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House vacation rentals in Montgomery

Find and book unique houses on Airbnb

Top-rated house rentals in Montgomery

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Superhost
A modern tiny house is set amongst trees, featuring a combination of dark and bright blue exteriors. A wooden deck is equipped with a picnic table, inviting guests to enjoy outdoor meals. Nearby greenery complements the natural surroundings.
Home in Johnson
4.89 out of 5 average rating, 200 reviews

Maple Sugar Shack Tiny House w/hot tub & river by

Welcome to The Maple Sugar Shack! Updated photos coming soon! Nestled along the Lamoille River in the charming town of Johnson, Vermont, this cozy retreat invites you to immerse yourself in the essence of Vermont's maple sugaring traditions. Featuring a warm and inviting buffalo check décor, local Vermont maple syrup information, and thoughtful details inspired by classic sugar shacks, this unique getaway is perfect for a quintessential Vermont experience. This chic tiny house offers two sleep

Superhost
A welcoming living area features a modern couch adorned with several cushions, positioned near a white coffee table. A wall-mounted sign reads 'be our guest' above the seating. Natural light enters through the window beside a door, enhancing the simple and inviting design.
Home in Irasburg
4.81 out of 5 average rating, 573 reviews

Eco friendly. Military discount available.

If you are looking for a serene location that is nestled in the woods off a quiet country road and only 1 mile from the town square with its locally owned grocery store and gas station, you’ve come to the right spot! We are centrally located between Burke Mtn and Jay Peak resort, both being 30 minutes away and are near several lakes and hiking trails and the Craftsbury Outdoor Ctr. You will be expected to strip your beds, clean up any messes you made and return used items to their original space

Guest favourite
A blue house with a pitched roof is set against a clear blue sky. Lush green grass surrounds the property, and trees provide a natural border. A person is seen walking across the spacious lawn, highlighting the outdoorsy setting.
Home in Montgomery
4.96 out of 5 average rating, 136 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.

Top guest favourite
A spacious open concept living area is visible from above, featuring a comfortable seating arrangement around a fireplace. The room is complemented by large sliding glass doors that lead to a balcony. A modern kitchen island with a sink and bar stools enhances the design.
Home in Johnson
4.96 out of 5 average rating, 116 reviews

The Barn - Modern Living in Small Town Vermont

Built this summer! 1800's barn converted to a modern 2 bedroom home with 16ft sliding glass doors overlooking the Green Mountains from the second floor living space! Designed to enjoy time with family, friends, and pets while taking in amazing views. Enjoy our huge lawn, walk to the local shops and restaurants, and experience all that small town Vermont offers. 30 minutes to Stowe, Smugglers Notch, and tons of micro breweries. Walking distance to Northern Vermont University. Come and relax!

Top guest favourite
Home in Montgomery
4.92 out of 5 average rating, 116 reviews

Rustic Converted Barn near Jay Peak w/Pizza Oven

Located right on Main St. Montgomery Center, you’ll love our Barn because of its quaint and rustic Vermont country atmosphere. Ye Olde Barn has been lovingly renovated and updated while preserving and emphasizing its old farm charm. The Barn offers you the best value in town because of its size and its multiple living spaces. We are Vermonters and love our environment. We have installed solar panels to help reduce our carbon footprint. We strongly encourage you to recycle while in our home.

Top guest favourite
A spacious living room showcases original woodwork and a baby grand piano. Comfortable sofas and armchairs are arranged around a central table, with art displayed on the walls. A television is mounted near a window, allowing natural light to fill the space.
Home in Montgomery
4.93 out of 5 average rating, 254 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 & 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.

Top guest favourite
A serene winter landscape displays gently rolling snow-covered hills, with distant mountains rising under a clear blue sky. Small structures are scattered across the meadow, surrounded by sparse trees, creating a peaceful and open atmosphere.
Home in Richford
4.99 out of 5 average rating, 153 reviews

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!

Superhost
A rustic exterior of the Sugar House is visible, showcasing a deep red facade. The building features multiple windows allowing natural light, with a stone chimney prominently located on one side. Lush greenery and a small stone pathway surround the structure, enhancing its natural setting.
Home in Johnson
4.88 out of 5 average rating, 170 reviews

The Sugar House, Maple Hill Road

The Sugar House on Maple Hill Road was once the site of a traditional Sugar House. The post and beams, wooden ceiling boards, 26 foot ceiling enhances the interior beauty. The house sits on 7 acres of woods with a small stream. Stowe Mountain Resort, The Trapp Family Lodge, Smugglers Notch, Long Trail, are just a few of the near by points of interest. Other activities near by include biking, fly fishing, golf, the Rail Trail. Stowe, Morrisville , Johnson, Hyde Park are just minutes away

Top guest favourite
An aerial view captures a cabin surrounded by a vibrant forest, showcasing an array of fall colors from lush green to bright oranges and reds. The home features a green roof and a gravel area, with mountains visible in the background under a clear sky.
Home in Westfield
4.95 out of 5 average rating, 209 reviews

Jay Peak 3mi - ski here via Big Jay!

Best backcountry skiing in New England - mountain getaway with stunning views! • Jay Peak Resort 3 miles away! • Ski home from Jay Peak via Big Jay! • Backcountry ski 6 mountains from your door! • Tour Long Trail, Catamount Trail, Big Jay & Little Jay from here! • Backcountry guiding available (15% discount for guests!) Note: There is also an apt in the main house that sleeps 8. • Vermont Mountain Experience: guests get a 15% discount for photography, backcountry & resort guiding!

Top guest favourite
A countertop coffee station is displayed against a wall with a subtle floral pattern. The setup includes a coffee maker, a tray with creamers, and neatly arranged cups on shelves above. Below, a cabinet offers storage space, complementing the cozy kitchen environment.
Home in Irasburg
4.95 out of 5 average rating, 191 reviews

Lord’s Creek Private Haven

Take a break at this peaceful, private getaway. We are located on a quiet road just a mile from our small-town square. Only three quarters of an hour from three ski resorts, Jay Peak, Burke Mtn and Smugglers Notch, we’re the perfect place to stay for your skication. There’s also plenty of hiking and beautiful lakes (Memphremagog, Crystal and Willoughby) to explore close by. Craftsbury Outdoor Ctr, Creek Hill Barn and, snowmobile trails are nearby. We offer a full kitchen and coffee bar!

Top guest favourite
A quaint guest home is nestled amid a snowy landscape, surrounded by bare trees and low shrubs. The property features a metal roof and a spacious porch, providing scenic views of the distant, snow-covered mountains.
Home in Waterville
4.99 out of 5 average rating, 170 reviews

4CR Farm Guest House 4 Season Vacation Destination

We are conveniently located within 45 mins of 3 great ski - snowboard mountains, a water park, zip lining, wineries, breweries, and shopping. A 10 minute walk will get you to The Long Trail, to do some hiking. The Lamoille Valley Rail Trail is another great trail for walking and biking. Vermont also has over 100 covered bridges for you to explore. Our guest house is the perfect little spot to call home while in Vermont. Come and enjoy the peace and quiet of our county setting.

Top guest favourite
A wooden picnic table is situated near a gently flowing river, surrounded by lush greenery. Large rocks are visible along the water's edge, and trees provide a natural backdrop under a partly cloudy blue sky.
Home in Montgomery
5 out of 5 average rating, 277 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. Price info can be found in the Photos section. It changes each year***

Popular amenities for Montgomery house rentals

When is the best time to visit Montgomery?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$365 CAD$365 CAD$360 CAD$315 CAD$315 CAD$336 CAD$336 CAD$348 CAD$336 CAD$315 CAD$308 CAD$342 CAD
Avg. temp-6 °C-5 °C0 °C8 °C15 °C20 °C22 °C21 °C17 °C10 °C4 °C-2 °C

Quick stats about house rentals in Montgomery

  • Total vacation rentals

    Explore 20 vacation rentals in Montgomery

  • Nightly prices starting at

    Montgomery vacation rentals start at $210 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,390 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Montgomery vacation rentals include wifi 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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