Family-friendly holiday rentals in Chester

Nice place thanks Mike

Stop scrolling, you found your next vacation. Bob is a fantastic host with a stunning home. We have stayed with Bob many times and he continues to invest in the property and ensures your stay is nothing short of fantastic. Cannot recommend the ski chalet enough.

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

We had a wonderful stay! It's such a beautiful and unusual cabin. It would be great for two couples as there are 2 equally great bedrooms that are quite separate, and a very nice sitting area around the amazing wood stove. (Which we didn't use because it's June and not necessary.) The hot tub was such a treat, and the bedroom with the boat was so cool. (OK, so maybe the bedrooms aren't quite equally great.) The kitchen is outstanding! We sat out on the porch a lot looking over the meadow, and I really liked that we were able to bring our dog. About the notes and instructions: they didn't bother us at all. There's a few non-intuitive features of the cabin, and it was useful to have clear guidance on those things. I want to make clear why I gave 4 stars for "cleanliness". I think they do an excellent job cleaning this cabin! But a rustic cabin like this is impossible to make "5-star clean". If you want or need that level of cleanliness, then "rustic" isn't for you! Go find a nice hotel.

We could not have found a better home for our Killington ski week. The ski in ski out directions were perfect and so easy. The home comfortably accommodated 8 adults and provided privacy for each of us as well. Fabulous dining area for our family that provided many happy memories. We've never rented a home where every single bed was so luxurious either. Each night we slept so soundly. On days we did not ski there was plenty to do at the house, a beautiful neighborhood to walk in and such close proximity to Killington Rd with so many dining options.

Had an awesome weekend here with the family! The cabin had everything we needed, super comfy and well-stocked. The hot tub was a huge bonus, and the hosts were super friendly. Would definitely come back!

My wife and I have visited twice already and hope to go back again soon. We met the owner and her wonderful fiancé while we were visiting. Wonderful people. Very private and beautiful location. If you need to unwind and relax this is the location for you. Thank you for hosting us and congratulations..

We stayed at Susan place for 4 nights for a family member graduation it was amazing stay, we live in the city so being out in the woods with surrounding nature it was beautiful spot. Will definitely come back to stay next time.

Really lovely Airbnb in a beautiful location! I came with my dogs and they were right at home. This spot was truly a dog friendly location. They even provided dog bowls and beds! There was also a ton of room to run and play with them. You really can’t beat the location and view if you want to get away. I love that there are chairs both on the patio and in the lawn to enjoy the view. My husband and I were looking for a place to truly check out and get away from work and this was the perfect spot for that. The bed and couches were really comfy, the kitchen had all the basics and I love that there was a fireplace option, even if we didn’t need it. It rained a ton while we were there and the yard gets pretty soggy, so if you’re planning for outdoor playtime on a rainy day, bring your rainboots! 10/10 stay and we’re already talking about booking another weekend there.

Great host, great location. Very relaxing and close to many attractions. Loved watching all the birds coming into the yard

Heidi's place is a wonderful cabin in the woods with all you need to enjoy the nature in Vermont. Super peaceful and the property is well maintained. I would highly recommend staying here to enjoy your vacation!

Wonderful place with great family room with fireplace especially when your weather doesn’t cooperate. The house is well kept and the instructions for everything were placed all around where needed. Fenced yard was great for the dog. The bed in the master is super comfortable with great linens. Loved the house-would live in it in a heart beat. Plenty of games, air hockey table, darts and another game table…grill, firewood- even poop scoops for the dog! Well done!

This was the perfect place for a peaceful Vermont getaway! The house is unique and a great balance of historical farmhouse and modern comfort. Very clean and easy to use amenities. Would love to stay again!

It’s very well maintained and private. Everything was as in the pictures and it was a breeze to take care of.

It was a wonderful stay. Whether you’re just looking to relax or for a little adventure this stay offers it all. Even though it was a rainy stay they offer plenty of movies, books and games.

We have enjoyed Erin's cute cottage very much. It has everything you might need, plus the location is great. Would definitely return and recommend)

Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.

all around the house was so pretty! flowers and felt like you're in the middle of the forest, the house standing on a small hill and the only exit is through one driveway on a mini bridge, which is very cute and secluded. The only downside is sooooo many mosquitoes, but thats honestly everywhere especially if you're in the forest. This place gives off you're visiting your grandparents home, which felt very nice and refreshing especially since we're from a rowdy city.

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.

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!

The place was great, clean, nice bathrooms. The oven seemed like it wouldn't go up to temperature at one point so I messaged the host and they responded right away to get the maintenance folks over. But it turned out that it was just set to Celsius and I was able to look up how to change it online (Hold down the broil button!). There were PLENTY of towels/linens which was nice.

Great spot near the mountain. nice community pool and hot tub.

We enjoyed the stay. Good weather so did not need AC. Good thick towels.

Diana and family were amazing super friendly, accommodating and checked in on use through out. We arrived later than expected but Diana waited for us and showed us around the property. We even got to see her dogs, meet her family, met the horse on the property behind and great conversations with Diana. She made us feel right at home. She prepped the pool for us, left us some good snacks and offered lots of recommendations. When you visit check out the theater set up, it’s pretty cool with insane sound system and clear video. Comfortable beds and all around beautiful property. If you visit in the summer it is a little warm on the second floor but we cooled off in the pool and just made sure to turn the fans on. It was the perfect birthday trip, relaxing, private and homey. My family and I are already looking forward to the next trip. Thank you to Diana for everything and hope we can meet again! 100% recommend.