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Philadelphia Winter Rentals & Holiday Homes

Discover winter rentals Philadelphia - We found 980 exact matches

About Philadelphia Winter Rental on SunSkiResorts

Planning a winter vacation in Philadelphia? Discover 980 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Philadelphia, PA 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 Philadelphia start at US $322. The most popular properties in Philadelphia 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 Philadelphia, 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 Philadelphia and unlock incredible deals.

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Frequently Asked Questions About Philadelphia Winter Rentals

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

The average cost for winter rentals in Philadelphia is $322 per night. SunSki has a wide list of great winter places to stay near Philadelphia 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 Philadelphia that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Philadelphia on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Philadelphia to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 980 private swimming pools or indoor pools accommodations near Philadelphia along with other great amenities.

About 980 holiday rentals in Philadelphia 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 Philadelphia for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Philadelphia with all the best amenities for your next trip.