottomans. Natural light streams in through the window, illuminating the space. Decorative shelves with plants and artwork add a touch of greenery and charm to the room.

Home in Stoneham

4.92 out of 5 average rating, 387 reviews

Entire Apartment in Stoneham

Welcome to our cozy, beautiful, and well-equipped home—your perfect retreat in the heart of Stoneham. Wake up in this bright and inviting apartment, just 20 minutes from the airport and the historic city of Boston. You’ll be conveniently close to shopping malls, restaurants, coffee shops, grocery stores, and the stunning nature of Middlesex Fells Reservation and Stone Zoo. Whether you’re here to explore or unwind, this charming home will make your trip both enjoyable and stress-free.

Indoor spacesKitchenHospitality

Top Guest favourite

A dining area is presented with a rustic wooden table surrounded by white chairs. Lush green plants are displayed throughout the space, enhancing its natural light. A geometric pendant light hangs above, while large windows provide views of the bright, open living area beyond.

Home in Medford

4.99 out of 5 average rating, 122 reviews

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.

FamilyKitchenCheckout

Top Guest favourite

The exterior of a two-family home features a front porch with white railings and hanging flower baskets. A staircase leads to the entrance, flanked by flower pots. The entrance door is bright red, and the surrounding garden adds greenery to the welcoming facade.

Home in Melrose

4.96 out of 5 average rating, 139 reviews

Quiet Melrose Home

Two bedroom apartment on the first floor of a two family home located in a quiet neighborhood just a few blocks from downtown Melrose. Convenient 6.5 miles from Boston. One block from the commuter rail, bus at the end of the street, and 1.2 miles to MBTA. You will have 2 bedrooms with queen size beds plus extra single bed off of back bedroom, sunny full kitchen, living room, dining room 1 bathroom with walk in shower, and laundry room, back deck and yard . Owner lives upstairs.

Indoor spacesKitchenValue

Top Guest favourite

A private entrance to the basement suite is framed by a modern railing and steps leading down. Lush greenery surrounding the entrance enhances the serene setting, while a light fixture is positioned above the door. A children's playset can be seen in the background.

Guest suite in Lexington

4.97 out of 5 average rating, 182 reviews

Modern Farmhouse Suite in Historic Lexington

Enjoy a modern farmhouse themed private suite in a peaceful setting in historic Lexington. Our home is perfect for : -Travelers visiting Boston and surrounding historical sites -Visitors seeking to stay in close proximity to family and friends in Lexington or surrounding communities -Locals in need of temporary housing -Business professionals needing accommodations within commuting distance to Boston -Families with kids, couples, or solo guests

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Guest favourite

Apartment in Everett

4.95 out of 5 average rating, 100 reviews

Curated Designer Retreat • Pool • Gym • Dining

Experience modern Everett living in this bright 2BR/2BA home! Enjoy a fully equipped kitchen with stainless steel appliances, in-unit laundry, and spacious sunlit living areas. Relax by the courtyard pool, stay active in the 24/7 fitness center, or unwind in the outdoor lounges and fire pits. Close to Encore, Assembly Row and major highways for easy access to Greater Boston.

KitchenIndoor spacesValue

Top Guest favourite

A spacious living area features a comfortable sofa adorned with textured pillows and a cozy throw. A wooden coffee table holds magazines and a remote. Natural light enters through a nearby window, enhancing the soft, neutral decor.

Guest suite in Woburn

4.97 out of 5 average rating, 189 reviews

Private apartment with driveway parking in Woburn

Enjoy your private retreat in this spacious 1-bedroom lower-level apartment, comfortably accommodating up to 4 guests. Features a fully equipped kitchen, a cozy living room with a 65" Smart TV, and access to a beautiful, enclosed backyard. Located minutes from shops and restaurants, it's the perfect blend of comfort and convenience for your stay.

Indoor spacesFamilyHiking

Top Guest favourite

An inviting open-concept living area features a brown sectional sofa with a chaise, accented by throw pillows. A round coffee table sits in front, surrounded by a welcoming atmosphere of honeybee-themed decor, such as hexagon shelves on the wall. A workspace with a chair is positioned nearby.

Apartment in Billerica

4.99 out of 5 average rating, 215 reviews

Bee-Themed Retreat Near Boston - Unique Stay

Experience a one-of-a-kind stay at the Bee Hive in Billerica, a delightful apartment uniquely themed around honeybees. Located just 21 miles from vibrant Boston, enjoy close proximity to city attractions while relaxing in a charming, peaceful garden setting. Perfect for couples, families, or remote workers seeking inspiration and tranquility.

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