Family-friendly holiday rentals in Waitsfield

4.93 out of 5 average rating, 195 reviews

A cozy kitchen area features a combination of modern and rustic design elements. Light wood paneling complements the yellow walls and a large window allows natural light to illuminate the space, highlighting a dining table and chairs, along with contemporary appliances.

Cottage in Waitsfield

Casa Rio Loco!

This charming guest cottage affords well appointed privacy while being centrally located in convenient proximity to all the activities the Mad River Valley has to offer. Nestled along a quiet oxbow of our namesake waterway, if you have come for the winter sports you will be a 5/7 minute drive to the Sugarbush base areas, and 10 minutes will bring you to Mad River Glen ("ski it if you can"). Explore the towns of Waitsfield and Warren Village in less than 5... Snowshoeing? Walk out the front door!

4.91 out of 5 average rating, 109 reviews

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!

4.98 out of 5 average rating, 173 reviews

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.

Large glass doors frame a stunning mountain view, showcasing the surrounding landscape. A spacious deck with outdoor seating is visible. Inside, a wooden dining table with several chairs is positioned nearby, illuminated by pendant lighting, and a spiral staircase offers access to the upper level.

4.96 out of 5 average rating, 188 reviews

Mid century modern gem with views of Sugarbush

Wake up to stunning views of Sugarbush in this “Flat Roof A-Frame". Four bedrooms, a sleeping loft, three bathrooms, two living rooms, a dining room, a newly renovated kitchen, a desk area with wifi, two decks (one w/gas grill), and a laundry room/game room provide plenty of space for family gatherings. Located 3 minutes from town. Not suitable for small children/toddlers or guests with mobility issues. During summer we are only renting out 6+ night rentals with changeovers on Friday.

The luxury log home is situated on a spacious property surrounded by vibrant autumn foliage and rolling green mountains. The property includes a winding driveway and a large lawn, creating a serene and private atmosphere amidst the natural landscape.

4.96 out of 5 average rating, 100 reviews

Ridge House with Mountain Views

This large 5 bed 3 bath luxury log home with lovely views of the green mountains is one of a kind. The 16 acre property sits at the end of a private road in the Mad River Valley, with a great central location just minutes away from all local attractions. Highlights include the luxurious kitchen and dining area, a lovely master bedroom with spacious en-suite and the great room with floor to ceiling windows, a custom stone fireplace and a large deck which runs the entire length of the home

4.97 out of 5 average rating, 153 reviews

A spacious living area is showcased, featuring a red sectional sofa positioned around a round coffee table. Natural wood beams cross the ceiling, complementing the stone fireplace. Two modern chairs are arranged nearby, with a decorative plant on a side table, enhancing the welcoming ambiance.

Chalet in Waitsfield

Warm Luxury Mid-Century Modern Chalet

Woodward Haus is a stylish MCM retreat with wood, glass, & stone design. Perfect for remote work, a romantic weekend, a multifamily gathering, a girls' weekend, or retreat. MRV offers all season fun: farmer's market, swimholes, farms, hiking, road & mtn bike, golf, climbing, tubes on the river and lake, can't be beat. The house is nestled in the woods w/ beautiful views mountains. The area's food & breweries, including Lawsons are phenomenal. 1 min to MRG & 14 min to Sugarbush. Exp Wifi

4.94 out of 5 average rating, 259 reviews

A cozy living room is depicted, featuring a brown leather sofa adorned with decorative pillows. A wooden coffee table stands in the center, holding various items. A lampshade softly illuminates the space, and a mirror is mounted on the wall, reflecting light from a ceiling fixture.

Flat in Waitsfield

Historic District Overlooking the Mad River Studio

This beautiful apartment is located the second floor of Bridge Street's most popular building, neighboring the Covered Bridge with views of the Mad River. The setting is gorgeous, the apartment is immaculate and charming. 15 minutes from Sugarbush and Mad River Glen Ski Resorts, endless hiking trails, Mt. biking, kayaking, golfing, swimming, fishing and walking distance to Lawson's Finest Liquids Brewing Company. Please check out our reviews as they have been nothing but positive!

4.94 out of 5 average rating, 580 reviews

An elevated cabin nestled among trees features a wooden exterior with large windows. A spacious deck is furnished with seating, providing a serene outdoor space surrounded by lush greenery.

Treehouse in Moretown

Gorgeous Treehouse Fall Foliage Amazing Views!

Lilla Rustica is an elevated cabin among the trees. Private, with Stunning views this was built by "The Tree House Guys" a local Vermont company whom can be found having a season on the DIY network. Tons of detail, while keeping the design natural and simple. Unbelievable views of Camels hump State park. A loft with one queen bed and downstairs has a queen bed with three sides of the bed having windows facing the views. Hiking offered right from the cabin. An awesome getaway!

4.94 out of 5 average rating, 201 reviews

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.

A spacious deck features comfortable seating with plush cushions and a wooden table. The railing provides unobstructed views of rolling green hills and distant mountains, creating a serene outdoor space ideal for relaxation. Overcast skies enhance the natural colors of the surrounding landscape.

4.94 out of 5 average rating, 107 reviews

Sunny Retreat, Mountain Views on 4 Private Acres

Incredible views from this fantastic house set on 4 acres central to all activities in the Valley - hiking, biking, skiing, fun at the river. A mile to downtown Waitsfield for groceries, shopping, etc. The house gets tremendous sun and all rooms have an exceptional view of the mountains and the valley, which are spectacular year round. The kitchen has everything you need for cooking, and there’s also a gas grill. Spend the day out exploring and then relax on the deck!

4.97 out of 5 average rating, 187 reviews

The exterior of the Little House is showcased, featuring a wooden facade and a gray door. The structure is framed by vibrant autumn foliage, with leaves in shades of yellow, orange, and red. A wooden deck leads up to the entrance, surrounded by a serene forest atmosphere.

Cottage in Waitsfield

von Trapp Farmstead Little House

Come stay in the beautiful Mad River Valley! Our guest house named the Little House is surrounded by forest and 3.5 miles from the town of Waitsfield. Located on the North East corner of our farmland you'll find yourself less than a mile from our Farm Store where you can stock up on our organic cheeses, yogurts, and meats or beer, wine, and other provisions from over 40 local producers. Enjoy a quiet vacation or a skiing, hiking, biking, or rafting adventure!

4.97 out of 5 average rating, 202 reviews

The exterior of The Wolf's Den features a welcoming entrance with a wooden sign and vibrant flower baskets. A shaded porch is visible, along with a barbecue grill. The surrounding gravel area is complemented by well-maintained landscaping and a stone wall, enhancing the overall appeal.

Flat in Waitsfield

The Wolf's Den at Sugarbush Mt Ellen

The Wolf's Den at Sugarbush Mt. Ellen is a brand new fully equipped custom 1st floor studio apartment at the foot of SUGARBUSH MT ELLEN enjoy the luxurious bedding, and accessories. Also provided is a continental breakfast with a Vermont flair! This property abuts the CATAMOUNT X-C SKI TRAIL!! From here you can walk or bike to many of the Valley's hot spots! Off of German Flats Road. THE VALLEY'S GREATEST LOCATION !!! One well-behaved pet is allowed!

Popular amenities for Waitsfield family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Superhost

4.9 out of 5 average rating, 134 reviews

Mountain Retreat |Hot Tub, Firepit, Game Room

4.99 out of 5 average rating, 334 reviews

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

Superhost

A spacious post and beam home is nestled among trees displaying vibrant autumn foliage. The property features a green metal roof and blue windows reflecting the colorful landscape. A grassy area in the foreground provides an inviting contrast to the rich hues of fall.

Home in Moretown

South Hill Lodge- 5 BR Post & Beam Home

4.92 out of 5 average rating, 152 reviews

A spacious living area features a large sectional sofa positioned to take in views through floor-to-ceiling windows. A coffee table sits in the middle, complemented by wooden dining chairs and a table in the background. Natural light enhances the wood-paneled ceiling.

4.92 out of 5 average rating, 121 reviews

4br, 3ba with 2 master bedrooms, Sauna, Hot Tub

4.96 out of 5 average rating, 244 reviews

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

Snow-covered grounds are visible, framed by tall evergreen trees. In the background, a mountain slope is partially visible, marked by ski trails. A white fence and signs of winter's chill set the scene, with cloudy skies overhead.

4.97 out of 5 average rating, 141 reviews

TWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO

4.99 out of 5 average rating, 140 reviews

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

4.98 out of 5 average rating, 125 reviews

Farm stay in Huntington

The Barn at Fielder Farm

Family- and pet-friendly home rentals

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.

4.9 out of 5 average rating, 115 reviews

Architectural House Prickly Mountain

4.99 out of 5 average rating, 178 reviews

The single-story home features a modern wooden exterior with large windows that allow natural light to enter. A spacious deck is equipped with outdoor seating and leads to a grassy area surrounded by trees. The inviting structure presents a blend of warmth and contemporary design.

Home in Starksboro

Forest Hideaway

4.93 out of 5 average rating, 252 reviews

A two-story log house is set among trees with snow covering the ground. A wide wooden deck features multiple chairs, and a door is visible on the base level. The structure showcases earthy tones and has a circular window above the entrance, enhancing its rustic appearance.

Home in Roxbury

Captain Tom's Cabin - Secluded Vermont Getaway

4.95 out of 5 average rating, 210 reviews

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!

4.97 out of 5 average rating, 145 reviews

A cozy log cabin interior is illuminated by natural light from windows. A comfortable blue couch faces a stone fireplace. Above, a sleeping loft is accessed by sturdy wooden steps and bordered by wood railing. Maple hardwood floors and bookshelves add warmth to the space.

Cabin in Warren

Stetson Hollow Cabin by Stetson Brook

4.97 out of 5 average rating, 251 reviews

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.

The charming home is set back from a gravel driveway, surrounded by trees. A large front porch features double doors framed by decorative windows. A vibrant red outbuilding is visible on the left, enhancing the rustic atmosphere of the property.

4.98 out of 5 average rating, 202 reviews

Cozy 3 BR ski town home tucked away retreat

4.91 out of 5 average rating, 113 reviews

A cozy living area is arranged with two beige sofas positioned around a wooden coffee table. A small television is placed on a stand, and large windows allow natural light to fill the space. A patterned rug adds warmth to the floor.

Home in Moretown

Cozy net zero apartment

Family-friendly home rentals with a pool

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.

4.88 out of 5 average rating, 219 reviews

Ski In/Ski Out with upgrades!

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.

4.88 out of 5 average rating, 112 reviews

Sugarbush Mountainside Retreat - Ski in Ski out

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.

4.98 out of 5 average rating, 144 reviews

NEW: Stylish Ski On/Ski Off Mountainside Retreat

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.

4.83 out of 5 average rating, 132 reviews

Charming Sugarbush Standalone Condo

Guest suite in Starksboro

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.

Private Suite in the Green Mountains

4.95 out of 5 average rating, 156 reviews

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.

4.99 out of 5 average rating, 96 reviews

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

The living room features a comfortable sofa adorned with decorative pillows, a wooden coffee table, and an armchair with a patterned fabric. A lamp provides soft lighting, while a framed wall art piece and a window with blinds bring a sense of warmth to the space.

4.84 out of 5 average rating, 38 reviews

Convenient Mad River/Sugarbush Condo