East Hampton Ski Chalets Rentals & Holiday Homes

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

• Mid-Century Home with Pool, Private Beach Access, and Long-Stay Summer Savings
• Charming East Hampton cottage w/pool, near Georgica beach
• The Roundtree, Amagansett
• 2026 Summer Rental Available in East Hampton. Private Bay Beach Community!
• East Hampton- Beautiful 4 Bedroom Home, Large Heated Pool, Private Backyard
• Perfect Mid-Century Private Waterfront East Hampton Retreat!
• Spacious Open Floor Plan on 1.5 Acresnn
• Beautiful East Hampton Home, Pets welcome
• East Hampton Village: Beautifully Renovated 3 Br Classic Cottage Walk To All
• Family Friendly Bright Home With Pool, Hot Tub, 1 Mile to Bay & Maidstone Beach

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

• Spectacular 5 acre secluded private gem
• Villa Chantal
• 2026 Summer Rental Available in East Hampton. Private Bay Beach Community!
• 434 on Main
• Beautiful East Hampton Retreat with Hot Tub and Pool!

Villa Bay 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 East Hampton.

At Villa Bay most of our ski chalets are perfect for families. Check out the complete list of ski chalets in East Hampton to find what works for you.

Yes, there are plenty self-catering family ski chalet in East Hampton that have hot tubs & other amenities.