Family-friendly holiday rentals in West Windsor

4.96 out of 5 average rating, 198 reviews

A charming cottage is set against a backdrop of lush trees, with a deck extending from the front. The warm, orange sky creates a serene atmosphere, casting soft light on the exterior of the house and surrounding landscape.

Guesthouse in Hartland

Cozy Getaway- Ski, Woodstock, Hanover

Luxurious, well appointed cottage - Beautiful sunrise view located between Woodstock VT and Hanover NH. Inspiring treat for musician’s getaway is a fully restored 1929 Steinway Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer. VERY comfortable queen bed. Romantic getaway in the woods, relax, work in peace, explore the beauty and history of the area. Hiking, biking, fishing, hot air balloon rides and shopping are all close by. Long (90 day) or weekend rental

4.98 out of 5 average rating, 119 reviews

Home in Windsor

Fresh Snow- Luxury Cabin near Ski Areas

On a cold winter morning Wake up in a luxurious bed in a stylish cabin with panoramic Vermont views. Grab a hot coffee with a book from our library. Hot mug in hand, step out to the porch, look at faraway hills. Make breakfast in the Chefs kitchen. Snowshoe/slide/talk/play with your favorite people/animals in the world. Take a scenic drive to Woodstock, Simon Pearce, Okemo, or the Harpooon Brewery. Kick back with a night around the firepit stargazing Sharing our Red House with you.

4.95 out of 5 average rating, 147 reviews

Cottage in Hartland

Adorable Dog Friendly Cottage w/FIOS

Just 5 miles from Woodstock, this bright two-story cottage sits on a peaceful 20-acre oasis of woods, pasture, and hill views. Especially cozy in winter, it’s quiet, warm, and welcoming year-round. The cottage has two bedrooms (queen upstairs, full downstairs), one bath with shower, and an open kitchen/living/dining area. February stays include a warm Arrival Comfort setup and late checkout. Guests using only one bedroom receive a 10% discount, applied after checkout (not combinable).

4.96 out of 5 average rating, 274 reviews

The rustic cabin, surrounded by lush trees, features a porch with a picnic table. The wooden structure is designed with a gabled roof and large windows, providing a welcoming entrance. Flower boxes adorn the front, enhancing the natural setting.

Cabin in West Windsor

Sunset Cabin - your private romantic hideaway

Your private woodlands retreat awaits. Nestled atop a beautiful 10 acre meadow with 25 acres of woods for you to enjoy; this rustic, pet friendly cabin is a perfect romantic hideaway. Two trout ponds are steps from your door for fishing and swimming. Just minutes from Mt. Ascutney's hiking/biking trails and in the middle of fantastic cycling country. Near local race including the VT100, Vt overland, VT50. Sunset Cabin is a marvelous spot for enjoying fall foliage and exploring VT!

4.97 out of 5 average rating, 433 reviews

The private guest house is surrounded by lush greenery, featuring a covered porch with a chimney and hanging planters. A well-maintained lawn leads to the house, while a backdrop of rolling hills enhances the tranquil setting.

Cottage in Windsor

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

4.99 out of 5 average rating, 718 reviews

A cozy living area features a mixture of seating options, including a tufted sofa and a vintage-style sofa adorned with decorative cushions. Natural wood floors enhance the warmth of the space, while artwork on the walls and a circular coffee table complete the inviting atmosphere.

Barn in Chester

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. I am as close or as far away as you would like me to be with my house right next door.

4.95 out of 5 average rating, 110 reviews

A modern kitchen features sleek white cabinetry and open shelving displaying glassware and kitchen essentials. A wooden dining table with black chairs provides a gathering space. Stainless steel appliances, including an oven and microwave, complement the stylish design, while a fresh plant adds a touch of greenery.

Apartment in Ludlow

Peaceful Ludlow Base 5 minutes to Okemo

Newly renovated, clean 1 BR apt. in historic house 2 blocks to town, 5 minute drive to Okemo, Buttermilk Falls, and 2 minute walk to the Ludlow Farmers Market. Enjoy complimentary coffee and local maple syrup while overlooking the town of Ludlow. Make yourself at home with a full kitchen/bath, wall-mounted flat screen TV, king bed, and comfortable futon. Free EV charging available. Kayaking, hiking, and golfing close by. We are dedicated to ensuring a top-notch experience!

4.98 out of 5 average rating, 168 reviews

A well-appointed bedroom showcases a spacious bed dressed in white linens, complemented by decorative pillows. A wooden bench is situated at the foot of the bed. A large mirror and artful wall decor enhance the serene atmosphere, while natural light enters through a large window.

Home in West Windsor

Birdie's Nest Guesthouse

Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

4.94 out of 5 average rating, 148 reviews

A cozy room features a full-sized bed covered with a white blanket and accent pillows. A kitchenette with cabinetry, coffee maker, and compact fridge is visible. A framed landscape print adorns the wall, with natural light coming through windows beside the bed.

Guesthouse in Lebanon

Private guesthouse in Lebanon

This cozy one-room guesthouse is located on a quiet street off the green in downtown Lebanon, NH. It offers a private entrance with access to a lovely outdoor patio and gas grill. The room has high ceilings, a full-sized bed, a bathroom/shower, and a kitchenette with coffee maker, electric kettle, microwave, toaster, and compact fridge. A short walk away from restaurants and cafes and a 12-minute drive to Dartmouth College. Please note that there is no kitchen sink or stove.

Apartment in Weathersfield

The exterior of a modern blue house is depicted, featuring a combination of angular roofs and large windows allowing for ample natural light. A stone wall borders the property, which is surrounded by lush greenery and trees in the background.

4.99 out of 5 average rating, 185 reviews

The Loft at Weathersfield

Close to Okemo, The Loft at Weathersfield, is just 1/2 hour south of Woodstock / Hanover area and 22 minutes from Okemo Mountain. The Loft, is located in a private agricultural setting with easy access to Vermont's best biking, hiking, fly fishing, skiing, and many equine trails. The loft is 900 square feet with a kitchen/dining room, living room, full bath, one bedroom with a queen bed and one twin bed. There is a spacious deck off the kitchen and a car port underneath.

4.97 out of 5 average rating, 117 reviews

The exterior of a two-story home is set among vibrant gardens filled with colorful flowers. A neatly maintained lawn extends toward a shaded area featuring rustic seating. Lush trees and greenery complete the serene landscape, providing a peaceful and inviting outdoor atmosphere.

Home in West Windsor

Vermont Retreat Near Okemo | 3BR w/ Fireplace

Peaceful 3BR Vermont Estate Near Woodstock & Mt. Ascutney Escape to our serene Vermont retreat on 7 private acres. Just 5 minutes from Mt. Ascutney trails and 15 minutes from Green Mountain Horse Association. Perfect for families, riders, and nature lovers, our modern country home blends comfort with classic Vermont charm. Whether you’re planning a quiet couples’ retreat or a family getaway full of Vermont adventure, you’ll find space, serenity, and style here.

4.93 out of 5 average rating, 160 reviews

A view of the snow-covered path leading to the ski slopes is framed by the C Building’s balconies. Sunlight casts long shadows across the pristine snow, highlighting the tranquil winter scene. The surrounding area is clear and inviting, with ski signage visible in the distance.

Condo in Ludlow

Okemo Ski-in/Ski-out, Steps to lift Condo

Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

Popular amenities for West Windsor family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A cozy living room features a dark leather sofa adorned with decorative pillows. Above the couch, three framed nature-themed art pieces display serene mountain landscapes. A dog rests comfortably on the carpet, with soft lighting from two side lamps enhancing the peaceful ambiance.

4.95 out of 5 average rating, 160 reviews

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails

A cozy living space features a warm wood-burning fireplace, with flames gently glowing behind a glass screen. A soft beige leather sofa is complemented by a bright red decorative pillow. A standing lamp provides soft illumination next to the fireplace, enhancing the inviting ambiance.

4.93 out of 5 average rating, 109 reviews

Right at Killington !

4.92 out of 5 average rating, 107 reviews

A comfortable living area features a wood fireplace with tools nearby and a mounted television above it. Two armchairs flank a rustic coffee table, creating a cozy space. Large windows allow natural light to fill the room while offering views of the snowy outdoors.

Home in Killington

Ski Back to Trail Creek!

4.9 out of 5 average rating, 115 reviews

A comfortable living area features a soft, light-colored sofa and two armchairs upholstered in a cozy texture. A coffee table is centered on a patterned rug, and a large bear photograph is displayed on the wall, contributing to the inviting ambiance.

Home in Killington

TheGrizz! Shuttle on/off!

4.93 out of 5 average rating, 195 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 w/ private hiking trail

4.95 out of 5 average rating, 106 reviews

The living area features a cozy fireplace surrounded by stone, with a wooden mantel. A dining table with white chairs is positioned near the kitchen, complemented by bar stools at the counter. Light floods in through large windows, enhancing the open layout.

Condo in Ludlow

Winterplace - Steps away from Slopes

4.96 out of 5 average rating, 133 reviews

A cozy living area features a brick fireplace with a warm fire. A comfortable sofa adorned with decorative pillows is positioned nearby, accompanied by a wooden coffee table. Wall-mounted art and soft lighting enhance the welcoming ambiance.

Townhouse in Killington

Beautiful Spacious Condo at Killington Resort

A cozy living area is furnished with a grey sofa and two patterned chairs. A wooden coffee table sits center stage, complemented by a stone fireplace. A large television is positioned on a wooden media console, while sliding glass doors offer access to an outdoor balcony, revealing greenery.

4.93 out of 5 average rating, 212 reviews

Newly renovated ski retreat at Killington

Family- and pet-friendly home rentals

Guest suite in West Lebanon

A comfortable bedroom features a spacious bed with dark bedding, flanked by two decorative lamps. Art pieces hang above the bed, and a large closet with wooden doors is visible. A small table and plant are situated near the window, allowing for natural light.

4.87 out of 5 average rating, 143 reviews

Convenient and chic private suite with 2 bedrooms!

4.86 out of 5 average rating, 117 reviews

A sign reading 'The Oaks' is prominently displayed in front of the property. Colorful metal flowers are set in the lush green grass, framed by a backdrop of blooming trees and a partially visible building. Soft clouds pass overhead, creating a serene outdoor atmosphere.

Home in Plainfield

The Oaks - secluded rural estate w/ amazing views

4.95 out of 5 average rating, 169 reviews

The exterior of a red cabin is surrounded by a snowy landscape. Large windows allow natural light to illuminate the front space, while a simple wooden bench rests on the porch. Pine trees are visible in the background, creating a serene atmosphere.

Cabin in Cavendish

The Cozy Little Red Cabin

4.95 out of 5 average rating, 344 reviews

An open living space is captured, featuring a comfortable couch, a colorful chair, and a round coffee table. Natural light brightens the room, highlighting a kitchenette area and coordinating furnishings across the suite. High ceilings contribute to an airy atmosphere, creating a welcoming environment.

Apartment in Clarendon

Dog heavenly! Private, beautiful and relaxing.

4.93 out of 5 average rating, 300 reviews

Townhouse in Killington

Dog Friendly Mountain Condo w/Spa, Pool, Sauna

4.96 out of 5 average rating, 143 reviews

A historic white house with a metal roof is surrounded by vibrant autumn foliage. A landscaped area with pumpkins and colorful flowers is visible in the foreground, while the expansive green lawn leads to tree-lined boundaries in the background.

Apartment in Hartland

Hearth House Farm

4.95 out of 5 average rating, 1,031 reviews

The spacious interior of the yurt features a circular design with natural wood and fabric elements. Comfortable seating areas include a queen-sized futon and a wooden sofa. Large windows allow natural light to fill the space, while a wood stove provides warmth.

Guesthouse in Hartland

Yurt In The Woods - Private Refuge

4.97 out of 5 average rating, 220 reviews

A warmly lit cabin emerges from the surrounding trees, framed by a quiet, snow-covered dirt road. Soft light spills from the windows, creating a welcoming glow in the tranquil, darkened landscape.

Home in Rochester

The Guest House at Sky Hollow

Family-friendly home rentals with a pool

Superhost

Aerial view of a snow-covered landscape, showcasing rolling hills and a winding road. The scene includes a mix of bare trees and patches of evergreen, while the distant mountains hint at recreational opportunities. A clear sky and soft sunlight enhance the serene atmosphere.

Home in Killington

4.89 out of 5 average rating, 236 reviews

Luxury Condo Tucked in the Heart of Killington

4.92 out of 5 average rating, 25 reviews

A cozy living area features a stone fireplace with a warm fire, surrounded by a modern sofa. Above the fireplace, a wall-mounted television is visible. A rustic chandelier with multiple bulbs hangs over a dining table, while decorative items are placed on a nearby side table.

Home in Ludlow

Ski-In/Ski-Out Hike Okemo Condo Solitude Village

4.98 out of 5 average rating, 95 reviews

A cozy living area features exposed beam ceilings and wood floors. Two comfortable sofas face each other, complemented by a coffee table and side tables with lamps. A staircase leads to the upper level, and a small workspace with a chair is visible in the corner.

Cabin in Hartford

Cozy Quechee Cabin near Woodstock and skiing

A modern kitchen with a circular dining table surrounded by four wooden chairs is featured. Stainless steel appliances, including a microwave and oven, are present. A stylish light fixture hangs above the table, while the fireplace and sports equipment are visible in the background.

4.91 out of 5 average rating, 197 reviews

Cozy 1BR, Shuttle/Walk to Lifts, Covered Parking

4.93 out of 5 average rating, 115 reviews

A view of an open-concept suite showcases a kitchen countertop with a sink and decorative flowers. A cozy living area is visible, featuring a red sofa and a dining table. The master bedroom is visible in the background, fitted with a king bed and soft lighting.

Condo in Proctorsville

One Bedroom Suite Near Okemo

Superhost

The exterior of a contemporary timber home is visible, featuring a sloped green metal roof and warm wood siding. Surrounding snow-covered ground reflects nearby evergreen trees. The property is situated on a spacious lot, offering a serene winter landscape.

Townhouse in Killington

4.84 out of 5 average rating, 108 reviews

SKI ON/OFF Spruce Glen C | Sauna| Fireplace | AC

4.95 out of 5 average rating, 155 reviews

A cozy living area features a pair of brown sofas with decorative cushions. A wooden coffee table is centered in front of the seating. Artwork is displayed on the light green walls, and a lamp provides soft illumination, complementing the natural light from the window.

Condo in Stratton

Cozy condo within walking distance to the slopes.

A modern studio space is presented with wood paneling and a vaulted ceiling. Stainless steel kitchen appliances are featured alongside a dining table and a comfortable seating area. Two vintage ski boards are mounted on the wall, and a sliding glass door provides access to a private balcony.