Hudson Valley Ski Chalets Rentals & Holiday Homes

There are a lot of options in Hudson Valley. If you plan on staying in the Hudson Valley area, consider making a reservation for a few nights at one of these properties as these have been rated the top Ski Chalet Rentals in Hudson Valley:

• Romantic Luxury Chalet For 2
• Woodstock mountainside retreat, nicest view in the Catskills! RELAX!
• Exquisite Chalet by Ashokan water & Woodstock’s most scenic sites-WITH GENERATOR
• Beautifully decorated & immaculate log chalet on 3 acres, winter views.
• Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style
• Windham Log Cabin on 35 Acres. Family friendly.
• Chalet nestled right in Windham Mountain's quiet beauty-private access to trails
• Belleayre View: Paramount Views, Hot Tub + Firepit
• Cozy A FRAME ski retreat, walking distance into Hunter Mountain. New 2026 Rates
• Mountain Luxury: Pool, Theater & Outdoor Kitchen

There are many ski chalets available in Hudson Valley; however, here are the most popular ski chalets listed in Hudson Valley:

• Lakefront on the quiet side of main lake!
• Hudson Valley Farmhouse on 4 acres, pets allow
• Conveniently Secluded, 1 Mile From Slopes and Festivals
• Fantastic 2 family vacation home with EV charger

Vacationpirate offers availability throughout the year, but you can book pre-Christmas, mid-January, or before and after the school break at Easter are the best times for renting in Hudson Valley.

At Vacationpirate most of our ski chalets are perfect for families. Check out the complete list of ski chalets in Hudson Valley to find what works for you.

Yes, there are 201 self-catering family ski chalet in Hudson Valley that have hot tubs & other amenities.