
Ski-in/Ski-out holiday rentals in Rutland County
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Top-rated ski-in/out rentals in Rutland County
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Ski-in/out house rentals

Stay at our renovated Okemo chalet
Wonderful house for our ski trip to Okemo! We are glad we saw a reviewer who also mentioned that there is a fun sledding hill in the yard for our kids, so we packed our sleds and they had a blast sledding after we finished skiing! We are also glad we noticed a few reviews who explained that it was not technically ski in/ski out but rather a short walk to the mountain so we knew what to expect. The driveway/road was rather icy when we went so we opted to do the short drive to get to the base of the mountain instead. Overall, we really enjoyed staying here and it was an extremely convenient location for our trip to Okemo mountain!

Golf, Bike, Fish, or Hike!
Ashley was super friendly and responsive and her place was as described with everything I need and more to make me feel right at home. Would love to stay here again. Thank you so much for letting us stay at your beautiful place!

Killington Condo Near Mountain Biking Trails
Awesome spot. Stayed off season for an event at Pico. Plenty of space for four adults. Colby was great to work with.

Ski-In/Ski-Out Hike Okemo Mountain Condo
Words can’t describe the experience we had this weekend. Linda was the best host we have ever worked with and the place was extraordinary to say the least! Extremely clean, comfortable and well located! Kid friendly and close to downtown! We will highly recommend it to friends and family and if we could leave more stars than a 5-star review we would! Looking forward to booking this place again in the near future! Thank you Linda for your amazing hospitality!

Ski On/Off Sunrise at Killington
We had a great weekend at Liz's place! The place is super cozy and had everything we needed. It's really spacious and loved all the decorations. They also have a bunch of board games which was fun with the fam. It was really clean and I felt right at home. I'd love to come back in the future! Skiing in an out is totally doable but a little difficult to find your way back if you're not familiar with the sunrise condos. Keep in mind it's not directly on the Sun Dog trail so it was a tad more difficult starting with beginners from there. It ended up better for them to drive to snowshed. Overall would definitely recommend for a large family or bigger group. We had a blast. OH and fantastic DVD collection! Needed to add that in there. 😊

Okemo Condo – Ski In/Out
Great location - ski in/out! Close to Jackson Gore base and easy ski lift / drive access to Clock Tower base. Condo was perfect for our family of 4 with 2 kiddos, could accommodate more for sure. Well stocked kitchen. We enjoyed the kids board games! Very comfortable all around and good value for typical cost during winter ski season. Would definitely return!

Walk to Okemo Ski Lift - Private Classic VT Ski Ch
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.

Mountainside 5-BR Ski-In/Out Okemo Estate
Wonderful stay. Ski on ski off. Lots of games to play and puzzles to do. Skiing was great. Only note is to check with okemo on morning star triple to make sure it’s running. It doesn’t during the week. So you can ski off but not on. Weekend including Friday was perfect.
Family-friendly, ski-in/out home rentals

Come to Killington this summer!
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.

Slopeside condo at the base of Okemo-steps to lift
Loved Kristin’s place, the best part was that it was right on the mountain. Perfect for a family of 4, will definitely comeback. Beds were comfortable and the living room was very cozy. Loved the mural. Thank you Kristin!

THE CABIN....a Vermont log home
Bill's cabin was excellent. Rustic and rural but close to Killington and Pico, and a quick ride to Rutland. It was clean, comfy and had all we needed for a great little stay. It got a thumbs up from my wife and that is a high standard to meet. She even liked the king bed so much she was looking for the label to get one like it for home. I'm a guy and don't need much. The cabin made me feel like I was staying at a friend's house. You can nit-pick about the lighting and other minor stuff, but to me this place was a 10 out of 10 stars. We may be back next year for a longer ski vacation. Thanks Bill.

Right at Killington !
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!

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

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace
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!

Nicely decorated 2 bedroom Ski on/ski off L3
This was one of the best places we have ever stayed and perfect for a ski trip! It is the definition of ski in/ski out - right along the trail that takes you to a lift and easy to ski back to for lunch or at the end of the day. The beds were comfortable and the place fit our group of six very comfortably. We loved using the fireplace, and the kitchen was well stocked with cooking supplies to make full meals. We loved using the outdoor hot tub at the sports center (a 3 min drive away). When we called maintenance with a question on a Sunday, they were quick to respond and even brought us more paper towels and toilet paper. The place is very clean and updated (a previous review said that it wasn't and we felt the exact opposite). Please note: if the trail and lift that this condo skis on/off from are closed, the guests need to drive to a base. We got lucky with the weather and snow accumulations, but it is important to have this in mind. We will definitely stay at this condo again!

Cozy 3BR/2BA Chalet – Mins to Mtn & Biking Trails
Dray was thorough and the airbnb was clean, comfortable, and close to everything! I hope to stay here next time I visit!
Ski-in/out apartment rentals

Luxury Condo - with Garage Parking and Pool
Clean and updated condo. Great location. Short walk to snowshed and ramshead lifts.

2 BR/2BA Ski In/Ski Out Condo on Okemo- Sleeps 6
This was our second time staying at Lauren's beautiful home, and it certainly won’t be our last! The location is absolutely perfect—right on the mountain, making it incredibly convenient! The condo itself is beautifully appointed and stocked with everything you could possibly need for a comfortable stay. One of our favorite features was the wood-burning fireplace, which added a wonderful touch to our evenings after a long day on the slopes. Lauren is a gracious host, always attentive and ready to help with anything we needed. We recommend her place to all our family and friends and look forward to returning next year for more unforgettable memories! Thank you, Lauren, for another fantastic stay!

Ski Haven: 1-Bed Ski-in/out Condo, Okemo Base Area
Wonderful place with perfect location near slopes. Would definitely stay here again.

Mountain Vista 3-BR Haven at Jackson Gore Resort
Noah’s place on the mountain was amazing! Ski in and ski out was so convenient. The place was exactly as described and was beautiful. The beds were super comfortable and the house was extremely clean. The indoor parking was the best ! Noah was great through the whole communication process. I would definitely rent this place again and we plan to go back this year.! Absolutely a must stay if you’re going to Okemo!

1 BR Best Location w/ Pools/Massage Chair/Hottub!
The Condo Unit: The one bedroom was exactly what I needed. Great wifi and plenty of space. The Complex: Mountain Green is a gem. 10 minute walk to the slopes. Free shuttle. Amazing spa and fitness area- hot tub, steam room, sauna a& heated pool. Plus a very safe area. The Host: Andres was extremely easy to work with and very fast to respond. If anything came up, he was very quick to resolve the issue. What more can you ask?

Killington Mnt Escape Ski/Golf/Bike/Hike/Pool
It was a pleasure staying at Shirley's place for our last trip to Killington this season. The place was nice and clean, the kitchen had everything we needed to cook our meals, and the amenities in the building were great!

Cozy 1BR/1BA Mt Green Condo. Pool. Hot Tub. Bus.
Amazing spot. I feel at home as I write this review. I wound up book an additional night because it felt right. Thank you team!

1BR Ski-Home Pool/HotTb, Walk 2 Lifts, golf
Location was perfect! The weekend shuttle to Snowshed was very convenient and the trail to ski home was an easy way to get back. Also loved the spa amenities after a long day of skiing. Will definitely try to come back to this place for future visits!
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- Stratton Mountain
- Sugarbush Resort
- Okemo Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Pico Mountain Ski Resort
- West Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth Skiway
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Dorset Field Club
- Fort Ticonderoga
- Autumn Mountain Winery
- Lake George Expedition Park
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Hooper Golf Course
- Fox Run Golf Club
- Gooney Golf
- Adirondack Extreme Adventure Course
- Lincoln Peak Vineyard
- Killington Adventure Center
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