Windsor Ski Chalets Rentals & Holiday Homes

There are a lot of options in Windsor. If you plan on staying in the Windsor 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 Windsor:

• Highland Lake Waterfront home perfect for family, fun, outdoors, and S’Mores!
• 2 Mi to Boat Ramp: Log Cabin in New Hampshire
• Gorgeous 4-bedroom house with WiFi in charming Stoddard
• Lakefront Cabin/314` Shoreline
• Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
• Lakefront Log Cabin on 2 acres
• Lakefront Ski Log Cabin on 2 acres
• Lakeside Retreat 2hrs from Boston
• Charming Cottage On Highland Lake
• Pristine Waterfront, Charming Home, Breathtaking Views

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

• Direct Waterfront, Year-Round, A-Frame Cabin
• Highland Haus- Cozy 1975 Aframe Cabin- short walk to lake
• Highland Lake Waterfront home perfect for family, fun, outdoors, and S’Mores!
• Lakefront Log Cabin on 2 acres
• 2 Mi to Boat Ramp: Log Cabin in New Hampshire
• Lakeside Retreat 2hrs from Boston

Longislandholidays 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 Windsor.

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

Yes, there are 2 self-catering family ski chalet in Windsor that have hot tubs & other amenities.