Family-friendly holiday rentals in Middlesex

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Middlesex

Total holiday rentals
Explore 70 holiday rentals in Middlesex
Nightly prices starting at
Middlesex holiday rentals start at €69 per night before taxes and fees
Verified guest reviews
Over 5,910 verified reviews to help you choose
Pet-friendly holiday rentals
Find 20 rentals that welcome pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
70 of Middlesex holiday rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Middlesex rentals
4.9 Average rating
Middlesex stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated family-friendly rentals in Middlesex

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

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Top guest favourite

A spacious studio apartment features a high, sloped ceiling and large windows that provide views of the surrounding greenery. The area includes a queen bed, cozy seating options, and a well-equipped kitchen with a breakfast bar, creating a welcoming and functional living space.

Guest suite in Waterbury Center

Cozy Mountain Retreat with a View of Mt Hunger

Nestled in the heart of Vermont's best skiing, hiking, dining + golfing right between Waterbury and Stowe. We're just minutes to downtown yet the private driveway that opens to 10 acres feels like you're a world away. The apartment has a private locking entrance through a shared garage, well stocked kitchen, cozy sitting area with a view of the mountains, full bathroom, memory foam mattress and blackout shades. We are family friendly with a highchair, pack n' play + changing table upon request!

4.88 out of 5 average rating, 230 reviews

Top guest favourite

A vibrant red barn is framed by greenery, with a full rainbow arching across a darkening sky. The barn's luminous white roof contrasts with the moody backdrop, creating a serene countryside image.

Barn in Middlesex

Jules Gem

Reconditioned Barn Apartment. One large room with 4 large windows creating much natural light with kitchenette, no oven at this time, but there is a toaster oven & BBQ Grill for your use Overlooking Mountains and situated next to a river. Enjoy the sounds and views of country on this 90 acre property. All new amenities and full bath with shower. Private swimming hole on property, steps from sought after hiking, 12 minutes to downtown Montpelier with fine dining, bars and unique shopping.

4.98 out of 5 average rating, 254 reviews

Top guest favourite

The farmhouse is displayed with a classic white exterior and a metal roof. A welcoming front porch is flanked by steps leading up to the entrance. Surrounding fields stretch into the distance beneath a clear blue sky, showcasing the home's peaceful rural setting.

Home in East Montpelier

The 1919 Mountain Farmhouse, new hot tub and patio

Welcome to your charming mountain getaway—The 1919 Mountain Farmhouse! Located just 10 minutes away from Montpelier and 40 from Stowe proper, this newly renovated 1919 farmhouse comfortably sleeps 8 and is the perfect choice for a relaxing stay. Nestled among quiet farmland, you and your guests will enjoy sipping coffee/wine on the back deck with full mountain views. After a fun day enjoying local trails, shops, mountains, and more—a table inside or outside awaits a meal to be shared with all.

4.99 out of 5 average rating, 138 reviews

Top guest favourite

A circular fire pit is surrounded by three rustic wooden benches, positioned on a grassy area among lush trees. Two adults and a child sit comfortably, enjoying the warm glow of the fire. Behind them, the unique treehouse structure, with large windows, blends into the natural setting.

Treehouse in Moretown

4-Season Treehouse @ Bliss Ridge; Best Views in VT

Insulated, thermostat control! LUXURY! 1-of-a-kind, 5⭐️Interior bathroom, @Bliss Ridge - 88acre, OG farm, private estate surrounded by 1000s acre of wilderness. NEW SAUNA& cold plunge!!! Our 2 architectural wonders = real treehouses, built withIN the living trees, not stilted cabins. Fabulous “Jotul” fireplace, indoor hot shower / plumbing, fresh mtn spring water, stable access ramp. Our original treehouse, "The Bird’s Nest" is open May-Oct. WiFi avail at the barn! Cell svc works! No pets.

4.98 out of 5 average rating, 167 reviews

Top guest favourite

Home in Waterbury

Perry Pond House

Come with your family, friends or by yourselves to enjoy a restful stay at our newly built secluded hillside home. Perry Pond is located close to many recreation opportunities (ski, bike, hike, swimming holes, paddling), restaurants, breweries, and scenic attractions in the Waterbury-Stowe-Waitsfield-Montpelier area. Its private setting overlooking a pond and distant views provides the perfect getaway for those seeking a peaceful break from their daily routine or to relocate remote work.

4.98 out of 5 average rating, 100 reviews

Top guest favourite

An open living area features a wooden dining table surrounded by black chairs. A cozy lounge area includes a navy blue sofa and a wooden coffee table, complemented by a patterned area rug. Exposed beam ceilings add a rustic touch to the bright space.

Home in Waterbury Center

Stunning Views near Stowe /Mountain private home

Retreat and relax at this incredibly located & uniquely designed home nestled in the heart of ski country. This three bedroom, two bathroom vacation home is perfect for families or couples looking to enjoy Vermont's beauty and recreation. Very private location minutes to the attractions of Stowe, Waterbury and Mad River Valley. Enjoy the hiking trails very close to this cozy home or the nearby ski slopes of Stowe. Sweeping views of the mountains throughout the house. Serene and lovely.

4.99 out of 5 average rating, 169 reviews

Guest favourite

A charming single-story house sits on a well-manicured lawn, surrounded by lush greenery and flowering shrubs. The exterior features large windows that invite natural light indoors, and a gentle sloping landscape leads towards a serene backdrop of trees.

Home in Moretown

Home on Flower Farm near VT’s best skiing & brews!

Country setting adjacent to a flower farm only 3 minutes off 89 perfectly nestled between mountains that boast hiking, skiing and mountain biking and the best of Vermont's brewery and restaurant scene. 20 minutes to Sugarbush and Mad River Glen, 30 minutes to Stowe and 25 minutes to Bolton Valley (night skiing!). With Waitsfield and Waterbury being less than 10 minutes away, it's an easy drive to two of the finest breweries, Lawsons and Prohibition Pig, that Vermont has to offer.

4.95 out of 5 average rating, 209 reviews

Top guest favourite

A panoramic view reveals rolling green mountains under a partly cloudy sky. The foreground features a lush meadow filled with tall grass, bordered by a tree line. The vibrant greens of the trees contrast beautifully with the scenic backdrop, inviting a sense of tranquility.

Guest suite in Waterbury Center

Farmhouse with Sunset Mountain Views

Unbeatable Vermont setting, panoramic mountain views and gorgeous sunsets. Located one mile off Rt 100, minutes from the best skiing, bike trails, kayaking, and hiking in the east. The apartment is a sunny, bright and private space, cheerfully decorated, with the comfiest beds and coziest linens. And great outdoor spaces to relax in at the end of the day! 10 min to Stowe Village, 18 to lifts, 30 to Sugarbush, 35 min Burlington. The pictures and our 5 star reviews say it all!

4.95 out of 5 average rating, 319 reviews

Top guest favourite

A serene landscape showcases rolling hills silhouetted against a pastel sky at sunset. The subtle gradient of pinks and purples transitions into deeper hues, while trees cresting the hills add depth to the tranquil scene.

Guest suite in Middlesex

Morningstar Meadow - your home in Vermont

You have a home in Vermont! 5-star one-bedroom apartment has country charm and contemporary panache. A perfect retreat to enjoy rural serenity, stunning views, woods and fields. Everything you need: well-appointed with attractive, high quality furnishings, separate entrance, full kitchen, open living/dining area, cozy bedroom with queen bed. Cable TV, WiFi, and cell service. Plentiful free parking. Recent guests claimed heat an issue. It is not. No complaints before or since.

4.98 out of 5 average rating, 368 reviews

Top guest favourite

A wooden bridge leads to the entrance of the treehouse, surrounded by trees displaying autumn colors. The structure features large windows and a unique architectural design, blending nature with handcrafted elements.

Treehouse in Waterbury

The Roost - Recharge & Relax

Enjoy being immersed in nature when you stay in this unique treehouse to unwind while experiencing some of the best sights and nature in Vermont. This cabin up on stilts and bordering one of Vermont's beautiful state parks. Views of the walkable Waterbury reservoir can be seen from its perch in the trees. "The Roost" aims for a balance of rustic meets elegance. With a tiled shower and heated flooring through out- one can truly reconnect and recharge in this unique experience.

4.94 out of 5 average rating, 194 reviews

Guest favourite

A spacious living area is filled with natural light from large windows, showcasing a comfortable sofa and a small dining table with two chairs. Refinished maple floors create a warm ambiance, while vintage wallpaper adds character to the space.

Guest suite in East Montpelier

Cottage Farmhouse Apartment in Heart of Vermont!

Welcome to our charming second-floor cottage-apartment in our historic 1830s brick farmhouse! This cozy space is completely redecorated for guests and features a comfortable queen bed in the sleeping area, a vintage farmhouse kitchen, and a lovely living/dining room with maple floors and travertine in the bathroom. Enjoy the peaceful country setting with eastern mountain views and active farm fields. Wake up to glorious morning sun and blackout shades for a good night’s sleep.

4.92 out of 5 average rating, 344 reviews

Top guest favourite

A private mountain home is nestled among lush greenery, featuring a wooden exterior and a metal roof. The structure is complemented by a welcoming porch and surrounded by a neatly maintained lawn, creating a serene atmosphere against the forest backdrop.

Home in Middlesex

True Mountain House

This is a very private mountain home surrounded by green and peace. Your private forest. Amazing Views. Very romantic. Open layout. Lots of light. Wood floors and electric heating. Very quiet, relaxing and cozy. It has a decompressing effect on it's guests. Perfect to rest your head. Not suitable for children under 12 years old. Amazing gourmet kitchen. WE HAVE HIGH SPEED INTERNET. Fly into Burlington and rent a car, it will be approximately a 40min. Drive to Middlesex.

4.94 out of 5 average rating, 199 reviews