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

Newly renovated Ski house stratton mountain
Rented Joseph’s great place for me and my friends yearly Stratton trip. Awesome space, perfect location. Joseph was super responsive and helped us figure out the shuttle. We will definitely try to book his place next year!

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!

Mt Snow Townhouse - Ski On/Off
We had a great stay at Matthew's. he was so helpful getting us situated and settled in. The space has everything needed for a cozy winter stay. Perfect Family set up

A Family Place
Donald's place is awesome. About 15 minutes to Stratton. Easy to get to. You might need the all-wheel drive for the driveway during the snow season. If not, it's okay. The caretaker was responsive and helped us sand the driveway right away. The house itself is big enough for 12 people. The kitchen is well-equipped and the living room is lovely. We had a great time here. Will definitely visit again!

Serene getaway in the Vermont National Forrest
Great location, 30 min from MASSMOCA. Beautiful home and property. Lots of room. We had two families with kids and had a great time.

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!

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!
Family-friendly, ski-in/ski-out home rentals

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.

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.

Stone's Camp on Stamford Stream
This was our second stay at Stone's Camp. It was just as great as the first stay. It's very private, peaceful and relaxing. We enjoyed hiking around the area and never had to leave the property in our car during our 4 night stay. The walk from the camp down the abandoned road to the washout is perfect. Our dogs enjoyed being off leash and exploring the woods and stream. It was especially nice for our 15 yro dog who is now unable to tackle larger hikes. Nights were spent enjoying a campfire by the babbling stream on rain free nights. Rainy nights were spent playing cards and games around the table indoors. If you are looking for something quiet, private and love to be outside and away from it all this is the place for you. If you have dogs it's the place for them as well. Thank you again, Chuck, for sharing your piece of paradise and thanks for accommodating our daughter and her boyfriend at the last minute who surprised us with a visit from the West Coast. We hope to be back!

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!

Landgrove Charm - Post and Beam Barn House
Instantly honey. So many places are sterile. This home truly feels lived in. And, at once, you can feel at home. Well equipped for all of our needs (four adults, three children). Special mention to Matt, the caretaker, for being super responsive and on top of things. Wake up early to watch the bobolinks, or get comfortable on the porch in the afternoon to watch the hawks hunt. A perfect stay in every way
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.

Walk to Lift - 2 Bedroom Condo - Newly Renovated
This place is AWESOME hence why we have come back multiple times and plan to come back again. James is very responsive and his place is perfectly clean and orderly every time we stay. 10/10

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!
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Six Flags Great Escape Lodge & Indoor Water park
- Jiminy Peak Mountain Resort
- Pico Mountain Ski Resort
- Albany Center Gallery
- Stratton Mountain Resort
- West Mountain Ski Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Saratoga Spa State Park
- Berkshire East Mountain Resort
- Lake George Expedition Park
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Canterbury Farm
- Pineridge Cross Country Ski Area