
Ski-in/Ski-out vacation rentals in Londonderry
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Top-rated ski-in/ski-out rentals in Londonderry
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Ski-in/ski-out house rentals

The Sugar House
Nice place, probably better in summer than winter, simply due to more amenities (like screened porch) and better able to appreciate the location, but it was nice as a winter spot, too, to sit and read by the fire. Kitchen was well-equipped, and the place was very clean.

Hot tub | Shuttle | Ski back home!
Four of us have stayed in 25 Vermont airbnb type places for ski trips in the last 35 years and this is one of the 5 best. The huge living room (comfortable even up to 8), the wood-burning fireplace, and the hot tub are the extra special features of the house. The backyard is very private and peaceful in case you plan to visit in the summer. There is a hawk nest within view of the hottub. Saying the kitchen is stocked with utensils is an understatement. We will return.

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!

Multi-Level Ski Retreat at Stratton Mountain
We had a wonderful stay Duojia’s residence! Peaceful location, clean, and the Stratton Mountain view was icing on the cake. There is privacy and so much space at this home. Thank you!

Summit View Ski and Golf Retreat w/hot tub & Sauna
We came up to celebrate a 40th birthday. Jason’s home was absolutely beautiful and exactly what we were looking for. We had a great time relaxing playing games and soaking in the hot tub. Pictures of Stratton Mountain do not do it justice, it’s so much closer in person and stunning. We loved the fireplace indoors and the outdoor fire pit. We had great weather so we were able to utilize the fire pit and then fireplace at night when it was chilly. Very cozy vibes! We would absolutely recommend this gem and would love to come back! Also, Pearl’s Place Southern Kitchen was delicious, get the bbq!

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.

MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts
Place was great! Less than 10 minutes to Mount Snow. We had fun playing ping-pong, air hokey, pool, and darts! Relaxed by the wood burning stove. Lots of rooms and beds.

Family Lodge at Jiminy Peak - Pools & Adventure
This is the second year we have stayed at Morgan’s home, and it is spacious, welcoming, clean, and very well equipped! This year we had much better conditions than last year (snow!) and walked down the road and skied right on to the mountain. It’s a few minutes, but is not any worse than trying to find a parking space when there are none and walking up all of those steps! It was awesome! Morgan is attentive and communicative and our large family absolutely love staying and can’t wait to come back!
Family-friendly, ski-in/ski-out home rentals

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!

Beautiful 2 Bedrooms in Mountains w/ full kitchen
Nancy is a responsive host who provides clear instructions and offers local recommendations. The apartment we stayed in worked perfectly for our ski weekend at mount snow with 2 teens. Plenty of room and amenities within to foster a fun and relaxed family weekend. The maple syrup for purchase was a delicious touch. Would definitely stay again if we returned to the area.

Killington Chalet - Hot Tub, Sauna, Boot Dryer
Nice space for a group, plenty of room for dining and relaxing. Clint was very responsive and gave excellent instructions. Appreciated the hospitality!

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

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

Sunset Bay: Amazing waterfront w/ dock on 5 acres!
We had an amazing stay! The house was wonderful - super clean, tons of space and gorgeous views of the river. Beth responded to all of my messages extremely quickly. She was easy to work with and very flexible and accommodating. I would definitely recommend this house to larger groups; the set up with lots of single beds was perfect for what we needed. There was also a basement full of games that would be just perfect for kids and families. Everyone who stayed would absolutely stay here again!

*Killington Summer Rental: 3 Bdrm, 2 Bth*
Dray was thorough and the airbnb was clean, comfortable, and close to everything! I hope to stay here next time I visit!

Large Chalet; Sauna, Hot Tub; Walk to Trail
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.
Ski-in/ski-out cabin rentals

‘Owls Nest’ nature retreat In the trees
I came up to the cabin for my birthday, and ended up having three more people than I thought I would - not only was Ashley super helpful and friendly in getting us set up, but she was extremely reasonable/flexible in pricing for the other guests! The cabin was more than enough to comfortably sleep everyone, and was nice and toasty when we woke up that morning. It was an amazing birthday, for sure because we choose such a great spot !!! I’ll definitely be coming back.

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.

The Cozy Little Red Cabin
Marinas little red cabin was perfect for our ski trip! The WiFi is a little rough but we didn’t spend much time on our phones Bring dvd’s (the collection is solid but more the better) Perfect distance to okemo, Stowe is less than two hours so it was great! The cabin felt so cozy and felt right at home! Would def book again!

400+ Airbnb Visits: Incredible Mountain Cabin
Excellent place to stay considering the location and and beautiful views. Owners were excellent, very helpful and did what ever they could to make our experience enjoyable!

The Run-In - Beautiful Country Cabin with Hot Tub
What a beautiful spot for some R&R! Had some days of rain, but still enjoyed the spot to the fullest! The run-in was perfect for me and my dog. It was cozy, the hot tub was perfect, and the sauna was not even a minute walk from the run-in. The piece of land is so peaceful, my dog and I enjoyed walking the space. The views are breath taking and the sound of nature is so peaceful. It was so easy to find, all amenities were working, the hosts were responsive to questions! Looking forward to coming back and exploring the other cabins!

Rustic charming camp cabin
Beautiful cabin in the woods , nestled at the foothills of the mountains, we went around Peak Foilage in early October and couldn't have asked for better weather and accomodations. Elizabeth, an excellent host, Reccomended some people hikes and look out points by the river, and surprised us with breakfast goodies on a Sunday morning!! Looking forward to be back and would definitely recommend to others as well

Green Mt Getaway: <30m to Bromley Stratton Okemo
Cliff is very easy to communicate with. The house is in a great location, easy to find, and close to several ski resorts, making it very convenient for skiing. The room is comfortable and warm, and the kitchen is well-equipped, allowing you to cook your own meals. The game room, in particular, is a paradise for children, with countless games for you to enjoy. This was a wonderful experience, and I will definitely come back in the future.

The Gourmet Cabin at Stitchdown Farm
Andrew’s place is one of a kind, a true escape from the mundane. If you’re looking for luxury and high-tech, this may not be the stay for you. If you’re looking for comfort, a disconnect from reality, and complete peace…. This is THE place! We are looking forward to coming back and checking out Babes Bar and seeing the flower farm while it’s active, we were just exhausted from our ski days to do anything besides enjoy the space.
Quick stats about vacation rentals that are ski-in ski-out in Londonderry
Total rentals
10 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
520 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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- Stratton Mountain
- Okemo Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Saratoga Race Course
- West Mountain Ski Resort
- Berkshire East Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Pineridge Cross Country Ski Area
- Ekwanok Country Club
- Hooper Golf Course
- The Shattuck Golf Club
- Lake George Expedition Park
- Baker Hill Golf Club
- National Museum of Racing and Hall of Fame
- Stump Sprouts Ski Touring Center
- Northern Cross Vineyard
- Clarksburg State Park
- Hildene, The Lincoln Family Home
- Dorset Field Club
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