Family-friendly holiday rentals in Rutland County

We had an issue with our previous rental and needed to find a place to stay that is pet friendly and available. Rad and Carol responded quickly to our reservation request. The house was made available to us early in the day and hot tub prepped last minute for us to enjoy! The Chalet is beautiful and spacious, the location is private and relaxing. The wood stove kept us warm and cozy while we enjoyed watching light snow fall. We would definitely stay there again and bring our family with us!

Our family had a wonderful stay at the condo in Killington. The location could not be beat! A very short 5 minute walk to the lifts and Snowshed lodge. The complex had an amenity building with pool/hot tub that the kids loved and the condo was quite spacious and clean. Ruslana was a great host and very responsive! There is a solid chance we will be back next year!

We are fishermen from CT who stay at Bob’s place every year. This place accommodates us comfortably. We are able to walk to restaurants and love the location. Bob is so proactive making our stay so easy. He always communicates well and responds quickly to our needs. Until next year.🎣

The hosts let me check in early and they were extremely responsive to any questions or concerns I had during my stay. The building and property were dated, however, no complaints on cleanliness. My only gripe, not huge, most of the TV remote batteries were dead and there was a light bulb missing from the over table light fixture, I ended up taking a bulb from one of the bedroom lamps. Keep in mind, my stay was right after 2 back to back weeks of school vacation. I’d recommend to anyone that is looking to be close to the mountain base and have access to a hot tub, steam room, pool, & sauna. Oh, there is also a pro shop in the main building! If I do Killington next year, I’d stay here again.

This is our second time renting Clinton's ski lodge place is great super host. Always responsive will be renting again next season.

This space was perfect for our family. With walking distance to the entrance of the slopes, this location was ideal for our ski getaway. I appreciated the small touches that made this experience feel luxurious, the provided coffee, wine, wood for the usable fire place. The beds were comfortable and the space was spacious. We would definitely visit Jim’s place again!

Great place to stay for okemo mountain!! Very close to local restaurants and the mountain

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!

A very clean, cozy, and comfortable home! We came to ski at Okemo and were pleased that the house is only about a 10 minute drive from the resort and the town of Ludlow where there are great restaurants and shops. The living area of the home is spacious and great for hanging out - there were tons of movies on DVD and video games to enjoy. The kitchen was well-equipped and perfect for cooking meals at home. The beds were comfy. Overall a wonderful stay! We hope to be back in the future.

Nice place thanks Mike

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

Very responsive host who went above and beyond to display hospitality. Clear instructions and let us enjoy the place in peace. Space itself was warm and inviting and perfect for a couple's weekend away.

We had a great time at David's place. The kitchen was well stocked, plenty of firewood, and the hot tub was ready to go. The house was very clean. All the bedrooms had plenty of linens, and extra blankets. We would definitely stay at David's again!

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 place to stay! The hot tub after a long day of snowboarding was amazing. Dean responds fast to any questions you have too. Definitely recommend

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.

Great stay. Location is prime, especially if you need some ski tuning at Black Dog Sports and want to be close to the mountain. Plenty of space and clean. Bed was a little firm but thats okay. Will be coming back in the future.

Convenient to the slopes via the shuttle that picks up out front. Able to walk to a good restaurant, Still on the Mountain. Place is comfortable and has everything we needed for a weekend skiing.

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.

WhiffleTree was exactly what we were looking for in a long weekend skiing//snowboarding at Killington. We were able to walk to the a base lodge and there is a ski home trail that’s right across the street. The fireplace was really nice after a cold day—we couldn’t figure out how to work it at first, so we called Killington group and they helped us and we had it on within 5 minutes. We mixed cooking at home for breakfast and getting takeout for dinner. Not much within walking distance but everything within 10min drive. Would definitely come back again.

Our family really enjoyed our stay at the trailside chalet! A quick walk up the road to the ski lifts and plenty to keep us entertained after a day of skiing. We really enjoyed the fire place and pool table!! Prescott was a great host, quick to respond to our questions.

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

Great place in ideal location

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.