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Family-friendly holiday rentals in Addison County

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Top-rated family-friendly rentals in Addison County

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

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Guest favourite
Farm stay in Bristol

Private constructed yurt on organic farm

Take it easy at this unique and tranquil getaway. The entire constructed yurt is yours to enjoy privately. Nestled on an organic farm, it sits a bit above Bristol offering sweeping views of the valley and the beautiful Adirondack mountains. There are many farm animals on the property and farm tours are available upon request. PLEASE NOTE: The queen bed is only accessible by a ladder. The property is located up a steep driveway. During the winter months all wheel drive vehicles are required.

4.92 out of 5 average rating, 132 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!

Romantic Honeymoon or fun family fantasy come true this treehouse has it all! Built by The DYI Network Treehouse Guys! Every detail custom crafted in this home in the tree tops makes your ultimate Vermont experience. All just 8 minutes to the lifts at Sugarbush. Kitchenette, cast iron stove, clawfoot tub, washer/dryer, AC, & outdoor shower all encased in a whimsical perch near skiing, waterfalls, biking and hiking. Incredible hillside views from your private deck! Romantic Hot tub in the trees!

4.91 out of 5 average rating, 109 reviews
Top guest favourite
A serene landscape is captured, showcasing a reflective pond surrounded by lush greenery. A variety of trees are positioned nearby, some displaying vibrant yellow leaves against a backdrop of rolling hills and a dramatic sky filled with clouds.
Barn in Ripton

Lovely Vermont Breadloaf Barn Stay Near Middlebury

Stay at our lovely renovated barn guesthouse in the Green Mountains of Vermont near Middlebury College. Perfect spot for a visit to campus, a quiet retreat, or home base for your outdoor adventure! 3 min. to Middlebury College’s Bread Loaf campus and Rikert Nordic Center, 9 min. to Middlebury SnowBowl. 40 min. to Sugarbush. 1 hr to Killington. Sleeps 1-6 people: entry level living area w/ laundry; mid-level with kitchen, bedroom, and bathroom ; upstairs loft suite with living area and desk.

4.95 out of 5 average rating, 271 reviews
Top guest favourite
Cottage in Middlebury

The Cottage Apartment in downtown Middlebury.

This charming, 1st floor two-bdr. cottage apartment is steps from Main Street, downtown Middlebury, & walking distance to shops, restaurants, and the College. An historic college town, Middlebury is replete with great restaurants, shops and cultural events to enjoy, all within walking distance. The comforts of this home include private parking, gardens, separate entrance, full kitchen and bath, and sleeps four. It is only a half hour from The Middlebury College Snow Bowl, and Lake Champlain.

4.92 out of 5 average rating, 161 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, 202 reviews
Top guest favourite
A unique treehouse is seen perched among tall trees, with a blend of rustic wood siding and large windows that reflect the surrounding greenery. The structure stands elevated from the ground, supported by slender pillars, blending harmoniously with the natural forest environment.
Treehouse in Hancock

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses

4.98 out of 5 average rating, 182 reviews
Top guest favourite
A simple yet inviting guesthouse features wooden siding and a metal roof. The front is lined with large windows, enhancing natural light. A wooden deck provides seating, with a grassy lawn extending towards the surrounding trees and fields.
Farm stay in Cornwall

Cozy country guest house

Our guesthouse is nestled in the Lemon Faire River Valley. This 1 bedroom with kitchen, bathroom, and extra sleeping loft gives you a quiet experience of the Vermont countryside. The outside entry deck overlooks over a 1000 acres of open field and farmland. Middlebury is only 3 miles away and offers museums, restaurants, and shopping. This is an active farm: horses, dogs, geese, a duck, and chickens. Please read the house manual as it has lots more information about the house and property.

4.94 out of 5 average rating, 257 reviews
Top guest favourite
The cozy cottage is softly illuminated at night, with warm light emanating from the windows. A sliding door is positioned at the entrance, complemented by two outdoor chairs on the lush lawn. The moonlight adds a serene ambiance to the rural scene.
Farm stay in Salisbury

Quaint 1-bedroom cottage on Blue Ledge Farm

This cozy cottage is on Blue Ledge Farm- a working goat dairy. It is a one-bedroom with a double fold-out futon in living room to potentially fit 4 guests. It is within 15 minutes of both Brandon and Middlebury, 1 hour south of Burlington. Pets are allowed, on leash. It can possibly include a farm and cheese tasting for an extra $20 per person (contact host in advance). It is the perfect place if you're an animal or cheese lover looking for a rustic and relaxing stay on a beautiful farm.

4.95 out of 5 average rating, 469 reviews
Top guest favourite
Cottage in New Haven

Hilltop Cottage With a View

Our newly built cozy and relaxing guest cottage is located in New Haven . It has stunning views and gorgeous sunsets!! Located just seven miles from Middlebury ,Vergennes and Bristol . All of which have great shops and restaurants! Close to many local attractions including ,Woodchuck Cider house, Lincoln Peak Vineyard, Ski areas, Hiking , rivers, lakes, restaurants and much more! Our goal was to provide guests with a home away from home! We feel our cottage offers that and much more.

4.99 out of 5 average rating, 199 reviews
Top guest favourite
A bright living area features large windows that frame views of the surrounding forest. Natural light enhances the wood-paneled walls. A comfortable sofa and chair are positioned around a central coffee table. A small, modern wood stove provides warmth, creating a cozy atmosphere.
Cabin in Goshen

The Berghüttli: Glowing Swiss Hut in the Forest

The Berghüttli ("little mountain hut") is a Swiss-inspired hut and farm stay surrounded by National Forest in Goshen, VT (pop. 168). A completely private escape—no other structures in sight, just woods and quiet. Inside, a wall of windows brings the forest right up to you, while glowing maple plywood fills the space with warm light. High-speed fiber internet runs a reliable 300 Mbps. Stay connected or switch off completely. Search "The Berghüttli" on YouTube for a video tour.

4.97 out of 5 average rating, 150 reviews
Top guest favourite
An open-concept kitchen and dining area is furnished with modern appliances and sleek cabinetry. A central island provides additional counter space, while a dining table with four chairs is positioned nearby. Natural light filters through windows, enhancing the space's bright and airy feel.
Home in Weybridge

Close to college-cheerful, quiet, 2 bedroom home

This recently renovated home is conveniently located 1.5 miles from Middlebury College campus and all that Middlebury has to offer! The back deck and spacious yard are perfect for relaxing outdoors. The open floor plan is cozy for one and accommodates families well. The master bedroom is furnished with a queen bed and the second bedroom has two twin beds. Pack 'n Play and highchairs are available for young children upon request.

4.99 out of 5 average rating, 129 reviews
Top guest favourite
A large farmhouse is set against a backdrop of vibrant autumn foliage. The structure features a modern design with a metal roof and expansive glass windows, allowing for abundant natural light. A spacious lawn complements the serene rural setting.
Home in Rochester

Modern Farmhouse on 25 Acres - Superb Views

This Truex Cullins designed Farmhouse is inspired by the iconic old farmsteads found throughout northern New England. Embracing the dramatic beauty of Rochester's north hollow the house is a serene retreat where connection to your partner, family and the environment will thrive. Unplug, recharge, renew and enjoy all that mountain living has to offer.

4.97 out of 5 average rating, 156 reviews

Popular amenities for Addison County family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favourite
A modern house with wooden exterior is shown from an elevated perspective, surrounded by autumn foliage. A hot tub is positioned on a spacious deck, which includes a seating area with four chairs and a small table. Scenic mountain views and vibrant trees enhance the natural setting.
Tiny home in Warren

Luxury Glass Tiny House - Mountain View + Hot Tub

4.99 out of 5 average rating, 330 reviews
Top guest favourite
A historic two-story home with blue siding is showcased, featuring white trim and black shutters on its windows. A welcoming front porch is visible, surrounded by well-manicured lawns and garden plants, creating a serene outdoor atmosphere.
Home in Middlebury

Walk Everywhere and Enjoy a Historic Vermont Home

4.96 out of 5 average rating, 109 reviews
Top guest favourite
A sunlit room features large windows and a skylight, allowing natural light to fill the space. A hot tub is surrounded by wooden decking, adorned with various potted plants that enhance the serene atmosphere. Scenic views of the outdoors are visible through the windows.
Farm stay in Roxbury

Moonlight Farm Studio · Hot Tub · Vermont Retreat

4.96 out of 5 average rating, 239 reviews
Top guest favourite
Cabin in Ripton

#7 - Hemlock Hideaway Cabin

5.0 out of 5 average rating, 121 reviews
Top guest favourite
A spacious living area features large windows allowing natural light to fill the room. A gray sofa with decorative pillows is centered on a decorative area rug. The open layout connects to the kitchen and dining area, enhancing the inviting atmosphere.
Home in Salisbury

Lake Dunmore Retreat 15 min to Middlebury College

4.96 out of 5 average rating, 146 reviews
Top guest favourite
The exterior view showcases the Barn at Fielder Farm, its red facade reflecting on the tranquil pond below. Lush green lawns and trees frame the scene, enhancing the sense of serenity in the Vermont countryside.
Farm stay in Huntington

The Barn at Fielder Farm

4.98 out of 5 average rating, 124 reviews
Guest favourite
Home in Warren

HYGGE HAUS - Mountain Views Minutes from Sugarbush

4.93 out of 5 average rating, 115 reviews
Guest favourite
The spacious living area features a large sectional sofa and a coffee table made from natural wood. A flat-screen television is mounted on the wall. Sliding glass doors lead to the outdoor space, while wooden floors and a vaulted ceiling create a warm ambiance.
Cabin in Starksboro

Charming getaway tucked away in the Green Mtns

4.88 out of 5 average rating, 312 reviews

Family- and pet-friendly home rentals

Top guest favourite
A custom home is surrounded by lush greenery and flowering shrubs. Two blue Adirondack chairs are placed on a stone path leading to the front door. Sunlight filters through the trees, creating a serene atmosphere in the peaceful rural setting.
Home in Cornwall

Custom Home, minutes from Middlebury

5.0 out of 5 average rating, 120 reviews
Top guest favourite
The historic brick farmhouse features a central entrance adorned with a small landing and wooden steps. Flanking the door, two windows allow natural light to enter. Flower pots filled with vibrant blooms sit at the base of the steps, surrounded by lush greenery.
Guest house in Middlebury

Historic Farmhouse in Middlebury

4.87 out of 5 average rating, 162 reviews
Guest favourite
The exterior of a contemporary concrete home is showcased, featuring a unique asymmetrical roof design with solar panels. The structure is surrounded by trees, and large windows allow glimpses into the interior. Natural stone accents provide contrast against the smooth concrete façade.
Home in Warren

Architectural House Prickly Mountain

4.9 out of 5 average rating, 114 reviews
Guest favourite
A spacious living room is depicted featuring comfortable sofas and a stylish coffee table. Natural light enters through a window with dark curtains, while a decorative rug adds warmth to the wood floor. A welcoming entryway is visible in the background.
Flat in Middlebury

Spacious Home • Near Downtown Middlebury.

4.97 out of 5 average rating, 147 reviews
Top guest favourite
The entrance of the cottage features a small wooden porch with a smooth surface. A decorative bench is adorned with flower pots filled with colorful blooms, creating an inviting and cheerful entryway. The door is painted a calming blue, complemented by matching shutters.
Home in Middlebury

The Middlebury Cottage

4.91 out of 5 average rating, 104 reviews
Guest favourite
A serene outdoor setting features a two-story house surrounded by greenery. A small pond reflects the landscape, while a fire pit is visible nearby. Rustic wooden chairs provide seating, and smoke can be seen rising from the fire, creating a cozy atmosphere in nature.
Home in Goshen

Nature Lover's Paradise

4.84 out of 5 average rating, 331 reviews
Top guest favourite
The interior of a cozy yurt features an orange clay wall and a wooden ceiling with exposed beams. A spacious bed is dressed in white linens, and a small desk with a chair sits nearby. A wood stove is positioned next to a area rug, enhancing the inviting atmosphere.
Earthen home in Granville

Sculpted Earthen Yurt in Green Mtns

4.93 out of 5 average rating, 179 reviews
Top guest favourite
Guest house in Salisbury

VT Getaway Near Middlebury & Lake Dunmore

4.95 out of 5 average rating, 166 reviews

Family-friendly home rentals with a pool

Top guest favourite
A bright and spacious loft area is highlighted by tall windows allowing natural light to illuminate the room. A well-equipped kitchenette is visible, along with a cozy seating arrangement featuring a small table and two chairs, next to a large bed dressed in soft linens.
Guest suite in Starksboro

Private Suite in the Green Mountains

4.95 out of 5 average rating, 154 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, 134 reviews
Top guest favourite
A clear in-ground pool is framed by lush greenery and concrete patios. A shaded area features a table and chairs, while a large umbrella rests nearby. The peaceful setting invites relaxation with calm blue waters reflecting the surrounding landscape.
Cabin in Bridport

Champlain Valley Alpacas

4.93 out of 5 average rating, 168 reviews
Guest favourite
A cozy living area is highlighted by a flat-screen TV displaying Netflix, positioned above a minimalist fireplace. A tabletop showcases two glasses of red wine beside a wooden platter of assorted cheeses and fruit, complemented by flowers in a vase and flickering candles.
Apartment in Warren

Ski In/Ski Out with upgrades!

4.88 out of 5 average rating, 218 reviews
Top guest favourite
The living area features a light-colored sofa, two armchairs, and a coffee table with a decorative tray. A large window offers natural light and leads to the balcony. A patterned area rug anchors the space, alongside a cozy electric fireplace set into the wall.
Apartment in Warren

Sugarbush Mountainside Retreat - Ski in Ski out

4.87 out of 5 average rating, 111 reviews
Guest favourite
A modern stand-alone condo is set against a backdrop of vibrant autumn foliage. The light gray exterior features large windows, allowing natural light to fill the interior. A wooden deck and stairs lead to the entrance, surrounded by well-maintained landscaping.
Home in Warren

Charming Sugarbush Standalone Condo

4.83 out of 5 average rating, 132 reviews
Top guest favourite
The dining area features a circular white table surrounded by four modern white chairs with wooden legs. Two black-and-white framed photographs adorn the walls alongside a decorative letter 'VT', adding character to the neutral-toned space.
Apartment in Warren

NEW: Stylish Ski On/Ski Off Mountainside Retreat

4.98 out of 5 average rating, 144 reviews
Top guest favourite
A spacious living area features a light-colored sofa with decorative pillows and two armchairs, one in yellow upholstery. A wooden coffee table sits centrally, while a stone fireplace offers a focal point. Large windows allow for natural light and views of the outdoors.
Home in Warren

Spacious 5-bed with hot tub, 12 min to Sugarbush

4.99 out of 5 average rating, 94 reviews

Destinations to explore