Kid-friendly holiday rentals in Middlesex

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Middlesex

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

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Guest favourite

Home in Plattsburgh

5 out of 5 average rating, 44 reviews

Comfy 3 bedroom home tucked away on the bay

Bring the whole family to this comfy lake house with a 'home away from home' feeling. Lots of indoor and outdoor space for fun, relaxation, swimming, fishing; equipped for adults and kids alike. Tucked away on the bay on Lake Champlain, and bordering the national wildlife park, there's no need to worry about cars or noisy neighbors; very safe environment. Centrally located; minutes to beaches, trails, shopping, golf, skiing, ferry to Vermont, and restaurants. Beautiful views, peaceful, and clean

Top guest favourite

Cottage in Burlington

4.98 out of 5 average rating, 209 reviews

Brand-new house steps away from downtown and lake!

Enjoy everything Burlington has to offer in this brand-new, cozy, stylish cottage. This adorable house was completed in January of 2023 and has a master bedroom plus a sleeping loft, as well as a full-sized bathroom, washer and dryer, and parking. The dining/living area has a partial view of Lake Champlain! You're tucked away on a quiet residential street near a park & playground but are just a 10-minute walk to downtown and a 5-minute walk to the lakefront and a gorgeous shoreline bike path.

Guest favourite

Home in Rutland

4.81 out of 5 average rating, 347 reviews

Home Sweet Home

Single family house within walking distance of downtown Rutland. Many restaurants, bars, movies, bowling, farmer's market, etc to do. 15-20 minute drive to Pico and Killington. 30 minutes to Okemo. Mountain bike parks near by- Pine Hill, Killington and Okemo. Adventure park at Killington. 4 bedrooms, 1.5 baths. House sleeps 8+comfortably. Room for more if needed. Keurig coffee maker in kitchen, microwave, toaster, crock pot. Kitchen is fully furnished. AC units on first floor and second.

Guest favourite

Home in Enfield

4.95 out of 5 average rating, 19 reviews

Upper Valley Shaker-Style Home, close to Dartmouth

Located within minutes to Dartmouth Health Medical Center and Dartmouth College, this home offers a comfortable, warm place to gather with friends and family during your visit to the Upper Valley. Just off Route 4, this home offers easy access to I-89 and I-91. This home is unique in its location and proximity to Mascoma Lake. A common right of way and short walk will lead you to the lakefront park and rail trail, where the views are breathtaking. Snowmobile access to rail trail

Guest favourite

Flat in Essex Junction

4.88 out of 5 average rating, 141 reviews

Apartment with SO MUCH SPACE -Burlington & airport

NEW FLOORING & BATHTUB: Feb 2025. This 1,000-sqft spacious basement apartment is in the heart of Essex Junction in a great neighborhood — near Burlington, ski resorts, Essex Expo, and the airport. Restaurants and bars nearby! Great for quick work trips or longer stays. We have a few toys and a Pack ‘n Play for your little one! Fully furnished and equipped for an easy stay — including an air-fryer, panini press, etc. (NO ridiculous cleaning fees!) Come visit — we'd love to host you!

Superhost

Cabin in Woodsville

4.88 out of 5 average rating, 317 reviews

Cabin Getaway, Pool Tb, Darts, Poker Tb, ATV Trail

Log cabin getaway in White Mountains, NH. Located in Mountain Lakes community, it is a perfect location from which to enjoy outdoors. You can fish, swim, hike, ski and then come back to a comfortable home. Sit on the deck and pick at the mountains or enjoy a get together by the big fire in the yard. Easy walk to the lakes. Close to trails for ATV and snowmobiles. Visit nearby towns of Lincoln, Littleton, Franconia with lots of restaurants and activities.

Top guest favourite

Home in Addison

4.96 out of 5 average rating, 224 reviews

Brthtkng New Premier Lake Champlain Wfrnt Escape!

7/19/20 : UPDATE - We are fully compliant with all local, state and federal safety protocols. Call /text Us fir any questions, at 978-502-6282 . Be Well, Be Safe & We Look Forward to Having You as Our Guests! We are the #1 Premier Lake Champlain Breathtaking New Property with 250'+ Prime Lake Champlain West/Sunset/Adirondack Mtn. facing w/Amazing Sunsets & Jacuzzi Tub in Master Bath Overlooking Lake,Mountains & Amazing Sunsets and 250+ 5 Star Reviews!

Guest favourite

Home in Burlington

4.93 out of 5 average rating, 114 reviews

Cozy, safe, conveniently located, newly renovated.

"Bienvienue" to our charming, recently renovated house to provide a comfortable stay in our quiet safe neighborhood and beautiful city. Suitable for a small family or two couples. Pet friendly with nice fenced back yard, pergola patio with grill. Also screened in front porch for bug free summer lounging. Five minute walk to Lake Champlain and waterfront park , ten minute walk to market place restaurants and nightlife or North Beach Park.

Guest favourite

Apartment in Killington

4.78 out of 5 average rating, 176 reviews

Amazing,Ski, Golf, Hike, Bike, Adventures

Killington has become a wonderful 4 season resort area that satisfies many tastes. You can hike, play golf ,swim, bike, ski-snowboard, or just lay back and enjoy the surroundings. You can go to the Killington website to find out what is happening. Please go to the Killington website to get complete information before you go. There is also a Mountain Green website that will let you know which amenities are available during your stay. mountaingreen.com

Guest favourite

Home in Glover

4.86 out of 5 average rating, 21 reviews

Cheerful 5-bedroom house offered by Lakeside Haven

Bring the whole family to this great place with lots of room for fun over looking Shadow Lake with access to the beach with a short walk. Skiers and Snowmobiles at welcome all winter with VAST trails access and several X-country and down hill skiing facilities with in 1 hour drive. Near by Ski mountains (Jay Peak, Burke Mountain, Stowe, Smugglers Notch) Cross Country Skiing (Craftsbury Outdoor Center, Jay. and Burke) also just off the Skidoo trails

Guest favourite

Flat in Burlington

4.94 out of 5 average rating, 130 reviews

No tariffs here! Will refund all taxes!

Now accepting reservations until Sept 2025. Situated on Lake Champlain in the desirable, artsy, historical south end of Burlington. Cozy, newly renovated, 1 BR apartment with 1 comfy queen bed, fully equipped kitchen, and all the comforts of home. Located on the city bike path, less than a mile to downtown. EV charger available. Longer stays: WORK at Hula Lakeside! Traveling nurses also encouraged!

Guest favourite

Home in Plattsburgh

4.92 out of 5 average rating, 111 reviews

Enjoy every season in the Lake Champlain Region

3 bedroom home on a cul-de-sac. Off street parking Deck with patio seating and grill Double lot yard Dishwasher, washer/dryer, filtered drinking water Internet, Hulu Live TV One full bath, one half bathroom Lake rights and private beaches 2 blocks from park with playground, tennis and basketball courts 1.5 miles from bike paths