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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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A modern living area features a gray sofa adorned with decorative pillows, paired with a simple coffee table atop a patterned area rug. Large glass doors open to a balcony, allowing natural light to enhance the atmosphere.

Apartment in Waltham

4.88 out of 5 average rating, 139 reviews

2bed/2bath Apt at Waltham Landing. Middle Unit

This apartment complex was built in 2016. It is 1 block from The Charles River and Waltham's famous Moody Street, aka "Restaurant Row." Across the street from Waltham Station: Fitchburg Line - Commuter Rail. Bentley and Brandeis are 1 mile away. Monthly rentals accepted (inquire for best rate), discounts for groups and long-term rentals. Perfect for business travelers, families, anyone in between housing or visiting town! Free parking in the parking lot. Yes there is an Elevator.

A two-story grey house with white trim is visible, featuring large windows and a front porch. A white car is parked in the driveway, leading to a closed garage door. Lush trees provide greenery around the property.

Guest suite in Worcester

4.89 out of 5 average rating, 447 reviews

Private Suite with separate entrance in Worcester

The suite allows maximum of two pets per reservation for $50 per a pet. Our guests privacy starts from check in to check out with private entrance. The living room has mini library for guests, a 65 inch smart TV with high speed Internet and complimentary YouTubeTV local channels. The suite has a mini kitchen with mini refrigerator, freezer, microwave, air fryer, and coffee maker. It also has stocked cabinet utensils, cleaning supplies, linen closet and electric pump air mattress if necessary.

An open living area features a cozy striped sofa and a bright red pub table. A winding black staircase leads to the upper sleeping area. Natural light enters through a nearby door. A flat-screen TV is mounted on the wall, enhancing the space's functionality.

Barn in Carlisle

4.88 out of 5 average rating, 423 reviews

✨Private Studio w/ Loft Center Historic Carlisle✨

ENTIRE PLACE. This is a private charming studio completely separate with no shared areas located in the center of beautiful Carlisle. Close proximity to Routes 128, 495 and 3. Just 25 mins from Cambridge, Somerville, Boston. A pleasant 10 min to historic downtown Concord's lively events, shops and restaurants. 1.6 miles to Hiking/bike trails of Great Brook Farm State Park. Explore nearby hiking, conservation land and farms. *Only a 15 min drive to Lowell via the Lowell Connector*

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, 412 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, 300 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!

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

4.91 out of 5 average rating, 511 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!

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, 410 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.

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.

4.89 out of 5 average rating, 467 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.

An open and spacious room is highlighted by natural light from large windows. A cozy leather settee and a small marble breakfast table with two chairs provide seating. The queen bed is dressed with a deep purple coverlet, and a decorative rug adds warmth to the wooden floor.

Apartment in Concord

4.93 out of 5 average rating, 401 reviews

Cottage Suite "A" - Walk to Shops, Train, History

This is a private unit with no shared areas. It is the front corner of our house and is completely separate. However, you will share walls like in an apartment. Kitchen includes: sink, microwave, fridge, Keurig, and water boiler. Private gated outside lawn and patio. History, nature, dining & shopping are very close by. Open and welcoming to ALL types of people. There is TV with internet (Prime & Netflix) but NO LIVE TV OR CABLE

A spacious living area features soft furnishings with patterned upholstery and a light-colored coffee table. Natural light filters through the large windows draped with sheer curtains. The kitchenette is visible, along with a small dining table and chairs, creating a welcoming environment.

Apartment in Newton

4.96 out of 5 average rating, 431 reviews

Sunny apartment in gracious Victorian

Relax into your Boston stay! We offer a sunny in-law apartment on the first floor of a gracious owner-occupied Victorian house. Quiet, safe residential neighborhood. Private entrance. Spacious bedroom, living room with sofabed, kitchenette & bath. Strong Wi-fi. Driveway parking. Contactless check-in, Easy access to Boston, Cambridge, Rts. 128 & 90, and Charles River bike path. Let us welcome you!

Top guest favorite

A cozy sleeping area is separated by wooden bookshelves, showcasing an array of books. A queen size bed is placed against a wall, complemented by warm lighting. A small dining table with two chairs is situated nearby, enhancing the functional layout.

Apartment in Natick

4.98 out of 5 average rating, 367 reviews

Scandi-Modern Apartment

Charming walk-out ground level apartment in a quiet residential neighborhood. Conveniently located west of Boston with easy access to highways. Walkable to grocery store, pharmacy, banks and restaurants. Walk the nearby trail to Lake Cochituate and the Cochituate Rail Trail is less than 1 mile away. Natick Mall is 1.3 miles.

A cozy bedroom features a four-poster bed dressed in white linens and accented by a decorative pillow. Soft light from a bedside lamp illuminates the space, which includes a wooden nightstand. A closet with double doors is visible in the background.

Apartment in Concord

4.94 out of 5 average rating, 244 reviews

Bishop Suite - Private suite in historic Concord

I live in historic Concord, Massachusetts, 4 miles from Concord Academy, Fenn School, Middlesex School, and many historical sites, and less than 30 miles from downtown Boston. About 4 miles from the commuter rail (train) to downtown Boston, and 2 miles to restaurants, grocery, and any kind of store you would need.

Vacation rentals for every style

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Apartments

Convenient locations with everyday essentials

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A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Middlesex County family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The kitchen features modern cabinetry and high-end stainless steel appliances, including a refrigerator and microwave. A dark countertop extends to a breakfast bar with two white stools. Warm hardwood floors and soft overhead lighting create an inviting cooking space.

Apartment in Boston

4.91 out of 5 average rating, 67 reviews

South Boston. Minutes away from Convention Center

A spacious living area features a large sectional sofa adorned with decorative pillows. A glass coffee table sits atop an area rug, complemented by a flat-screen TV on a console table. Natural light filters through a window, creating a bright and welcoming atmosphere.

Condo in Brookline

4.77 out of 5 average rating, 183 reviews

Brookline Village, Central Air, 2B, Near Longwood

A spacious living room features a comfortable white sofa paired with an accent chair. Natural light floods in through multiple windows, creating a bright atmosphere. A large area rug lies on the hardwood floor, and a decorative painting adds a touch of color above the fireplace.

Home in Brighton

4.96 out of 5 average rating, 269 reviews

Spacious 3 bed, in unit laundry, central Air

The living room features a comfortable couch and chairs arranged around a circular coffee table. Natural light enters through two windows, illuminating the hardwood floors and wall mirrors. Soft curtains frame the windows, while a decorative plant adds a touch of greenery to the space.

Apartment in Brookline

4.66 out of 5 average rating, 29 reviews

Sunny,spacious, sleeps 4, steps to MBTA,Hospitals.

The open layout showcases a living area with a comfortable sofa and decorative pillows. A granite counter separates the kitchen from the space, which features natural light from large windows adorned with light-filtering shades. A piece of framed art and a potted plant complete the ambiance.

Apartment in Boston

4.78 out of 5 average rating, 331 reviews

Modern, Spacious 1BR for 4 - Easy Marathon Access!

Family- and pet-friendly home rentals

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

4.96 out of 5 average rating, 271 reviews

Welcoming 7-room house <15 miles to Boston & Salem

An outdoor space is presented, featuring a wooden picnic table surrounded by a sprawling lawn. A slide is integrated into the landscape, complemented by vibrant greenery and a nearby garden area. Outdoor seating is also visible in the background, enhancing the communal atmosphere.

Condo in Boston

4.93 out of 5 average rating, 204 reviews

Family Home + Near Downtown + Cool Backyard!

A room features a queen bed with crisp white bedding against a vibrant red wall. Two nightstands with lamps flank the bed, and a colorful piece of wall art adds character. Bright windows allow natural light to fill the space.

Townhouse in Boston

4.91 out of 5 average rating, 355 reviews

Spacious Family-Friendly Townhome Near Harvard

A serene bedroom is presented with soft blue walls and natural light flowing through the windows. A spacious bed is centered in the room, complemented by bedside tables, a lamp, and decorative wall art. A comfortable bench is positioned at the foot of the bed.

Apartment in Milton

4.85 out of 5 average rating, 120 reviews

Retreat Milton/Boston line (transit close) Pets

A sitting area features a classic blue wall with two framed botanical prints above a marble fireplace. An orchid in a pink pot and a small potted plant add color. A comfortable armchair and a leather sofa complete the cozy layout, enhancing the inviting atmosphere.

Apartment in Boston

4.96 out of 5 average rating, 381 reviews

Charming South End Duplex (Pets Ok)

A compact laundry area is visible, featuring stacked white washer and dryer units against a bold red wall. A set of shelves holds neatly folded white towels, while a fire extinguisher is positioned on the floor near the shelves.

Condo in Cambridge

4.9 out of 5 average rating, 143 reviews

#1A Harvard MIT Central location! in unit W/D

A light-filled living room features a pair of grey sofas, accented with decorative cushions. A glass coffee table is centered on a patterned rug, while large windows allow natural light to brighten the space. A front door is visible in the background.

Townhouse in Everett

4.89 out of 5 average rating, 306 reviews

#7 Comfortable Spacious Home Near Boston + Parking

A sunlit living room features a comfortable sofa with striped cushions and two armchairs with red accents. Soft rugs cover the wooden floor, while large windows with draped red curtains allow natural light to fill the space. A central coffee table adds functionality to the cozy setting.

Home in Medford

4.85 out of 5 average rating, 143 reviews

Sunny home minutes from Boston. Free parking.

Family-friendly home rentals with a pool

An open-concept kitchen and dining area features modern furnishings, including a long dining table surrounded by black chairs. Large windows offer views of greenery, allowing natural light to fill the space. A sleek kitchen island with bar stools complements the contemporary design.

4.71 out of 5 average rating, 7 reviews

Luxury Ultra Modern House in Newton ; Boston

The backyard features a tranquil swimming pool with sunlit reflections, surrounded by elegant outdoor seating arranged on a stone patio. Large windows in the main house offer views of the inviting outdoor space, enhancing the serene atmosphere.

Home in North Andover

4.94 out of 5 average rating, 162 reviews

Nana-tucket Inn

An outdoor swimming pool is surrounded by a spacious patio and lush greenery. Sun loungers are arranged around the pool, with a shaded seating area nearby. The house features a multi-level deck overlooking the pool, creating a relaxing outdoor space for guests.

Home in Hopkinton

4.95 out of 5 average rating, 157 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

A spacious backyard is shown, featuring a wooden playset with a slide and swings. Lush greenery surrounds the yard, with tall trees providing shade and privacy. The grass is well-maintained, creating a suitable area for outdoor activities.

Guest suite in Canton

4.72 out of 5 average rating, 114 reviews

Newly renovated, close to Foxboro and Boston

A spacious outdoor pool area is surrounded by lounge chairs and tables, offering a relaxing atmosphere. The pool is clear and inviting, with steps leading into the water. A rustic building with large windows is positioned nearby, set against a backdrop of lush greenery.

Cottage in Westford

4.92 out of 5 average rating, 39 reviews

Beach & pond cottage ! Westford MA and Boston!

Top guest favorite

A historic yellow home with multiple gables and an inviting front porch is surrounded by manicured greenery. The driveway leads to a garage, while shrubs and trees create a peaceful ambiance. Sunlight streams onto the exterior, highlighting the charming architectural details.

Townhouse in Groton

5 out of 5 average rating, 82 reviews

Potager Farm Private Townhouse

A tranquil outdoor pool area is surrounded by lush greenery, featuring a swimming pool with a waterfall. Colorful chairs in pink and turquoise are positioned nearby, inviting relaxation. A hot tub is situated adjacent to the pool, contributing to the serene atmosphere.

Apartment in Holliston

4.96 out of 5 average rating, 122 reviews

Lake Link

Destinations to explore