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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 €70 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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Guest favourite
A white farmhouse is set against a clear blue sky, surrounded by lush greenery and large trees. A private pool reflects the house and trees, creating a serene outdoor space. A rustic barn can be seen in the background, indicating the property's charm.
Home in Plainfield

Mountain View Farmhouse w/ Orchard, Pool is Open!

This magical property is Vermont at its finest. Bring the whole family to this idyllic farmhouse with panoramic mountain views, large private pool, apple orchard, flower gardens, fire pit and much more. Be as free as you imagine on 14 private acres of lawn, perennial gardens, fruit trees and lush woods with a meandering stream. Let the kids swim in the pool all day while you read in the shade of old locust trees while taking in one of the best views in Vermont.Find us on insta: @upper_east_eden

4.82 out of 5 average rating, 153 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 entrance features a white door with a glass panel, surrounded by soft green siding. A decorative white planter box holds flowers beneath the window. A wooden overhang provides shelter at the entryway, enhancing the welcoming appearance of the space.
Guest house in Montpelier

The North Cottage

La Casita del Norte is a private, bright, self-contained apartment in a small building separate from our home – a relaxing retreat in a quiet neighborhood within easy walking distance of Vermont College, State House and downtown Montpelier. Warm in the winter, cool in the summer -- we just installed air conditioning! WE ARE FOLLOWING AIRBNB’S ENHANCED CLEANING AND SANITIZING PROTOCOL TO MAKE YOUR STAY AS SAFE AND WORRY-FREE AS POSSIBLE. And we use green cleaning products wherever possible.

4.89 out of 5 average rating, 519 reviews
Top guest favourite
Aerial view of the vibrant Vermont landscape, showcasing rolling hills adorned with a diverse palette of fall foliage. The rustic barn sits among expansive fields, framed by trees displaying bright autumn colors, with distant mountains in the background under a partly cloudy sky.
Barn in Morristown

200 acre Stowe area Bunkhouse.

Hello and welcome to our Red Road Farm 'Bunkhouse' -- We're so happy to host you! Sitting on our 200 acre estate this authentic barn offers our guests a chance to relax in the beautiful rolling hills of Vermont. Access the vast majority of our historic Stowe area land -- from our apple orchards to our extensive walking paths in fields and woodland. We hope that you can experience such fun and quiet time in our cozy, western-style bunk room. Located only a 10 minute drive from downtown Stowe.

4.97 out of 5 average rating, 251 reviews
Top guest favourite
A charming treehouse is nestled among lush green trees, featuring large windows that glow warmly at dusk. A connecting bridge is illuminated with string lights, creating a welcoming pathway. Ferns and forest foliage add to the natural surroundings, enhancing the serene woodland atmosphere.
Treehouse in Moretown

Treehouse at Bliss Ridge Farm - Best Views in VT!

This treehouse, the Birds Nest, is open May-Oct. Our “4-Season Treehouse @ Bliss Ridge,” is open year-round: https://www.airbnb.com/h/bigtreehouseatblissridgefarm — NEW SAUNA on property! Dr. Seuss-inspired tree home perched @top of 88-acre, organic hill farm, surrounded by 1000s acres of wilderness. Designed by B'fer Roth, DIY network host of The Treehouse Guys - built WITHIN living trees, not stilts! Private hiking & panoramic views of Worcester range, MR valley! No pets or animals please.

4.97 out of 5 average rating, 209 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, 102 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, 172 reviews
Top guest favourite
The log cabin features a charming exterior with a prominent stone chimney and rustic red accents. It is surrounded by lush greenery and tall trees, with a serene yard that conveys a peaceful retreat in nature. A welcoming wreath adorns the front door.
Cabin in Stowe

Charming log cabin w/ fireplace in Stowe village

The Ginger House: experience the warmth of this charming rustic log cabin, situated in the woods but close to the main village of Stowe. The open floor plan allows you to be in the new kitchen while still enjoying the real fireplace. Also located on the first floor is a full bath and spacious bdrm. Upstairs is where you’ll find the master with full bath. There is a large deck and fire pit which is great for just hanging out. All this and easy access to the Mountain Road shuttle.

4.97 out of 5 average rating, 263 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, 210 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, 323 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, 370 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, 201 reviews

Popular amenities for Middlesex family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favourite
A modern treehouse features a warm wooden exterior, elevated on a platform among vibrant autumn foliage. Large glass windows provide a view into the inviting interior space. Steps and a small deck lead to seating arranged on the ground level, surrounded by natural scenery.
Treehouse in Newport

Secluded Luxury Treehouse - Hot Tub + Projector

4.97 out of 5 average rating, 341 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

4.99 out of 5 average rating, 140 reviews
Top guest favourite
Two white Adirondack chairs are positioned on a grassy expanse, surrounded by autumn foliage. Trees with vibrant orange and yellow leaves create a scenic backdrop against a clear blue sky, showcasing the natural beauty of the 8-acre property.
Home in Waterbury Center

Peaceful setting with Mountain Views

4.96 out of 5 average rating, 148 reviews
Top guest favourite
A hot tub emits steam under the soft glow of string lights, creating a relaxing ambiance. The wooden deck features outdoor seating, inviting guests to enjoy the night. The rustic home blends with the surrounding nature, offering a peaceful retreat.
Home in Waterbury Center

Mountain Oasis/10 Mins to Stowe/Hiking/HotTub

4.99 out of 5 average rating, 146 reviews
Top guest favourite
Cabin in Morristown

Modern Post&Beam w/ Hot Tub, Waterfall, Mtn. Views

4.97 out of 5 average rating, 185 reviews
Guest favourite
The A-frame treehouse is illuminated by warm string lights, showcasing a spacious deck above the ground. The structure is nestled among trees, featuring a mix of wooden materials and large windows that highlight the inviting interior. A cozy seating area is visible on the deck.
Treehouse in Johnson

Designer A-Frame Treehouse | Hot Tub & Sauna

4.91 out of 5 average rating, 111 reviews
Guest favourite
A charming treehouse is perched among vibrant autumn foliage, surrounded by trees displaying shades of yellow and red. The wooden structure features a red roof and a spacious deck that offers a scenic view, harmonizing with the natural hillside landscape.
Treehouse in Warren

The Birch Perch! Treehouse with spa and fire pit!

4.91 out of 5 average rating, 109 reviews
Top guest favourite
Home in Waterbury

Cozy Hideaway w Hot Tub — Bike, Hike, Play & Relax

4.96 out of 5 average rating, 160 reviews

Family- and pet-friendly home rentals

Superhost
A farmhouse is positioned in a scenic landscape, with a gravel driveway lined by greenery leading towards it. The sunrise casts warm tones across the sky, reflecting on puddles in the foreground, while a distant tree stands amidst the open fields.
Farm stay in Elmore

Cozy rustic Cottage // Close to Stowe

4.96 out of 5 average rating, 373 reviews
Top guest favourite
A sun-filled living area features large windows that offer views of the surrounding trees. A cozy seating arrangement includes a blue couch and a brown accent chair. A low coffee table sits atop a vibrant, striped rug, complemented by a soft bean bag nearby.
Cabin in Moretown

Waldhaus - Modern Forest Cabin

4.94 out of 5 average rating, 266 reviews
Top guest favourite
A large house featuring a blend of stone and timber architecture is set against a backdrop of lush greenery. The exterior showcases a prominent gable roof, large windows, and a welcoming porch. A separate structure with a barn-like design is visible in the background.
Home in Stowe

Cozy Mountain Home w/Million $ View

4.97 out of 5 average rating, 131 reviews
Top guest favourite
An open living area features wooden walls and a light wood floor. A small kitchenette is visible with seating at a bar. A table with two patterned chairs is positioned next to a doorway, leading to the stairs. Natural light enters through a nearby window.
Flat in Montpelier

Travelers Oasis in Montpelier

4.92 out of 5 average rating, 131 reviews
Top guest favourite
Home in Stowe

Vermont Cedar Cottage | Fireplace & Pond Views

4.96 out of 5 average rating, 165 reviews
Top guest favourite
The exterior of the duplex is showcased, featuring a welcoming porch with two umbrellas over a seating area. Steps lead up to the porch, surrounded by lush greenery and neatly arranged flower beds, and the house is embraced by mature trees.
Flat in Montpelier

Entire 2nd Floor Walk to Montpelier

4.88 out of 5 average rating, 803 reviews
Top guest favourite
The house is set against a backdrop of vibrant fall foliage, with a blend of yellow and red leaves surrounding it. Large windows reflect the colors of the trees, while the modern architecture adds to its charm. The scene conveys a harmonious connection with nature.
Home in Stowe

Spacious Eco-Friendly Stowe Home for Family Fun

4.98 out of 5 average rating, 203 reviews
Top guest favourite
A cozy sitting area features a couch and an armchair, complemented by decorative cushions. Wall art is displayed above a television, and a kitchenette is visible in the background. Warm lighting enhances the inviting atmosphere in this thoughtfully arranged space.
Guest suite in Waterbury Center

Waterbury Center Guest Bedroom - 244 Howard

4.94 out of 5 average rating, 499 reviews

Family-friendly home rentals with a pool

Guest favourite
A cozy living area features a built-in conversation pit surrounding a modern fireplace. Natural light streams in from large windows, illuminating comfortable seating adorned with colorful cushions. Wooden bookshelves filled with books create a warm and inviting backdrop.
Townhouse in Stowe

Ski In Ski Out, Chic, Fun, Cozy, Grt Location!

4.94 out of 5 average rating, 158 reviews
Guest favourite
A dining area is presented with a long wooden table, surrounded by several gray chairs. Two built-in benches with patterned cushions and pillows are positioned along the wall. A round mirror is mounted above the table, reflecting the space's natural light.
Townhouse in Stowe

Stowe, Newly Renovated Topnotch Resort Townhouse

4.95 out of 5 average rating, 171 reviews
Top guest favourite
A spacious two-story home is set among lush greenery, with a large front deck featuring white railings. The exterior showcases a mix of light-colored siding and dark shutters, while tall trees provide a natural backdrop, creating a peaceful atmosphere.
Home in Stowe

EPIC Stowe Getaway - Great For Families & Friends

4.98 out of 5 average rating, 315 reviews
Superhost
A serene lake scene is framed by lush greenery and trees. A canoe rests on the grassy shore, with soft water reflections of the surrounding landscape. The sky displays gentle pastel hues, indicating a calm evening atmosphere.
Home in Haverhill

Lakefront Peaceful Getaway in Mountain Lakes

4.8 out of 5 average rating, 196 reviews
Guest favourite
Villa in Stowe

World-Class Villa @ Trapp & Stowe

4.98 out of 5 average rating, 103 reviews
Guest favourite
Flat in Williamstown

Cozy/Private, close to hospital, i-89

4.91 out of 5 average rating, 187 reviews
Top guest favourite
A vibrant garden surrounds a pool area, featuring blooming tulips and a variety of colorful flowers. A patio umbrella provides shade over seating near the pool, with scenic views of rolling hills and distant mountains visible in the background.
Flat in Monkton

Spacious Private Apartment w/ Green Mountain Views

4.99 out of 5 average rating, 136 reviews
Top guest favourite
A spacious living room features a large brown leather sofa with decorative pillows, accompanied by two armchairs. A wooden coffee table sits on an oriental-style rug, and a couple of framed artworks adorn the walls. Floor-to-ceiling windows provide an airy atmosphere.
Townhouse in Stowe

Gorgeous panoramic views - 4 miles to the mountain

4.89 out of 5 average rating, 253 reviews

When is the best time to visit Middlesex?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price€226€255€198€188€199€214€197€180€195€208€175€248
Avg. temp-6°C-5°C0°C8°C15°C20°C22°C21°C17°C10°C4°C-2°C

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