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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 $190 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,600 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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Top guest favourite
An aerial view showcases the home nestled among vibrant autumn foliage, with red, orange, and yellow leaves contrasting against the tranquil lake. A private dock extends into the water, complemented by a row of chairs facing the scenic landscape.
Home in Eden
4.95 out of 5 average rating, 216 reviews

LakeView Manor

YEAR-ROUND outdoor in-deck HOT TUB! You’ll be ON THE WATER! Perfect for any size group. Spectacular sunsets from the covered porch or private dock. Relax in the OUTDOOR HOT TUB. Enjoy a peaceful lake view and listen to the loons. SKIERS, we are a short drive to three major ski resorts; Stowe, Jay Peak, and Smugglers Notch. Amazing restaurants and pubs are nearby, and a great general store is down the road. Bring your snowmobiles and snow shoes! Trails are everywhere, right outside the doorstep.

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Top guest favourite
Home in Montgomery
4.92 out of 5 average rating, 124 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.

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Guest favourite
The wooden cabin, characterized by a pitched roof and large front deck, is nestled in a grassy area surrounded by trees. A stack of firewood is neatly arranged beneath the deck, while a dog is seen exploring the green lawn.
Home in Westfield
4.95 out of 5 average rating, 262 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!

ValueLocationAccess

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, 279 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.

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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, 304 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!

FamilyValueSleep quality

Top guest favourite
A charming Victorian house is showcased in a snow-blanketed landscape. The exterior features blue siding and intricate detailing, with festive wreaths adorning the front. A red barn, accompanied by several outbuildings, is visible in the background against a clear blue sky.
Home in Jeffersonville
4.94 out of 5 average rating, 139 reviews

Jeffersonville/Smuggler's Notch near Wedding Barns

Our house is a 5 bedroom Victorian built in 1835- restored with modern amenities and sits in the middle of the historic village of Jeffersonville. We are 5 minutes from Smuggler's Notch Ski area. 4 VT ski areas are close; Stowe 40 minutes, Sugarbush 70 minutes, Jay Peak 52 minutes & Bolton Valley 50 minutes. Minutes from The Barn at Smugglers Notch and Barn at Boydens. We are walking distance to restaurants, bars & stores. WIFI is excellent! Check us out on Insta- the parsonageairbnb

LocationFamilyQuiet

Top guest favourite
Home in Waterville
4.99 out of 5 average rating, 183 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.

ValueFamilyCondition

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
5.0 out of 5 average rating, 300 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***

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Guest favourite
Home in Eden
4.93 out of 5 average rating, 178 reviews

SleepUnderThe Stars-Lakefront|Hot Tub|GameRm|Pets!

Enjoy a quintessential Vermont getaway at this lakefront home. It’s the perfect place for remote workers and families looking for a perfect base for outdoor activities. Relax in the newly added Hot Tub and admire gorgeous lake views, and enjoy direct access to the water. Rainy days are no less fun, with a game room and fireplace to keep you busy. Recently added a brand new Star gazing dome - Glampers welcome !!! Lake Eden –Frontyard! Jay Peak - 25 min drive Stowe – 30 Min Drive

ValueFamilySleep quality

Top guest favourite
Home in Enosburg
5.0 out of 5 average rating, 71 reviews

The Gambrel Mountain Retreat at Twin Ponds

Escape to our charming gambrel-style retreat nestled in the Cold Hollow Mountains. Unplug in nature or settle in for a productive workcation with reliable Wi-Fi. Wake to peaceful views, cook in the fully equipped kitchen and unwind by the fire pit under the stars. Reconnect with nature and explore the peaceful forest trails just steps outside the door. Whether you're seeking adventure or quiet relaxation, you'll find the perfect balance of comfort, serenity, and mountain charm.

FamilyLocationIndoor spaces

Guest favourite
The exterior of The 1860 Farmhouse is showcased, featuring a blue clapboard facade with white trim. A spacious porch extends along the front, with multiple gabled roof peaks. Lush green lawns surround the house, complemented by colorful flower beds and a glimpse of the countryside in the background.
Home in Berkshire
4.94 out of 5 average rating, 169 reviews

1860 Farmhouse

Enjoy a restful getaway at The 1860 Farmhouse. We purchased the farmhouse in 2018 from a family that had done extensive renovations to the interior. Keeping true to its historic roots, the farmhouse offers modern amenities in a historic setting. A convenient location close to Jay Peak and Smuggler's Notch, and many Vermont and Quebec attractions within an easy drive. Swiss and Bloom wedding venue and Phoenix Manor are close by. The house is 6 bedrooms and sleeps 12 people.

ValueLocationBiking

Top guest favourite
A colorful sunset displays soft hues of pink and purple across the sky, with the silhouette of trees in the foreground. The modern home is seen at the right, revealing a corner of the structure against the twilight backdrop.
Home in Troy
4.94 out of 5 average rating, 142 reviews

Jay Mountain Retreat

Our modern home is just 8 miles to Jay Peak. We have long range mountain views, you can check if the tram is running and enjoy exquisite sunsets all from the couch. The loft upstairs has an open floor plan with a comfortable living space, bathroom and platform bed, where you can view Jay Peak conditions. We now have Starlink high speed internet. There are 8 private acres half woods half open meadow feel free to walk around the property and enjoy the quiet sounds of nature.

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Popular amenities for house rentals in Montgomery

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Avg. price$359 SGD$332 SGD$310 SGD$274 SGD$304 SGD$281 SGD$304 SGD$314 SGD$304 SGD$304 SGD$285 SGD$352 SGD
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