Kid-friendly holiday rentals in Windsor County

Perfect location for skiing, and cosy home that we all enjoyed (including our pup). We appreciated the thoughtful touches provided by the host, and the apple orchard was a beautiful setting. Would definitely stay again!

Awesome place right off the access road in Killington. Beautiful property and perfect for our group! Will definitely stay here again.

This home is absolutely beautiful, with stunning views that make for a perfect Vermont getaway. The house is well-equipped with everything you need for a comfortable and relaxing stay. The location is fantastic—close to local attractions yet peaceful and private. Whether you’re looking for a cozy weekend retreat or an adventure in nature, this spot has it all. Highly recommend!

Excellent place for our group. Definitely would recommend. 10 out of 10

We had a great stay, lovely welcoming home and great location - short walking distance to nice places in town and 30min drive to either Sugarbush or Killington/Pico. Thank you!

Chris isn't joking that he likes to keep the kitchen well stocked. It was great having everything that a typical kitchen would have at your convenience. The views were gorgeous and were really enjoyable when relaxing in the hot tub. Our three boys loved the kids room and that there were toys to play with. The location made our Vermont stay all that much more enjoyable, thank you for the great memories!

My friends and I had a great time at this place! The home was beautiful and very spacious - we were able to all hang out in the hot tub, kitchen, living room, and no place felt cramped.

My friends and I had a great stay at Jennifer’s home. We wanted a winter escape from the city and got exactly that! Jennifer was super friendly and communicative and left no questions unanswered. The home was so welcoming and cozy and had everything we needed for a fun weekend.

This rental was perfect for our family’s overnight ski trip to Okemo. We have two teenaged sons who shared a bedroom. The kitchen had everything we needed to cook breakfast and (most importantly) to meet the AM caffeine needs. The rental was approximately 10 minutes away from Okemo, which was the best part for us. Already planning next February’s ski trip!

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

We had a fantastic stay at Phils place. The airbnb was spotless and incredibly well outfitted. It is a short 3 minute walk to the Amtrak station and local free transportation, plenty of restaurants, bowling, art galleries, the public library and movie theatre. We found the wifi and t.v to be easy to use and nice to have once settled in for the night. We hope to return one day soon.

Sam is a friendly, generous, helpful host! He and his family live upstairs in this fun, modern building; the apartment is on the ground floor/daylight basement, but the house sits on a steep hill so the unit has plenty of natural light and does not feel like a basement. The separate entrance is located at the far end of the structure so it feels like a standalone unit with plenty of privacy. The neighborhood rises steeply from downtown Woodstock, up narrow, steep, windy roads. The streets were pretty consistently plowed, but drive slowly and cautiously, especially with snow. Also, like Sam says, don't just enter the address into Google Maps; it will try to take you elsewhere through someone's house and yard (haha!) Instead, follow Sam's directions. We loved the casual, yet carefully curated decor and found the bedroom super cozy with the most comfortable bed and linens. Our favorite was going on a cross-country ski adventure right out the back! Thank you, Sam, for a great stay!

Dick and Dorothy are some of the most lovely, hospitable folks we have ever met and we feel so lucky to have gotten to know them through our extended stays at their apartment for the the last 5 winters. Hancock is a truly special community and the apartment is an excellent choice for anyone looking to visit the area. It is conveniently located, well-stocked, and delightfully quaint. We are already excited to return!

This was such an amazing Airbnb to stay at for our weekend ski trip to Okemo. The location is perfect, less than 5 minutes from everything (Okemo, great restaurants, grocery store etc). Brandon is an incredibly friendly host who checked in with us multiple times throughout our stay to ensure everything was going well! I have nothing but great things to say about this Airbnb and would 100% stay here again for another trip as well as recommend to anyone looking to explore the Ludlow area!

We enjoyed our stay at this cute apartment. Easy check in, a porch to sit on, lots of decorative touches and lots of space to spread out. It was so convenient to be able to walk into town. A bit of traffic/train noise since it’s closer into the center of things bet so worth it.

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 Lauren's beautiful home, and it certainly won’t be our last! The location is absolutely perfect—right on the mountain, making it incredibly convenient! The condo itself is beautifully appointed and stocked with everything you could possibly need for a comfortable stay. One of our favorite features was the wood-burning fireplace, which added a wonderful touch to our evenings after a long day on the slopes. Lauren is a gracious host, always attentive and ready to help with anything we needed. We recommend her place to all our family and friends and look forward to returning next year for more unforgettable memories! Thank you, Lauren, for another fantastic stay!

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 for our ski weekend! Spacious, clean, super comfortable beds, kitchen had everything needed, even spices! close easy drive to slopes! Great host- it was easy to communicate, we felt really welcome in this beautiful place! Would love to come back again and again!

Very clean, cozy and spacious place to stay. Well-equipped kitchen, clean bed sheets and towels. Very easy access to Killington ski resort Ramshead Base. Tina is a great host!! I would recommend this apartment!

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 wanted to take my 3 children on a ski trip as a single mom. The location and Blaine's communication and clear instructions made it a seamless trip. The condo is right at Pico Mountain and just a short 10-15 minute car ride to Killington, with lots of restaurant choices close by. The condo is beautifully decorated and made it a cozy space to relax after spending a day on the mountains. The location made it such an easy ski trip that I would definitely stay longer next time!

Dray was thorough and the airbnb was clean, comfortable, and close to everything! I hope to stay here next time I visit!

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.