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House holiday rentals in Montgomery

Find and book unique houses on Airbnb

Quick stats about house rentals in Montgomery

  • Total holiday rentals

    Explore 30 holiday rentals in Montgomery

  • Nightly prices starting at

    Montgomery holiday rentals start at $193 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,540 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Montgomery holiday 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!

Top-rated house rentals in Montgomery

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

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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, 137 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
An aerial view of a spacious mountain home surrounded by vibrant autumn foliage. The house features multiple levels, large windows, and is complemented by a grassy expanse. Nearby, a green shed and parked vehicle are visible, with rolling hills and colorful trees creating a picturesque backdrop.
Home in Westfield
4.96 out of 5 average rating, 253 reviews

Jay Peak 3 miles - secluded with spectacular view!

Mountains, streams & seclusion! • Hike the Long Trail • Road, gravel & mountain biking • Jay Peak Resort is three miles away! • Waterpark • Golf • Backcountry guiding - hiking, kayaking, gravel & mountain biking (15% discount) • Photography and videography (15% discount) This is the mountain getaway you dream about! Our only neighbors are animals in the surrounding mountains & forests. Note: There is also an apt in the main house that sleeps 8. Welcome to Vermont Mountain Experience!

Top guest favourite
Home in Montgomery
4.92 out of 5 average rating, 123 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/batteries to reduce 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
4.94 out of 5 average rating, 272 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
Home in Richford
4.99 out of 5 average rating, 159 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!

Guest favourite
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
4.89 out of 5 average rating, 188 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
The red wooden house features a welcoming entryway with a prominent front door framed by large windows. Bright green foliage lines the path, enhancing the natural setting. The garage is visible on the left, with sunlight illuminating the exterior.
Home in Hyde Park
4.97 out of 5 average rating, 295 reviews

CLASSIC VT STYLE

This is an authentic VT house tucked between two of the state's most celebrated ski resorts, Stowe and Smuggler's Notch. We are about 30 minutes north of Mount Mansfield with tons of hiking and exploration opportunities. In this area you can enjoy some of the state's most popular outdoor recreational attractions and activities. The space is private and serene and works for all different kinds of local adventures in any season. Come experience a unique part of VT in your own unique VT home!

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, 177 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, 290 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***

Top guest favourite
A hot tub is positioned with a view of the lake, surrounded by trees and an open landscape. The water is calm, reflecting the colors of the sky. In the distance, a dock is visible along the shoreline.
Home in Saint Albans City
4.89 out of 5 average rating, 149 reviews

Sunrise Lake House! Comfort-Hot Tub-Beach

Relax and recharge with family and friends at the lake! It’s the perfect place to stay year round. We aim to provide a place of comfort and relaxation with essential and fun amenities. Enjoy private lakefront access, a screened porch to relax on, kayaks and paddle boards provided in the summer. Enjoy the NEW 4 person Hot Tub with Lake views! Minutes to downtown St. Albans, offering delicious eateries and shopping at local boutiques. Burlington is 35 minutes away.

Top guest favourite
A single-story house is framed by lush greenery and a clear blue sky. The front deck is accessible from a winding gravel driveway, with neatly trimmed bushes bordering the yard. Large windows invite natural light into the living space.
Home in Craftsbury
4.94 out of 5 average rating, 108 reviews

Relaxing Craftsbury Retreat

One bedroom house in pastoral setting with deck, small pond and screened in sitting area. Newly renovated kitchen and full bath. Kick back with a book in front of the stove after a day on the trails or out on the amazing NE kingdom gravel roads at the Craftsbury Outdoor Center (4 mi). Short stroll to maple buns at the Genny or Creemees at Village Store (1/2 mi). Spend the day on the lake at Caspian (8 mi). Stock up at Hill Farmstead Brewery (10 mi).

Top guest favourite
A spacious living area features large windows framing mountain views and a cozy fireplace. Natural wood accents complement the soft furnishings, including a circular glass coffee table atop a patterned area rug. A dining table for two is positioned near the sliding doors leading to the outdoor deck.
Home in Moretown
4.98 out of 5 average rating, 332 reviews

Dramatic Views at the Above the Clouds Guesthouse

As featured in Conde Nast Traveler (1/21/22) Peaceful & impeccable retreat with a 180 degree view of Vermont's tallest mountains. Near Vermont's premier skiing, hiking, & outdoor adventures, you’ll love the sunset views and cozy atmosphere (huge sheepskin in front of the fireplace) and the attention to detail (live-edge wood details, spa-like bathroom). This is an incredible retreat for couples and families, adventurers and business travelers alike!

Popular amenities for house rentals in Montgomery

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Avg. price$364 SGD$337 SGD$315 SGD$289 SGD$289 SGD$308 SGD$308 SGD$319 SGD$308 SGD$308 SGD$289 SGD$357 SGD
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