
Family-friendly vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
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

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
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.
Family- and pet-friendly home rentals

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!

Vermont Chalet
Had a wonderful stay at the “Birdhouse on wheels.” Waking up to the stream was so peaceful. Make sure to look up at the stars on a clear night. Just a heads up (pun intended) to those on the taller side for the sloped roof.

Nature Lover's Paradise
We always love staying here. It’s so peaceful and the sound of the brook is so relaxing! Philip responds quickly and is an excellent host!!

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! 😀

Stunning Rustic Apple Barn - hot tub & sauna
Ben was very helpful as a guide to the area to help make the most out of a rainy weekend in Vermont. The cabin itself was perfectly rustic and great place to relax and recharge.

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!

Martin’s Breezy Acres
We had a wonderful stay — the house was quiet, peaceful and on a beautiful property. Everything was comfortable and we felt right at home. Very short drive to downtown Bolton Landing or the Lake George area and tons of great hikes only minutes away. Looking forward to coming back soon.

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.

⭐️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.
Quick stats about vacation rentals that are family-friendly in Castleton
Total rentals
50 properties
Nightly prices starting at
$130 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
Destinations to explore
- Hudson Valley Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- The Hamptons Vacation rentals
- Long Island Vacation rentals
- Plainview Vacation rentals
- Cape Cod Vacation rentals
- East River Vacation rentals
- New York Vacation rentals
- Pocono Mountains Vacation rentals
- Québec City Vacation rentals
- Jersey Shore Vacation rentals
- Cottage rentals Castleton
- Pet-friendly rentals Castleton
- Rentals with a fire pit Castleton
- House rentals Castleton
- Rentals with a patio Castleton
- Rentals with a fireplace Castleton
- Waterfront rentals Castleton
- Rentals with lake access Castleton
- Rentals with a washer and dryer Castleton
- Rentals with beach access Castleton
- Rentals with outdoor seating Castleton
- Family-friendly rentals Rutland County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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
- Lincoln Peak Vineyard
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes