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Family-friendly vacation rentals in Westfield

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Top-rated family-friendly rentals in Westfield

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

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Top guest favorite
The exterior of a contemporary timber frame house is shown, featuring a covered porch with seating arrangements. Wood stacked neatly at the base adds to the rustic charm. A sloped roof peaks at the top, and large windows allow natural light to enter.
Apartment in Jay
4.87 out of 5 average rating, 365 reviews

Jay Apartment

Only 10 minutes to Jay Peak Ski Resort. Secluded in the woods right next to Starr Brook, yet only a 2 min drive to the Jay Village Inn restaurant and bar and the Jay Country Store. Fire pit with cooking grate next to the brook you are welcome to use weather permitting. Great hiking, biking trails, snow showing and Nordic skiing minutes away. Some trails are accessible directly from the property. Very comfy bed, wonderful place to sleep. . Vermont Meals and Rooms Tax ID number is MRT-10126712

Top guest favorite
An aerial view of a spacious mountain home surrounded by vibrant autumn foliage. The house features multiple levels, large windows, and is complemented by a grassy expanse. Nearby, a green shed and parked vehicle are visible, with rolling hills and colorful trees creating a picturesque backdrop.
Home in Westfield
4.96 out of 5 average rating, 255 reviews

Jay Peak 3 miles - secluded with spectacular view!

Mountains, streams & seclusion! • Hike the Long Trail • Road, gravel & mountain biking • Jay Peak Resort is three miles away! • Waterpark • Golf • Backcountry guiding - hiking, kayaking, gravel & mountain biking (15% discount) • Photography and videography (15% discount) This is the mountain getaway you dream about! Our only neighbors are animals in the surrounding mountains & forests. Note: There is also an apt in the main house that sleeps 8. Welcome to Vermont Mountain Experience!

Top guest favorite
The living room features tall windows that provide ample natural light and overlook the surrounding wooded area. A stone fireplace is flanked by a television and cozy seating options, including a leather sofa and lounge chairs. A patterned rug adds texture to the wooden floor.
Chalet in Westfield
4.96 out of 5 average rating, 140 reviews

Cozy Chalet at Jay Peak

The house is set up with everything to make your stay cozy, comfortable & fun. Gas Fireplace, 5br, 2.5 Bath, 2 separate Living Room areas. Large Deck with Gas Grill overlooks small brook. Private wooded setting with panoramic mountain views once leaves have fallen. Seasonal Pool, Disc Golf, Volleyball, Playground & Hiking Trails a short walk from the house. 3 mi to Jay Peak. Air Conditioning is in three bedrooms which are installed by the 2nd Sunday of June then removed the last Sunday of Sep.

Guest favorite
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
4.97 out of 5 average rating, 321 reviews

Secluded Luxury Treehouse - Hot Tub + Projector

Our treehouse is a haven of well-being, peace, and elegance. In our stunning modern treehouse we have brought relaxation to a whole new level. Surrounded amongst us is nothing but woods & wildlife. An experience not to be missed. Put your favorite movie on the projector, get Zen in the cozy sun room, jam out to music on the record player, or grab a towel, and head for the custom cedar hot tub. It is time to create core memories that will never be forgotten. Welcome to a little slice of heaven.

Top guest favorite
A green two-story house is viewed from a snow-covered path leading to its entrance. Thick layers of snow blanket the yard, while tall trees stand in the background against a clear sky, indicating a serene winter setting.
Chalet in Montgomery
4.93 out of 5 average rating, 137 reviews

Montgomery Meadows Chalet near Jay Peak

Located on beautiful, historic Hazens Notch Road, Montgomery Center, Vermont. This “hidden gem” of a house sets back from the road in a private setting on 5 spectacular acres of cleared land, with views of Jay Peak Ski and Golf Resort. A perfect location for skiing, hiking, biking, golfing, etc. Only 15 minutes from the resort and all of the great amenities (water park, ice rink, movie theater, climbing wall, arcade). Only 3 miles from local amenities (grocery store, top rated restaurants).

Guest favorite
The front exterior of a historical cottage is framed by lush green trees and blooming lilac bushes, providing a vibrant contrast against the structure. A small porch is visible, offering a view of the surrounding nature.
Cottage in Westfield
4.91 out of 5 average rating, 191 reviews

Historic Schoolhouse Minutes From Jay Peak

After a long day of hiking, biking, or skiing, come take a swing at our charming historical cottage. Dating back to the mid 1800s it was one of the first schoolhouses in the area, today it is filled with all the modern luxuries one would need. Our quaint porch is perfect for bird watching or leaf peeping. The inside includes high ceilings, a bedroom and a cozy loft- both with queen beds. French culture is only a 10 min drive away; Vermont culture is abound with maple syrup and warm locals.

Top guest favorite
A guest cabin nestled in the woods is visible, featuring a spacious green yard and a flowing brook nearby. A hammock hangs between trees, while red outdoor chairs are arranged around a stone fire pit. The cabin's elevated deck overlooks the serene landscape.
Guesthouse in Montgomery Center
4.97 out of 5 average rating, 403 reviews

Cabin in the Woods VT - Discount Jay Peak Lift Tix

Come enjoy the ski season and a relaxing weekend at our private guest cabin in the woods. A brook flows through the backyard, providing a peaceful natural backdrop and a stone outdoor fire pit for great campfire fun. The main floor bedroom has 1 queen bed and the loft has 1 queen and 1 twin. There is also a living room couch. Just 5 min to town, 15-20min to Jay Peak! Use our vouchers for discount lift tickets! **We recently added “The Loft” listing on the other side of the same property**

Top guest favorite
The exterior of the cottage is showcased, featuring a charming wooden structure with a peaked roof. Light wooden siding complements the rustic feel. A door and windows offer glimpses of the interior, surrounded by a grassy area and trees under a partially cloudy sky.
Farm stay in Fairfield
4.97 out of 5 average rating, 452 reviews

Meadow Cottage on Organic Farm with Mountain Views

The Meadow Cottage is perched on a picturesque knoll in the back of our 300 acre working dairy farm. We are located in between two of Vermont's best ski resorts, Jay Peak and Smuggler Notch. Come for a winter adventure full of downhill skiing, riding or x-country touring. Stay for the local breweries, distilleries, restaurants and antique stores. Or just relax at the farm, watch us milk the cows or cook up some delicious farm raised food for dinner. Well behaved dogs are welcome anytime!

Top guest favorite
The chalet's inviting exterior features beautiful wooden walls and a warm red roof, harmonizing with the surrounding snowy landscape. A spacious deck wraps around the front, providing views of the trees and hillside, while a wooden stack is neatly arranged beneath it.
Guesthouse in Westfield
4.99 out of 5 average rating, 148 reviews

Beautiful Chalet minutes to Jay Peak Resort

Our guest house "Le Petit Chalet" is only a few years old, has very beautiful wooden walls and floors, and is both elegant and warm. We love all dogs and your well behaved pet is welcome The house is very comfortable, with all utilities big and small including coffee machine, nespresso machine, food processor, etc Jay Peak is the best ski resort of the East, guaranteed the best snow no matter the conditions. Great for skiing and snowboarding, on the slopes and in the glades.

Guest favorite
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
4.93 out of 5 average rating, 168 reviews

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.

Top guest favorite
A modern living area features a comfortable brown sofa beside a wooden coffee table. Exposed wooden beams run across the ceiling, while a staircase leads to an upper level. Natural light fills the space through large windows, creating a warm and inviting environment.
Cabin in Montgomery
4.94 out of 5 average rating, 179 reviews

Jay Peak Retreat

The Jay Peak Retreat – Experience the Northeast Kingdom’s premier destination at Jay Resort, known for record snowfall and Vermont’s largest indoor waterpark. This warm, stylish cabin offers an open-concept layout perfect for cozy gatherings and après-ski lounging. Blending upscale comfort with rustic charm, enjoy a creek out back, river across the street, patio, fire pit, and plush outdoor chairs. Just 1 hour from Burlington, 2 from Montreal, 35 minutes to Sutton Quebec!!

Top guest favorite
A rustic cabin stands surrounded by autumn foliage, showcasing wooden siding and two front windows. The covered porch features a set of outdoor chairs, inviting guests to sit and enjoy nature. Layers of fallen leaves create a colorful carpet at the cabin's base.
Cabin in Danville
4.99 out of 5 average rating, 127 reviews

The Cabin

Welcome to The Cabin! This cozy, rustic cabin is a part of 85 private acres in Danville, VT, just up the road from The Forgotten Village at Greenbank’s Hollow. Perched at the crest of a 12 acre pasture, enjoy both local and long range views of the Presidential Range. Trails lead you in various directions throughout the woods. The Cabin is a place to breathe deep, enjoy nature, and simply get away from it all!

Popular amenities for Westfield family-friendly rentals