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Penn Yan Winter Rentals & Holiday Homes

Discover winter rentals Penn Yan - We found 266 exact matches

About Penn Yan Winter Rental on Rent By Owner

Planning on a winter vacation in Penn Yan? Discover 266 places to stay in Penn Yan, for those traveling with their family, friends, in groups, or for a wedding retreat.

At Rent By Owner, we have a wide range of listings for accommodations in Penn Yan, NY that are perfect for your winter trip or seasonal escape. Our listings have private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that you would love. RBO winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Penn Yan winter accommodation starts at GB £374, and the most popular properties in Penn Yan are cabins, bungalows, and rental homes by owner. Planning snowboarding on your next winter vacation? We have many snowboard-friendly ski resorts, chalets, and cabins that are available for you to rent. These rentals are available for both short-term stays and long-term stays, whether you are traveling for a weekend, monthly, or a longer stay, RBO will make your winter trip memorable.

Rent By Owner offers a great deal for travelers planning on renting a place in Penn Yan, to enjoy these benefits and to book your winter vacation homes, go to RBO filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of our winter vacation rentals without hassle. Our interactive map is also available, to view all places to stay in or around Penn Yan and unlock even more amazing deals.

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Frequently Asked Questions About Penn Yan Winter Rentals

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

The average cost for winter rentals in Penn Yan is $502 per night. RBO has a wide list of great winter places to stay near Penn Yan 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 Penn Yan that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Penn Yan on Rent By Owner

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Penn Yan to find what works for you.
As of 2025, the data from Rent By Owner shows that there are over 266 private swimming pools or indoor pools accommodations near Penn Yan along with other great amenities.