Long Island Ski Chalets Rentals & Holiday Homes

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

• WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
• Fabulous Waterfront Property in the Heart of Wine Country
• Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
• Waterfront Cottage Perfection
• Stunning Beachfront Home ~ 5BR/3BA Family Friendly
• Beach House W/Short Walk to Ditch Plains Beach
• Private & Spacious Five Room Suite.Steps To Bay Beach and walk to Village.
• Montauk House with Lake View
• Charming, Convenient & Spacious 2BR Carroll Gardens Brownstone
• Lovely North Fork Beach Cottage (2 BR/2 bath)!

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

• Spectacular 5 acre secluded private gem
• Hamptons retreat w/ hot tub + loft only minutes to the beach
• 3 bed, 3 full bath, beachfront, AMAZING views, fireplace
• Summer 2026 Now Available! Grab an Amazing Property in the Heart of the Hamptons
• Separate big room near JFK and LaGuardia airport
• Cozy Cottage
• 2026 Summer Rental Available in East Hampton. Private Bay Beach Community!

Selectvacationvillas 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 Long Island.

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

Yes, there are 3 self-catering family ski chalet in Long Island that have hot tubs & other amenities.