Family-friendly holiday rentals in Montgomery

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

Hillwest Mountain View

We are close to Jay Peak and Canada including Montreal. If you like hiking, the Long Trail is close by. If you like star gazing you will love seeing the Milky Way in our backyard. Our house is good for both couples and families. We have a private hiking trail that leads down to a cool mountain stream where you can cool off. Take a dip in the nearby Hippie Hole or go fishing or canoeing in nearby lake Carmi. There are three bedrooms and a master bath with a spa tub. Wifi, fireplace and more.

200 acre Stowe area Bunkhouse.

Hello and welcome to our Red Road Farm 'Bunkhouse' -- We're so happy to host you! Sitting on our 200 acre estate this authentic barn offers our guests a chance to relax in the beautiful rolling hills of Vermont. Access the vast majority of our historic Stowe area land -- from our apple orchards to our extensive walking paths in fields and woodland. We hope that you can experience such fun and quiet time in our cozy, western-style bunk room. Located only a 10 minute drive from downtown Stowe.

Great Old Farmhouse near Jay Peak

Updated farmhouse built in 1860 located 8mi. from Jay Peak, in the heart of the village of Montgomery Center. There’s a bar/ restaurant & supermarket across the street but only the Trout River & forest out back. Easy access to skiing, mountain biking, hiking, and a quick walk to a great swimming hole. One of a few places locally with access to fast internet (Gigabit). The house, now solar powered, sleeps 6-8 and is spacious, well insulated, and well furnished. 8 people + 2 infants max.

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**

Jay Peak 3 miles - ski home via Big Jay!

Best backcountry skiing in New England - mountain getaway with stunning views! • Jay Peak Resort 3 miles away! • Ski home from Jay Peak via Big Jay! • Backcountry ski 6 mountains from your door! • Tour Long Trail, Catamount Trail, Big Jay & Little Jay from here! • Backcountry guiding available (15% discount for guests!) Note: There is also an apt in the main house that sleeps 8. • Vermont Mountain Experience: guests get a 15% discount for photography, backcountry & resort guiding!

Alder Brook Cottage: A Tiny House in the Woods

From the moment you cross the cedar footbridge over Alder Brook, you'll know you're somewhere special. Featured in Boston Magazine and CabinPorn, Alder Brook Cottage is an inspired, rustic dream cabin located in the woods of Vermont's Northeast Kingdom. Surrounded by a crystal clear stream and 1400 acres of rugged forest, it is the perfect getaway for glampers looking to experience the tiny house life. Minutes away from Caspian Lake, Hill Farmstead Brewery & Craftsbury Outdoor Center.

Serene Mountain Cabin with Private Pond & Hot Tub

Take advantage of spring discounts in April and May when you stay 4 nights or longer Escape to our incredible and luxurious cabin set on 24 acres of untouched forested mountains, with a large private pond, 8 person hot tub and gorgeous mountain views. Only 20 minutes from Jay's Peak Resort, our spacious and cozy 4 bedrooms, 3 full bathrooms can comfortably accommodate 8 guests. Whether you are looking for a base to go skiing, hiking or want to sit back and relax, this is the place.

Crofter's Green @ Jay Peak: O'Shea Farmhouse

The O'Shea Farmhouse is one of five micro-cottages at Crofter's Green - our small, thoughtfully-designed lodging property in the heart of Vermont. This cozy woodland retreat is just minutes from Jay Peak Ski Resort and the warm, eclectic town of Montgomery Center. this bright 2-story cottage sits at the forest's edge and offers a peaceful home base for exploring the Northeast Kingdom. It's simple, comfortable, and surrounded by nature. Find us on social media! @croftersgreen

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, and 3.5 from Boston.

Cozy Jay Condo

Welcome to our Mountainside Jay condo! This cozy 525 sq foot studio has a queen murphy bed, a queen sofa bed & a gas burning fireplace. Located directly across the street from the golf course/nordic center, next to the Ice Haus & the Water Park. Walk to the tram in the morning. Great destination for a small family, couples getaway or just a place to rest your head after a long day skiing/boarding. Newly renovated bathroom. Sweet and simple. Pets welcome!

Beautiful lake-front cottage, Lake Champlain

Lakefront cottage located in Highgate Springs, Vermont, on the Canadian border. The 2-bedroom cottage sits adjacent to the owner-occupied main house, on a large one-acre lot, with 120 feet of Lake Champlain shoreline. Enjoy the stunning sunset views while sitting on the deck overlooking the water. Private dock included. Montreal and Burlington each 45 minutes away. Available level-2 car charger. Well-behaved pets allowed. Super-fast WIFI!