
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$22,995 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.
Indoor spacesFamilyBiking

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!
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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.
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Cozy Chalet at Jay Peak
The house is set up with everything to make your stay cozy, comfortable & fun. Gas Fireplace, 5br, 2.5 Bath, 2 separate Living Room areas. Large Deck with Gas Grill overlooks small brook. Private wooded setting with panoramic mountain views once leaves have fallen. Seasonal Pool, Disc Golf, Volleyball, Playground & Hiking Trails a short walk from the house. 3 mi to Jay Peak. Air Conditioning is in three bedrooms which are installed by the 2nd Sunday of June then removed the last Sunday of Sep.
FamilyKitchenPool

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.
KitchenIndoor spacesHot tub

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).
KitchenIndoor spacesWifi

Treehouse at Bliss Ridge Farm - Best Views in VT!
This treehouse, the Birds Nest, is open May-Oct. Our “4-Season Treehouse @ Bliss Ridge,” is open year-round: https://www.airbnb.com/h/bigtreehouseatblissridgefarm — NEW SAUNA on property! Dr. Seuss-inspired tree home perched @top of 88-acre, organic hill farm, surrounded by 1000s acres of wilderness. Designed by B'fer Roth, DIY network host of The Treehouse Guys - built WITHIN living trees, not stilts! Private hiking & panoramic views of Worcester range, MR valley! No pets or animals please.
FamilyKitchenBreakfast

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!
KitchenFamilyPets

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.
KitchenFamilyLayout

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.
KitchenIndoor spacesHeating

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***
Indoor spacesFamilyAccess

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.
KitchenFamilyAccuracy
Popular amenities for Montgomery family-friendly rentals
Family-friendly home rentals with a hot tub

Modern 3-BD Mountain Cabin w/ Hot Tub, Deck, Loft
Indoor spacesFamilySkiing

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

Townhouse at Jay with Sauna + Jacuzzi
Indoor spacesKitchenGrill

La Cabine Potton
Indoor spacesFamilyComfort

Metcalf Pond Cottage Convenient to Smugglers Notch
KitchenIndoor spacesBiking

La Binocle: Peaceful Architect Cottage
FamilyKitchenGrill

Maple Sugar Shack | Hot Tub, Sauna, River & Views
KitchenIndoor spacesAccess

LakeView Manor
FamilyKitchenCondition
Family- and pet-friendly home rentals

Streamside Treehouse in the Woods with Sauna
KitchenFamilyShared spaces

Cady’s Falls Cabin
KitchenFamilyAccess

Mountain views of Jay Peak- with 2nd cabin add-on!
Indoor spacesKitchenBiking

Peaceful + Cozy Farmhouse Near Jay Peak + Sutton
KitchenFamilyDecor

Cozy rustic Cottage // Close to Stowe
Indoor spacesKitchenCheck-in

Journeys End Chalet - Minutes to Jay Peak!
Indoor spacesFamilyLayout

Meadow Cottage on Organic Farm with Mountain Views
KitchenFamilyOutdoor spaces

Jay Apartment
KitchenFamilyLocation
Family-friendly home rentals with a pool

Jay Peak Ski in Ski out Condo
KitchenIndoor spacesLocation

Quiet stay on 76 acres land with pool!
Indoor spacesFamilyAccess

L'Absolut Lac Champlain, Venise-en-Québec
KitchenFamilyAccuracy

The House of the Setting Sun, Private Apartment
Indoor spacesFamilyOutdoor spaces

Chalet Potton Cottage - spa, sauna & pool
FamilyIndoor spacesAccess

The Gîte des Sœurs Racines
KitchenIndoor spacesAccess

Fall Peeping and/or SKI 30 minutes Jay's Peak!
Indoor spacesKitchenAmenities

Château Chavis
KitchenFamilyHot tub
When is the best time to visit Montgomery?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$61,668 GYD | G$61,877 GYD | G$54,770 GYD | G$47,035 GYD | G$50,171 GYD | G$50,171 GYD | G$50,171 GYD | G$53,934 GYD | G$50,380 GYD | G$51,216 GYD | G$50,380 GYD | G$61,041 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
- Mont Sutton Ski Resort
- Jay Peak
- Ski Bromont
- Stowe Mountain Resort
- University of Vermont
- Jay Peak Resort Golf Course
- Kingdom Trails
- ECHO, Leahy Center for Lake Champlain
- Mont-Orford National Park
- Spa Bolton
- Snow Farm Vineyard & Winery
- Shelburne Museum
- Shelburne Vineyard
- Pump House Indoor Waterpark
- Cold Hollow Cider Mill
- Bleu Lavande
- Fairbanks Museum & Planetarium
- Elmore State Park
- Waterfront Park
- Marais de la Rivière aux Cerises





