Family-friendly holiday rentals in Waitsfield

4.96 out of 5 average rating, 193 reviews

The cabin complex is illuminated with warm lighting, surrounded by snow-covered trees. An outdoor fire pit is visible in the foreground, and decorative evergreens add a festive touch. The rustic architecture and inviting decorations create a charming winter setting.

Cabin in Waitsfield

Peaceable Nation at Sugarbush Mt. Ellen

Peaceable Nation at Sugarbush Mt. Ellen, a world class experience at the foot of Mt Ellen Sugarbush and on the Catamount X-C ski Trail is available as a fun group rental for 2-4 people. The entire cabin complex is yours! Enjoy the The Bear Den, a rustic cabin with Loft (Queen) and pull out Queen, the Whiskey Bunkhouse with a full size and a drop down table twin bed if requested, This charming Village is part of a larger compound. Stunning views. Winter tubing run! One well behaved pet allowed

4.93 out of 5 average rating, 188 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!

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, 110 reviews

Architectural House Prickly Mountain

This architectural showpiece is a high-concept concrete manse featuring well-designed details from FAIA Architect David Sellers, such as a curving staircase, exposed concrete structural elements, double height ceilings and open views. PLEASE READ description carefully and ask questions prior to booking. There are 3 beds, 3 baths, open floor plan kitchen, living and dining area and small grassy yard with a view, tucked away in the forest on Prickly Mountain Rd, Warren in the Mad River Valley

4.97 out of 5 average rating, 190 reviews

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, 151 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

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, 140 reviews

TWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO

Enjoy all the MRV has to offer in our renovated 2 Bedroom, 1 bath condo at the Bridges Resort. The Resort features two outdoor pools, one indoor pool, hot tub, indoor and outdoor clay and Har-Tru tennis and Pickleball courts, updated fitness center, volleyball, basketball, horseshoes, badminton and children's playground. Tennis lessons and clinics available on site. Both gas and charcoal grills are available. Two Fire pits located just outside outdoor. Plenty of convenient parking.

4.94 out of 5 average rating, 255 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.

Apartment 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!

4.95 out of 5 average rating, 565 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 High on Mountain-Amazing View!

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!

4.93 out of 5 average rating, 174 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.

4.94 out of 5 average rating, 106 reviews

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.

Home in Waitsfield

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!

4.98 out of 5 average rating, 162 reviews

The spacious kitchen features wooden cabinets and countertops with an array of modern appliances, including a stainless steel refrigerator and oven. Pot racks hang from the ceiling, and a window provides natural light, enhancing the inviting atmosphere of the cooking area.

Home in Moretown

Private Mad River Valley Cabin: Chef’s Kitchen

Discover a private Vermont retreat in the heart of the Mad River Valley. Shielded in the pines, our well-appointed cabin offers a quiet escape within a scenic 25-minute drive to Sugarbush and Mad River Glen. It’s an ideal base for skiing, hiking, swimming holes or fly fishing the nearby Mad River. After a day of adventure, enjoy local dining or cook a gourmet meal in our chef’s kitchen. Perfect for those seeking both outdoor thrills and total relaxation. Follow @mrvstays

4.97 out of 5 average rating, 155 reviews

A cozy queen bed is adorned with white linens, positioned next to a bedside lamp and a small clock. A dining table sits nearby, complemented by green foliage, while large windows invite natural light and showcase views of surrounding trees.

Guest suite in Moretown

The Nest Studio

Off a quiet dirt road set up in the mountains, The Nest Studio is a bright and cozy space. Great for couples, the studio has a queen bed with an additional small twin pull out sofa, best for a little one. The newly remodeled Moretown studio is close to skiing, mountain biking, hiking and several wedding venues. Coffee and tea is provided. The Nest has a full kitchen, washer, dryer, and tiled shower. Secure bike storage and bike wash are present on the property

Popular amenities for Waitsfield family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.92 out of 5 average rating, 130 reviews

Mountain Retreat | Hot Tub, Game Room, Sleeps 10

4.99 out of 5 average rating, 135 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

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

4.92 out of 5 average rating, 150 reviews

South Hill Lodge- 5 BR Post & Beam Home

4.99 out of 5 average rating, 160 reviews

The charming exterior of a classic cabin is surrounded by lush greenery, with a well-maintained front yard featuring flowering shrubs. A covered porch, adorned with hanging plants, invites relaxation, while the cabin’s traditional wood siding and gabled roof contribute to its rustic appeal.

Cabin in Stowe

Adorable Stowe Cabin w/ Hot Tub, River, Wood Stove

4.94 out of 5 average rating, 220 reviews

A cozy living space is highlighted by a modern pink chair positioned near a wood stove, which emits a warm glow. Large glass doors offer views of the wooded surroundings, while a Moroccan rug adds texture to the concrete floor.

Chalet in Royalton

Scandinavian design Chalet hiking trail + hot tub

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

4.93 out of 5 average rating, 113 reviews

HYGGE HAUS - Mountain Views Minutes from Sugarbush

Home in Waterbury Vermont

A spacious living area features a large, sectional grey sofa adorned with colorful cushions. A coffee table sits in front, accompanied by a small decorative bowl. Natural light filters through large windows, enhancing the warm wooden flooring and inviting atmosphere.

4.95 out of 5 average rating, 155 reviews

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

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 228 reviews

A two-story house features a sloped green metal roof, with large windows adorning its beige exterior. A welcoming deck is accessible through a set of stairs, surrounded by landscaped grass and greenery. A storage shed is positioned to the left, tucked among the trees.

Cottage in Moretown

Cozy Cottage in the Mad River Valley

4.97 out of 5 average rating, 302 reviews

A tiny house features a wooden exterior with a light-colored door framed by large windows. A small porch with two chairs and a table provides an inviting entrance, while additional seating is arranged on a grassy area, surrounded by trees and natural greenery.

Tiny home in Duxbury

Tiny House at Camp Comyns

4.97 out of 5 average rating, 154 reviews

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

4.98 out of 5 average rating, 405 reviews

A warm wooden cabin is set against an autumn backdrop, with vibrant orange and yellow foliage surrounding it. Steps lead to a pair of French doors, inviting guests inside, while a smaller structure sits nearby, complementing the serene natural setting.

Farm stay in Topsham

Fairytale cabin at The Wild Farm

4.93 out of 5 average rating, 107 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

4.96 out of 5 average rating, 184 reviews

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.

Home in Waitsfield

Mid century modern gem with views of Sugarbush

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, 200 reviews

Cozy 3 BR ski town home tucked away retreat

Earthen home in Granville

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.

4.93 out of 5 average rating, 172 reviews

Sculpted Earthen Yurt in Green Mtns

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, 216 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.

4.87 out of 5 average rating, 109 reviews

Sugarbush Mountainside Retreat - Ski in Ski out

A snow-covered slope is flanked by trees adorned with frost, creating a winter wonderland. Skiers can be seen navigating the path under a sky filled with clouds and sunlight filtering through. The serene atmosphere captures the essence of outdoor winter activities.

4.91 out of 5 average rating, 76 reviews

Powder Hound Condo

4.94 out of 5 average rating, 477 reviews

A custom-made yurt is nestled among lush greenery, surrounded by tall trees. Sunlight filters through the foliage, illuminating the yurt's circular structure and chimney. Wildflowers and grasses frame the foreground, creating a natural, serene setting.

Yurt in Randolph

Lower Yurt Stay on VT Homestead

4.83 out of 5 average rating, 131 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.

4.94 out of 5 average rating, 145 reviews

Private Suite in the Green Mountains

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.