
Family-friendly holiday rentals in Montgomery
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Montgomery

Total holiday rentals
Explore 50 holiday rentals in Montgomery

Nightly prices starting at
Montgomery holiday rentals start at $141 SGD per night before taxes and fees

Verified guest reviews
Over 3,480 verified reviews to help you choose

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Montgomery holiday rentals include wifi 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.

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!

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.

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).

La Cabine Potton
La cabine est un mini chalet de style scandinave qui plaira aux adeptes de la nature, du calme et des pentes de ski l'hiver comme le vélo et la randonnée l'été. Ce chalet a été conçu en harmonie avec son environnement. D'ailleurs, sa taille permet de profiter de la nature tout en réduisant son empreinte écologique. Avec ses deux chambres, son foyer, sa grande terrasse et son spa, il est tout équipé pour répondre à vos besoins. Venez relaxer dans ce logement unique! Certificat CITQ #311739

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.

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!

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 stay in bed and take in the views. And with plenty of woods to explore, it's your perfect escape at your pace.

Private Studio Nestled in the Hills of Vermont
With a private entrance and mountain views, this studio features lots of natural light in the spacious bedroom and a fully-equipped kitchen, daybed nook and private bathroom with shower. Sitting up high in the fields and forest of northeast VT, Feel Good Farm is rich with wildlife, prime for woods walking/cross-country skiing, star gazing, and slowing down. Our 150 acres abut a 968-acre East Hill Wildlife Management Area. Hunters welcome! We're an easy drive to VT's best attractions.

Château Chavis
Indulge in a serene retreat at Chateau Chavis, a captivating and picturesque residence nestled on over ten acres of tranquil rural land in Johnson, Vermont. Conveniently situated just twenty minutes from Stowe and twenty-five minutes from Smugglers Notch, Chateau Chavis offers easy access to breathtaking waterfalls, scenic hiking trails, and the rail trail. Regardless of the season, this idyllic haven serves as an ideal destination for a staycation or a quintessential Vermont vacation.

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***

Gorgeous Treehouse! Big views, Cozy warm fireplace
Lilla Rustica is an elevated cabin among the trees. Private, with Stunning views this was built by "The Tree House Guys" a local Vermont company whom can be found having a season on the DIY network. Tons of detail, while keeping the design natural and simple. Unbelievable views of Camels hump State park. A loft with one queen bed and downstairs has a queen bed with three sides of the bed having windows facing the views. Hiking offered right from the cabin. An awesome getaway!
Popular amenities for Montgomery family-friendly rentals
Family-friendly home rentals with a hot tub

Romantic NEK Log Cabin w/ Hot Tub & Fireplace

Metcalf Pond Camp Convenient to Smugglers Notch

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

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

Sunrise Lake House! Comfort-Hot Tub-Beach

Secluded Luxury Treehouse - Hot Tub + Projector

The Binocular: Peaceful Architect Cottage

*Hot tub | Ravens Nest
Family- and pet-friendly home rentals

Secluded Riverside Loft next to Smuggs

Peaceful Treehouse in Woods with Sauna & Stream

Relaxing Craftsbury Retreat

Cady’s Falls Cabin

Cozy Chalet at Jay Peak

Charmante Tiny House bord de l'eau

Peaceful + Cozy Farmhouse Near Jay Peak + Sutton

The Original Montgomery Lodge - Tried and True!
Family-friendly home rentals with a pool

Lower Yurt Stay on VT Homestead

Sunset Cottage on the Richelieu River CITQ#302701

The House of the Setting Sun, Private Apartment

Cute Cottage - Poolside - Minutes To Activities

Chalet Potton Cottage - spa, sauna & pool

Beautiful Chalet minutes to Jay Peak Resort

Serene Mountain Studio Spruce Peak Lodge | 1328

Cozy/Private, close to hospital, i-89
When is the best time to visit Montgomery?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $378 SGD | $380 SGD | $336 SGD | $289 SGD | $291 SGD | $305 SGD | $308 SGD | $331 SGD | $309 SGD | $314 SGD | $309 SGD | $375 SGD |
| 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
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Island of Montreal Holiday rentals
- Capital District, New York Holiday rentals
- Rentals with breakfast Montgomery
- Rentals with outdoor seating Montgomery
- Rentals with a washing machine and dryer Montgomery
- Rentals with a firepit Montgomery
- Pet-friendly rentals Montgomery
- House rentals Montgomery
- Rentals with a hot tub Montgomery
- Rentals with a fireplace Montgomery
- Waterfront rentals Montgomery
- Rentals with a patio Montgomery
- Family-friendly rentals Franklin County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Jay Peak Resort
- Owl's Head
- Zoo de Granby
- Mont Sutton Ski Resort
- Stowe Mountain Resort
- Bolton Valley Resort
- Ski Bromont
- Parc Safari
- Jay Peak Resort Golf Course
- Jay Peak
- ECHO, Leahy Center for Lake Champlain
- University of Vermont
- Pump House Indoor Waterpark
- Spa Bolton
- Shelburne Museum
- Elmore State Park
- Snow Farm Vineyard & Winery
- Shelburne Vineyard
- Mont-Orford National Park
- Cold Hollow Cider Mill
- Fairbanks Museum & Planetarium
- Kingdom Trails
- Waterfront Park
- Bleu Lavande





