Family-friendly holiday rentals in Montgomery

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Top-rated family-friendly rentals in Montgomery

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

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.

21–28 Nov

$236 SGD 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.

5–12 Jul

$206 SGD per night

Guest favourite

Guest suite in Sutton, Canada

4.95 out of 5 average rating, 218 reviews

Charming Studio close to Sutton's. Queen bed.

The studio is attached to our house, but very private. 2 miles from Sutton’s Village, 9 miles from the Us Borders. In the village you will find delicatessen,microbreweries , restaurants , art galleries , shops . It’s near ski centres, golf courses and spas. The area is known for its wine route , bike rides , hiking trails and local produces . Enjoy the atmosphere of the studio, the quality of its equipment , its brightness , its peaceful environment. Perfect for couples and solo travellers.

27 Apr – 4 May

$110 SGD per night

Guest favourite

Home in Richford, Vermont, US

4.99 out of 5 average rating, 117 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!

22 Feb – 1 Mar

$195 SGD per night

Guest favourite

Flat in Montgomery, Vermont, US

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.

3–10 Aug

$192 SGD per night

Guest favourite

Home in Mansonville, Canada

4.85 out of 5 average rating, 160 reviews

Chalet for rent in Potton Owl's head

Beautiful rustic cottage located on the mountainside in the canton of potton.In a wooded area just 5 minutes from all services (SAQ grocery CLSC pharmacy, etc.) Same distance from several tourist attractions such as : Mount Owl's Head,Golf Owl's head and Vale Perkins Beach of Lake Memphremagog which gives access to a beautiful boat descent.You will be not far from several other tourist attractions such as Mount Sutton, Jay Peak and Orford all less than 25 minutes from the cottage.

11–18 Jun

$149 SGD per night

Guest favourite

Cabin in Newport, Vermont, US

4.98 out of 5 average rating, 296 reviews

Sugar Hill

Come and embrace the majestic beauty of Vermont from Sugar Hill, a quaint log cabin nestled on 24 acres of beautiful countryside. Enjoy the views of the Canadian mountains from the front porch with a cup of coffee or a glass of wine; or wander around the pasture or woods behind the cabin. Close to both Jay Peak and downtown Newport, you can enjoy all those locations have to offer, or simply relax. Please note that the stairs to the 2nd floor are steeper than usual.

19–26 Sep

$236 SGD per night

Superhost

Home in Irasburg, Vermont, US

4.82 out of 5 average rating, 443 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 yet 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. We sit 1/4 mile from the VAST trail and are near several lakes and hiking trails. Also close by is the Craftsbury Outdoor Ctr, Creek Hill Barn and breweries.

30 Aug – 6 Sep

$160 SGD per night

Guest favourite

Flat in Sutton, Canada

4.96 out of 5 average rating, 276 reviews

Sutton - Large terrace - 10 min to the mountain

Located in the middle of nature and only a few minutes from the village of Sutton, nice independent 4-season apartment - in the same main house of the hosts. Fully equipped. Large outdoor terrace for exclusive use by visitors and BBQ to enjoy the beautiful summer and autumn evenings. 10 minutes from Sutton ski resort and its many activities. Cycling, skiing, golf, hiking, kayaking, wine route. Peace and quiet and birdsong guaranteed ! Establishment Number 296758

17–24 May

$144 SGD per night

Guest favourite

Guest house in Highgate, Vermont, US

4.98 out of 5 average rating, 530 reviews

Beautiful lake-front cottage, Lake Champlain

Lakefront cottage located in Highgate Springs, Vermont, on the Canadian border. The 2-bedroom cottage sits adjacent to the owner-occupied main house, on a large one-acre lot, with 120 feet of Lake Champlain shoreline. Enjoy the stunning sunset views while sitting on the deck overlooking the water. Private dock included. Montreal and Burlington each 45 minutes away. Available level-2 car charger. Well-behaved pets allowed. Super-fast WIFI!

14–21 Mar

$148 SGD per night

Guest favourite

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

30 Jun – 7 Jul

$148 SGD per night

Guest favourite

Cottage in Dunham, Canada

4.98 out of 5 average rating, 173 reviews

Cozy Little Orchard House in Dunham

This newly built house is located on our 90 acre property. It is surrounded by an orchard and forest. The quaint and natural setting is perfect for couples, solo travellers or families. Cross country skiing, running and hiking can be practiced on the property. Bromont and Sutton downhill ski slopes are a 35 minutes drive away. Jay Peak, Vermont is 1h15 away by car. The surrounding country roads provide for wonderful bike rides.

7–14 Oct

$119 SGD per night