Family-friendly vacation rentals in Montgomery

The Rustic Retreat at Twin Ponds

Take it easy and make yourself right at home in our woodsy cabin tucked away in the Cold Hollow Mountains. As you head down the drive, let your worries fade away - you’re now on cabin time. Relax in the clawfoot tub after a day of travel or prepare a home-cooked meal in the well equipped kitchen. When morning comes, enjoy your coffee while cozied up in front of the fireplace. Or simply stay in bed and admire the view. With plenty of land to explore, a hike is always welcome. The choice is yours!

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.

Bright new cottage in exquisite Vermont setting

Relax in "Findaway" cottage. Centrally located between Burlington and Montpelier and directly adjacent to Sleepy Hollow cross country ski and bike area, Birds of Vermont museum and the Vermont Audubon Center. Settle in and relax, hike right out the door, or sip a drink on the deck overlooking a beaver pond where you may see beaver, otters, deer, birds or even a moose! Surrounded by gardens and not far from downhill skiing and hiking options, swimming, sailing, dining and Lake Champlain.

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.

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.

Off Grid Vermont Cabin-Hike-Write

An off grid cabin in the hills of Vermont with a spectacular view of Camel's Hump. Not for everyone, (no running water, spotty cell service) but if you want quiet, beauty and solitude, this place is for you. A writer-hiker's dream. If it's chilly, the cabin's heated. There's also an ice pack (provided) fridge, propane stove, solar electricity for lights, composting toilet (no smell. Really), pots, cooking utensils, dishware etc We allow one dog (only ONE, please!) for a fee $25 per stay.

Trout River Lodge - Discount Jay Peak Lift Tix

Welcome to the Trout River Lodge! Check out the “Three Holes” swimming hole and waterfalls, just a few hundred yards up the river. We are located right in the heart of Montgomery Center, VT. Live music at the Snowshoe Pub, breakfast at Bernies, and groceries from Sylvester’s are all just steps away. You can also enjoy the mountain biking and hiking trails just minutes away! ***Discount vouchers for Jay Peak Ski. Price info can be found in the Photos section. It changes each year***

The Binocular: Peaceful Architect Cottage

Cosy timeless chalet conceptualized by the architects of _naturehumaine. Nestled into the cliffside at an altitude of 490 meters (1600 feet), its unique design is distinguished by boldness and originality and fits with harmony in its environment. Surrounded by forest, the cottage offers breathtaking views of Mount Glen and the surrounding nature largely protected by the Appalachian Corridor. The perfect silent place to relax and unwind. Photo: Adrien Williams / S.A. CITQ #302449

Crofter's Green @ Jay Peak: Sugar Shack

The Sugar Shack 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 light-filled studio cottage sits at the forest's edge ad 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.

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!

Cozy Little Orchard House in Dunham

This newly built house is located on our 90 acre property. It is surrounded by an orchard, a vineyard and forest. The quaint and natural setting is perfect for couples, solo travellers or families. Cross country skiing, running and hiking can be practiced on the property. Bromont and Sutton downhill ski slopes are a 35 minutes drive away. Jay Peak, Vermont is 1h15 away by car. The surrounding country roads provide for wonderful bike rides.