Kid-friendly holiday rentals in Rutland County

We enjoyed our stay immensely! We visit Rutland often and will continue to stay here as long as it is available! Everything was better than anticipated!

This is my third time staying at Virginia’s house. She is very responsive, checking in via a message to see if everything is going well. It’s an easy walk to the shops and restaurants in the center of the village. I plan to be back again next year.

Brandon’s place was perfect for my family and I visiting for a graduation. Plenty of room to host and we all had our own space. Perfect for a large family vacation.

We enjoyed our stay. we felt at home. very spacious and cozy. this house has everything you need for your stay. Very close to Rutland. The fresh baked apple pie was a bonus. It was so delicious. Everything was perfect for us! Thank you! We will definitely be back again!

Dan & Holly’s place was fantastic! Although we didn’t spend much time there due our busy schedule whenever we returned we found the place be extremely homey and comfortable! The house was very clean organized and I could find everything I needed. I felt comfortable throughout my stay and really enjoyed the air conditioning at night due to the humid weather lately! 10/10 would stay again!

Philips place was literally perfect! The location, the awesome house filled with super cool art, the cozy feel of the house, the amazing outdoor area we had available to us all made this a perfect experience! Philip was great with communications and I would recommend this place to anyone looking for a perfect place to stay in this area of VT. My dad and I were up there for a quick 2 day stay. We'll both be returning with our significant others to vacation there and will absolutely be coming here in the future whenever we travel to this area!!!

We had an amazing stay! The place is in a fantastic location—perfect for exploring Woodstock or Killington—and it was super cozy, clean, and well-equipped. Robyn and Trevor were outstanding hosts, always quick to respond and incredibly helpful. The easy communication made the entire experience seamless and stress-free. Highly recommended!

My family stayed at Thomas' house during a weekend ski trip. The house was perfect for our family's needs. We skied at Okemo and it was a short drive to the mountain. After a long day of skiing, it was nice to come back to a comfortable house to relax. The house we very well stocked to include a drying rack (which we forgot to bring) and a boot dryer. We highly recommend this house for your ski adventure.

We enjoyed our stay here, very convenient location with lots of good food around. The place had all the amenities you would need for an extended stay.

Cindy and Doug were phenomenal hosts and their suite was so lovely to spend the weekend in while skiing at Killington. Their suite was very clean and cozy, and they went above and beyond to make our experience a great one. They provided homemade banana bread, fresh fruit, snacks, coffee, and even left us a bottle of champagne to celebrate our anniversary. This was one of our favorite airbnbs we’ve ever stayed at, and we hope to stay here again on future trips!

This was a wonderful spot for myself this past weekend! And had I been joined by my friend and Doggo as initially planned, it would have very comfortably accommodated the three of us. Casey was very prompt in responding to my inquiries before and during my stay. I will definitely reach out for availability the next time I visit the area…

Beautiful area. Cozy house. We loved the cows on pasture next to the lawn. They were adorable.

This is a return visit to Pam's place. It was exactly as I remembered it. A magnificent setting in a beautiful part of VT. The space is sweetly decorated and accessorized in an appropriate horse theme. Everything is in pristine condition. The cleanliness is matchless. Fully equipped as described. A bed that's hard to get out of in the morning!! Pam takes this business seriously and is a consummate professional - at the same time warm and welcoming.

Amazing and great hosts! Very clean. Perfect for our ski team. we loved enough bed and beautiful views. We will definitely be back. ♡♡♡♡♡♡♡

I really like Sam's place! This was a repeat stay, and what really works for me is the location. I like to be able to park and walk to the downtown area. Sam provides lots of choices for bath amenities, and he provides all the fixin's for morning coffee/tea as well as snacks and sweet treats. The bed is very comfortable and the shower water is nice and hot. He has also installed a window unit a/c for comfort. I would highly recommend his place for your stay in the Rutland area

Can't say enough! Steve was quick to have information and respond. His knowledge of the area is massive and he knows all the great spots to go. Their place was perfect and everything you'd expect from the pictures and description. During our stay we got a large ice storm. Some locals called it the worst ice storm since 1996. Steve was texting me throughout the storm to make sure we were ok and had power and internet. He asked if there was anything he could do for us... And he was located hours away.. Steve and LA went above and beyond in so many ways.. Their place will be the first place I look to stay on return trips!

Tom was super helpful with Checking in as well as checking out. Place is always clean and super close to our event. Thanks so much.

Great place, great host, zero complaints.

This was our second time staying at Caitlyn’s condo in Killington, we chose it again for a reason !! The vibe of the condo is super relaxing, the decor is thoughtful and cool. The fire place makes coming back after a day on the slopes so cozy! We love coming to Killington and this condo is so close to the snowshed lot, it’s perfect!

Great place! We enjoyed our stay so much that we extended it an extra day. Hosts made it super easy to extend.

Couldn’t have asked for more. Cozy, clean and such a comfortable place to stay and exactly what was described in the listing. I’ll certainly be booking again! Tricia’s communication was perfect, everything very clear and didn’t have to reach out with extra questions.

We had an amazing stay at this place! The location was perfect—just a short walk to all the incredible relaxation amenities like the pool, steam room, and sauna, which made our trip feel like a true escape. Going for a walk while taking in the views of the mountains were absolutely stunning and made every morning feel special. The unit itself was spotless and had everything we needed for a comfortable, short stay. The kitchen was well-stocked, the bed was cozy, and everything felt thoughtfully arranged. It was the perfect home base for exploring Killington and unwinding after a day of adventure. Would absolutely recommend and may come back during the Peak of the Snow Sport Season!

Amazing experience! Will be back soon!!

We loved it. Although it’s not the newest or fanciest condo the location can’t be better right at the Clocktower Base. Our family of for had an amazing time snowboarding and exploring the area. Great restaurants close by and we will definitely be back next year.