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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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Top guest favorite

A comfortable living area features a combination of leather sofas and armchairs arranged around a coffee table. A stone fireplace serves as a focal point, while large windows allow natural light to fill the space. Decorative elements include a patterned area rug and light wooden walls.

Cabin in Lake George

4.87 out of 5 average rating, 178 reviews

Cozy cabin, private beach access, near LG village

Cozy authentic cabin, with access to a private beach and right next door to Hearthstone State beach (day pass included). Use of beach towels, chairs, umbrella, toys, and a cooler included. Filtered lake views from the enclosed porch, deck, and patio. Weber gas grill, Adirondack chairs, fire pit, and plenty of firewood. Fully equipped kitchen. Convenient to everything in LG Village and in Bolton: boat/kayak rentals, hiking, biking, entertainment, shopping, and restaurants. Trolly stop nearby.

An elevated view of a wooden house is set amidst a sprawling green landscape. The spacious back deck features a sturdy railing, with outdoor seating below on a stone patio. Lush trees and rolling hills are visible in the background, contributing to the natural surroundings.

Home in Warrensburg

4.85 out of 5 average rating, 233 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!

A spacious living area is showcased, featuring a red sectional sofa positioned around a round coffee table. Natural wood beams cross the ceiling, complementing the stone fireplace. Two modern chairs are arranged nearby, with a decorative plant on a side table, enhancing the welcoming ambiance.

Chalet in Waitsfield

4.96 out of 5 average rating, 140 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

A serene view across Lake Champlain stretches to the distant mountains, framed by trees with autumn foliage. A pathway is visible in the foreground, leading along the lakeshore, while the expansive sky showcases soft clouds.

Guest suite in Burlington

4.92 out of 5 average rating, 382 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.

A cozy living room is displayed, featuring plush seating arranged around a central coffee table. A ceiling fan provides light, while natural light filters through glass-paneled doors. A fireplace is centered between the doors, adding warmth to the space.

Home in Rutland

4.81 out of 5 average rating, 347 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.

Top guest favorite

A spacious living area features a cozy sofa and wooden furniture, complemented by a glass coffee table. Natural light illuminates the room through large windows, while soft drapes provide privacy. A warm wooden ceiling enhances the inviting ambiance.

Home in Chestertown

4.95 out of 5 average rating, 231 reviews

Adirondack Lake House

Adirondack beauty all year! Fully furnished home has lovely great room, fireplace , two bedrooms, one bath, basement family room, large deck, outdoor fire pit, screened porch with lake glimpse, limited air conditioning, rights to private lake, kayaks, canoes, w/d, fire pit with wood, in quiet wooded setting. Central location. This is NOT a lakefront property. It comes with lake access and is located across the street from the lake. Please see complete listing for accurate information.

Top guest favorite

The exterior of the chalet features a warm and inviting facade with a covered entryway, accented by a star motif. Surrounded by trees, the driveway is lined with gravel, leading to a spacious front yard with decorative seating and a sauna barrel.

Home in Wilmington

4.94 out of 5 average rating, 220 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.

Top guest favorite

A wooden dock extends over calm waters, reflecting a clear blue sky dotted with fluffy white clouds. The distant mountains along the shoreline provide a picturesque backdrop, enhancing the serene lakeside environment.

Home in Addison

4.96 out of 5 average rating, 225 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!

Townhouse in Stowe

4.89 out of 5 average rating, 167 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!

The exterior of a large, multi-level home showcases a wraparound porch with a red awning and is surrounded by well-maintained green lawns and decorative rocks. Tall trees provide natural shade, creating a welcoming outdoor atmosphere.

4.83 out of 5 average rating, 161 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.

The serene lake reflects vibrant fall foliage on the surrounding trees, creating a warm tapestry of orange and yellow. Soft gray clouds drift above, adding depth to the autumn landscape. A small boat is anchored nearby, contributing to the tranquil scene.

Home in Whitehall

4.93 out of 5 average rating, 139 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

A green, grassy area is framed by tall, slender trees. Two benches are positioned on either side, offering a place to sit and admire the expansive view of distant hills and valleys under an overcast sky.

Apartment in Chester

4.89 out of 5 average rating, 501 reviews

Beautiful 2 Bedrooms in Mountains w/ full kitchen

Ready for a Vermont getaway? In heart of ski area w/ A+restaurants & charming villages are two cozy bedrooms on 2nd fl of larger apt complex. Each bedroom has separate toilet/sink room, shared shower room for your and your guests alone. Hallway living room at one end with 2 couches, desk and TV Other end is full compact kitchen with dishwasher, stove and over, full size refrigerator, coffee maker and microwave.

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Popular amenities for Middlebury family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A wooden dining table is surrounded by upholstered chairs, with an antler chandelier overhead. A vibrant artwork featuring a buffalo hangs on the wall, adding color to the white-paneled room. Natural light enters from an adjoining living area, enhancing the space's inviting feel.

4.93 out of 5 average rating, 353 reviews

The Rabbit Hole - Luxury Cabin in heart of Stowe

A captivating sunset paints the sky with hues of orange, pink, and purple, with rolling hills silhouetted in the foreground. The distant mountains create a serene backdrop, accentuating the natural beauty of the secluded setting.

Home in Plymouth

4.95 out of 5 average rating, 251 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

A private hot tub is illuminated with soft blue lights, creating a relaxing atmosphere. The hot tub features multiple jets and is surrounded by wooden walls and a partially covered area, ensuring privacy. Warm ambient lighting enhances the tranquil setting, inviting relaxation.

Chalet in Killington

4.84 out of 5 average rating, 249 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

A well-lit outdoor Jacuzzi features soothing water jets, creating a relaxing ambiance. The water is illuminated with soft lights, enhancing the tranquil setting. Visible edges and seating areas allow for comfortable relaxation. Surrounding space remains dark, emphasizing the warm glow of the Jacuzzi.

Chalet in Stockbridge

4.92 out of 5 average rating, 181 reviews

Killington ski house winter MTbike -new jacuzzi

An inviting entryway features warm wood paneling and a bench against the wall. Hooks are mounted for coats, and a spacious mat lies underneath. Natural light enters through a window, illuminating the area, with a door leading to the main living space.

Chalet in Killington

4.87 out of 5 average rating, 248 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

A spacious living area features large windows allowing natural light to fill the room. A comfortable sectional sofa is arranged around a coffee table, and a TV is positioned near a wood-burning fireplace. A decorative artwork of a bull's head adorns the wall.

Condo in Killington

4.97 out of 5 average rating, 144 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

A comfortable living area features a light-colored sectional sofa, two armchairs, and a wooden coffee table. Natural light fills the space through large windows with wooden blinds. Artwork and framed photos decorate the walls, while a piano is positioned near the window.

Home in Waterbury Center

4.96 out of 5 average rating, 131 reviews

Peaceful setting with Mountain Views

Top guest favorite

A modern bathroom features a sleek design with a circular mirror above a contemporary sink. A white shower curtain with a subtle pattern hangs in front of the shower area, complemented by dark wooden accents on the walls.

4.97 out of 5 average rating, 158 reviews

Ski Chalet with Hot Tub on Okemo Mountain

Family- and pet-friendly home rentals

Home in Bristol

4.88 out of 5 average rating, 155 reviews

Large New England Home w/ Gorgeous Mountain Views

The bathroom features a double sink vanity with wooden cabinetry and a spacious countertop. A vibrant plaid shower curtain adds color, while neatly stacked blue towels are accessible on a metal shelving unit. A large mirror reflects the inviting space.

Home in Wilmington

4.88 out of 5 average rating, 166 reviews

Birchwood Lodge - Our Home in the Woods

Home in Rochester

4.95 out of 5 average rating, 196 reviews

The McKinley House

The image captures a view of the shoreline of a scenic lake, where the water appears choppy under a cloudy sky. Trees line the edge of the shoreline, with some areas illuminated by sunlight, revealing the textures of land and foliage.

Cabin in Burlington

4.83 out of 5 average rating, 506 reviews

The Sunrise Cabin

A welcoming porch is presented with a rocking chair and small side table. Hanging planters add greenery, while a flower basket enhances the inviting atmosphere. The wooden flooring is complemented by a small welcome mat, creating a cozy outdoor space for relaxation.

Apartment in Montpelier

4.87 out of 5 average rating, 696 reviews

Entire 2nd Floor Walk to Montpelier

A bright living area features a dark sectional sofa adorned with patterned pillows. Sunlight pours in through skylights and windows, illuminating the cozy space. A wooden coffee table and a floor lamp enhance the inviting environment, while the walls display a neutral hue.

Home in Burlington

4.84 out of 5 average rating, 477 reviews

The Sanctuary: 3 Bedrooms, Easy Walking, +Parking!

Top guest favorite

Chalet in Wells

4.9 out of 5 average rating, 143 reviews

Views! Entire Chalet, FAST Wi-Fi, All 18 Acres

A well-lit living area features a comfortable white sofa and a wooden coffee table at the center. A light wood bookshelf is lined with books, while a storage cabinet is positioned in the corner. A ceiling fan circulates air, enhancing the room's inviting atmosphere.

Farm stay in Jay

4.96 out of 5 average rating, 142 reviews

Blue Pepper Farm in Jay, New York

Family-friendly home rentals with a pool

A clean bathroom features a light-colored countertop and a sink, accompanied by a towel neatly folded beside it. A colorful shower curtain with intricate patterns enhances the space, while a full-length mirror reflects the room's details. Light-colored tiles cover the floor.

4.81 out of 5 average rating, 284 reviews

Spacious Stowe condo Amzing views w/shared hot tub

Top guest favorite

A breathtaking view showcases the sun rising above the horizon, casting warm orange and yellow hues across the sky. The silhouette of Camel's Hump is visible in the distance, framed by softly illuminated clouds. The scene evokes a sense of tranquility and natural beauty.

Apartment in Barre

4.94 out of 5 average rating, 163 reviews

Relax in Recreation Paradise!

Guest suite in Killington

4.95 out of 5 average rating, 145 reviews

Cozy, spacious, 3 bedrooms, 4 beds, 5 mi to K Rd.

A swimming pool is surrounded by lush greenery, inviting relaxation and enjoyment. The clear blue water reflects the surrounding landscape, providing a refreshing appeal. A person is seen in the water, engaged with a floating device, highlighting the leisure activities available at the property.

Guesthouse in Granville

4.9 out of 5 average rating, 894 reviews

Moon Valley Country Retreat no clean fee pets yes

An indoor swimming pool is depicted with clear blue water, featuring multiple lanes marked by buoy lines. Surrounding areas include seating and wood-paneled walls, providing a spacious and inviting atmosphere for relaxation and recreation.

Condo in Killington

4.82 out of 5 average rating, 257 reviews

Ski, Ride, Walk On/Off Condo On Pico at Killington

An outdoor pool area is showcased with a well-maintained pool surrounded by a paved deck. Sun loungers are placed at various points, accompanied by red umbrellas for shade. The backdrop features a multi-story building, enhancing the serene atmosphere of the space.

Condo in Killington

4.78 out of 5 average rating, 307 reviews

Serene Top Floor Condo (resort style amenities)

A dining area is set with a wooden table adorned with plates and glassware, complemented by a stylish chandelier overhead. In the background, a comfortably furnished living area features a sofa and a smart TV, creating a welcoming environment.

Condo in Killington

4.89 out of 5 average rating, 162 reviews

Modern Killington Farmhouse Condo: Close to Resort

Top guest favorite

A spacious two-story home is set among lush greenery, with a large front deck featuring white railings. The exterior showcases a mix of light-colored siding and dark shutters, while tall trees provide a natural backdrop, creating a peaceful atmosphere.

4.98 out of 5 average rating, 262 reviews

EPIC Stowe Getaway - Great For Families & Friends

Quick stats about vacation rentals that are family-friendly in Middlebury

Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ331 before taxes and fees
Total number of reviews
2.2K reviews
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool

Destinations to explore