Kid-friendly vacation rentals in Montgomery

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Top-rated kid-friendly rentals in Montgomery

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Guest favorite

Apartment in Jay, Vermont, US

4.86 out of 5 average rating, 298 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

Sep 1 – 8

G$22,630 GYD per night

Guest favorite

Home in Montgomery, Vermont, US

4.96 out of 5 average rating, 116 reviews

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.

Sep 10 – 17

G$35,617 GYD per night

Guest favorite

Guest suite in Sutton, Canada

4.93 out of 5 average rating, 104 reviews

Guest Studio with Beautiful Mountain Views

Our 30 acre farm property is located on a quiet country road just 6 kms from Sutton Village, a haven for cyclists, hikers, skiers and wine enthusiasts. The village features 2 brewpubs, a good choice of restaurants, fun shops and beautiful Mt. Sutton to explore. Enjoy spectacular views and sun rises from your private balcony or patio, the walking paths in our forest behind, cycle along the surrounding backroads or just enjoy some quiet time in front of the wood burning stove or outdoor fire pit.

Jun 26 – Jul 3

G$13,693 GYD per night

Guest favorite

Home in Montgomery, Vermont, US

4.94 out of 5 average rating, 212 reviews

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 and supermarket across the street but only the Trout River & forest out back. Easy access to skiing, mountain biking, hiking, and just downstream from a great swimming hole. One of a few places locally with access to fast internet (Gigabit). The house, now solar powered, sleeps 6-8 comfortably and is spacious and well furnished. 8 people + 2 infants max.

Aug 10 – 17

G$35,024 GYD per night

Guest favorite

Chalet in Montgomery, Vermont, US

4.94 out of 5 average rating, 101 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).

Jun 16 – 23

G$39,426 GYD per night

Guest favorite

Cottage in Westfield, Vermont, US

4.92 out of 5 average rating, 108 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.

Apr 11 – 18

G$22,451 GYD per night

Guest favorite

Farm stay in Fairfield, Vermont, US

4.97 out of 5 average rating, 327 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!

Mar 30 – Apr 6

G$29,012 GYD per night

Guest favorite

Home in Montgomery, Vermont, US

5.0 out of 5 average rating, 229 reviews

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/Golf Round/Water Park. Price info can be found in the Photos section***

Apr 11 – 18

G$74,374 GYD per night

Guest favorite

Apartment in Montgomery, Vermont, US

4.93 out of 5 average rating, 121 reviews

The Original Montgomery Lodge - Tried and True!

We are The Montgomery Lodge and we've been doing it right since 2008. That's 15 years of clean, affordable ski (and summer) lodging. Compare us to other area vacation rentals and you'll see that we cannot be beat. Located on Main Street in beautiful Montgomery Center -- the heart of the Jay Peak Region and gateway to VT's North East Kingdom! Walk to shops, grocery, bars, restaurants, spas and enjoy a rare, genuine, non-commercial ski-town experience that will beg your return.

Aug 3 – 10

G$29,024 GYD per night

Guest favorite

Cabin in Montgomery, Vermont, US

4.92 out of 5 average rating, 190 reviews

Remote yet convenient cabin

Escape to a remote yet convenient spot in the mountains. This cabin is an open space with a kitchen, bathroom, and loft bedroom. 1000 square feet of rustic coziness inside with all the conveniences. It is located on 15 acres with amazing views, walking/ hiking/ X country Skiing/ biking/ ATV/ snowmobiling options, foliage season, and a pond in the summer. While this cabin is situated outside of town, it is close to all the local restaurants and 20 minutes from Jay Peak Resort.

Oct 13 – 20

G$19,779 GYD per night

Guest favorite

Chalet in Mansonville, Canada

4.95 out of 5 average rating, 169 reviews

A-Frame river access

This Swiss chalet is an ideal place to unplug from the city, relax and enjoy the outdoors. Whether it's reading, sleeping, yoga, drawing, tea or board games, everything is well arranged. The land gives direct access to the river to the walking path as well as private access for a bonfire. Where the stars shine even brighter, the beautiful Potton area offers a range of playgrounds in the heart of nature. It's up to you to discover it!

Jul 13 – 20

G$23,092 GYD per night

Guest favorite

Chalet in Frelighsburg, Canada

4.91 out of 5 average rating, 299 reviews

Frelighsburg. Charming mountain log pavillon

SPECIAL RATE for APRIL & MAY: $99. This authentic 4 season log cottage with its large stone fireplace and 2 bedrooms can accommodate 4 people. Ideal for a couple with 2 children. Fully equipped. Large sunny terrace. BBQ. High Speed Wifi. An ideal place for nature lovers, for biking, hiking, skiing or just relaxing. A haven of peace and inspiration for writers, poets at heart and dreamers... Quebec Tourism Reference number : 297222

Dec 5 – 12

G$22,648 GYD per night