Family-friendly holiday rentals in Chittenden

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Chittenden family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Plymouth
4.95 out of 5 average rating, 251 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

MichaelRating, 5 stars3 months ago
Nice place thanks Mike
Guest favourite
Chalet in Killington
4.84 out of 5 average rating, 251 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

ScottRating, 5 stars4 weeks ago
This is our second time renting Clinton's ski lodge place is great super host. Always responsive will be renting again next season.
Top Guest favourite
Guesthouse in Randolph
4.96 out of 5 average rating, 259 reviews

Macintosh Hill Farm

MadelynRating, 5 stars3 months ago
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.
Superhost
Home in Pittsfield
4.84 out of 5 average rating, 238 reviews

Killington area home - 4-seasons & hot tub

KenleyRating, 5 stars3 months ago
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!
Guest favourite
Chalet in Killington
4.87 out of 5 average rating, 248 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

AudreyRating, 5 stars3 months ago
We could not have found a better home for our Killington ski week. The ski in ski out directions were perfect and so easy. The home comfortably accommodated 8 adults and provided privacy for each of us as well. Fabulous dining area for our family that provided many happy memories. We've never rented a home where every single bed was so luxurious either. Each night we slept so soundly. On days we did not ski there was plenty to do at the house, a beautiful neighborhood to walk in and such close proximity to Killington Rd with so many dining options.
Guest favourite
Chalet in Stockbridge
4.92 out of 5 average rating, 181 reviews

Killington ski house winter MTbike -new jacuzzi

ZachRating, 5 stars3 months ago
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
Top Guest favourite
Home in Ludlow
4.97 out of 5 average rating, 160 reviews

Ski Chalet with Hot Tub on Okemo Mountain

ImanRating, 5 stars4 weeks ago
Had an awesome weekend here with the family! The cabin had everything we needed, super comfy and well-stocked. The hot tub was a huge bonus, and the hosts were super friendly. Would definitely come back!
Top Guest favourite
Cabin in Ripton
5 out of 5 average rating, 106 reviews

#7 - Hemlock Hideaway Cabin

ChrisRating, 5 stars3 months ago
Home now after a couple days at the cabin. Feeling fully rested and can’t express enough how much we needed this getaway. Ago and Marty go above and beyond to make you feel comfortable and provide you with everything you could need to relax and have a great time. We will be coming back here. Hopefully soon.

Family- and pet-friendly home rentals

Guest favourite
Cabin in West Windsor
4.96 out of 5 average rating, 144 reviews

Cowshed Cabin Farm

JefferyRating, 5 stars1 week ago
Great host, great location. Very relaxing and close to many attractions. Loved watching all the birds coming into the yard
Superhost
Cabin in Cavendish
4.95 out of 5 average rating, 159 reviews

The Cozy Little Red Cabin

LaurenRating, 5 stars3 months ago
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!
Guest favourite
Home in Danby
4.96 out of 5 average rating, 228 reviews

Comfortable farmhouse with stunning views

ErinRating, 5 stars2 weeks ago
This was the perfect place for a peaceful Vermont getaway! The house is unique and a great balance of historical farmhouse and modern comfort. Very clean and easy to use amenities. Would love to stay again!
Guest favourite
Home in Rochester
4.95 out of 5 average rating, 196 reviews

The McKinley House

GarethRating, 5 stars4 months ago
We had a great stay, lovely welcoming home and great location - short walking distance to nice places in town and 30min drive to either Sugarbush or Killington/Pico. Thank you!
Top Guest favourite
Cabin in Pawlet
4.94 out of 5 average rating, 156 reviews

Hickory Ridge, Vermont Log Cabin, no cleaning fee

ReneeRating, 5 stars1 week ago
Fantastic and authentic Vermont experience. Top 3 AirB&Bs I’ve stayed in. Off the beaten path, but close enough to everything you need. Rik is great host and makes it easy. Book if you can find availability.
Top Guest favourite
Chalet in Wells
4.9 out of 5 average rating, 144 reviews

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

TomRating, 5 stars3 months ago
Rita’s chalet is really clean and the view around it is amazon. The place is well stocked with games for fun and firewoods for warmth. Upon request, Rita was able to accommodate our late checkout request with a reasonable surcharge. We have enjoyed our stay at Rita’s place and would definitely come back next time when we are around
Top Guest favourite
Cabin in Warren
4.97 out of 5 average rating, 132 reviews

Stetson Hollow Cabin by Stetson Brook

MicheleRating, 5 stars2 months ago
Adorable, cozy cabin 10 minutes from Sugarbush ski resort. Very relaxing atmosphere. Well stocked with linens and firewood. Jill left us a little delicious treat. Would stay here again
Top Guest favourite
Home in Leicester
4.97 out of 5 average rating, 104 reviews

Lakefront home with stunning views

YokoRating, 5 stars1 month ago
Beautiful place to spend relaxing weekend by the Lake Dunmore. Her art filled home is comfortable and clean. Thank you , Ashley. We can’t wait for next visit.

Family-friendly home rentals with a pool

Guest favourite
Yurt in Randolph
4.94 out of 5 average rating, 457 reviews

Upper Yurt Stay on VT Homestead

GabriellaRating, 5 starstoday
We loved our stay with Jonathan! It was the perfect place to get away and unplug - the pool was wonderful, esp in the summer heat. My boyfriend was obsessed with the little frogs that cohabitated the pool. Jonathan was very communicative about the check in instructions and the operation of the sauna - another gem of this Air B&B even amid the summer heat. Thank you again!
Superhost
Condo in Killington
4.92 out of 5 average rating, 106 reviews

Right at Killington !

CrossanRating, 5 stars4 months ago
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!
Guest favourite
Guest suite in Killington
4.95 out of 5 average rating, 146 reviews

Cozy, spacious, 3 bedrooms, 4 beds, swimming pool.

DiannaRating, 5 stars1 day ago
all around the house was so pretty! flowers and felt like you're in the middle of the forest, the house standing on a small hill and the only exit is through one driveway on a mini bridge, which is very cute and secluded. The only downside is sooooo many mosquitoes, but thats honestly everywhere especially if you're in the forest. This place gives off you're visiting your grandparents home, which felt very nice and refreshing especially since we're from a rowdy city.
Guest favourite
Home in Granville
4.96 out of 5 average rating, 145 reviews

Epic Views of the Green Mountains

ColbyRating, 5 stars2 weeks ago
We had a great stay at William’s. The location was beautiful and the house was comfortable. We had a great mix of day-tripping and relaxing with a view. We also ran into William and he was very helpful and friendly.
Guest favourite
Condo in Killington
4.95 out of 5 average rating, 105 reviews

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

PatriciaRating, 5 stars3 months ago
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!
Superhost
Condo in Killington
4.82 out of 5 average rating, 257 reviews

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

ZacharyRating, 5 stars4 months ago
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.
Superhost
Condo in Killington
4.78 out of 5 average rating, 308 reviews

Serene Top Floor Condo (resort style amenities)

NikitaRating, 5 stars4 weeks ago
Amazing view and cozy vibes. Hot tub and a pool are fun amenities to have. Building has freshly renovated pool and tubs. If you like it there are also sauna pods. So do not forget your swimsuit. It was clean and if you cook there is a kitchen. On top of that it was great to have a balcony with a view. May is a nice time to come even if you are not skiing because it’s not crowded and nature is stunning. And there are plenty of spots for mountain bike. Scott is a great host and local recommendations are helpful and honest. Visit liquid art, if you want a good cup of coffee that’s the right place. Great place!
Superhost
Condo in Killington
4.89 out of 5 average rating, 162 reviews

Modern Killington Farmhouse Condo: Close to Resort

RodneyRating, 5 stars4 months ago
Great home near the mountain, exactly how described and shown in pictures. We had a wonderful stay.

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

  • Total rentals

    80 properties

  • Nightly prices starting at

    $167 NZD 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

Destinations to explore