Family-friendly vacation 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 favorite

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.

Oct 22 – 29

G$35,617 GYD per night

Guest favorite

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.

Apr 12 – 19

G$39,988 GYD per night

Guest favorite

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.

May 6 – 13

G$16,602 GYD per night

Guest favorite

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!

Apr 20 – 27

G$29,423 GYD per night

Guest favorite

Apartment in Montgomery, Vermont, US

4.93 out of 5 average rating, 121 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.

Aug 3 – 10

G$29,024 GYD per night

Guest favorite

Home in Mansonville, Canada

4.85 out of 5 average rating, 160 reviews

Chalet for rent in Potton Owl's head

Superb rustic chalet located on the mountainside in the canton of Potton.In a wooded area just 5 minutes from all services (SAQ pharmacy CLSC grocery store, 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 chalet.

Jun 15 – 22

G$22,956 GYD per night

Guest favorite

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.

Oct 18 – 25

G$36,768 GYD per night

Superhost

Home in Irasburg, Vermont, US

4.82 out of 5 average rating, 444 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.

Aug 23 – 30

G$25,703 GYD per night

Guest favorite

Chalet in Mansonville, Canada

4.91 out of 5 average rating, 112 reviews

Private & Intimate Cottage In Eastern Townships

We have 8 acres of beautiful wood and IMHO a beautiful spot that we're continuing to gradually improve every year. It may be small but we really love it and it's got everything we need. I built this place myself based on plans I bought online in 2001 while working full-time and doing a masters degree. One day, we'll build our dream cottage at the top of our land to take in the spectacular views. But for now, the 3 kids and the jobs are keeping us more than busy.

Oct 24 – 31

G$23,408 GYD per night

Guest favorite

Apartment 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 - same as the hosts' main house. Completely 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. Bicycle, skiing, golf, hiking, kayaking, wine route. Tranquility and bird songs guaranteed! Property number 296758

Dec 16 – 23

G$22,987 GYD per night

Guest favorite

Guesthouse in Highgate, Vermont, US

4.97 out of 5 average rating, 531 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!

Apr 9 – 16

G$22,413 GYD per night

Guest favorite

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

Nov 11 – 18

G$22,648 GYD per night