Kid-friendly holiday rentals in Middlesex County

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Middlesex County

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

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Guest favourite

Guest suite in Winchester

5.0 out of 5 average rating, 109 reviews

Warm and cozy 1st flr sweet guest suite w parking

Easy living at this peaceful and centrally-located guest suite. Winchester is the quintessential New England town located just 8 miles from Boston with an easy drive or 16 minute by train from Winchester Center or Wedgemere. Or check out historic Lexington and Concord next door, bustling Arlington Center or hip Davis Square. Tufts University, Harvard Square, Harvard University and MIT nearby. Your comfortable home away from home for fun excursions, get aways, business meeting or college visits

28 Mar – 4 Apr

$136 SGD per night

Guest favourite

Guest suite in Tyngsborough

4.98 out of 5 average rating, 217 reviews

Lakefront Suite Two-Room, Comfy, Tranquil

Guests can enjoy our home's private suite on a lovely small lake with a panoramic view, a spa-like bathroom, cotton linens, and a comfy bed. A/C and a fireplaced living room. Quietly watch lake nature or boats going by, or venture out to swim, kayak, or fish. Enjoy Lowell's mill history and it's national park, take a forest walk nearby, or drive 10 min. to Nashua, NH for its many restaurants and tax-free shopping. 1 hr from Boston and central to New England highlights. Low cleaning fees!

5–12 Aug

$169 SGD per night

Guest favourite

Flat in Framingham

4.92 out of 5 average rating, 259 reviews

Spacious 2 Br with All The Comforts Of Home

This a quaint apartment . Not your typical hotel room. In a country setting but 5-10 minutes from great shopping, restaurants, parks, colleges and major highways. Boston is 22.5 miles away. Fenway Park is 20 miles. Worcester is 17 miles. Private location overlooking conservation land. Walk to great hiking and biking trails but car needed for other activities. Full kitchen, laundry room and living room in addition to 2 br and bath. It has the comfort of a home away from home. Please NO PETS.

17–24 Jan

$213 SGD per night

Guest favourite

Cabin in Littleton

4.98 out of 5 average rating, 114 reviews

Private & Remote, Enjoy Outdoors, Sleep in Luxury

A bit of a wonderland (57 Acers, 50+ 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.

15–22 Jul

$252 SGD per night

Guest favourite

Barn in Carlisle

4.84 out of 5 average rating, 513 reviews

✨Entire Secluded Barn Suite Ctr 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*

15–22 Mar

$168 SGD per night

Guest favourite

Flat in Maynard

4.91 out of 5 average rating, 443 reviews

New Renovated Attic Apartment in Downtown Maynard

Newly renovated private attic apartment 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!

20–27 May

$187 SGD per night

Guest favourite

Guest suite in Dover

4.98 out of 5 average rating, 184 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

Graceful country oasis in a renovated 125 year old historic home, 35 minutes driving time from downtown Boston. (Important-stairs climbing required to reach bedroom suite.) I welcome quiet, mature guests. We are located on a scenic road in sophisticated Dover, Ma, a commuter/country setting, with miles of hiking trails and roads ideal for cycling, and surprisingly close to downtown Boston. I have owned and loved this home for 33 years and take great joy in its charm and outdoor spaces.

29 Oct – 5 Nov

$202 SGD per night

Guest favourite

Guest suite in Bolton

4.97 out of 5 average rating, 112 reviews

Vaughn Hill Hideaway & Sauna

Tucked into the slope of Vaughn Hill on 3 wooded acres, the entire lower level of our home is yours to enjoy. The Hideaway is a cozy 2-bedroom unit with “the BEST BEDS at an Air BNB ever!" to quote one guest. Take it slow with a wine tasting at Nashoba Valley Winery (5 min away), coffee at Harvard General Store (8 min), apple-picking at a local orchard, or hiking Vaughn Hill trails with your dog. Unwind in the backyard wood-fired sauna, available by request at $30 per firing.

12–19 Sep

$201 SGD per night

Guest favourite

Guest suite in Littleton

4.91 out of 5 average rating, 315 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.

26 Aug – 2 Sep

$143 SGD per night

Guest favourite

Flat in Hudson

4.85 out of 5 average rating, 295 reviews

Private Mother-In-Law apartment on the lake!

Waterfront on the Lake with a private beach and dock. Relax on your deck and Patio with Wonderful Views. This is a mother-in-law private downstairs apartment complete with kitchen and separate entrance. Enjoy the lake with a fire pit and use of paddle boat and kayaks (life jackets provided). Enjoy the wonderful eclectic restaurants in downtown Hudson including a Micro Brewery, Pub, Martini Bar, Micro Creamery and even a SpeakEasy.

12–19 Nov

$124 SGD per night

Guest favourite

Flat in Concord

4.94 out of 5 average rating, 207 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. For guests staying over 2 weeks, discounts can be negotiated, and an additional $75 cleaning fee will be assessed.

29 Mar – 5 Apr

$154 SGD per night

Guest favourite

Guest suite in Marlborough

4.88 out of 5 average rating, 252 reviews

Professional Accommodations!

Across from Lake Williams near 20 and 495, completely separate entrance and parking, all newly renovated, central air, high speed fios internet, 43 inch smart tv, desk, mini fridge, microwave in separate eating area, walk to Dunkin Donuts, Your completely private space! Walk to restaurant with indoor and outdoor seating. For your safety during Covid I keep 72 hours Between guests and have unit professionally cleaned!

9–16 Jan

$92 SGD per night