
Ski-in/Ski-out vacation rentals in Windham County
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Top-rated ski-in/ski-out rentals in Windham County
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Ski-in/ski-out house rentals

Entire Craftsman House Rental
A spacious place with character, Rebecca's place had everything we needed, and she was an extremely attentive host. Quiet neighborhood. Being close to I-91 made Rebecca's house an excellent jumping off point for day trips to various places in Vermont.

The Mountain Escape
Great space! We were comfortable with a big group here, and loved being so close to the slopes. Hot tub seems new and is in great condition.

Private chalet tucked in the green mountains
Liz's place was the great! Beautiful, clean, and conveniently located to the mountain. Everything we needed for a long ski weekend with friends! Thank you!

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!

Rustic home near skiing & lakes, walk to downtown
Very welcoming home, amenities were a great way to entertain ourselves during the night while kids were sleeping. The spacious living room, dining room and kitchen were an absolute dream! Would stay here again!

Modern Chalet: Magic Mountain
Tyler’s place exceeded expectations! The home was exactly as advertised—beautiful, spotless, and in a fantastic location. Check-in and check-out were seamless, making our stay even more enjoyable. Tyler was an outstanding host, incredibly responsive, and went above and beyond by providing detailed information and fantastic restaurant recommendations. I’d highly recommend staying here to anyone looking for a top-notch experience!

Brand new, 5 BR, next to Hermitage Club&Hermt Inn
We loved this house! And plan to come back again soon! Beautiful home with great amenities. Host was very responsive. We had a great visit!

Spring Getaway @ Mt Snow! Hike, Bike, Sleeps 8.
We had such a great time staying here! The house was so cozy and clean and was perfect! Felt like being at home and not staying in an Airbnb. Super close to the mountain, especially if you park in carinthia! Loved the guest book that they have in the kitchen, a fun added touch! Robert was extremely responsive to any messages and super accommodating with us and our needs! Absolutely would recommend staying here!!
Family-friendly, ski-in/ski-out home rentals

Beautiful Art Studio with hot tub/sauna #1 Airbnb
The cabin was beautiful and perfect for a getaway from the city! We loved watching the sunset from the hot tub and cooking in the beautiful kitchen.

Slopeside at MT Snow VT
Perfect location to get on and off the mountain. Responsive and helpful. We had a great weekend!

Mt. Snow, VT scenic views, 3decks
Great place! Clean, spacious, with plenty of amenities. Owner was great. Flexible. Communicated clearly and promptly. Would definitely stay again.

Summer or Winter Slope side on Bromley Mountain!
Talk about great location! This was the best ski-in/ski-out condo we've used. Bonus: the sledding hill is at the end of the parking lot. The beds were very comfortable and the fireplace was easy and so cozy. Corinne was very attentive and took care of any questions promptly.

Large tent platform at wood's edge
G’O was amazing! Very friendly and accommodating! Will definitely book next time I go visit my family! Her property is beautiful and peaceful, exactly what I was looking for.

Summer Living On Hillside Condo on Mount Snow
We had a nice getaway at Paul's place. The place fit our needs perfectly. We enjoyed the use of both the indoor and outdoor pool. You do need to reserve times online for use of the pools or other activities but we never had any issue with that. There are several great restaurants nearby and we enjoyed walking the nearby trails and shopping in Wilmington and Dover.

Stratton Mountain House
We stayed with four adults and two young children. The beds were great - we all had excellent separate spaces. The common room was spacious as was the dining area. It was easy to walk to the shuttle bus pick-up spot. Chris was so great to let us stay a bit later on Sunday to enable us to ski a bit and then organize ourselves for departure.

The Amos Brown House.
This is a really special antique house that has been very well cared for. we visited in the midst of pretty narly presidents dy snow storm and the howling winds and multiple feet of snow outside only made the old house feel even cozier and more special. in the winter, the house sits on the end of a dirt road, due to the southern portion of it being covered in snow so we were nervous that we would get completely snowed in, but the town plowed the road multiple times each day and we had no problems getting in and out! Our big highlights were cross country skiing on the trail that crosses the property, puzzling by the gas fireplace, and the huge mounds of dog toys for our pup! Also, big thank you to Michelle for being so accommodating about our late check out. Our time here makes me want to check out all of the landmark trusts locations!
Ski-in/ski-out condo rentals

Cozy 2BR Condo Walking Distance to Mount Snow
Think this is our third time staying at the condo and again it was great. Love being able to walk across the street to the mountain, renting equipment from Equip Sports is very convenient. In our opinion the condo has everything you need for a family of 4. Can’t wait until next year.

Cozy Mountain Condo - Let's Hike!
Laura's place was great. It was clean, right on Bromley Mountain (ski on and ski off), and a quick drive to Manchester. Laura was very responsive and helpful. Even sent me a youtube video to help with my technical challenges of working with two remotes for the Smart TV. I highly recommend this AIRBNB.

Slopes N Seasons | Trailside Condo at Mount Snow
This place is so welcoming and tasteful. Lots of in-house activities for the evening, when it's raining, or just when you feel like staying in. An easy recommendation.

Perfect 3 Br. Getaway Condo in Stratton, Vermont!
Lina was so responsive and helpful. Location could not have been more perfect. Such a lovely find! Thank you, Lina!

Ski In/Out, Cozy 3BR Condo steps to Village
Exactly as described. Beautiful condo, right in the heart of Stratton. Easy ski in/ski out. Excellent proximity to everything the village has to offer. The kitchen is well equipped and the bedrooms are really comfortable. Brian was a great host! We will absolutely book again for future Stratton ski trips!

Condo w/ great amenities 4-seasons! Ski in Ski out
Excellent location and central to all things fun in southern Vermont. Loved the sports center amenities. Very peaceful considering it was end of mud season and not busy at all. We used the pool, workout facilities and locker room. Even had a fireplace we could use ! Christine was incredibly responsive and welcoming. Would recommend to others and would stay again if in the area.

Cozy Condo-4 Minute Walk to Skiing at Mount Snow!
We had a great late season long ski weekend at Elizabeth’s condo at Mount Snow and would definitely recommend this place to others. It was clean and cozy and we had good communication with the host. The condo wasn’t the most renovated but it was clean and comfortable, had all of the desired amenities (dishwasher, washer/dryer, fireplace, good heating system, large comfy couch, and two full bedrooms and bathrooms with a third loft room) and had more than enough space for our group of four. We were able to easily walk in about 5 min to the Sundance parking lot and lift (only open during the weekend during our trip). Elizabeth sent some good restaurant recommendations as well. We hope to come back soon! Thank you for a great trip!

Stratton Duplex Condo Steps to Lifts, Village!
Great walkable location. Loft space granted nice privacy for 2 couples or extended family. Fireplace and living room were cozy.
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- The Shattuck Golf Club
- Dorset Field Club
- Baker Hill Golf Club
- Pineridge Cross Country Ski Area
- Clarksburg State Park
- Hildene, The Lincoln Family Home
- Ekwanok Country Club
- Brattleboro Ski Hill
- Hooper Golf Course
- Bretwood Golf Course
- Fox Run Golf Club