
Family-friendly holiday rentals in Chittenden
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chittenden
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Killington-Pico ski in/out Studio at base of Pico
At the base of Pico and 10 minutes from Killington. Free shuttle service from my place to Killington. I have a free ski locker and free wood for the fireplace. There is a laundry room with coin operated machines. There is a brand new 50” flat screen tv with cable. It’s a smart tv, that’s hooked up to WiFi, so you can use your Netflix, Amazon or Hulu account if you want. The kitchen is fully equipped. Towels, soap, shampoo and conditioner provided for 1 day. No daily cleaning service. No parties.

Charming tiny house with great VT location!
Curious about tiny home living!? This newly constructed 180 sq ft. house will let you experience comfort in charming farmhouse/cottage style. (Shiplap walls anyone?) Only 25 min to Killington, and 12 min from Mtn Top Inn, Downtown Rutland, or Brandon VT makes the location very convenient. 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.

Howling Wolf Farm Yurt--A Magical Glamping Retreat
Our 88-acre farm spreads up a steep hillside above the village of Randolph, one mile away. The land is a mixture of open areas where we rotate our sheep flock daily, and wooded land with trails and old stone walls. You might hear the occasional car or truck on a nearby road, but more likely you'll hear our sheep baaing to one another or the cows across the valley trumpeting, or the abundance of birdsong. The energy here is calming and peaceful--we know you will love it as much as we do.

Quaint 1-bedroom cottage on Blue Ledge Farm
This cozy cottage is on Blue Ledge Farm- a working goat dairy. It is a one-bedroom with a double fold-out futon in living room to potentially fit 4 guests. It is within 15 minutes of both Brandon and Middlebury, 1 hour south of Burlington. Pets are allowed, on leash. It can possibly include a farm and cheese tasting for an extra $20 per person (contact host in advance). It is the perfect place if you're an animal or cheese lover looking for a rustic and relaxing stay on a beautiful farm.

Cabin on The Hill
Relax with the whole family at this peaceful place. Private, cozy, clean, comfortable getaway in Chittenden Vermont. This beautiful cabin is off the grid with solar power and push button generator. Chittenden is a small drive to endless recreational activities for every season. It is the perfect rustic space for a couple or a small family. It is centrally located between Killington and Rutland. Everything you need is within a 20 to 30 minute drive.

Baby Queens Barbie-core Studio Apt (dog friendly)
Enjoy a stylish experience at this centrally-located place. This studio apartment is perfect for the solo traveller or couple. The queen bed is super comfy. Brand new and renovated throughout. The kitchen is stocked for basic cooking. I'll make sure there is always coffee and cream for you. Pets are welcome if they do not get up on the furniture. It's easy access to downtown Rutland to enjoy yoga studios, restaurants, and coffee shops.

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.

Cozy Poultney Village Apartment
I enjoy booking my two-story in-law apartment with a private entrance, which is attached to my 1850 Poultney Village home. I am located a block from Main Street with shops, books, and eateries. I am in the lakes region of Vermont, close to both Lake St. Catherine and Lake Bomoseen. Killington is 35 miles away. We am also located a mile from the NY border and the entrance to Lake George and the Adirondacks.

Suite in the Green Mountains
We have a first-floor,two-room suite with its own entrance in our home, located on an official Vermont Scenic Highway, in the middle of the Green Mountains. The suite has a large sitting room with a kitchenette; a bedroom with queen bed and A/C; and bathroom with tub/shower. NOTE: We have a second, larger unit in our home called "Two-Bedroom Apartment in the Green Mountains".

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

Vermont Country Suite
Located in Chittenden, VT, we are in the heart of the Green Mountains. We are just down the road from the Mountain Top Inn wedding venue and Cross Country Skiing Center. The apartment is an easy 15-20 minute drive to Pico and Killington ski areas. The suite is perfect for winter and summer adventuring or just a quiet get away in Vermont.

The Berghüttli: The Coziest Cabin in Vermont
The Berghüttli is a Swiss-inspired mountain hut and farm stay located in Goshen, VT (population 168). Inspired by the tradition of mountain huts in the alps, the Berghüttli provides a completely private mountain escape surrounded by National Forest. Take a VIDEO TOUR: search "The Berghüttli" on Youtube
Popular amenities for Chittenden family-friendly rentals
Family-friendly home rentals with a hot tub

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

Upper Yurt Stay on VT Homestead

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

Lake Dunmore Getaway — Foliage Views & Ski Retreat

Scandinavian design Cabin w/ private hiking trail

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

Beautiful Spacious Condo at Killington Resort

Newly renovated ski retreat at Killington
Family- and pet-friendly home rentals

Vermont Hill Top Studio

Ranch at Mendon Mt Orchards

Moon Valley Country Retreat no clean fee pets yes

Cozy Contemporary Downtown Texaco

Earthen Yurt in Green Mtn Wonderland

Cozy Home in Poultney, Vermont.

Vermont private retreat with gorgeous views.

Breadloaf Hut. Glamping, hiking, biking, foliage
Family-friendly home rentals with a pool

Luxury Condo Tucked in the Heart of Killington

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

Epic Views of the Green Mountains

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

⛷☃️Close to lifts. Rustic. Mountain Green Resort🏂❄️…

SKI ON/OFF Spruce Glen B | AC | Sauna| Fireplace

Serene Top Floor Condo (resort style amenities)

Modern Killington Farmhouse Condo: Close to Resort
When is the best time to visit Chittenden?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $716 NZD | $844 NZD | $659 NZD | $532 NZD | $530 NZD | $489 NZD | $468 NZD | $500 NZD | $523 NZD | $484 NZD | $466 NZD | $657 NZD |
| Avg. temp | -7°C | -6°C | 0°C | 7°C | 14°C | 18°C | 21°C | 20°C | 15°C | 9°C | 3°C | -3°C |
Quick stats about holiday rentals that are family-friendly in Chittenden

Total holiday rentals
Explore 80 holiday rentals in Chittenden

Nightly prices starting at
Chittenden holiday rentals start at $213 NZD per night before taxes and fees

Verified guest reviews
Over 3,360 verified reviews to help you choose

Pet-friendly accommodation
Find 20 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
80 of Chittenden holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Chittenden rentals

4.9 Average rating
Chittenden stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with a hot tub Chittenden
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- Family-friendly rentals Rutland County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Magic Mountain Ski Resort
- Bolton Valley Resort
- West Mountain Ski Resort
- Fort Ticonderoga
- Dartmouth Skiway
- Cochran's Ski Area
- Pico Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Lake George Expedition Park
- Dorset Field Club
- Lucky Bugger Vineyard & Winery
- Bromley Mountain Ski Resort
- Whaleback Mountain
- Autumn Mountain Winery
- Fox Run Golf Club
- Northeast Slopes Ski Tow
- Country Club of Vermont
- Ekwanok Country Club
- Montshire Museum of Science




