
Family-friendly vacation rentals in Montgomery
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Montgomery
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Jay Apartment
Only 10 minutes to Jay Peak Ski Resort. Secluded in the woods right next to Starr Brook, yet only a 2 min drive to the Jay Village Inn restaurant and bar and the Jay Country Store. Fire pit with cooking grate next to the brook you are welcome to use weather permitting. Great hiking, biking trails, snow showing and Nordic skiing minutes away. Some trails are accessible directly from the property. Very comfy bed, wonderful place to sleep. . Vermont Meals and Rooms Tax ID number is MRT-10126712

The Rustic Retreat at Twin Ponds
Take it easy and make yourself right at home in our woodsy cabin tucked away in the Cold Hollow Mountains. As you head down the drive, let your worries fade away - you’re now on cabin time. Relax in the clawfoot tub after a day of travel or prepare a home-cooked meal in the well equipped kitchen. When morning comes, enjoy your coffee while cozied up in front of the fireplace. Or simply stay in bed and admire the view. With plenty of land to explore, a hike is always welcome. The choice is yours!

Hill Top Apartment With Amazing View Near Stowe
Charming one-bedroom suite high on a hill with one of the best views in the county. Very private setting on a country road. You will have the whole top floor to yourself including a bedroom, open kitchen/dining/living space, a wardrobe room, bathroom complete with 2-person jet tub and an enclosed porch. Ramble around our large property, or use as your base of operations for your Vermont Adventure. We're right in the heart of northern Vermont, a modest drive from best things to see in the area!

A-Frame accès à la rivière
Ce chalet suisse est un endroit idéale pour décrocher de la ville, se reposer et profiter du plein air. Que ce soit pour faire de la lecture, dormir, du yoga, dessiner, prendre le thé ou jouer aux jeux de société; tout y est bien aménagé. Le terrain donne un accès direct à la rivière au sentier de marche ainsi qu'un accès privé pour un feu de joie. Là où les étoiles brillent encore plus, la belle région de Potton offre une panoplie de terrain de jeu en pleine nature. À vous de la découvrir!

Montgomery Meadows Chalet near Jay Peak
Located on beautiful, historic Hazens Notch Road, Montgomery Center, Vermont. This “hidden gem” of a house sets back from the road in a private setting on 5 spectacular acres of cleared land, with views of Jay Peak Ski and Golf Resort. A perfect location for skiing, hiking, biking, golfing, etc. Only 15 minutes from the resort and all of the great amenities (water park, ice rink, movie theater, climbing wall, arcade). Only 3 miles from local amenities (grocery store, top rated restaurants).

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.

Alder Brook Cottage: A Tiny House in the Woods
From the moment you cross the cedar footbridge over Alder Brook, you'll know you're somewhere special. Featured in Boston Magazine and CabinPorn, Alder Brook Cottage is an inspired, rustic dream cabin located in the woods of Vermont's Northeast Kingdom. Surrounded by a crystal clear stream and 1400 acres of rugged forest, it is the perfect getaway for glampers looking to experience the tiny house life. Minutes away from Caspian Lake, Hill Farmstead Brewery & Craftsbury Outdoor Center.

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***

Serene Mountain Cabin with Private Pond & Hot Tub
Take advantage of spring discounts in April and May when you stay 4 nights or longer Escape to our incredible and luxurious cabin set on 24 acres of untouched forested mountains, with a large private pond, 8 person hot tub and gorgeous mountain views. Only 20 minutes from Jay's Peak Resort, our spacious and cozy 4 bedrooms, 3 full bathrooms can comfortably accommodate 8 guests. Whether you are looking for a base to go skiing, hiking or want to sit back and relax, this is the place.

Crofter's Green @ Jay Peak: O'Shea Farmhouse
The O'Shea Farmhouse is one of five micro-cottages at Crofter's Green nested on twenty-five beautiful acres of land just minutes from Jay Peak Ski Resort and the warm, eclectic town of Montgomery Center, Vermont. Whether you're looking for a relaxing escape from the hustle and bustle, or want a cozy home-base from which to ski, hike, shop, or explore the nearby cities of Montreal and Burlington, the O'Shea Farmhouse is your ideal destination. Find us on social media! @croftersgreen

Charmante Tiny House bord de l'eau
Découvrez notre charmante Tiny House, idéale pour un séjour chaleureux au bord de la rivière. Profitez de sentiers sur le site et d’un accès privé à l’eau. Ce projet, conçu avec amour, reflète notre bonheur d’avoir un havre de paix où se ressourcer et pratiquer des activités de plein air. Nous souhaitons partager cette expérience avec ceux qui recherchent un doux moment de bien-être en campagne. Offrez-vous un moment de sérénité, seul ou en amoureux, dans notre petit cocon.

Jay Peak 3 miles - secluded with spectacular view!
Mountains, streams & seclusion with stunning views! • Hike the Long Trail • Road, gravel & mountain biking • Jay Peak Resort is three miles away! • Waterpark • Golf • Backcountry guiding available (15% discount!) This is the mountain getaway you dream about! Our only neighbors are animals in the surrounding mountains & forests. • Vermont Mountain Experience - 15% discount on photography & backcountry guiding! There is an apt in the main house that sleeps 8.
Popular amenities for Montgomery family-friendly rentals
Family-friendly home rentals with a hot tub

Cabin Sutton 264 - Relaxation en pleine nature !

Metcalf Pond Camp Convenient to Smugglers Notch

Spring Hill Farm, coffee & hot tub

Chalet forêt avec spa et sauna privés

Geodome 1min to Smuggler's Notch w/hot tub & River

Northern Vermont Country Escape/ The Martin House

La Cabine Potton

Secluded Luxury Treehouse - Hot Tub + Projector
Family- and pet-friendly home rentals

Le petit refuge

Dream Cabin in Vermont

Sympathique pied-à-terre dans Brome-Missisquoi

Super Cozy Cabin with WiFi

Fairytale cabin at The Wild Farm

Journeys End Chalet - Minutes to Jay Peak!

CH'I TERRA gîte-ressourcement entre lac et rivière

Peaceful Log Cabin in the Woods
Family-friendly home rentals with a pool

Jay Peak Ski in Ski out Condo

Quiet stay on 76 acres land with pool!

Lovely Ski-in / Ski-out Studio at “Smuggs”⭐️

Cozy Chalet at Jay Peak

Condo bord de l'eau avec piscine intérieure et ext

Spruce Peak Lodge Studio Mnnt Views! | 1516

Ski in Ski out - fantastic location on the trail

The House of the Setting Sun, Private Apartment
When is the best time to visit Montgomery?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$54,790 GYD | G$56,044 GYD | G$54,372 GYD | G$47,052 GYD | G$47,471 GYD | G$49,771 GYD | G$50,189 GYD | G$53,953 GYD | G$50,398 GYD | G$47,052 GYD | G$46,843 GYD | G$53,535 GYD |
| Avg. temp | -6°C | -5°C | 0°C | 8°C | 15°C | 20°C | 22°C | 21°C | 17°C | 10°C | 4°C | -2°C |
Quick stats about vacation rentals that are family-friendly in Montgomery

Total vacation rentals
Explore 50 vacation rentals in Montgomery

Nightly prices starting at
Montgomery vacation rentals start at G$25,095 GYD per night before taxes and fees

Verified guest reviews
Over 3,110 verified reviews to help you choose

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
50 of Montgomery vacation rentals include wi-fi 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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- Jay Peak Resort
- Owl's Head
- Parc Safari
- Ski Bromont
- Amazoo Park
- Mont Sutton Ski Resort
- Bolton Valley Resort
- Le Vignoble du Ruisseau - Winery & Cidery
- Sherbrooke Golf Club
- Cochran's Ski Area
- Jay Peak Resort Golf Course
- Pump House Indoor Waterpark
- Ethan Allen Homestead Museum
- Country Club of Vermont
- Leahy Center for Lake Champlain
- Burlington Country Club
- Val Caudalies - Vignoble & Cidrerie
- Le Club De Golf Memphrémagog
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- Domaine Cotes d'Ardoise - Winery & Cidery
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