Family-friendly holiday rentals in Rutland

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Rutland family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Apartment in Townshend
4.93 out of 5 average rating, 240 reviews

Private Apt. on Farm, Hot Tub with views!

MathildeRating, 5 stars2 weeks ago
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!
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 stars3 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.
Guest favourite
Yurt in Randolph
4.95 out of 5 average rating, 434 reviews

Lower Yurt Stay on VT Homestead

AlinaRating, 5 stars1 week ago
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.
Guest favourite
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.
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 stars3 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!
Guest favourite
Apartment in Londonderry
4.96 out of 5 average rating, 582 reviews

Vermont Getaway Apartment

AshleyRating, 5 stars5 days ago
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

Guest favourite
Cabin in Mount Holly
4.92 out of 5 average rating, 196 reviews

Cozy Vermont Cabin near Okemo.

MarlaRating, 5 stars3 months ago
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.
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!
Top Guest favourite
Cabin in Topsham
4.99 out of 5 average rating, 293 reviews

Pine Cabin, Galusha Hill Farm, incredible view!

BridgetRating, 5 stars3 weeks ago
We loved our stay and hope to come back again!
Guest favourite
Cabin in Danby
4.89 out of 5 average rating, 298 reviews

Mountain treasures await.

DustinRating, 5 stars1 month ago
Very nice people loved the small conversation we got to have love the cabin will be back next year.
Top Guest favourite
Guesthouse in Hartland
4.95 out of 5 average rating, 993 reviews

Yurt In The Woods - Private Refuge

KristieRating, 5 stars4 days ago
It’s very well maintained and private. Everything was as in the pictures and it was a breeze to take care of.
Top Guest favourite
Home in Corinth
4.99 out of 5 average rating, 317 reviews

Dawnside - Green Mtns Home with White Mtns View

LovinskyRating, 5 stars1 week ago
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!
Top Guest favourite
Chalet in Wells
4.9 out of 5 average rating, 143 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
Guest favourite
Home in Whitehall
4.93 out of 5 average rating, 142 reviews

Lakefront A-Frame Home Emerald Lake, NY

SubinRating, 5 stars3 weeks ago
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

Guest favourite
Home in Salem
4.98 out of 5 average rating, 192 reviews

Magical Farm Getaway - a must visit!

BriannaRating, 5 stars2 weeks ago
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!
Top Guest favourite
Guesthouse in Ticonderoga
5 out of 5 average rating, 212 reviews

Chilson Brook Alpacas

DerekRating, 5 stars1 month ago
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.
Superhost
Condo in Killington
4.92 out of 5 average rating, 106 reviews

Right at Killington !

CrossanRating, 5 stars3 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, 145 reviews

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

JoshRating, 5 stars2 months ago
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.
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 stars2 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!
Guest favourite
Condo in Ludlow
4.93 out of 5 average rating, 110 reviews

One Bedroom Suite Near Okemo

ChristopherRating, 5 stars2 months ago
Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.
Superhost
Condo in Killington
4.8 out of 5 average rating, 107 reviews

Cozy 3BR/2BA Chalet – Mins to Mtn & Biking Trails

MikeRating, 5 stars3 months ago
Dray was thorough and the airbnb was clean, comfortable, and close to everything! I hope to stay here next time I visit!
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 stars3 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.

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