Kid-friendly holiday rentals in Chester

Really nice peaceful place to stay. Was super clean and a most interesting house with many antiques, brought back many memories from childhood. Host was very responsive and very friendly. Would definitely stay there again!

This was truly an oasis for me and my family during our stay in beautiful Vermont. Collin was an excellent host and was accommodating during my entire stay. It is a large beautiful farm house with the antique charm but updated amenities. My children enjoyed the hot tub and the large outdoor area while I had the space to cook some excellent meals. The town is just lovely with friendly people everywhere you go. I highly recommend Smitty’s for a local small grocery store. Our host Collin even gave us a gift card to a local pizza place that is superb. I will certainly stay again!

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!

The Grafton house was perfect for our multi-family with the big space, bedrooms, and bathrooms. We loved the living room area where we could all sit together for family games. The property and house are beautiful and the perfect Vermont vibes. As a skiing family, we liked the location between our favorite ski resorts. Raphael was a wonderful host in providing instructions before our arrival and helpful advice. We really enjoyed our stay at the Gafton house.

Loved our stay! Everything was cozy and easy; no issues at all. The heated bathroom floor ended up being one of our favorite parts (so nice!), and the whole place just felt super relaxing. Didn’t need to contact the host because everything was smooth from start to finish. Would definitely come back!

Great stay! The Chalet is nice and secluded. A Great way to getaway with friends and/or family. The size of the stay is great for those looking to spend time intimately. Everything you see is what you get. There were no complaints with our stay and that is why it deserves a 5 ⭐️. The hosts are kind enough to have had firewood available for use of the fire pit. The hosts were both hospitable and responsive. I hope to stay there again maybe in the winter to go skiing or snowboarding. The towns of Ludlow and Springfield are roughly 15 minutes away in their respective directions with tons of dining options and activities. New England Cider donuts is right on Main St. in Ludlow which is a great spot for breakfast sandwiches and pastries. Okemo Mountain is a great hiking experience also found in Ludlow. If you find yourself looking for a quiet and peaceful getaway, don’t give it a second thought and just book this place you won’t regret it!

We loved staying at this cozy home. It had beautiful grounds and we enjoyed sledding and walking around thoroughly and made a cozy fire to warm up after being outdoors. The hosts left fresh eggs, milk, coffee and other treats. Overall it was an excellent experience.

Amazing view, great and comfy Airbnb. The hot tub is such a nice plus with the incredible view over the mountains. It was so well equipped we had most of our meals in the Airbnb because the kitchen was so functional. I highly recommend this Airbnb!

Great apartment with privacy and ample space. Clean, tidy, lots of natural light. Great hosts! Very responsive and helpful but also absolutely unobtrusive. Would definitely stay here again.

Nancy's place was a great place to stay, very private and quiet with beautiful surroundings. Easy access to Quechee and Woodstock (~20 min). Skunk Hallow Pub and Farmer's Market just down the street and Harpoon, Simon Pearce factory in Windsor easy to get to. Hope to visit again soon. Nancy's is a fantastic host!

Exceptional! Dave and Donna are the best! Beautiful property! Immaculate! Friendly. Beyond highest rating we can give. We will be back! Thank you for everything!

Cute room above the brewery was a nice get away for my wife, our little dog, and I. John was friendly and so were all of the other employees and guests. The Irish band was great and the patio by the brewery was very cozy the beers were also delicious too. The room itself was spacious and well furnished with a good size bed and additional day bed. Fun weekend get away for all ages.

We had an exceptional stay at this Airbnb! It was perfect for two people with plenty of room. It was so cozy. We loved the Vermont specific decor. The ingredients for pancakes and the basic ingredients in the fridge were a thoughtful touch. I could not recommend staying here more!!!

The getaway apartment was just as described. Peaceful, private, and with ample space and amenities for a family of three. We enjoyed our weekend!

Really great, efficient, comfortable lodging on a residential street but in good walking distance to restaurants, coop, and shops downtown. Very easy to find and easy instructions, good communication, all around great place to stay, especially given the reasonable rate! Will return!

Easy access to downtown Ludlow! We loved the walkable amenities in the area. Loads of good restaurants and amazing views right outside the building! We thought this AirBnb was super cute and practical for a family with young kids. Extremely clean and well set up! Parking out front was extremely easy to access for quick check in/ check out. We message Wendi with questions and she got back to us super fast and was understanding when we didn’t message right back because of poor reception where we were hiking.

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.

⭐️⭐️⭐️⭐️⭐️ 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!

Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.

Claudia was super responsive and the place was amazing!! Within 5 minutes of a lot of great restaurants and very close to great hiking trails. Would love to come back again!

Such an amazing place. Great location for walking to restaurant. Breath taking views especially the river. Extremely homey feel. We will definitely be back. thank you for your hospitality.

We are repeat visitors. Staying here is always a pleasure. The apartment is wonderful. Just as described and perfect for day trips or just staying in. Mary and Lance are friendly and courteous. Hope to be able to stay here again when in the area.