
Family-friendly holiday rentals in Rutland
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Rutland
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Rutland family-friendly rentals
Family-friendly home rentals with a hot tub

Private Apt. on Farm, Hot Tub with views!
Amazing view, great and comfy Airbnb. The hot tub is such a nice plus with the incredible view over the mountains. It was so well equipped we had most of our meals in the Airbnb because the kitchen was so functional. I highly recommend this Airbnb!

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

Killington Chalet - Hot Tub, Sauna, Boot Dryer
This is our second time renting Clinton's ski lodge place is great super host. Always responsive will be renting again next season.

Lower Yurt Stay on VT Homestead
Beautiful spot to relax, reconnect and leave refreshed! We enjoyed everything about our stay, especially the sauna, living pool, and hike to the yurt! We would love to return, thank you for sharing such a peaceful place with us, it was exactly what we needed.

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!

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.

Ski Chalet with Hot Tub on Okemo Mountain
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!

Vermont Getaway Apartment
The getaway apartment was just as described. Peaceful, private, and with ample space and amenities for a family of three. We enjoyed our weekend!
Family- and pet-friendly home rentals

Cozy Vermont Cabin near Okemo.
A very clean, cozy, and comfortable home! We came to ski at Okemo and were pleased that the house is only about a 10 minute drive from the resort and the town of Ludlow where there are great restaurants and shops. The living area of the home is spacious and great for hanging out - there were tons of movies on DVD and video games to enjoy. The kitchen was well-equipped and perfect for cooking meals at home. The beds were comfy. Overall a wonderful stay! We hope to be back in the future.

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!

Pine Cabin, Galusha Hill Farm, incredible view!
We loved our stay and hope to come back again!

Mountain treasures await.
Very nice people loved the small conversation we got to have love the cabin will be back next year.

Yurt In The Woods - Private Refuge
It’s very well maintained and private. Everything was as in the pictures and it was a breeze to take care of.

Dawnside - Green Mtns Home with White Mtns View
Dawnside is just as beautiful in person as in the photos. We had a wonderful time and appreciated the views, privacy, and cleanliness of the property. Erich is a great host and the house manual is detailed and useful. We would visit again!

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

Lakefront A-Frame Home Emerald Lake, NY
The house was very charming and had a stunning view of the lake from most rooms of the house. Spacious bedrooms too with nice big basement and sunroom. Loved the lake environment. Great spot for fishing and water activities. The family had great time with the kayaks and pedal boat. Great spot for a relaxing and peaceful getaway.
Family-friendly home rentals with a pool

Magical Farm Getaway - a must visit!
We had a wonderful & relaxing weekend here with a large group for my sister's lowkey bachelorette party. Even with a day of non-stop pouring rain, we were perfectly content with staying in and enjoying the coziness of the house. We had a blast watching the chickens roam around and hanging out with the overly-friendly barn cats while we sat outside. The goats & pigs were happy to greet us at the fence every time. The hot tub and pool were perfect! Highly recommend staying here if you're looking for a beautifully scenic and peaceful getaway. Thanks, Sarah & BBVF team!

Chilson Brook Alpacas
This was my third time staying at this property. With every visit, it feels more and more like a home away from home. The property has great views and a calming environment. I enjoy cracking the windows at night to hear owls hooting and the stream running. The owners are fantastic people. It's a short 5-minute drive into town where you can find some good food.

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, swimming pool.
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!

One Bedroom Suite Near Okemo
Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.

Cozy 3BR/2BA Chalet – Mins to Mtn & Biking Trails
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.
Quick stats about holiday rentals that are family-friendly in Rutland
Total rentals
80 properties
Nightly prices starting at
$84 NZD before taxes and fees
Total number of reviews
4.1K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Wi-Fi availability
80 properties include access to Wi-Fi
Destinations to explore
- Hudson Valley Holiday rentals
- Boston Holiday rentals
- Montreal Holiday rentals
- The Hamptons Holiday rentals
- Long Island Holiday rentals
- Plainview Holiday rentals
- East River Holiday rentals
- New York Holiday rentals
- Pocono Mountains Holiday rentals
- Québec City Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Apartment rentals Rutland
- Pet-friendly rentals Rutland
- House rentals Rutland
- Rentals with outdoor seating Rutland
- Villa rentals Rutland
- Rentals with a fireplace Rutland
- Cottage rentals Rutland
- Rentals with a fire pit Rutland
- Kid-friendly rentals Rutland
- Rentals with a patio Rutland
- Rentals with a washing machine and dryer Rutland
- Family-friendly rentals Rutland County
- Family-friendly rentals Vermont
- Family-friendly rentals 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
- Sugarbush Resort
- Okemo Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Pico Mountain Ski Resort
- West Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth Skiway
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Dorset Field Club
- Autumn Mountain Winery
- Fort Ticonderoga
- Lake George Expedition Park
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Northeast Slopes Ski Tow
- Baker Hill Golf Club
- Ekwanok Country Club
- Hooper Golf Course
- Fox Run Golf Club
- Willard Mountain
- Santa's Land USA
- Adirondack Extreme Adventure Course