Kid-friendly holiday rentals in Rutland County

Very nice place easy access to routes 4 and 100 with plenty of things to do

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.

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!

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.

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!

beautiful white pine floors and cabinets, comfortable feeling as soon as you walk through the door. can see neighbors horses and hear them in the morning to relax to. Great nature light due to the amount and type of windows. we had a very relaxed wedding week off here. 5 minutes from Rutland, vt so quick to go out .

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.

Great spot right next to Okemo! The cabin was better than the photos, felt really homey and clean.

I'm always happy when a place looks like the pictures, but this apartment was even better. It was more spacious than it looked in the pictures, and everything was perfect - spotlessly clean and ready for us to move in for our short 2-night stay. We arrived earlier than check in and were able to get in early, which was SO nice - we were on bikes and it was raining. It's always nice to "land" at the end of a long day on the bike, so getting in early was really appreciated. The apartment also has lots of nice touches that clearly have guests in mind - hooks in the bathroom, living room and bedroom for coats and towels, etc., detergent to do laundry, a table to play games (nice on a rainy day!), televisions in both the living room and bedroom, great dishes and silverware, lamps with plug openings for all our charging needs. It's hard to overstate the case - this apartment was super!

Extremely convenient place next to the mountains, nearby restaurants and shops. The bedrooms can get cold, but the blankets are quite warm and comfy.

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!

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.

Apartment was clean including the bathroom, just as described by the listing. The place was very comfortable to stay at.

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!

My family and I had an awesome stay in Tina's apartment. We took full advantage of the outdoor pool and the indoor spa space, which were both fantastic. The unit was a clean, cozy and comfortable place to return to at the end of busy days. Tina was an exceptional host - one of the most responsive/helpful experiences I've had with an Airbnb host. We would definitely stay here again!

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.

I took my 13 yo son for a weekend visit to ski Killington for the first time and Gregory’s condo made our stay worthwhile! It was easy to access, clean, and equipped with all necessities. We will be sure to return!!

Amazing view and cozy vibes. Hot tub and a pool are fun amenities to have. Building has freshly renovated pool and tubs. If you like it there are also sauna pods. So do not forget your swimsuit. It was clean and if you cook there is a kitchen. On top of that it was great to have a balcony with a view. May is a nice time to come even if you are not skiing because it’s not crowded and nature is stunning. And there are plenty of spots for mountain bike. Scott is a great host and local recommendations are helpful and honest. Visit liquid art, if you want a good cup of coffee that’s the right place. Great place!