Kid-friendly holiday rentals in Chester

Steal of a deal for this place. Perfect for any couple or family looking to do a vermont ski vacation. Has all the amenities you need, it’s super spacious, it’s right by town, and it’s a short drive to stratton or bromley. Easy 5 stars.

A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!

we enjoyed our stay and it met all our expectations.

It was a pleasure staying here ! Everything is clean and the house is such a nice size !

Absolutely incredible place! Tons of room, bathrooms for each bedroom was a big hit. Amazing location. Views were magnificent after 8 inches of snow and some freezing rain. Perfect excuse to not leave the house and enjoy the peaceful serenity over a nice margarita. Fall views must be totally awesome. Don’t need to bring anything except you, your friends and some food. The home has everything you need, all set and ready to go, and I mean everything you’ll need. The house manager Teri was an absolute peach. Her connection to the house and knowledge of the local history was amazing. 5 STARS doesn’t do this place justice. Already planning a return visit.

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!

This is a wonderful place to stay in Peterborough, NH. Lori is a great host and the place really feels like home. Definitely recommend and will try to get back there for sure?

It was a great two week stay.. I enjoyed being at this lake house. The lake is across the road, and pretty to look at on the balcony. The clear view of the lake walking and driving in the morning was very peaceful. His dock is the nicest in comparison to his neighbors. Kitchen was very well equipped, top notch washer and dryer, excellent lighting , beds and linens were comfortable, couch was large, easy to sprawl out and take a nap. Michael was available and easy to communicate. The high reviews are true, he cares and is thoughtful . I look forward in future stays .

Rachel was super quick to respond which was very helpful for me when last minute planning. In addition, I was traveling solo with my dog and she (and her super seeet dog)was sooooo nice to hang out with him when I had to go to my jobsite. The bedrooms are all super cozy, it was hard to pick one for the two nights I was there solo. The bed was very comfortable and a great night sleep away from home is hard to find. Love the natural light and the plants throughout. Made me feel right at home. Would stay again next time I’m in town for work!

Location can’t be beat! This is our second stay in one of Susan’s apartments and the basic needs — linens, dishes, tea etc—are well provided for. She has artful taste which we really appreciated. They also contacted us when we left a shirt behind. They are upfront about the smoke in the stairwell , but the smell does seep into the back bedroom a bit. Also, we were there in April but the building heat was still running. It took us a while to realize that is why it was so stifling hot. We ended up using the AC units to make it comfortable enough to sleep.

Great space, very conveniently located in town. The host was great, and would definitely stay here again

Our stay was in the cold of winter and there was ample heating in the form of radiators spread about, extra blankets, and a very powerful space heater in the living room. The artwork, furniture and layout gave a comfortable and cozy feeling. I stayed with two friends and we cooked all our meals easily with what was provided in the kitchen as far as pots, pans and utensils. During our stay John was extremely responsive and accommodating over the air bnb messages. The house is older so outlets were oddly placed with only two prongs, most of the lights were hand pull to turn on and off, and the bedroom doors locked with a hook and latch. It all felt very clean and comfortable and we were very happy with our stay.

Perfect stay for our short trip! Whitney is wonderful and so responsive!

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

This property is a very welcome getaway and we felt right at home. Thanks again! I'll be back again. 👍

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!

this condo is the perfect set up for our family! we had 3 adults staying, with a dog and a cat. there were three separate full bathrooms which helped a TON. everyone had their own area to wind down. we stayed for easter and were able to cook in the kitchen. Lyn was super responsive with any questions we had! we’re hoping to stay again next easter with Lyn!!

Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.

The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.

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!

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.

Great place to stay conveniently located by the mountain base! We enjoyed walking into the village after skiing. Very clean and cozy and had everything we needed and more. Dana was very responsive! Hope to come again next year!!

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.