
Family-friendly vacation 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.

Near Salem! Air Bee-n-Bee Hive Oct 29-30 Open!
Plan a unique and memorable stay at the Hive, a bee-themed apartment in a Boston suburb 21.1 miles from the city. Delight in the charming honeybee-inspired décor. Relax on the patio and enjoy the nearby chickens and geese – and especially their fresh eggs. You’ll love the entertainment options – 100s of free movies plus cable TV and access to streaming channels. Everything you need is here, from a full kitchen with a coffee bar to EV charger. Got work? A workspace and super-fast Wi-Fi await you.

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!

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!

Corner Cottage - cozy studio just north of Boston
Whether you’re a tourist visiting Boston for the weekend, a traveling nurse in search of a medium-term stay, or a pilot/flight attendant needing overnight accommodations, this completely renovated and professionally cleaned AirBnB is perfect for you! Finding living accommodations is tough; finding a reliable and responsive host is even tougher. Not only is this unit well equipped with almost everything you may need, but I will do my best to ensure your stay is the most comfortable.

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.

Luxe Serene 1BR 15 min from Boston with Gym & More
You will love this beautifully designed 1 Bedroom 1 Bath luxury unit that is in a central location between many great cities! You will be staying in a gorgeous private community with a gym, dog park, kids playground, tennis court, and tons of outdoor space. Have peace of mind knowing you’re in a safe space. Our luxury suite has a Queen Medium Firm bed along with a Queen Air Mattress for any additional guests. Check out more of our amenity spaces below!

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

Chic/Cozy2BR-nearAirport & Beach
LOCATION, LOCATION, LOCATION! Located right in the middle of great cities (Boston, North End, Seaport District and Encore Casino). Your family will be close to everything when you stay at this centrally-located place. The airport is about 10 mins away, the train station is about 2-3 min drive, Salem is about 25 min drive and the beach is 3 mins drive as well with amazing restaurants and food all around.
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

Sanctum by the Lake

Oceanfront Pool. Close to Boston. Free Parking.

Winery Studio w/ Private Hot Tub,Fireplace,Tasting

Little Lake House, the Bungalow

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

Spacious 3 Bedroom Apartment with King Bed

Beautiful renovated 3 bedroom apt near Boston.

Charming Studio downtown Salem, MA *Parking

Ocean Park Retreat

#7 Comfortable Spacious Home Near Boston + Parking

Modern, Cozy 3 BR Apartment! Minutes to Downtown!

Renovated Cozy City Getaway

Modern Suite Near Boston, Airport & Downtown
Family-friendly home rentals with a pool

Cozy, with Lots of Space

Peaceful suite in Boston with city views

Boston Modern Apt: Luxe Stay w/ Gym, Parking

Spacious vacation unit in premium suburban town

Modern Space With Pool Close To Singing Beach

Stylish and Cozy at Revere Beach

Country Cottage in the City

Headers’ Haven
Quick stats about vacation rentals that are family-friendly in Wakefield
Total vacation rentals
Explore 20 vacation rentals in Wakefield
Nightly prices starting at
Wakefield vacation rentals start at R871 ZAR per night before taxes and fees
Verified guest reviews
Over 1,090 verified reviews to help you choose
Pet-friendly vacation rentals
Find 10 rentals that welcome pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
20 of Wakefield vacation rentals include wi-fi access
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Wakefield rentals
4.9 Average rating
Wakefield stays are highly rated by guests—averaging 4.9 out of 5!
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