Hamptons Ski Chalets Rentals & Holiday Homes

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

• WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
• Waterfront Cottage Perfection
• Beach House W/Short Walk to Ditch Plains Beach
• Montauk House with Lake View
• Private, Charming, Lovely Farmhouse in Wainscott, East Hampton
• Enjoy the beach, Fireplace , Hot Tub the wine ! July and August 5 day min
• Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!🏖️
• Relaxing Lake Retreat
• Luxury 9 Acre Sagaponack/Sag Harbor Compound Retreat & Year-Round Spa
• Waterfront, Pool, HotTub, Strong WIFI, Pingpong, Paddleboard, Kayak, Bocce Court

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

• Spectacular 5 acre secluded private gem
• Hamptons retreat w/ hot tub + loft only minutes to the beach
• Summer 2026 Now Available! Grab an Amazing Property in the Heart of the Hamptons
• Villa Red Hut
• 434 on Main
• 2026 Summer Rental Available in East Hampton. Private Bay Beach Community!

Old Mansions 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 Hamptons.

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

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