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.

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Guest favorite

Chalet in Waitsfield

4.96 out of 5 average rating, 137 reviews

Warm Luxury Mid-Century Modern Chalet

Warm, clean & comfortable chalet w/ thoughtful & stylish touches. Perfect for remote work, a romantic weekend, a multifamily gathering, a girls' weekend, or retreat. MRV offers all season fun: farmer's market, swim holes, farms, hiking, road & mtn bike, golf, climbing, tube on the river and lake, can't be beat. The house is nestled in the woods w/ beautiful views of surrounding mountains. The area's food & breweries, including Lawsons are phenomenal. 1 min to MRG & 14 min to Sugarbush. Exp Wifi

Guest favorite

Cabin in Lyman

4.93 out of 5 average rating, 206 reviews

White Mountain Bliss on 33 Acres

Gorgeous private secluded 33 acres of fields & forest. Sit in your private hot tub and enjoy the view of the woods and once inside your feet will be cozy with the radiant floor heating and the steam room downstairs. Beautiful nearby lakes to swim in summer, 10 miles from Franconia Notch State Park and Cannon Mountain ski area. Explore charming New England towns for antiquing, dining & shopping. A lovely place to visit with small or large family group or friends, great for kids. Sleeps up to 8.

Guest favorite

Guest suite in Burlington

4.91 out of 5 average rating, 383 reviews

3 Cozy Rooms ,2 Bathrooms,2 Bedrooms,Beach,Bike

This quiet, charming neighborhood is a treasure. Lake Champlain , on the 14 mile bike path. Bikes available. microwave, small fridge, toaster oven, Keurig coffeemaker provided, Wifi, HD Smart TV, Netflix , Amazon Prime, DVD, Roku, HuluTV, CD player, screened in front porch. Locking gate at the top of the stairs.There is not a kitchen. Not recommended for guests who what to cook. Two bedrooms one full bath and one half bath. LGBTQ always welcome. Well behaved doggie parents and dogs allowed.

Guest favorite

Home in Cambridge

4.99 out of 5 average rating, 174 reviews

Close to Smuggler's Notch Resort! High speed Wifi!

NOTE: Minimum age of 25 years required to rent our house and to be a guest here. Children traveling with parents are exempt from this age requirement. Exceptions made on a case by case basis. Beautiful, bright, and spacious 4 bedroom home in the heart of Smuggler's Notch area with views of the mountains. Less than 4 miles to Smugglers Notch Resort and 1 mile from the Wedding Barn. Property consists of our primary residence with the rental being a separate and private "mother in law" home.

Superhost

Home in Belvidere

4.93 out of 5 average rating, 159 reviews

Cozy Adams Farmhouse - Ski Weekend Availability!

Welcome to the Adams Farmhouse, your dream ski weekend retreat in the heart of Vermont! Nestled just a short drive away from Jay Peak, Smuggler’s Notch, and Stowe Mountain Resort, our charming farmhouse is the ideal base for your winter adventure. Wake up to breathtaking mountain views and spend your day conquering the slopes. After an exhilarating day of skiing or snowboarding, come back to a warm, welcoming home. Book now and create unforgettable memories in Vermont’s winter wonderland!

Guest favorite

Home in Waitsfield

4.96 out of 5 average rating, 161 reviews

Mid century modern gem with views of Sugarbush

Wake up to stunning views of Sugarbush in this “Flat Roof A-Frame". Four bedrooms, a sleeping loft, three bathrooms, two living rooms, a dining room, a newly renovated kitchen, a desk area with wifi, two decks (one w/gas grill), and a laundry room/game room provide plenty of space for family gatherings. Located 3 minutes from town. Not suitable for small children/toddlers or guests with mobility issues. During summer we are only renting out 6+ night rentals with changeovers on Friday.

Guest favorite

Cabin in Barton

4.81 out of 5 average rating, 159 reviews

Charming lake cottage on Crystal Lake! Boats! R&R!

Lakeview Cottage is adorable and located on one of Vermont's cleanest and most beautiful lakes, Crystal Lake! It's in the heart of the Northeast Kingdom, in the charming town of Barton. Sit around the outdoor firepit and soak in the view! You're just steps away from beaches and a dock. You'll find great swimming, fishing, boating, hiking, golfing, and mountain biking. Use our canoe or kayaks! Plus, Hill Farmstead Brewery is a short drive away. Beers there are rated best in the world!

Guest favorite

Cabin in Hyde Park

4.96 out of 5 average rating, 276 reviews

Serene Country Cabins 2 In the heart of Vermont

My place is close to Stowe, Smuggler's Notch and within 15 minutes of 6 breweries. It is nestled in the woods with some views, art and culture, farms, hiking trails, lakes, 3 major ski resorts, snow machine trails, and 3 miles from the down town shopping plazas. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets). Our bedrooms offer a create a king to accommodate guests who prefer a king bed and guests who prefer twin beds.

Guest favorite

Cabin in Jeffersonville

4.93 out of 5 average rating, 190 reviews

Cozy two-bedroom cabin near Smugglers Notch

Our two-bedroom log cabins (we have several) are a long-time family and small group favorite. Equipped with one queen bed, two twin beds (that can be converted to a king), one bath, a kitchen, living space, a woodstove or traditional fireplace, TV, and free WiFi, these cabins are cozy, yet spacious enough for the whole family or two couples to enjoy. This cabin has a maximum occupancy of 6 adults/children. Close to skiing/snowboarding, hiking, horseback riding, wedding barns and more.

Guest favorite

Townhouse in Stowe

4.89 out of 5 average rating, 162 reviews

Stowe, Topnotch Resort-Best Mt & Luxury in Vermont

This beautiful Resort Condo is located in the award-winning, Top Notch Resort & Spa. Our spacious 2-bedroom, 2-bathroom condo is only 1 mile away from Stowe Mt. Resort while offering privacy and room to spread out on the resort’s 120 acres. It is perfect for families or couples. We are proud of our stellar reviews and competitive pricing. Newly updated, our home is ready for your perfect vacation! Enhanced Cleaning protocols in place!

Guest favorite

Home in Stowe

4.98 out of 5 average rating, 155 reviews

Spacious Eco-Friendly Stowe Home for Family Fun

Vacation/Work Remotely or both in this 5 BR and 5 BA gorgeous mountain eco-friendly home. FIBER 100 meg symmetrical wifi, a quiet workspace with desk, monitor, and printer. Fully stocked kitchen, ping pong, fire pit, large family space but quiet spaces too, and 3 ensuite bedrooms! Conveniently located close to town and a short drive to skiing. This is a great family space to reconnect or a space to work remotely for a change of pace.

Superhost

Home in Stowe

4.83 out of 5 average rating, 155 reviews

Great For Large Groups with Hot Tub

This property is not suited to noisy groups - please don’t book for partying. Recently renovated to meet every vacation need, this unique property has everything you require for a great trip. The property is huge, ideally located right on Mountain Rd - minutes to slopes, spas, breweries, restaurants, hiking, biking and swimming holes. With 4 large comfortable bedrooms, fun basement, huge living space with fireplace and private hot tub.