Upper East Side Winter Rentals & Holiday Homes

Discover winter rentals Upper East Side - We found 180 exact matches

About Upper East Side Winter Rental on SunSkiResorts

Planning a winter vacation in Upper East Side? Discover 180 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Upper East Side, WI perfect for your seasonal escape. Our listings include private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments. SunSki's winter vacation homes feature top amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Winter accommodations in Upper East Side start at US $770. The most popular properties in Upper East Side include cabins, bungalows, and rental homes. Planning a snowboarding adventure? Explore our snowboard-friendly ski resorts, chalets, and cabins available for short-term or long-term stays. Whether it's a weekend getaway, monthly retreat, or an extended stay, SunSki ensures a memorable winter trip.

To book your winter vacation homes in Upper East Side, visit SunSki's filter option, enter your travel dates, narrow down your preferences, and choose from our extensive list of rentals hassle-free. Explore our interactive map to uncover all accommodations in or around Upper East Side and unlock incredible deals.

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Frequently Asked Questions About Upper East Side Winter Rentals

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

The average cost for winter rentals in Upper East Side is $770 per night. SunSki has a wide list of great winter places to stay near Upper East Side that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in Upper East Side that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Upper East Side on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Upper East Side to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 180 private swimming pools or indoor pools accommodations near Upper East Side along with other great amenities.

About 180 holiday rentals in Upper East Side boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in Upper East Side for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Upper East Side with all the best amenities for your next trip.