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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Superhost

A cozy outdoor space features a stone fire pit surrounded by a paved patio. A wooden bench sits nearby, with a barbecue grill positioned to the left. Lush, manicured shrubs and small trees frame the area, providing a sense of privacy and tranquility.

Home in Wayland

4.78 out of 5 average rating, 486 reviews

Tiny house experience steps from the water!

-Tiny house experience in quiet private neighborhood on its own lot with great backyard & fire pit on private secluded St. -prof cleaned after each guest -High speed internet/ expanded cable -Built in full bed with queen sleeper futon bed that can sleep 2 more -Just a few steps from beautiful Dudley Pond for swimming/fishing and great walking trails Wayland is one of nicest towns in MA yet only a min or two from anything you need and less than half hour from Boston. texts returned instantly

Guest favorite

A cozy reading nook is situated next to a custom-built wooden bookshelf filled with books and decorative items. A rocking chair with a striped cushion invites relaxation. Soft natural light streams in, highlighting the warm wooden floors and the workspace's inviting ambiance.

Condo in Cambridge

4.89 out of 5 average rating, 138 reviews

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

WALK to Harvard, MIT and steps to all public trans & blue bikes! Gorgeous fully furnished monthly stays! Great for tourists, visiting nurses, Harvard, MIT fellows, etc! In-unit w/d and full eat in kitchen (granite counters, dishwasher/disposal (all cooking utensils, etc.). Light filled large bay windows living room with custom built in bookshelves & picture book library. Wood floors, AC/WIFI/all utilities included! Pets (yes large dogs too) welcome w. preapproval.

Guest favorite

A modern living area is highlighted by a sectional sofa in neutral tones and a large area rug. A flat-screen television is mounted above a stone accent wall. A Peloton bike is positioned nearby, and natural light filters through the windows adorned with sheer curtains.

Apartment in Boston

4.85 out of 5 average rating, 194 reviews

1st Flr 2BR unit with parking + steps from train

Modern ground floor apartment with all updated interior and furnishings. 2 blocks from Stony Brook Orange Line stop. Close to all Boston Universities (Northeastern, Boston University, Boston College, Emerson, Suffolk University, Simmons, etc) as well as all major Boston hospitals (Brigham & Womens, Beth Israel, Dana Farber, Mass General, Boston Medical, etc). Home is also close to Fenway Park, Boston Common, TD Garden, Downtown Boston and the Financial district.

Guest favorite

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

4.95 out of 5 average rating, 202 reviews

Family Home + Near Downtown + Cool Backyard!

Welcome to our family home. It's convenient, comfortable, safe, and close to downtown Boston! We have a backyard and open space with a beautiful deck. It's a great place to spend time and enjoy a peaceful outdoor setting in the city. Located in the waterfront neighborhood of Jeffries Point, East Boston. A 5-minute walk to lovely parks and the HarborWalk. And just ONE SUBWAY STOP to downtown Boston. We love Boston - and hope we can share it with you!

Top guest favorite

An aerial view captures the farmhouse in a vibrant red hue, surrounded by lush greenery and autumn foliage. The expansive yard includes several parked vehicles, while the mountains rise in the background under a clear blue sky.

Home in Sterling

4.94 out of 5 average rating, 205 reviews

Quiet country retreat with modern conveniences

Our mountain-view farmhouse sits on a 5 acre knoll, 300' from a quiet country road, surrounded by the sights and sounds of quintessential New England. The location of the property strikes a perfect balance between seclusion and convenience with access to hiking, kayaking, biking, parks, restaurants, grocery, and shopping close by. Restaurant food delivery of local favorites for Japanese (including sushi), Chinese, pizza, sub, salads, etc is available.

Guest favorite

A spacious bathroom features a marble countertop with a sink and vanity cabinet. A large mirror above the sink reflects soft lighting. A toilet is positioned beside the vanity, and neutral-toned tiles cover the floor, contributing to a clean and functional space.

Home in Westminster

4.94 out of 5 average rating, 127 reviews

Wachusett Mountain Get-Away

This family home is spacious and accommodating for those looking to relax while away from the ski slopes or simply wanting to get away from the city. Situated nearby a plethora of hiking and mountain biking trails, lakes for fishing and paddling, the home is perfect for those craving the great outdoors. The home is 6 min from Wachusett Mountain Ski Resort, 3 min from the Wachusett Brewery, and 1 min from the 1761 Old Mill Restaurant.

Guest favorite

A private backyard oasis is surrounded by lush greenery and blooming flowers. A swimming pool is featured in the foreground, reflecting blue skies. Outdoor seating areas are visible, providing space for relaxation and enjoyment.

Home in North Andover

4.94 out of 5 average rating, 152 reviews

Nana-tucket Inn

Charming historic town, home of Brooks School and Phillips Academy, 30 minutes to Boston and Seacoast. Families will enjoy our children’s park and town park, just a short walk from property. Enjoy pastural views while relaxing poolside (availability May 1 - Oct 1)in a quiet & private backyard setting. Hot tub is also open May 1 til Nov 1. Seven minutes to commuter rail for those who desire traveling into Boston, no hassle!

Superhost

Apartment in Milton

4.85 out of 5 average rating, 119 reviews

Retreat Milton/Boston line (transit close) Pets

The house is tastefully decorated and can accommodate a larger group , sleeps 6-8. 5 min to Boston , 1.3 miles to Central Ave Transit, or bus at end of street. The house is 20 min to Downtown Boston , it is a duplex totally separated for your own privacy. Reasonable alternative to Hotels , perfect for groups going to Convention Center. I recently added mini splits for additional cooling and heating needs , central ac .

Top guest favorite

A beautifully renovated Victorian home features a distinctive red exterior with large bay windows and a stone foundation. Lush greenery surrounds the entrance, complemented by flowering plants along the walkway. A spacious front porch invites relaxation and enjoyment of the serene neighborhood.

Home in Boston

4.97 out of 5 average rating, 163 reviews

Clean, spacious condo just steps from the MBTA

Perfect location for you to rest and relax during your Boston vacation. Located in a great area just 0.2 miles from the Green MBTA B Line, which will take you right to Fenway Park (3.4 mi) or Downtown Boston. The condo is 1.5 mi to Boston College, 3 mi from Longwood Medical area. Located on the top floor of a beautiful, fully renovated Victorian home. Central heat and air! Located on a very safe street in Brighton.

Top guest favorite

The front exterior of the house features a charming porch with white railings and hanging flower baskets. Lush greenery surrounds the entrance, complemented by a stone path and flower beds. A tall lamp post stands by the walkway, enhancing the inviting appearance of the property.

Home in Melrose

4.96 out of 5 average rating, 104 reviews

Spacious 5BR Near Boston | Family-Friendly Stay

Experience the best of Boston just 7 miles away in this 5BR, 2BA family-friendly home. Features include a chef’s kitchen, fenced yard, large deck, smart TV, central A/C, and parking for 3 cars. Families enjoy added perks like Pack ’n Plays, high chairs, stroller, and more. Transut is just 1,000 ft away for easy city access. Perfect for vacations, business trips, or long-term stays. Stylish, peaceful, and fully equipped!

Superhost

The exterior of a single-story house is depicted, featuring a grassy backyard and a deck. Green plastic chairs are positioned on the lawn. A section of the yard is enclosed by a fence, with trees providing shade in the background.

Home in Canton

4.83 out of 5 average rating, 168 reviews

3 bedroom impeccable private home, quiet street

Clean, quiet house with 3 bedrooms, full kitchen, fenced in yard, smart TVs (no cable). Quiet, safe, clean neighborhood, close to restaurants, and amazing outdoor destinations (Blue Hills reservation for hiking, swimming, photography, biking, etc), also golf course, horse barns, rock climbing, ice rink and more! Please note, the driveway and yard are shared with the downstairs unit.

Superhost

A dining area is presented with a wooden table set for six. A vase filled with vibrant flowers is centered on the table, and natural light illuminates the space through large windows adorned with sheer curtains. A living area is visible in the background.

Apartment in Waltham

4.83 out of 5 average rating, 390 reviews

Airy, Sunny, CLEAN 2 BR in Waltham- 15 min BOS

CLEAN 2 bedroom with updated kitchen (granite counter top) and bathroom. Minutes to vibrant Moody Street for restaurants (great selection range from good old American food to Asian), local homemade ice cream shop, shops and a movie theater. Quiet, convenient location- 15 minutes to Boston and close to Brandeis University, Regis College, Bentley College and Lasell College.