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Family-friendly holiday rentals in Chittenden

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Quick stats about holiday rentals that are family-friendly in Chittenden

  • Total holiday rentals

    Explore 90 holiday rentals in Chittenden

  • Nightly prices starting at

    Chittenden holiday rentals start at $169 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,680 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Chittenden holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chittenden rentals

  • 4.9 Average rating

    Chittenden stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Chittenden

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

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Top Guest favourite
A sunroom showcases high wooden ceilings with skylights, enhancing natural light. A comfortable seating area, set with a light-colored couch and side table, is positioned next to large windows offering views of the outdoors. A dining table, accompanied by four chairs, occupies one corner of the space.
Home in Rutland

Mountain Getaway Pet friendly

Escape to our charming getaway, ideally located in Rutland just 20 minutes from the world-famous Killington Ski Resort! Whether you're here for skiing, snowboarding, hiking, or simply enjoying the serene beauty of Vermont, our home offers the perfect base for all your adventures. Our home offers a cozy and welcoming environment, perfect for families, couples, and groups of friends. You'll love the combination of comfort, convenience, and proximity to the best of Killington's outdoor adventures.

Indoor spacesFamilySkiing

4.94 out of 5 average rating, 121 reviews
Top Guest favourite
A unique treehouse is seen perched among tall trees, with a blend of rustic wood siding and large windows that reflect the surrounding greenery. The structure stands elevated from the ground, supported by slender pillars, blending harmoniously with the natural forest environment.
Treehouse in Hancock

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses

KitchenIndoor spacesQuiet

4.98 out of 5 average rating, 182 reviews
Top Guest favourite
Home in Mendon

New Firepit, Great Location, Dog Friendly, Kitchen

Welcome to @MendonMtGetaway - my warm & cozy VT retreat! With 3 bedrooms, comfy living room, full kitchen, washer/dryer, AND office space - I hope you'll feel at home right away. You are in a wonderful location here. Turn left & you are just minutes down the road from ski heaven - Killington and Pico Mountains! Turn right, and you're just minutes from cute & historic Rutland. Either way you’ll find tons of great outdoor activities & hiking, and lots of local shops and restaurants.

FamilyIndoor spacesCheckout

4.98 out of 5 average rating, 170 reviews
Top Guest favourite
A bright living area features large windows that frame views of the surrounding forest. Natural light enhances the wood-paneled walls. A comfortable sofa and chair are positioned around a central coffee table. A small, modern wood stove provides warmth, creating a cozy atmosphere.
Cabin in Goshen

The Berghüttli: Glowing Swiss Hut in the Forest

The Berghüttli ("little mountain hut") is a Swiss-inspired hut and farm stay surrounded by National Forest in Goshen, VT (pop. 168). A completely private escape—no other structures in sight, just woods and quiet. Inside, a wall of windows brings the forest right up to you, while glowing maple plywood fills the space with warm light. High-speed fiber internet runs a reliable 300 Mbps. Stay connected or switch off completely. Search "The Berghüttli" on YouTube for a video tour.

Indoor spacesFamilyCleanliness

4.97 out of 5 average rating, 150 reviews
Top Guest favourite
The exterior of the building is shown against a backdrop of a green and orange hillside. Surrounding landscaping includes neatly trimmed bushes, with a paved parking area featuring two parked cars. The structure has a mix of stone and brick accents, complemented by gray roofs.
Condo in Mendon

105 Fox Hollow Village Pvt - Red Fox - Unit B-4

105 Fox Hollow Village is located near Pico and Killington ski areas. There are year round outdoor activities including access to trails for skiing/snowboarding, mountain biking, golfing, and hiking. Accommodations include 2 bedrooms, 2 full bathrooms (newly renovated), fully updated kitchen, living room, separate dining area, a mudroom at entrance, backyard access with sliding door, and a common pool area. No smoking/vaping, and no pets are allowed in or around the condo.

FamilyIndoor spacesLocation

4.89 out of 5 average rating, 124 reviews
Top Guest favourite
Apartment in Rutland

Red Rooster Fall Foliage Hub Near Downtown Rutland

Welcome to The Red Rooster, a private second-floor guest suite in a historic 1867 Greek Revival Victorian with ample parking. Located on urban micro-farm, tucked into Rutland's Historic District, enjoy peaceful views and perfect urban convenience. Walk right to downtown dining, Amtrak, and the Paramount Theater! We are minutes from Killington Resort, Pico, the VAST trail, Appalachian Trail, and Lake Bomoseen. Your Green Mountain basecamp awaits.

Indoor spacesKitchenNearby

4.94 out of 5 average rating, 111 reviews
Top Guest favourite
The exterior of a renovated one-room schoolhouse is presented, set amidst lush green foliage. A vibrant red door stands out against the white walls, while a well-maintained hedge borders the property. Surrounding trees provide a serene backdrop, creating a peaceful atmosphere.
Home in Rutland

One Room School House. No Cleaning Fees!

Renovated one room school house. Spacious, open space. Music room has been converted into a bedroom. European style kitchen area. High ceilings with fans and air-conditioner. Propane fireplace. Off-street parking. High speed internet and 65 inch Roku TV with surround sound. Three season screened porch. Also, we have recently introduced a NO CLEANING FEE policy as our way of saying "Thank You" for respecting our property and guidelines.

KitchenIndoor spacesWi-Fi

5.0 out of 5 average rating, 161 reviews
Top Guest favourite
The exterior of a traditional white house features a spacious covered porch lined with wooden railings and supported by columns. Potted plants and hanging baskets add greenery, while the entrance is framed by multiple windows. A gravel driveway leads up to the porch.
Apartment in Rutland

Your home away from home

Another glorious time of year in Vermont! Our house is close to the mountains (Killington, Pico, Okemo). You'll love our space for its central location to lakes, hiking, skiing, golf, restaurants and dining, downtown, art and culture, shopping and medical facilities.This first floor apartment with its home-like atmosphere has a separate entrance. It is good for couples, small families, solo adventurers, and business travelers.

FamilyKitchenValue

4.96 out of 5 average rating, 692 reviews
Guest favourite
A welcoming living area features a large fieldstone fireplace, with a soft couch and several armchairs arranged for comfort. A coffee table sits in the center of the space. Above, warm lighting illuminates an adjacent dining area, enhancing the cozy atmosphere.
Home in Pittsfield

Killington area home - 4 seasons - hot tub and A/C

Set on a private road in the hills of Pittsfield, our house welcomes you year-round. Right in the heart of the Northeast’s best winter-sports, it's convenient to Killington ski resort, VAST snowmobile trails, Mountain Meadows cross country skiing and Green Mountain National Golf course. Furthermore, there are wonderful hikes and mountain biking to be done on the property and beyond - particularly beautiful in the fall.

FamilyKitchenComfort

4.85 out of 5 average rating, 256 reviews
Top Guest favourite
A cozy living room area is presented with a dark gray sofa adorned with white pillows. A television is positioned on a light-colored console, with framed black-and-white nature photographs displayed on the wall. Natural light filters through the windows, enhancing the serene environment.
Home in Pittsford

Convenient Vermont Getaway

Conveniently located near the top ski and mountain bike attractions, incredible trails, resorts, and the towns of Woodstock, Middlebury, Killington, Pico, and Rutland. This historic property has been in existence since 1832 and has been lovingly maintained with a backdrop of the Adirondacks beyond the picturesque pasture. This one bedroom apartment is located downstairs in the two story duplex.

KitchenIndoor spacesHospitality

4.91 out of 5 average rating, 126 reviews
Guest favourite
A snow-covered pathway leads to a charming white house surrounded by trees blanketed in snow. The structure features a gabled roof and a small cupola, with snow drifts framing the entrance. The clear blue sky provides a bright contrast against the winter scene.
Home in Pittsford

Colburn's Carriage House

Only 30 minutes from Killington/Pico ski resorts, and 20 minutes from Mountain Top Inn and Chittenden Reservoir, Colburn's Carriage House is a charming and convenient getaway. Situated on over 2 acres of private back yard, overlooking beautiful Sugar Hollow Brook in the heart of Pittsford, Vermont. Walking distance to village general store, library and the Pittsford trail system.

Indoor spacesKitchenCheck-in

4.93 out of 5 average rating, 222 reviews
Guest favourite
A private deck with a hot tub is surrounded by colorful planters filled with seasonal flowers and pumpkins. The entrance to the cabin features a welcoming door framed by autumn decorations, backed by lush greenery from the surrounding forest.
Cabin in Chittenden

Outside Inn - Hot Tub/Killington/MtnTop Inn/VAST

Reconnect with nature at the Outside Inn, a four season retreat, locally known as the Labor of Love. A man fell in love with a woman, but when he asked for her fathers blessing he said, first you must build her a home. So he built this beautiful post and beam cabin and they lived happily ever after! *Decorated seasonally!* IG/TikTok: outside_inn_vt FB: Outside Inn VT

Indoor spacesKitchenCheckout

4.93 out of 5 average rating, 150 reviews

Popular amenities for Chittenden family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favourite
A cozy living space is highlighted by a modern pink chair positioned near a wood stove, which emits a warm glow. Large glass doors offer views of the wooded surroundings, while a Moroccan rug adds texture to the concrete floor.
Chalet in Royalton

Scandinavian design Chalet hiking trail + hot tub

FamilyIndoor spacesGetting around

4.94 out of 5 average rating, 226 reviews
Top Guest favourite
Chalet in Killington

The Overlook - Views | Hot Tub | Fire Pits | Games

Indoor spacesFamilySkiing

4.97 out of 5 average rating, 109 reviews
Top Guest favourite
Condo in Killington

FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym

Indoor spacesFamilyWalkability

4.96 out of 5 average rating, 217 reviews
Top Guest favourite
A new hot tub with jets is positioned under a wooden structure, surrounded by grass and landscaped areas. A tranquil view of distant mountains and trees is visible in the background, creating a peaceful outdoor setting.
Home in Rutland

Killington/Okemo, 7p Hot tub, Mtn.views, Spacious!

KitchenIndoor spacesLaundry

4.9 out of 5 average rating, 245 reviews
Guest favourite
A serene view of a lake is framed by lush green trees and grass. The still water reflects the surrounding nature, while a patio area with seating is visible near the water's edge, inviting relaxation in a peaceful outdoor setting.
Home in Whitehall

Well appointed lakehouse. Peaceful family fun.

KitchenFamilyDecor

4.87 out of 5 average rating, 269 reviews
Guest favourite
An A-frame cabin is nestled among trees with autumn leaves in vibrant shades. A large deck extends from the cabin, featuring a hot tub and outdoor dining area. A barrel sauna is positioned nearby, completing the inviting outdoor space.
Cabin in Mount Holly

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

FamilyKitchenDecor

4.87 out of 5 average rating, 173 reviews
Guest favourite
Chalet in Killington

Killington Chalet, Hot Tub, Sauna, Huge Boot Dryer

FamilyKitchenSleep quality

4.84 out of 5 average rating, 264 reviews
Guest favourite
A rustic cabin is nestled among the trees, showcasing its wooden exterior and a metal roof. Tall windows allow natural light to fill the space. Surrounding greenery, including ferns and bushes, adds to the secluded atmosphere. A stone wall and picnic table can be seen in front.
Cabin in Sharon

forest retreat; off-grid writers cabin

KitchenFamilyHeating

4.93 out of 5 average rating, 302 reviews

Family- and pet-friendly home rentals

Top Guest favourite
A vibrant bedroom features floral wallpaper and peach curtains. A spacious bed adorned with colorful pillows is positioned against one wall. Two windows allow natural light to fill the room. The pink door adds a cheerful touch, while a cozy chair is placed nearby.
Apartment in Rutland

Baby Queens Barbie-core Studio Apt (dog friendly)

KitchenIndoor spacesCheck-in

4.86 out of 5 average rating, 285 reviews
Top Guest favourite
Home in Woodstock

Cape Cod Home in Woodstock, Pet-Friendly & Wooded

KitchenFamilyDecor

4.99 out of 5 average rating, 170 reviews
Top Guest favourite
The cozy cottage is softly illuminated at night, with warm light emanating from the windows. A sliding door is positioned at the entrance, complemented by two outdoor chairs on the lush lawn. The moonlight adds a serene ambiance to the rural scene.
Farm stay in Salisbury

Quaint 1-bedroom cottage on Blue Ledge Farm

FamilyIndoor spacesCheckout

4.95 out of 5 average rating, 469 reviews
Top Guest favourite
A large farmhouse is set against a backdrop of vibrant autumn foliage. The structure features a modern design with a metal roof and expansive glass windows, allowing for abundant natural light. A spacious lawn complements the serene rural setting.
Home in Rochester

Modern Farmhouse on 25 Acres - Superb Views

Indoor spacesKitchenCleanliness

4.97 out of 5 average rating, 156 reviews
Top Guest favourite
A warmly lit cabin emerges from the surrounding trees, framed by a quiet, snow-covered dirt road. Soft light spills from the windows, creating a welcoming glow in the tranquil, darkened landscape.
Home in Rochester

The Guest House at Sky Hollow

KitchenIndoor spacesCheck-in

4.97 out of 5 average rating, 238 reviews
Guest favourite
The exterior of the renovated farmhouse is visible, showcasing a blend of historical charm and modern updates. Large windows allow plenty of natural light into the sunroom. The expansive yard is lined with mature trees, and the bright autumn foliage adds a warm, seasonal touch.
Home in Brandon

Rand’s Retreat

FamilyIndoor spacesCleanliness

4.93 out of 5 average rating, 136 reviews
Top Guest favourite
A serene view captures a green field leading to distant mountains, with a weathered barn nestled among trees. A small shrub occupies the foreground, providing a sense of depth. The landscape reflects a tranquil countryside setting.
Home in Bethel

Vermont private retreat with gorgeous views.

Indoor spacesKitchenSkiing

4.96 out of 5 average rating, 165 reviews
Guest favourite
A stationary white bus sits on a gravel path surrounded by green grass. In the background, sparse trees and expansive fields are visible. Two outdoor chairs and a small shed can be seen nearby, highlighting the serene, rural setting.
Bus in Granville

Serene Bus Getaway Among Rolling Farm Land

KitchenIndoor spacesGetting around

4.89 out of 5 average rating, 217 reviews

Family-friendly home rentals with a pool

Top Guest favourite
A cozy living area features a stone fireplace, providing warmth and a focal point in the room. Two brown sofas are positioned around a coffee table. Soft lighting from a nearby lamp creates a comfortable ambiance, complemented by large windows letting in natural light.
Condo in Killington

PEEP Pico Hike out back door 1 Bedrm 1 night okay

Indoor spacesKitchenAccuracy

4.93 out of 5 average rating, 500 reviews
Top Guest favourite
A cozy living area features a spacious sectional sofa and a wooden coffee table, with candles placed on top. Artwork depicting mountain scenes decorates the wall, while a glass door leads to the private balcony, allowing natural light to brighten the space.
Condo in Mendon

¤5-15 Mins to Mountains & Trails | Fast WiFi¤

KitchenIndoor spacesNearby

4.94 out of 5 average rating, 104 reviews
Top Guest favourite
A spacious living room features a comfortable sectional sofa facing a propane fireplace. A mounted TV is positioned above the hearth. Natural light enters through sliding glass doors leading to a private porch, surrounded by lush greenery.
Condo in Mendon

Hotel Chic - Home Comfort -Ski Easy.

FamilyKitchenAmenities

4.95 out of 5 average rating, 133 reviews
Guest favourite
Aerial view captures a large cluster of buildings nestled among vibrant autumn foliage, showcasing shades of orange, yellow, and green. Majestic mountains rise in the background, while a spacious parking area is visible, surrounded by trees.
Condo in Killington

Updated large condo across from AT and skiing

KitchenIndoor spacesLong stay

4.87 out of 5 average rating, 127 reviews
Top Guest favourite
The exterior of the chalet is shown in twilight, with soft light emanating from a window. The rustic wooden structure features a sloped roof and is surrounded by snow-covered ground and trees in the background.
Guesthouse in Granville

Moon Valley Country Retreat no clean fee pets yes

Indoor spacesFamilyWalkability

4.91 out of 5 average rating, 1019 reviews
Top Guest favourite
A gravel road leads through open fields bordered by manicured greenery. In the distance, rustic buildings and trees with autumn foliage are visible against a clear blue sky, creating a serene rural landscape.
Farm stay in Clarendon

Dream Catcher Farm

Indoor spacesFamilyOutdoor spaces

5.0 out of 5 average rating, 112 reviews
Superhost
Home in Killington

Luxury Condo Tucked in the Heart of Killington

FamilyKitchenAmenities

4.86 out of 5 average rating, 257 reviews
Top Guest favourite
A serene view of the Vermont horse farm features a spacious white house surrounded by lush green lawn. Horses can be seen grazing nearby, and the landscape is complemented by rolling hills and fluffy clouds in the sky.
Apartment in Clarendon

Vermont Horse Farm

Indoor spacesFamilyWalkability

4.92 out of 5 average rating, 157 reviews

When is the best time to visit Chittenden?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$684 NZD$777 NZD$610 NZD$530 NZD$505 NZD$503 NZD$446 NZD$476 NZD$498 NZD$518 NZD$545 NZD$652 NZD
Avg. temp-7°C-6°C0°C7°C14°C18°C21°C20°C15°C9°C3°C-3°C

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