Family-friendly vacation rentals in Middlebury

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Middlebury

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Ludlow

4.89 out of 5 average rating, 132 reviews

1st floor, Okemo contemporary country 3 BR 2 BA

Family-friendly, pet-friendly, clean, comfortable, contemporary country ski cabin on Okema shuttle buss route in Ludlow, VT, a few minutes from mountain. Very easy access to outdoor activities: skiing, hiking, lakes, boating, hunting, snowmobiling, fly-fishing. Updated, comfortable, light filled ambiance. Great location, 10 minute walk to downtown (2 minute drive). Great for groups, couples, families. Recently renovated. New butcher block counter-tops and island, all new kitchen, new bathrooms.

Superhost

Home in Warrensburg

4.84 out of 5 average rating, 223 reviews

INCREDIBLE Adirondack Home (Lake George/Gore Mtn.)

AMAZING Adirondack home set on a private and remote 130-acre mountainous property in Warrensburg, NY with INCREDIBLE views; 5 miles to Lake George, 11 miles to Bolton Landing & 17 miles to Gore Mountain. The charming town, only 2 miles away, includes antique shops, great restaurants, golf and plenty of family fun! This home is ideal for a group of friends or family wanting to explore the Adirondack region & enjoy outdoor entertainment/activities. There truly is something for everyone to enjoy!

Guest favorite

Chalet in Waitsfield

4.96 out of 5 average rating, 135 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 Lake George

4.87 out of 5 average rating, 178 reviews

Cozy cabin with private beach, near village

Cabin with private beach, lake views, enclosed porch, deck with grill, and patio with fire pit and firewood. Fully equipped kitchen. Easy lake access to our quiet and private association beach and also Hearthstone State beach, both just short walk/drive. Included beach towels, chairs, umbrella, and cooler. Nearby boat/kayak rentals, hiking, biking, entertainment, and restaurants in Bolton and LG Village. SuperHost for 8 years. Sat - Sat weekly rental. Great monthly / seasonal discounts!

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 Rutland

4.8 out of 5 average rating, 324 reviews

Home Sweet Home

Single family house within walking distance of downtown Rutland. Many restaurants, bars, movies, bowling, farmer's market, etc to do. 15-20 minute drive to Pico and Killington. 30 minutes to Okemo. Mountain bike parks near by- Pine Hill, Killington and Okemo. Adventure park at Killington. 4 bedrooms, 1.5 baths. House sleeps 8+comfortably. Room for more if needed. Keurig coffee maker in kitchen, microwave, toaster, crock pot. Kitchen is fully furnished. AC units on first floor and second.

Guest favorite

Home in Wilmington

4.93 out of 5 average rating, 203 reviews

Luxurious Chalet in the Woods!

CASCADE MOUNTAIN CHALET: Hot Tub, Sauna, 1 mile to Whiteface, 15 minutes to Lake Placid, Dog Friendly Fantastic 3 Bedroom (King beds), 2 Full Bath Chalet that sleeps 8 (queen-size foam mattress available to sleep up to 2 children). This home has a warm, stylish vibe in an ideal location! Amenities Include: Hot Tub, Fireplace, Finlandian Dry Sauna, Fire Pit, BBQ Grill, Deck, Huge Yard, Dogs welcome (no cats), fully equipped kitchen with 6 burner gas stove, granite counters, washer/dryer.

Guest favorite

Rental unit in Burlington

4.94 out of 5 average rating, 129 reviews

Enjoy the Lake and Bike Path!

Our guests had to sadly cancel their reservation so we’d like to offer you last minute 20% off during any time between Aug 28 and Sept 8. Situated on Lake Champlain in the desirable, artsy, south end of Burlington. Cozy, newly renovated, 1 BR apartment with 1 comfy queen bed. Fully equipped kitchen, and all the comforts of home. Located on the city bike path, less than a mile to downtown. Longer stays: WORK at Hula Lakeside! Traveling nurses also encouraged! EV charger available.

Guest favorite

Home in Addison

4.96 out of 5 average rating, 202 reviews

Brthtkng New Premier Lake Champlain Wfrnt Escape!

7/19/20 : UPDATE - We are fully compliant with all local, state and federal safety protocols. Call /text Us fir any questions, at 978-502-6282 . Be Well, Be Safe & We Look Forward to Having You as Our Guests! We are the #1 Premier Lake Champlain Breathtaking New Property with 250'+ Prime Lake Champlain West/Sunset/Adirondack Mtn. facing w/Amazing Sunsets & Jacuzzi Tub in Master Bath Overlooking Lake,Mountains & Amazing Sunsets and 250+ 5 Star Reviews!

Guest favorite

Townhouse in Stowe

4.89 out of 5 average rating, 160 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!

Superhost

Home in Stowe

4.82 out of 5 average rating, 151 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.

Guest favorite

Home in Whitehall

4.93 out of 5 average rating, 138 reviews

Lakefront A-Frame Home Emerald Lake, NY

A Frame style home with 100 + feet of lake frontage. 2 bedroom plus a loft bedroom with 2 twin beds. 1 and 1/2 baths and large open basement A-frame style home on a small, quiet lake in upstate NY in the town of Hampton/Whitehall, NY (not on Lake George), 5 miles from the VT border, 33 miles from Lake George village, with a screened in porch, a large deck, and a grill provided. Water activities 2 kayaks 1 - 4 person paddle boat