Holiday houses in Montgomery

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Top-rated holiday rentals in Montgomery

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Guest favourite

Apartment in Jay

4.86 out of 5 average rating, 295 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

16–23 Aug

$213 NZD per night

Guest favourite

Home in Montgomery

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.

25 Sep – 2 Oct

$348 NZD per night

Guest favourite

Cabin in Montgomery

4.93 out of 5 average rating, 42 reviews

Cozy Mountain Hideaway

“The Jay Peak Retreat” located up the road in the Northeast Kingdoms most hidden gem, Jay Resort with the highest annual snowfall in Vermont. Also the largest indoor waterpark. Upon entry you are greeted by an open concept modern layout best for intimate get togethers and Apres Ski! Our newly renovated cabin has all the comforts of a chic resort with the tranquility and privacy you've always dreamed of. In warmer month enjoy your private backyard oasis with modern patio furniture on the creek.

30 May – 6 Jun

$349 NZD per night

Guest favourite

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.

3–10 Dec

$330 NZD per night

Guest favourite

Chalet in Montgomery

4.94 out of 5 average rating, 100 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).

5–12 Jul

$358 NZD per night

Guest favourite

Guest suite in Waterville

5.0 out of 5 average rating, 112 reviews

Rivers Rock - a charming cottage in the woods

Warm, charming cottage, impeccably furnished with spacious cook's kitchen, nestled in a serene wooded hollow. Enjoy the cozy warmth of the gas fireplace in winter, the cool respite of river wading in summer, or brisk nights around the firepit after a day enjoying gorgeous fall foliage or biking on the Lamoille Valley Rail Trail. While rural, you're central: Smugglers Notch Resort 18 minutes, Jay Peak 30 minutes, Stowe Mountain Resort 40 minutes, Jeffersonville's art galleries 10 minutes.

11–18 Jul

$332 NZD per night

Guest favourite

Cottage in Westfield, Vermont, US

4.92 out of 5 average rating, 107 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.

19–26 Jan

$263 NZD per night

Guest favourite

Farm stay in Fairfield

4.97 out of 5 average rating, 324 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!

22–29 Jan

$270 NZD per night

Guest favourite

Home in Montgomery

5.0 out of 5 average rating, 228 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***

4–11 Dec

$665 NZD per night

Guest favourite

Apartment in Montgomery

4.93 out of 5 average rating, 120 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.

19–26 May

$259 NZD per night

Guest favourite

Cabin in Montgomery

4.92 out of 5 average rating, 189 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.

26 May – 2 Jun

$181 NZD per night

Guest favourite

Apartment in Montgomery

4.83 out of 5 average rating, 93 reviews

Good Vibes: Ski, Ride & Save Lodging

Find serenity by the Trout River at our private swimming and fishing hole, located only 10 miles from Jay Peak! Downtown Montgomery has music, dancing and the First Trax ski shop. ATVs/snowmobiles are welcome. Walk to the Comstock and Fuller Covered bridges. Save money staying at Good Vibes; go out locally to the Black Lantern for dinner and drinks, or stay home to bbq and relax by our fire pit. Make your travels into an epic adventure here at Good Vibes Lodging!

12–19 Nov

$145 NZD per night