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

Discover winter rentals Winchester-on-the-Severn - We found 256 exact matches

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

Planning on a winter vacation in Winchester-on-the-Severn? Discover 256 places to stay in Winchester-on-the-Severn, for those traveling with their family, friends, in groups, or for a wedding retreat.

At PickleTrip™, we have a wide range of listings for accommodations in Winchester-on-the-Severn, MD 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. PickleTrip™ winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Winchester-on-the-Severn winter accommodation starts at US $692, and the most popular properties in Winchester-on-the-Severn 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, PickleTrip will make your winter trip memorable.

PickleTrip™ offers a great deal for travelers planning on renting a place in Winchester-on-the-Severn, to enjoy these benefits and to book your winter vacation homes, go to PickleTrip™ 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 Winchester-on-the-Severn and unlock even more amazing 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 $692 per night. PickleTrip 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 PickleTrip

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 PickleTrip shows that there are over 256 private swimming pools or indoor pools accommodations near Winchester-on-the-Severn along with other great amenities.

About 256 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.