
Family-friendly vacation rentals in Montgomery
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Montgomery
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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

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.

Cady’s Falls Cabin
Welcome to our treehouse inspired, modern cabin overlooking The Kenfield Brook on Terrill Gorge. We are located 5 miles from Stowe and its attractions, and just a few minutes from downtown Morrrisville with all its amenities. Just upstream from the picturesque Cady’s Fall swimming hole and across the brook from the amazing Cady’s Falls bike trails, our cabin is perched atop the hillside. With its simple, minimalist design it’s easy to immerse yourselves in nature and feel at home in the trees.

Crofter's Green @ Jay Peak: Caribe Cottage
The Caribe is one of five micro-cottages at Crofter's Green - our small, thoughtfully-designed lodging property in the heart of VT. 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 and offers a peaceful home base for exploring the Northeast Kingdom. It's simple, comfortable, and surrounded by nature. This unit is pet-friendly! Find us on social media! @croftersgreen

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.

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!

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

The Book Barn: Newly Renovated Guesthouse
Enjoy all Vermont has to offer in this bright, airy space minutes away from Burlington and the mountains. On 14 acres with a brook, it’s a short walk down a dirt road to a historic covered bridge and town common. Fall colors are breathtaking when taken in from the barn deck, while Spring and Summer visitors enjoy free concerts on the town green on Sundays. Spectacular sunsets and hot air balloons are familiar sights. It doesn’t get much more Vermonty. *Note: No Cleaning Fee!

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.
Popular amenities for Montgomery family-friendly rentals
Family-friendly home rentals with a hot tub

Metcalf Pond Camp Convenient to Smugglers Notch

The Caterpillar House: Tiny w/ Hot Tub & Fire Pit

Forest Chalet • Private Spa & Sauna • Quiet

La Cabine Potton

The Country House in the Mountains

Garden Spa Terrasse Cozy Cottage near Lake Dunham

Nature Chalet, Private Hot Tub, ski and Pond

Guest Suite w/hot tub & fireplace
Family- and pet-friendly home rentals

Between village and summit – pet-friendly

Knowlton Village: Beautifully Designed 2BR Apt

Charming Tiny House bord de l'eau

Hydrangea House on the Hill

Waldhaus - Modern Forest Cabin

The Cabin

Beautiful lake-front cottage, Lake Champlain

The Original Montgomery Lodge - Tried and True!
Family-friendly home rentals with a pool

Luxury Alpine Studio Ski in Ski out mountainside

Secluded Paradise on the Connecticut River, VT

Jay Peak Ski in Ski out Condo

Quiet stay on 76 acres land with pool!

The House of the Setting Sun, Private Apartment

Chalet Potton Cottage - spa, sauna & pool

Waterfront condo in Magog

Beautiful Chalet minutes to Jay Peak Resort
When is the best time to visit Montgomery?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ962 | ﺩ.ﺇ984 | ﺩ.ﺇ955 | ﺩ.ﺇ826 | ﺩ.ﺇ834 | ﺩ.ﺇ874 | ﺩ.ﺇ881 | ﺩ.ﺇ948 | ﺩ.ﺇ885 | ﺩ.ﺇ900 | ﺩ.ﺇ885 | ﺩ.ﺇ1,072 |
| Avg. temp | -6°C | -5°C | 0°C | 8°C | 15°C | 20°C | 22°C | 21°C | 17°C | 10°C | 4°C | -2°C |
Quick stats about vacation rentals that are family-friendly in Montgomery

Total vacation rentals
Explore 50 vacation rentals in Montgomery

Nightly prices starting at
Montgomery vacation rentals start at ﺩ.ﺇ551 per night before taxes and fees

Verified guest reviews
Over 3,130 verified reviews to help you choose

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
50 of Montgomery vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Montgomery rentals

4.9 Average rating
Montgomery stays are highly rated by guests—averaging 4.9 out of 5!
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- Family-friendly rentals Franklin County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Jay Peak Resort
- Owl's Head
- Mont Sutton Ski Resort
- Ski Bromont
- Jay Peak
- Bolton Valley Resort
- Zoo de Granby
- Jay Peak Resort Golf Course
- Pump House Indoor Waterpark
- Stowe Mountain Resort
- University of Vermont
- ECHO, Leahy Center for Lake Champlain
- Shelburne Museum
- Boyden Valley Winery & Spirits
- Shelburne Vineyard
- Mont-Orford National Park
- Waterfront Park
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- Bleu Lavande
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- Lake Champlain Chocolates
- Elmore State Park
- Spa Bolton
- Marais de la Rivière aux Cerises




