
Family-friendly vacation rentals in Montgomery
Find and book unique family-friendly homes on Airbnb
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$23,012 GYD per night before taxes and fees

Verified guest reviews
Over 3,570 verified reviews to help you choose

Pet-friendly vacation rentals
Find 20 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!
Top-rated family-friendly rentals in Montgomery
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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.
FamilyIndoor spacesAccuracy

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!
KitchenIndoor spacesBiking

Charming Cottage by Jay Peak
Quaint cedar shake cottage perfect for a couples getaway. Bright open floor plan, comfortable and tastefully furnished. Gas fired stove in living room provides warmth and ambiance while the queen size bed is incredibly comfortable. Great galley kitchen fully equipped with everything you need to prepare your favorite meal or if you're not in the mood to cook there's four restaurants within walking distance. Jay Peak is only 8 miles from door to door. Easy parking. Discount ski tickets available.
KitchenFamilyQuiet

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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Secluded Luxury Treehouse - Hot Tub + Projector
Our treehouse is a haven of well-being, peace, and elegance. In our stunning modern treehouse we have brought relaxation to a whole new level. Surrounded amongst us is nothing but woods & wildlife. An experience not to be missed. Put your favorite movie on the projector, get Zen in the cozy sun room, jam out to music on the record player, or grab a towel, and head for the custom cedar hot tub. It is time to create core memories that will never be forgotten. Welcome to a little slice of heaven.
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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).
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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. Wake up to coffee on the deck or take a stroll around the pond. And you won’t regret kicking back in the evenings - star gazing is simply magical! We are certain that you‘ll have a hard time leaving!
Indoor spacesKitchenGrill

Jay Peak Retreat
The Jay Peak Retreat, Experience the Northeast Kingdom’s premier destination at Jay Resort, known for record snowfall and Vermont’s largest indoor waterpark. This stylish cabin offers an open-concept layout perfect for cozy gatherings and après-ski. Blending upscale comfort with rustic charm, enjoy a creek out back, river across the street, fire pit, and plush outdoor chairs. 1 hour from Burlington, 2 from Montreal, 35 minutes to Sutton Quebec!! Long Trail hiking entrance close to the cabin.
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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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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!
KitchenIndoor spacesHospitality

Meadow Cottage on Organic Farm with Mountain Views
The Meadow Cottage is perched on a picturesque knoll in the back of our 300 acre working dairy farm. We are located in between two of Vermont's best ski resorts, Jay Peak and Smuggler Notch. Come for a winter adventure full of downhill skiing, riding or x-country touring. Stay for the local breweries, distilleries, restaurants and antique stores. Or just relax at the farm, watch us milk the cows or cook up some delicious farm raised food for dinner. Well behaved dogs are welcome anytime!
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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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Popular amenities for Montgomery family-friendly rentals
Family-friendly home rentals with a hot tub

Scandinavian chalet • Sauna spa • Quiet nature
FamilyKitchenBiking

Metcalf Pond Camp Convenient to Smugglers Notch
FamilyIndoor spacesCheckout

Modern 3-BD Mountain Cabin w/ Hot Tub, Deck, Loft
KitchenIndoor spacesWifi

The Caterpillar House: Tiny w/ Hot Tub & Fire Pit
Indoor spacesKitchenBiking

Townhouse at Jay with Sauna + Jacuzzi
KitchenIndoor spacesLayout

The Old School | Spa | Natural Park | Countryside
KitchenFamilyOutdoor spaces

La Cabine Potton
KitchenFamilyWifi

La Binocle: Peaceful Architect Cottage
KitchenIndoor spacesComfort
Family- and pet-friendly home rentals

Streamside Treehouse in the Woods with Sauna
Indoor spacesKitchenLocation

Dream Cabin in Vermont
KitchenIndoor spacesBiking

Vermont Yurt Farm Stay | Vermont Glamping
Indoor spacesFamilyLong stay

Lakefront Cottage near Smugglers Notch Vermont
KitchenIndoor spacesGrill

Cady’s Falls Cabin
Indoor spacesFamilyAccess

Cozy Chalet at Jay Peak
KitchenIndoor spacesLocation

Journeys End Chalet - Minutes to Jay Peak!
Indoor spacesKitchenAir conditioning

Jay Apartment
FamilyIndoor spacesPets
Family-friendly home rentals with a pool

Jay Peak Ski in Ski out Condo
KitchenIndoor spacesSleep quality

Quiet stay on 76 acres land with pool!
FamilyIndoor spacesBreakfast

The House of the Setting Sun, Private Apartment
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The Cozy Condo at Smuggs Resort!
KitchenFamilyLocation

Studio Cabin near Smugglers Notch
Indoor spacesFamilyPool

Chalet Potton Cottage - spa, sauna & pool
FamilyIndoor spacesCondition

*10% off week*Cozy Lakeside Condo AND Heated Pool!
FamilyIndoor spacesGetting around

Château Chavis
FamilyKitchenNearby
When is the best time to visit Montgomery?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$61,713 GYD | G$61,922 GYD | G$54,809 GYD | G$47,069 GYD | G$50,207 GYD | G$50,207 GYD | G$50,207 GYD | G$53,973 GYD | G$50,416 GYD | G$51,253 GYD | G$50,416 GYD | G$61,085 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 |
Destinations to explore
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- Jay Peak Resort
- Owl's Head
- Zoo de Granby
- Bolton Valley Resort
- Jay Peak
- Stowe Mountain Resort
- Ski Bromont
- University of Vermont
- Jay Peak Resort Golf Course
- Kingdom Trails
- Mont-Orford National Park
- Snow Farm Vineyard & Winery
- Spa Bolton
- Pump House Indoor Waterpark
- Shelburne Museum
- Shelburne Vineyard
- Cold Hollow Cider Mill
- Bleu Lavande
- Fairbanks Museum & Planetarium
- Elmore State Park
- Waterfront Park
- Marais de la Rivière aux Cerises
- Boyden Valley Winery & Spirits
- Parc Jacques-Cartier





