
Family-friendly holiday rentals in Wakefield
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Wakefield
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Family Friendly Green Oasis Minutes from Boston
Oasis filled with natural light, plants & art in a quiet neighborhood minutes from Downtown Boston. Perfect for sightseeing & enjoying the best of the city and neighboring towns. Walk to Wrights Pond for a swim & hike the Middlesex Fellsway Reservation. Fully equipped chefs kitchen. Private backyard surrounded by trees. Wake up to birds chirping and relax after a long day of exploring while you watch your favorite TV show. Enjoy a bath in the soak-in tub. 3 parking spaces, office setup & laundry

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.

Comfy-Spacious-private 1BR conveniently located
This stylish, private place is perfect for a couple or a small family. Conveniently located minutes from Boston or the north shore whether you are traveling by car, Uber, or local train. Enjoy Boston adventures, north shore excursions, beaches, fall leaf peeping, skiing, historical visits to Massachusetts battle grounds, or some retail therapy at shops and malls nearby. An array of local and city restaurants and breweries provide a multitude of options for your pleasure. YMCA just steps away!

Cozy place to relax! 14min to Salem - 25 to Boston
Due to your allergies, we are unable to Host any animals Private entrance-Basement - H 6' - entrance 5' 6" Relax in this calm, stylish space after a day of exploration! Perfect for travelers /work trips. Stay with US! I live on-site to ensure a safe and welcoming stay You will get to enjoy: - Salem MA - - Boston MA - Beaches - Beverly MA - Gloucester MA - Marblehead MA - Trails Our mattress is fairly firm, which can provide a very good night sleep! - Illegal activities will be reported -

Welcoming 7-room house <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.

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!

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!

Prime location near Boston
Home in Everett, MA. Located just a 20 minute walk from Encore Boston Harbor Casino. This location is also just a 15 minute drive from downtown Boston. Room in the basement has a microwave, refrigerator, coffee maker, and hot water for making tea which is provided along with light snacks and coffee. There is a desk for laptop. Queen Tempurpedic Mattress topper as well as a pull out sofa. Private bathroom with spacious shower. See guide book for more info on the area!

Cozy West Peabody Guest Suite
Come enjoy this renovated studio guest suite in the quiet neighborhood of West Peabody! An easy drive to Salem or Boston, close to a woodsy bike trail, and a short drive to local shops and restaurants. Features a fully equipped kitchenette with a microwave and Keurig coffee. Make use of a Roku TV and fast, reliable WiFi to keep yourself entertained. This is a great space whether you are looking to explore the Boston North Shore or simply embark on a quiet getaway.

Modern Apartment - Easy Commute to Salem/Boston
This modern, spacious and cozy home was completely renovated at the end of 2022, thoughtfully designed for our family and guests when they visit. It is conveniently located close to popular spots such as Salem, North Shore and Boston (right off route 1 and highway 95). Grocery store, pharmacy, dry cleaners and other amenities are just down the road. In a quiet and friendly neighborhood. We open it up for Airbnb guests seasonally. We look forward to hosting you!

Couples Retreat - Apt in Charming Colonial Home
Newly renovated, open concept apartment in a private home located on a quiet residential street. Single, queen-sized adjustable bed, steam shower, and oversized bubble jet tub make this an ideal retreat for stress free relaxation. Includes off-street parking, full-size washer and dryer, and the use of both front and rear porches with seating in season. This apartment is great for couples or individuals looking to relax and get a break from their busy lives.

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
Popular amenities for Wakefield family-friendly rentals
Family-friendly home rentals with a hot tub

Nana-tucket Inn

Hopkinton Mass 3+ Bedrooms - Great location!

Your Cozy 1 BR Apt & Relaxing Retreat

BC/BU - Beautifully Renovated Penthouse 3-BR/2-BA

Pond-Front Passive Solar Architectural House

Oceanfront Pool. Close to Boston. Free Parking.

Winery Studio w/ Private Hot Tub,Fireplace,Tasting

Lakeside apartment, patio, hot tub, outside shower
Family- and pet-friendly home rentals

Private Studio 10 min from Airport

Flower Farm Getaway 2BR, 20 Min To Boston

Large One Bedroom Apartment

Renovated Cozy City Getaway

Ocean views, Large Deck, Grill, Kid/Dog Friendly

Ocean view studio with hot tub & access to Boston

Salem House

Luxe Serene 1BR 15 min from Boston with Gym & More
Family-friendly home rentals with a pool

Peaceful suite in Boston with city views

Spacious vacation unit in premium suburban town

Stylish and Cozy at Revere Beach

Modern Space With Pool Close To Singing Beach

Country Cottage in the City

Headers’ Haven

Cozy Private Studio Unit w/ Laundry and Parking!

4 Houses from Harbor - Private Pool - Parking
Quick stats about holiday rentals that are family-friendly in Wakefield
Total rentals
20 properties
Nightly prices starting at
$77 AUD before taxes and fees
Total number of reviews
1.1K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
20 properties include access to Wi-Fi
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Philadelphia Holiday rentals
- Mount Pocono Holiday rentals
- Jersey Shore Holiday rentals
- Quebec City Holiday rentals
- The Hamptons Holiday rentals
- Hampton Beach
- Fenway Park
- Boston Common
- TD Garden
- Harvard University
- Revere Beach
- Brown University
- Lynn Beach
- York Harbor Beach
- Duxbury Beach
- New England Aquarium
- Good Harbor Beach
- Canobie Lake Park
- MIT Museum
- Freedom Trail
- Crane Beach
- Faneuil Hall Marketplace
- Museum of Fine Arts, Boston
- Jenness State Beach
- North Hampton Beach
- Rye North Beach
- Quincy Market
- Prudential Center
- White Horse Beach