
Family-friendly holiday rentals in Castleton
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Castleton
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Castleton family-friendly rentals
Family-friendly home rentals with a hot tub

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

Killington Chalet - Hot Tub, Sauna, Boot Dryer
Nice space for a group, plenty of room for dining and relaxing. Clint was very responsive and gave excellent instructions. Appreciated the hospitality!

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

Okemo-Ludlow, fireplace, hottub, sleeps 13
My friends and I had a great time at this place! The home was beautiful and very spacious - we were able to all hang out in the hot tub, kitchen, living room, and no place felt cramped.

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

Large Chalet; Sauna, Hot Tub; Walk to Trail
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.

#45 Luxury Ski & Summer Condo with Private Sauna
Great spot near the mountain. nice community pool and hot tub.

#7 - Hemlock Hideaway Cabin
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

Cozy Log Cabin near Stratton/Mt. Snow-pet friendly
Christina was an excellent host who ALWAYS responded to any of my questions or concerns immediately and courteously. Her space was exactly as described and very spacious as well as a fantastic environment for a group to get together and have a great time! I highly recommend Christina’s place for a great time with a large group, she is the ideal host who works tirelessly to provide an amazing space for her guests!

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!

Cozy, Romantic, Historic Saratoga Apartment
We were extremely pleased with our stay at Roberta’s place. This was our first visit to Saratoga Springs, and we wanted a quiet place that was convenient to downtown and that would allow us to fully experience the community. We felt at home from the moment we walked into the place. The neighborhood was quiet and peaceful, and the apartment was very comfortable. The unit was exactly as described and came with coffee for the coffee maker and even a package of scones for us to enjoy. It was a short walk to the restaurants and shops of downtown, and we felt safe walking at all times. Overall, we highly recommend Roberta’s place. We will definitely stay again the next time that our travels take us to Saratoga Springs.

April/May special So Vt Cabin Mt Tabor Treasure
A great escape. We enjoy our stays here. We are booked again in June. Lori is so attentive. She is always one step ahead. Thank you! 😀

Entire HOUSE Walk to ALL Dogs OK
Nancy’s place was a great option for my stay in the area. The kitchen had everything I needed, and the couch was comfortable. As was the one bed I slept in. I was visiting for a work trip. Nancy was also incredibly responsive to any questions I had, and was offering suggestions for the area I found useful. I’m glad to have found this place. While on this trip, I did not bring my dogs, I will be sure to stay here on my next one to the area. I typically stay in hotels here, but I will do my best to stay at Nancy’s anytime visiting in the future.

Apple Blossom Cottage: A Tiny House
This tiny home is a charm! And, the location - if you are exploring south-central Vermont, as I was - is great. The tiny home has everything you need, and nothing that you don't. I had a perfect stay of two nights here - very enjoyable.

The McKinley House
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!

Views! Entire Chalet, FAST Wi-Fi, All 18 Acres
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
Family-friendly home rentals with a pool

Chilson Brook Alpacas
I keep coming back as it is a great place, everything is top notch and the hosts are such good people. Highly recommend it if you want a perfect get away

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.

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.

Modern Killington Farmhouse Condo: Close to Resort
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 Castleton
Total rentals
50 properties
Nightly prices starting at
£98 before taxes and fees
Total number of reviews
1.3K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
50 properties include access to wifi
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- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Gore Mountain
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Saratoga Spa State Park
- Saratoga Race Course
- West Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Mount Snow Ski Resort
- Fort Ticonderoga
- Ekwanok Country Club
- Lake George Expedition Park
- National Museum of Racing and Hall of Fame
- Northern Cross Vineyard
- Willard Mountain
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Gooney Golf
- Adirondack Extreme Adventure Course
- Cozy Cottages & Otter Valley Winery