Window on the Sea Winter Rentals & Holiday Homes

Discover winter rentals Window on the Sea - We found 14 exact matches

About Window on the Sea Winter Rental on SunSkiResorts

Planning a winter vacation in Window on the Sea? Discover 14 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Window on the Sea 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 Window on the Sea start at US $200. The most popular properties in Window on the Sea 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 Window on the Sea, 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 Window on the Sea and unlock incredible deals.

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Frequently Asked Questions About Window on the Sea Winter Rentals

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

The average cost for winter rentals in Window on the Sea is $200 per night. SunSki has a wide list of great winter places to stay near Window on the Sea 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 Window on the Sea that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Window on the Sea on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Window on the Sea to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 14 private swimming pools or indoor pools accommodations near Window on the Sea along with other great amenities.

About 14 holiday rentals in Window on the Sea 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 Window on the Sea for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Window on the Sea with all the best amenities for your next trip.