Family-friendly vacation rentals in Middlesex County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Middlesex County

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

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Top guest favorite

A cozy bedroom features a queen bed dressed in white bedding with honey-colored accent pillows. A wooden dresser is positioned against the wall, complemented by hexagonal decor and a charming light fixture. Soft lighting enhances the welcoming atmosphere, while a window provides natural light.

Apartment in Billerica

4.99 out of 5 average rating, 157 reviews

Air Bee-n-Bee Hive: Coffee Bar, Fresh Eggs & Charm

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.

Top guest favorite

A quaint cabin is positioned among trees, softly lit at night. An illuminated entrance is framed by colorful pots and surrounded by a cozy seating area with an Adirondack chair. Flickering firelight adds warmth to the inviting outdoor space.

Cabin in Littleton

4.99 out of 5 average rating, 201 reviews

Private & Remote, Enjoy Outdoors, Sleep in Luxury

Bit of a wonderland (57 Acres, 100+ 5-star reviews). A place you won't soon forget. Complimentary firewood, 1/2 hour from Boston, camp but sleep in luxury. This cabin is privately located on a retired Christmas tree farm, about a one-quarter mile off the public road. Listen to the water flow, and watch the sunset over the wetlands. This site is ideally suited for a couple looking for an outdoor experience retiring to the comfort and security of a luxury tiny house. Everything is solar-powered.

Top guest favorite

A charming farmhouse stands amidst a lush garden, surrounded by vibrant purple irises. The white exterior of the house contrasts beautifully with the greenery, providing a serene atmosphere. Tall trees and a manicured lawn enhance the inviting landscape of the property.

Guest suite in Weston

4.99 out of 5 average rating, 172 reviews

Flower Farm Getaway 2BR, 20 Min To Boston

Spacious two-bedroom in-law suite attached to 1700’s farmhouse, situated on our small flower farm and garden co-op just 20 minutes from Boston. Only a mile from the Mass Pike & Rt. 128 (I-95). Centrally located to all Rt. 128 businesses, colleges & hospitals. A 7-min drive to Riverside Green line “D” subway stop into Boston (parking available), or commuter rail stops (Auburndale, Wellesley & Kendal Green Stations). It's a 15-minute drive to Amtrak's "Route 128" station to NYC and points south.

Top guest favorite

The bedroom features a spacious bed adorned with navy bedding and accented by decorative pillows. Nightstands with lamps are positioned on either side. Natural light enters through a window, illuminating the warm wooden flooring.

Guest suite in Stow

4.98 out of 5 average rating, 103 reviews

Sisu Suite: Private one bedroom suite

Private suite with separate entrance. Locked door between suite and home. Sitting room with love seat, folding wall-mounted table/desk and chairs, tv, and kitchenette. Kitchenette includes mini fridge, microwave, coffeemaker, water kettle, and toaster. Bedroom with queen sized bed. New bathroom. 25 miles west of Boston. Minutes from pick-your-own apple orchards, winery, cider breweries, and golf courses. Backyard connects to conservation land trails. 3.3 miles from S. Acton Rail station.

Top guest favorite

A spacious living room area features hardwood floors and large windows allowing natural light. A dark wood cabinet holds a television, while a sofa and a colorful chair provide seating. An elegant kitchen island with seating is positioned in the background, showcasing warm wood cabinetry.

Apartment in Lexington

4.94 out of 5 average rating, 423 reviews

Warm home in Lexington, walk to town, nature trail

A newly built in-law apartment, located in the historical Lexington, is welcoming travelers home. Located in a safe and friendly community, the apartment is convenient to town center, Boston, restaurants, shops, tourist spots, and Lower Vine Brook forest trail (1 min walk)! The apartment follows enhanced cleaning protocol, with thorough ventilation and disinfecting. The HVAC system is private. Checkin and checkout are easy and no-contact. Registered with the town of Lexington: STML-21-2.

Top guest favorite

A spacious living area features a vaulted ceiling, large windows allowing natural light, and a comfortable sofa. A wooden coffee table sits at the center, complemented by patterned armchairs. Adjacent, a farmhouse dining table accommodates six, enhancing the open layout.

Place to stay in Sherborn

4.97 out of 5 average rating, 310 reviews

Entire Historic Carriage House with Fireplace & AC

Escape to our charming Carriage House in the Historic District of Sherborn which offers the feel of a country retreat without being far from civilization. Great for travelers looking for a peaceful getaway, checking out nearby colleges or attending a celebration like a wedding or graduation. You will love the feel of the Carriage House, its spacious living and dining room, well-equipped kitchen, and the beautiful grounds. Check us out on IG @carriagehousema. NEW in 2022: Mini-split AC!

Top guest favorite

A two-family home is set amidst lush greenery, featuring a light-colored exterior with large windows. Solar panels are visible on the roof, and a wide driveway leads to the attached garage. Nearby shrubbery and tall trees create a natural, serene backdrop.

Guest suite in Ayer

4.98 out of 5 average rating, 146 reviews

Peaceful, Private 1 Bedroom Apartment, & Porch

Quiet private 1 bedroom apartment with separate entry adjacent to the home. A private porch with an infrared grill offers relaxing outdoor space and ambiance. Great for couples, adventurers, and business travelers. A drive or short walk brings you to several restaurants and shopping stores. Downtown is a bicycling trail and commuter rail station from Ayer to Boston. Outdoor enthusiasts, rent kayaks at Nashua River or enjoy walks. Devens and Coed Boarding School in Groton is nearby.

Guest favorite

An open-concept living area is highlighted by hardwood floors and a vaulted ceiling. A maintenance-free reef tank with ambient lighting is displayed on the wall. Modern seating options include a sectional sofa and chairs arranged around a coffee table, with large windows providing natural light.

Apartment in Westford

4.94 out of 5 average rating, 109 reviews

Large One Bedroom Apartment

1,100 square feet, completely renovated, 1 bedroom with a walk-in closet. Large bathroom with two sinks and walk-in shower. Open concept living, dining and kitchen area with vaulted ceiling. Hardwood floors throughout. Central air. Apartment is connected to a main house but with no interior access between house and apartment whatsoever. (No interior connecting doors at all) It has its own private driveway and side yard. Reef tank will no longer be in the apartment after May 20th.

Guest favorite

A cozy living room is highlighted by a beige area rug featuring floral patterns. A wooden coffee table is centered, flanked by a futon adorned with pillows. Natural light filters through a large window dressed with sheer curtains, while a ceiling fan adds a touch of comfort.

Apartment in Maynard

4.9 out of 5 average rating, 523 reviews

Loft Apartment Suite in Downtown Maynard

Private apartment on top floor in downtown Maynard with full kitchen, living room and bedroom/office. A warm, cozy space with plenty of natural light! Free parking on site for 1 vehicle, and only 2 miles from the Fitchburg commuter rail line, which will bring you right into North Station in Boston! Walking distance to restaurants, cleaners, movie theater, gym, golf course, shopping... & lots more! Nearby there are lots of historical sites, ski areas, and areas for swimming!

Top guest favorite

A tranquil kettle pond is depicted, reflecting the surrounding wooded landscape and soft hues of the sky. The calm water creates a mirrored surface, enhancing the serene atmosphere of the natural setting.

Guest suite in Concord

4.98 out of 5 average rating, 130 reviews

Water front cabin-like guest suite on a quiet pond

Our home is located on a wooded lot overlooking a pristine kettle pond. Access to our home requires ascending a long but gradual set of stairs followed by a second set of stairs to the entrance of the guest suite. The two room suite has a bedroom and a kitchenette with a microwave, toaster, electric kettle and mini frig. There is a French press, coffee bean grinder, tea, cups, dishes and flatware in the cupboards. It does not have a full kitchen ( no stove/ no kitchen sink)

Guest favorite

A spacious loft area features a queen-sized bed with a cozy comforter and decorative pillows, alongside a daybed for seating or lounging. Wooden beams and a rustic brick hearth enhance the charm. Light enters through multiple windows, illuminating the inviting space.

Guest suite in Littleton

4.91 out of 5 average rating, 423 reviews

Historic Loft with bathroom & kitchenette

A beautiful 1840s barn loft steps away from miles of hiking trails. Fully separate and private entrance, bathroom, and kitchenette. Enjoy a serene, rustic cabin atmosphere with a historic brick hearth and exposed beams. Southeast facing windows overlook patio, garden and ruins. Off the beaten path but only 5 min. to Rte 2, Rte 495, and Boston commuter rail. Drive times w/o traffic: 45 min. Boston, 20 min. Lowell/ Rte 3, Burlington, Bedford, Nashua 30 min.

Guest favorite

The stone barn building is framed by vibrant lavender fields in the foreground. Evening light illuminates the windows, while a calm sunset creates a soft gradient in the sky, transitioning from warm hues to deep blues.

Barn in Holden

4.89 out of 5 average rating, 479 reviews

Farm stay in a Historic Ski Lodge turned Barn

Once a ski lodge, then a horse barn, the hayloft in this unique stone barn has been converted to a comfortable & peaceful getaway. Enjoy a tranquil farm stay on a working Lavender farm. Help feed (if you wish) the sheep and see the horses and chickens. Enjoy the serene views and take in a sunrise or sunset or the stunning evening stars and moon on the back patio, stroll around the farm and hike our 1 mile nature walk. Convenient to local skiing & golfing.