Family-friendly holiday 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, will you wake to coffee on the deck surrounded by nature? Or build a fire + cozy up on the couch? Perhaps a hike? Why not simply stay in bed and admire the view? The choice is yours!

Orchard House retreat near Jay Peak

Relax and unwind in this newly renovated house with peaceful overlook on apple orchard, woodland and hills. There are over 10 acres to play (snowshoe, cross country ski, sledding, hiking or just relaxing) and only 20 mins. to awesome skiing or riding at Jay Peak! Two bedrooms across two floors. Relax in the deep claw-footed tub in the large full bathroom. Fully outfitted kitchen: coffee maker, refrigerator, microwave, gas stove with oven. Grill on deck. Washer & dryer. Wifi for remote working.

Charming Cottage by Jay Peak

Quaint cedar shake cottage perfect for a couples getaway. Bright open floor plan, comfortable and tastefully furnished. Gas fired stove in living room provides warmth and ambiance while the queen size bed is incredibly comfortable. Great galley kitchen fully equipped with everything you need to prepare your favorite meal or if you're not in the mood to cook there's four restaurants within walking distance. Jay Peak is only 8 miles from door to door. Easy parking. Discount ski tickets available.

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).

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.

Peaceful + Cozy Farmhouse Near Jay Peak + Sutton

Our guest farmhouse, located 1 mile from the Canadian border, is close to Jay Peak Ski Resort and Mount Sutton. Mountain and meadow views are spectacular from every window! Here, you are perfectly poised to explore both the quaint, foodie-focused, French-Canadian, Eastern Townships, just across the border in Quebec AND the scenic back-roads, abundant lakes, family farms, mountain trails, local pubs, and old general stores of Northern Vermont. Or just enjoy the porch & peaceful atmosphere!

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.

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***

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.