Kid-friendly holiday rentals in Windsor County

Adam and Nicole's house is wonderful! Great view, spacious, and so clean. We all felt very comfortable and cozy. Great amenities, and a nice deck that unfortunately we didn't get to enjoy because of the rainy weather! Still, we enjoyed our stay and didn't let the rain dampen our spirits. Hosts were both very responsive, no issues with check in. Highly recommend if you're looking for something off the beaten path and quiet, but close enough to restaurants and sight-seeing. Thumbs up for sure!

David was very friendly and responsive. We enjoyed the location and the peaceful atmosphere. I was with my sister. The stay was a great experience and felt well worth it. Just a note—one bedroom is accessed via a spiral staircase, another by a ladder, and there’s a sleeper couch in the living room. Would definitely recommend!

I booked this spot for my birthday/ mother & daughter getaway and was not disappointed! The views were great and the whole place was very relaxing. Angela was quick to respond to any questions that we had. We traveled with my 3 year old rescue dog and he had the time of his life. There was plenty of space for him to run around! We will certainly be back!

The barnbrook house was lovely, private and rustic. It had everything our family needed as a base to explore VT/NH. The mountain views are sublime and the house is tucked away offering a lot of privacy. As far as amenities, we loved the toy chest, darts board, and den. There’s plenty of space for a family and Dana stocked up the kitchen with coffee and tea. If you need to be in Hanover for events, this location is a 45 minute drive so keep that in mind when planning.

John's place was perfect for us to enjoy three days of much needed family time. We played games sitting in the living room with morning coffee or evening wine. We made some simple meals, cooked fiddle heads. The high speed internet helped my daughter to complete some work. We basically enjoyed the second spring there as the field around the house were filled with tulips.

I can only say wonderful things about this property! Everything was beautiful both inside and out. The house was very clean and organized and was also extremely well stocked. Anything that we needed we found in this house. And everyone in our group said the beds were very comfortable… which is very important to me! Erik was great with communication and very proactive. He sent us a note about a week before we checked in that had everything we needed to know; it was quite helpful. I highly recommend this home….and as an added bonus, the view is spectacular! You will not be disappointed if you stay here!

We loved our stay here!! It was the perfect getaway for a long weekend. The property is beautiful and private but close to anything that you might need. The kitchen was super well stocked, beds were comfy, and we really appreciated the firewood supply. Nikki & Topher were great hosts - extremely responsive to all questions we had and proactive about check in/check out instructions. Would definitely come back!

This is my second time staying at one of Jess’s properties - and I’m sure it’s not my last. The property is beautiful inside and out and has everything you need. I was in town for a full week and this place was just what I needed to relax after long work days. I can’t recommend staying at one of Jess’s places enough. You won’t regret it!!

Our second stay here was great, river was a little higher but we wanted a peaceful weekend with friends and dogs. Apartment was warm given the unseasonable cold weather and we had all the amenities we needed even dog towels for wet pups. Did not see the host during our stay but she was in contact as needed.

What a lovely and serene spot to spend a few days in the Mountains of Vermont! Loved waking up to views of horses in the field by the private deck and a breathtaking mountain view. The hosts were kind and communicative. The space was clean and had just the right amount of amenities. Definitely recommend and hope to stay again!

We absolutely loved our stay with Bob and Sherry. They were so kind and attentive on the app, providing recommendations and checking in frequently when the weather turned on us. Although we were technically in their home, it still felt very private. The apartment is beautifully done and I’m obsessed with the pine wood everywhere. We would absolutely return and cannot recommend this little place highly enough!

My college roommate and I had a really nice stay at Chelsea’s place — clean, quiet and easy to get to. I really enjoyed the screened in front porch. We came to the area for a King Arthur Flour 3-day class and it was really convenient for that. Also, plenty of options for eating out (both in Lebanon and nearby Hanover).

All was great. We were in for an event at Dartmouth (graduation!) and this place is very convenient to Hanover. Just a short drive up the road. That was wonderful. It was more spacious than we expected, which was great! Really, it's a full apartment with plenty of room and a great layout. It's well named; it is an old farmhouse, and as a result, squeaky, uneven floors, slanted ceilings, somewhat funky where things like showers were added, but it works great. All was super clean and working, beds were comfortable, noise from street minimal, and just perfect for us. A fantastic deal if you don't need a fancy new place. Thank you David! We will come again if we have the chance, but sadly, post-graduation, we might not! We recommend this place highly.

Place was will organized and thought

This was our second, month+ long, stay at Dick & Dorothy's place. It was perfect for the two of us. The internet was reliable with fast speeds which worked great for remote work with zero issues for video calls. They are great hosts and respond quickly to any questions. They apartment is only about 100 yards off of VT 100 and has easy parking which was plowed quickly after any snowfall. There are plenty of options for ski/snowboarding/XC in every direction! Thank you!

No surprises for us, the apartment was exactly as described by previous renters: spacious, clean, charmingly appointed, and situated in a lovely hillside location with a rear deck that invites residents to put their feet up and relax. Easy walk into Woodstock itself. Brenda and Clay are very friendly and helpful while also being unobtrusive People who take such pride in and care of their property are bound to be good folks.

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 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!!

⭐️⭐️⭐️⭐️⭐️ Perfect Father–Son Getaway at CozyCub! My son and I stayed one night at the CozyCub condo in Killington, and once again, Dan and Holly delivered a flawless experience. From the moment we arrived, everything was spotless, cozy, and thoughtfully arranged—exactly what we look for in a mountain bike trip base. Comfort & Cleanliness: The condo was pristine, with comfy beds and fresh linens—like a home away from home. Attention to Detail: Every essential was readily available, from kitchen basics to crisp towels. Perfect for a Duo: Ideal layout and amenities for just the two of us—no waste, just well-tailored space. Consistent Excellence: We’ve stayed with Dan and Holly before, and CozyCub continues to meet our high expectations. This stay earned a full five stars. Thanks again to Dan and Holly for providing the perfect retreat—we’ll be back for our next biking adventure together!