Winchester-on-the-Severn Winter Rentals & Holiday Homes

Discover winter rentals Winchester-on-the-Severn - We found 258 exact matches

About Winchester-on-the-Severn Winter Rental on SunSkiResorts

Planning a winter vacation in Winchester-on-the-Severn? Discover 258 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Winchester-on-the-Severn, MD 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 Winchester-on-the-Severn start at US $691. The most popular properties in Winchester-on-the-Severn 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 Winchester-on-the-Severn, 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 Winchester-on-the-Severn and unlock incredible deals.

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Frequently Asked Questions About Winchester-on-the-Severn Winter Rentals

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

The average cost for winter rentals in Winchester-on-the-Severn is $691 per night. SunSki has a wide list of great winter places to stay near Winchester-on-the-Severn 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 Winchester-on-the-Severn that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Winchester-on-the-Severn on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Winchester-on-the-Severn to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 258 private swimming pools or indoor pools accommodations near Winchester-on-the-Severn along with other great amenities.

About 258 holiday rentals in Winchester-on-the-Severn 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 Winchester-on-the-Severn for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Winchester-on-the-Severn with all the best amenities for your next trip.