Family-friendly vacation rentals in Rutland County

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Rutland County family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Condo in Killington
4.92 out of 5 average rating, 106 reviews

Right at Killington !

CrossanRating, 5 stars2 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 favorite
A private hot tub is illuminated with soft blue lights, creating a relaxing atmosphere. The hot tub features multiple jets and is surrounded by wooden walls and a partially covered area, ensuring privacy. Warm ambient lighting enhances the tranquil setting, inviting relaxation.
Chalet in Killington
4.84 out of 5 average rating, 250 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

MauraRating, 5 stars3 weeks ago
Nice space for a group, plenty of room for dining and relaxing. Clint was very responsive and gave excellent instructions. Appreciated the hospitality!
Guest favorite
The bathroom features a neutral color palette with a single vanity topped with light-colored stone. A sizable mirror is mounted above the sink, and a framed sign reminding guests to wash their hands is displayed on the wall. Towels and amenities are neatly arranged.
Condo in Killington
4.95 out of 5 average rating, 105 reviews

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

PatriciaRating, 5 stars1 month 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
A wooden treehouse is elevated on a sturdy platform, featuring a green slide and swings. An American flag is displayed prominently. Surrounding greenery provides a natural backdrop, enhancing the outdoor play area designed for children and family activities.
Home in Killington
4.77 out of 5 average rating, 13 reviews

4 Bdrm house 5 min to skiing, hiking, golf, biking

GillianRating, 5 stars5 months ago
Awesome place right off the access road in Killington. Beautiful property and perfect for our group! Will definitely stay here again.
Superhost
An outdoor hot tub is nestled on a private rear deck, surrounded by snow-covered trees. Soft lighting illuminates the water, creating a serene atmosphere. Snowflakes gently fall around the hot tub, enhancing the winter ambiance of the setting.
Home in Ludlow
4.91 out of 5 average rating, 56 reviews

Walk to Okemo Base Lodge & Lifts. Private On Mount

LeoRating, 5 stars3 months ago
Fantastic home. Fantastic location. Excellent host. Could not have had a better experience.
Superhost
The exterior of the chalet is surrounded by a pristine blanket of snow, with two wooden balconies extending from the second floor. Snow-covered trees frame the structure, providing a sense of privacy and tranquility. A well-maintained path leads to the entrance.
Apartment in Killington
4.8 out of 5 average rating, 35 reviews

Luxury apartment in Hideaway Chalet best location

TarynRating, 5 stars19 months ago
We had a great stay. The space is clean and comfortable and close to many amenities. Our host was very responsive and helpful, both before and during our trip. We would gladly stay here again.
Superhost
A modern studio space is presented with wood paneling and a vaulted ceiling. Stainless steel kitchen appliances are featured alongside a dining table and a comfortable seating area. Two vintage ski boards are mounted on the wall, and a sliding glass door provides access to a private balcony.
Condo in Killington
4.78 out of 5 average rating, 307 reviews

Serene Top Floor Condo (resort style amenities)

JonRating, 5 stars1 month ago
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.
Superhost
A comfortable living area features a soft gray sofa adorned with pillows, positioned next to a wooden coffee table. A brick fireplace adds warmth, while large windows allow natural light to illuminate the space and provide views of the greenery outside.
Home in Killington
4.86 out of 5 average rating, 87 reviews

The Sundowner

PatrickRating, 5 stars2 months ago
Stay at the Sundowner hosted by Patrick was absolutely amazing. Very clean, had everything we needed for our stay and then some. Plenty of room for 8 grown men to move around and be comfortable/not on top of each other. Patrick was extremely responsive. We needed to get the hot tub maintenanced and he sent guys out to fix it immediately. We were able to use it and enjoy it after getting off the slopes the same day. Patrick was extremely friendly and responsive, even helped getting left behind clothing shipped to the correct address. Thank you, Patrick, we will definitely be staying here again with you the next time we visit Killington!

Family- and pet-friendly home rentals

Guest favorite
A cozy cabin is nestled among snow-covered trees, featuring a sloped roof blanketed in fresh snow. A woodpile is neatly stacked beside the structure, and a lightly snow-dusted wooden railing surrounds the entrance, enhancing the serene winter landscape.
Cabin in Mount Holly
4.92 out of 5 average rating, 196 reviews

Cozy Vermont Cabin near Okemo.

MarlaRating, 5 stars1 month 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.
Guest favorite
A charming farmhouse is displayed against a snowy backdrop, featuring a vibrant red exterior with white trim. A blue front door is adorned with a wreath, and light snowflakes are falling gently around the house, creating a serene winter atmosphere.
Home in Ludlow
4.86 out of 5 average rating, 191 reviews

2 Doors Down - Modern Farmhouse in Downtown Ludlow

GlennRating, 5 stars1 week ago
Great place. Extremely well stocked. The working fireplace and pool table were big hits. The requirement to pay $95 extra for sheets and towels took us by surprise -- even though it is mentioned in the house rules we missed it. Bob did offer that we could bring our own and avoid that extra charge so that is what we did.
Guest favorite
A chalet-style building with a wooden exterior stands in a snowy landscape. Sunlight illuminates the sloped roof, and smoke is seen rising from the chimney. Snow-covered evergreen trees frame the structure, set against a backdrop of distant wooded hills.
Guesthouse in Granville
4.9 out of 5 average rating, 895 reviews

Moon Valley Country Retreat no clean fee pets yes

AmberRating, 5 stars6 days ago
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.
Superhost
Home in Pittsfield
4.84 out of 5 average rating, 238 reviews

Killington area home - 4-seasons & hot tub

KenleyRating, 5 stars2 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 favorite
A comfortable living area features a warm-toned wooden floor, two armchairs, and a black swivel chair. A decorative rug adds color to the space, which is illuminated by natural light streaming through large windows. A fireplace and wall-mounted TV complete the cozy ambiance.
Home in Goshen
4.84 out of 5 average rating, 285 reviews

Nature Lover's Paradise

RobertRating, 5 stars1 week ago
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!!
Guest favorite
A snow-covered deck features a wooden railing and a pathway cleared of snow. A rocking chair is positioned to the side, while a grill is visible at the far end. The entrance to the interior is framed by large glass doors, adding a view of the surrounding trees.
Chalet in Stockbridge
4.92 out of 5 average rating, 181 reviews

Killington ski house winter MTbike -new jacuzzi

ZachRating, 5 stars1 month 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 favorite
The rustic log cabin is surrounded by greenery and vibrant flowering trees. A stone patio is visible in the foreground, with outdoor seating placed under a covered porch. Lush grass and blooming plants enhance the natural setting, offering a serene outdoor space.
Cabin in Pawlet
4.93 out of 5 average rating, 151 reviews

Hickory Ridge, Vermont Log Cabin, no cleaning fee

MaximRating, 5 stars3 weeks ago
One of my favorite AirBnB stays ever! If you're looking for a cool, comfortable, memorable experience, this is it. The photos don't do it justice. This beautiful home was spotless, had so many amazing handmade artful features, and comfortably hosted our group of 5. Communication with Rik was excellent throughout, and he gave us excellent local recommendations. There are so many great surprises and personal touches in the home, so much space to explore - all in the comfort of modern, cozy amenities. You're bound to leave with some great stories and adventures. Listen to all the reviews - stay here! And give the guestbook a look-see ;)
Guest favorite
An inviting entryway features warm wood paneling and a bench against the wall. Hooks are mounted for coats, and a spacious mat lies underneath. Natural light enters through a window, illuminating the area, with a door leading to the main living space.
Chalet in Killington
4.87 out of 5 average rating, 248 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

AudreyRating, 5 stars1 month 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.

Family-friendly home rentals with a pool

A well-maintained outdoor pool area features a rectangular swimming pool surrounded by a paved patio. Red umbrellas provide shade over several lounge chairs, creating a relaxed environment. A small pool house stands nearby, with trees and greenery framing the scene.
Condo in Killington
4.78 out of 5 average rating, 270 reviews

Come to Killington this summer!

SamuelRating, 5 stars1 week ago
Great stay. Location is prime, especially if you need some ski tuning at Black Dog Sports and want to be close to the mountain. Plenty of space and clean. Bed was a little firm but thats okay. Will be coming back in the future.
Guest favorite
A compact bathroom features a shower with a blue chevron curtain. A single vanity with storage is positioned beside a toilet. Soft white towels hang neatly, and a mirror is mounted above the sink. Natural light is provided by a ceiling fixture.
Condo in Killington
4.75 out of 5 average rating, 92 reviews

Still 89 Trails Open, Low, Low Rates

RyanRating, 5 stars1 month ago
Convenient to the slopes via the shuttle that picks up out front. Able to walk to a good restaurant, Still on the Mountain. Place is comfortable and has everything we needed for a weekend skiing.
Superhost
A spacious room features two queen beds adorned with vibrant patterned comforters. A flat-screen TV is mounted on the wall. A window allows natural light to fill the space, while an air conditioning unit is positioned nearby. A wooden dresser and lamps add functional touches.
Condo in Killington
4.59 out of 5 average rating, 100 reviews

NEW Killington Studio: Great Location! Comfy. 431

JohnRating, 5 stars2 months ago
Nice cheaper lodging on the access road
Superhost
Villa in Killington
4.56 out of 5 average rating, 9 reviews

Whiffletree base of Killington outdoor pool

MeganRating, 5 stars16 months ago
What a great condo in the best location! Unbeatable for the price. The condo was spotless, and had every amenity as described. Plenty of towels, soaps, kitchen necessities. Beds were comfortable! We really felt right at home. And the fire place was so nice! We’d definitely recommend this for a great weekend get away!
Superhost
A tennis court is set against a backdrop of lush trees and greenery. The court features a smooth, hard surface with clear white lines marking the boundaries. A net stands in the center, ready for play.
Condo in Killington
4.8 out of 5 average rating, 107 reviews

*Killington Summer Rental: 3 Bdrm, 2 Bth*

MikeRating, 5 stars2 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
A cozy living room features a large sectional sofa with decorative pillows, a wood-burning fireplace with a brick surround, and a wooden mantel adorned with small plants. A patterned area rug lies on the carpeted floor, complementing the warm atmosphere. Nearby, the dining area is visible.
Condo in Killington
5 out of 5 average rating, 3 reviews

Glazebrook J5: 3-Bedroom with Fireplace & Sauna

KeRating, 5 stars52 months ago
The property was super clean and tidy, everything had its own place and we were able to use most of the properties' amenities. The location was superb just a 5min drive to local ski shops and restaurants and the same amount of time the other direction to most of Killington's base lodges. Check-in was easy and fast, the employees at the Killington Rental office were very nice and even offered coupons for local shops and restaurants ! Communication was amazing I received fast email and message responses and they were only 1 call away when on the road. Price was exactly on the money, so worth the stay! Thanks!
Guest favorite
A wood stove is positioned within a brick fireplace, showcasing a warm fire glimmering behind a glass front. The surrounding brick offers a rustic touch, while stockings hang above, adding a seasonal element to the cozy ambiance.
Home in Chittenden
4.91 out of 5 average rating, 89 reviews

Comfortable, relaxing large country home

EdwardRating, 5 stars2 months ago
Great spot for a week of skiing! Danielle was very helpful and communicative throughout
Guest favorite
A cozy living area features a stone fireplace, providing warmth and a focal point in the room. Two brown sofas are positioned around a coffee table. Soft lighting from a nearby lamp creates a comfortable ambiance, complemented by large windows letting in natural light.
Condo in Killington
4.93 out of 5 average rating, 451 reviews

Pico discounted 1 bedroom 1 nght Ok shuttle

ScottRating, 5 stars1 week ago
Great place !

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