
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.

Upscale 5BR Family Home Near Boston
5-bdr, 2 full bath private house, 7 mi to Boston/airport, 1000 FT to bus & train and located in a quiet residential neighborhood. Luxury upscale furniture, hotel bedding, "5-star kitchen" per a famous chef who stayed, AC/heat (mini-splits) in all rooms, fenced yard with deck and grill, and 3-car driveway. Melrose was the #1 real estate market in the U.S. in 2015 and #4 in 2020 (search "hottest zip code melrose ma 2015"). Pls tell me about your group, pets & why you're visiting when inquiring.
4.95 out of 5 average rating, 145 reviews
Beautiful home next to train to Boston, near Salem
Boston and Salem location, 3-story condo in two-unit building with its own entrance. Kitchen is brand-new, with a large bar area and all the appliances. One bedroom with a king-size bed is located on the main 2nd level. Two bedrooms upstairs, with one King bed and one Queen bed. It is located within walking distance to the Wakefield commuter rail with trains running into downtown Boston. Also, adjacent to a walkable park around a stunning lake, and a small downtown with stores and restaurants.
4.83 out of 5 average rating, 125 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!
4.95 out of 5 average rating, 256 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!
4.99 out of 5 average rating, 128 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.
4.95 out of 5 average rating, 306 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!
4.89 out of 5 average rating, 169 reviews
Dixie’s House, 1BD in Arlington
1 bedroom, family-friendly apartment in the quiet Morningside neighborhood of Arlington. Can sleep 5. Free driveway & off-street parking. King bed + queen sofa bed in living room + extra twin. 1 full bath, kitchenette with dishwasher (No Oven or Cooktop). NEW washer/dryer combo! 1 mile from the bike path and short drive to Alewife/Davis T stations. Young kids and dog live above (expect some noise). Bus route to Harvard Square nearby. Also close to Wright-Locke Farm with stunning fall hikes.
4.88 out of 5 average rating, 234 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.
4.92 out of 5 average rating, 399 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.
4.99 out of 5 average rating, 126 reviews
Guest Suite with separate entrance
Guest Suite with open floor plan (kitchen with stove/oven, refrigerator, microwave, bottled water dispenser); living area (pullout couch, loveseat, 50" TV with Roku and Netflix); sleeping area, bathroom with shower, separate entrance, 1 off-street parking space. Convenient to public transportation (commuter rail - 5 min walk, 12 min ride to Boston/45 min ride to N Shore; subway - 2 min walk to bus/subway (25-40 min ride to Boston) or drive (25-45m to Boston or 45-60m to N Shore).
4.85 out of 5 average rating, 331 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
4.97 out of 5 average rating, 189 reviews
The Brickhouz at Arlington !
Just a little bit of everything for everyone to have a spectacular time in Boston, perfect for family gathering ! A funky and quirky cozy 4-bedroom brickhouse smack right in the middle of Arlington Center. 10 mins to Harvard Square, 15 minutes to Boston and Logan airport. Sleeps 8 - 2 bathrooms. Short 1 minute walk to cafes and restaurants. Discounts available for longer stays. Strictly no parties or unapproved pets.
4.99 out of 5 average rating, 119 reviewsPopular amenities for Stoneham family-friendly rentals
Family-friendly home rentals with a hot tub

Lakeside apartment, patio, hot tub, outside shower
4.98 out of 5 average rating, 221 reviews
Winery Farmhouse w/ Private Hot Tub & Wine Tasting
4.97 out of 5 average rating, 135 reviews
Nana-tucket Inn
4.95 out of 5 average rating, 184 reviews
Heart of Southie - Hot Tub + Walk to Top Bars
4.93 out of 5 average rating, 116 reviews
Oceanfront Pool. Close to Boston. Free Parking.
4.96 out of 5 average rating, 285 reviews
Modern, Spacious 1BR for 4 - Easy Marathon Access!
4.78 out of 5 average rating, 359 reviews
Hot tub - Arcade - Boston themed rooms
5.0 out of 5 average rating, 16 reviews
Headers’ Haven
5.0 out of 5 average rating, 89 reviewsFamily- and pet-friendly home rentals

Unique Loft/ Studio Guesthouse (super convenient)
4.74 out of 5 average rating, 274 reviews
Across the Subway · TD Garden · Concerts · Games F
4.89 out of 5 average rating, 104 reviews
Private Cozy Third Floor Space
4.95 out of 5 average rating, 143 reviews
3bed, 1 bath - Near Boston - Free parking
4.89 out of 5 average rating, 140 reviews
Sunny home minutes from Boston. Free parking.
4.86 out of 5 average rating, 165 reviews
Family Home + Near Downtown + Cool Backyard!
4.94 out of 5 average rating, 260 reviews
Luxury Grand Oasis | Pool · Gym · Parking · 2BR
4.92 out of 5 average rating, 130 reviews
Designer 3-BR Apt in Historic Charlestown, Boston
4.98 out of 5 average rating, 105 reviewsFamily-friendly home rentals with a pool

Amazing studio
4.87 out of 5 average rating, 209 reviews
Pool Is Open in Sept! Steps from Harbor + Old Town
4.99 out of 5 average rating, 168 reviews
Cozy Private Studio Unit w/ Laundry and Parking!
4.97 out of 5 average rating, 450 reviews
The Drew : Vibrant • Comfortable • W/D • City View
4.8 out of 5 average rating, 124 reviews
Country Cottage in the City
4.95 out of 5 average rating, 218 reviews
Private Pool Retreat w/Fire Pit Near Singing Beach
4.91 out of 5 average rating, 202 reviews
Private Suite• Pool • Sleeps 4 • Boston • Airport
4.97 out of 5 average rating, 348 reviews
Exquisite 1 Bedroom Suite-Charming,W/Private Entry
4.78 out of 5 average rating, 104 reviewsDestinations to explore
- Fenway Park
- Hampton Beach
- Harvard University
- TD Garden
- Boston Seaport
- Gillette Stadium
- Boston Common
- Revere Beach
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- New England Aquarium
- Boston College
- Northeastern University
- Canobie Lake Park
- Duxbury Beach
- North Hampton Beach
- MIT Museum
- Harvard Square
- Tufts University
- Crane Beach
- Quincy Market
- Snhu Arena
- Massachusetts Institute of Technology





