
Family-friendly vacation rentals in Chittenden
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Top-rated family-friendly rentals in Chittenden
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Popular amenities for Chittenden family-friendly rentals
Family-friendly home rentals with a hot tub

Upper Yurt Stay on VT Homestead
I needed a little break from my every day Vermont life. This was the perfect spot to get away from everything, but still not be far from home. I would definitely go back! Thank you so much!

Top of the World! Jacuzzi! Private Hiking Trails!
Nice place thanks Mike

Macintosh Hill Farm
A wonderful ski weekend! We spent two nights and spent the day (Saturday) skiing at Killington. Quiet drive there and back so it was a perfect location to come back to a peaceful evening. Hot tub was amazing after skiing and very clean! Laura and Aaron were very helpful and let us know the conditions of the roads prior to our arrival. Flexible, kind and friendly! Would stay again for sure.

Killington Chalet - Hot Tub, Sauna, Boot Dryer
Second time staying and it was better than the first time. Totally recommend and will definitely be going back for our annual ski trip. If it’s available of course!

Okemo Ski Chalet with Hot Tub
Bob’s place is great for several families. Many bedrooms, multiple bathrooms, great amenities and close to skiing!

Killington area home - 4-seasons & hot tub
We had a great time at David's place. The kitchen was well stocked, plenty of firewood, and the hot tub was ready to go. The house was very clean. All the bedrooms had plenty of linens, and extra blankets. We would definitely stay at David's again!

One Bedroom Suite Near Okemo
Great little studio . Lots of nearby dining options, and a short drive to Okemo.

Killington ski house winter MTbike -new jacuzzi
Great place to stay! The hot tub after a long day of snowboarding was amazing. Dean responds fast to any questions you have too. Definitely recommend
Family- and pet-friendly home rentals

The Cozy Little Red Cabin
Marinas little red cabin was perfect for our ski trip! The WiFi is a little rough but we didn’t spend much time on our phones Bring dvd’s (the collection is solid but more the better) Perfect distance to okemo, Stowe is less than two hours so it was great! The cabin felt so cozy and felt right at home! Would def book again!

Downtown Middlebury 3 BR Home - Walk Everywhere!
Ideal for a quick college visit. Walkable to campus and breakfast / dinner options. Dog friendly too - exactly what we needed!

Hideaway Cabin by the Stream on 27 Acres
We had an awesome getaway at Kevin and Lesley’s cabin! This was our last little getaway before we get married this fall and it was the perfect unplugged retreat to feel connected going into the stressful time before the wedding. The cabin is cozy, the bathroom is adequate and sort of surprisingly not as buggy as it could have been, and the porch was my favorite spot to feel connected to nature. Kevin was very communicative and the instructions in the cabin were very clear. Luce’s lookout was amazing at the top and a really great recommendation by our hosts. We would definitely go back!

Hancock hideaway
Heidi’s place was exactly what we wanted and needed. It was a beautiful location in the middle of the mountain. It is a private home, in a secluded location, but there were places available for food and entertainment not too far away. We got to hike and drive into towns to do some sight seeing and shopping. We absolutely enjoyed our stay

Quiet Vermont Farmhouse
This is a nice cozy attic apartment inside of a residence. Steep staircase. No living room. Wonderful walking area beside a river. Close to Woodstock and Dartmouth. Gracious host. Temperature a little difficult to regulate. Recommend.

Nature Lover's Paradise
Had a fantastic time. Went backcountry skiing before work and then worked from his place with multiple people doing zoom calls without issues. Perfect place for us

The Guest House at Sky Hollow
The house more than met our expectations! We skied at Killington and Sugarbush and snowshoed on trails behind the house. The house was very cozy and quiet with a large kitchen and very cozy spots to read and sleep in after a long day of being outside. I highly recommend staying here!

Hickory Ridge, Vermont Log Cabin, no cleaning fee
One of my favorite AirBnB stays ever! If you're looking for a cool, comfortable, memorable experience, this is it. The photos don't do it justice. This beautiful home was spotless, had so many amazing handmade artful features, and comfortably hosted our group of 5. Communication with Rik was excellent throughout, and he gave us excellent local recommendations. There are so many great surprises and personal touches in the home, so much space to explore - all in the comfort of modern, cozy amenities. You're bound to leave with some great stories and adventures. Listen to all the reviews - stay here! And give the guestbook a look-see ;)
Family-friendly home rentals with a pool

Right at Killington !
Our family had a wonderful stay at the condo in Killington. The location could not be beat! A very short 5 minute walk to the lifts and Snowshed lodge. The complex had an amenity building with pool/hot tub that the kids loved and the condo was quite spacious and clean. Ruslana was a great host and very responsive! There is a solid chance we will be back next year!

Cozy, spacious, 3 bedrooms, 4 beds, 5 mi to K Rd.
Amazing stay. Loved how close it was to the mountain. The pool also looked amazing so sad it was winter. Definitely recommend staying there were 4 beds and can comfortably fit 5-6 people.

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace
This space was perfect for our family. With walking distance to the entrance of the slopes, this location was ideal for our ski getaway. I appreciated the small touches that made this experience feel luxurious, the provided coffee, wine, wood for the usable fire place. The beds were comfortable and the space was spacious. We would definitely visit Jim’s place again!

Moon Valley Country Retreat no clean fee pets yes
There is not enough to say about the pristine beauty that is Loraine’s cabin. The instructions were helpful in navigating into the property and lights were turned on as it was dark to assure my comfortable arrival. The cabin feels like a nurturing home and is equipped with comforts and small touches. The bed was neatly made and felt like a picture walking in to see it. The stairs are cabin stairs and there is caution to take your time and step gently. Seemingly every question was answered with small notes around the cabin and a detailed welcome book. The care and attention to detail was perfection in a stay. I only wish I had been on a longer trip to fully enjoy the grounds and the surroundings. It was easy to feel at home and welcome with Loraine and Dean as hosts.

*Killington Summer Rental: 3 Bdrm, 2 Bth*
Dray was thorough and the airbnb was clean, comfortable, and close to everything! I hope to stay here next time I visit!

Ski, Ride, Walk On/Off Condo On Pico at Killington
Great location for pico mountain. The ski on ski off was pretty easy to find and nicely located. The location is slightly less ideal for killington, as you need to take a shuttle that has multiple stops. We also ended up on a bigger bus to take us back from Killington and the drop off was on the main road, which was a bit difficult to walk on in our snow gear. Overall, nice apartment and perfect for my group of friends.

Serene Top Floor Condo (resort style amenities)
A wonderful place situated close to the mountain. The amenities were fantastic as well. The only issue was getting the right pin to access the apartment...however Scott responded within seconds so it was minimally disruptive.

#45 Luxury Ski & Summer Condo with Private Sauna
Great spot near the mountain. nice community pool and hot tub.
Quick stats about vacation rentals that are family-friendly in Chittenden
Total rentals
80 properties
Nightly prices starting at
ﺩ.ﺇ367 before taxes and fees
Total number of reviews
3.4K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
50 properties have a dedicated workspace
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- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- West Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Cochran's Ski Area
- Lake George Expedition Park
- Fort Ticonderoga
- Dartmouth Skiway
- Northeast Slopes Ski Tow
- Country Club of Vermont
- Adirondack Extreme Adventure Course
- Gooney Golf
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Ekwanok Country Club
- Killington Adventure Center
- Whaleback Mountain
- Storrs Hill Ski Area
- Fox Run Golf Club