Pleasant Springs Winter Rentals & Holiday Homes

Discover winter rentals Pleasant Springs - We found 24 exact matches

About Pleasant Springs Winter Rental on Rent By Owner

Planning on a winter vacation in Pleasant Springs? Discover 24 places to stay in Pleasant Springs, 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 Pleasant Springs, WI 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.

Pleasant Springs winter accommodation starts at US $363, and the most popular properties in Pleasant Springs 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 Pleasant Springs, 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 Pleasant Springs and unlock even more amazing deals.

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Pleasant Springs Winter Rental Frequently Asked Questions

The average cost for winter rentals in Pleasant Springs is $363 per night. RBO has a wide list of great winter places to stay near Pleasant Springs 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 Pleasant Springs that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Pleasant Springs on Rent By Owner

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Pleasant Springs to find what works for you.
As of 2026, the data from Rent By Owner shows that there are over 24 private swimming pools or indoor pools accommodations near Pleasant Springs along with other great amenities.

About 24 holiday rentals in Pleasant Springs boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include: