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Annapolis Winter Rentals & Holiday Homes

Discover winter rentals Annapolis - We found 640 exact matches

About Annapolis Winter Rental on SunSkiResorts

Planning a winter vacation in Annapolis? Discover 640 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Annapolis, 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 Annapolis start at US $662. The most popular properties in Annapolis 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 Annapolis, 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 Annapolis and unlock incredible deals.

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Frequently Asked Questions About Annapolis Winter Rentals

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

The average cost for winter rentals in Annapolis is $662 per night. SunSki has a wide list of great winter places to stay near Annapolis 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 Annapolis that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Annapolis on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Annapolis to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 640 private swimming pools or indoor pools accommodations near Annapolis along with other great amenities.

About 640 holiday rentals in Annapolis 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 Annapolis for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Annapolis with all the best amenities for your next trip.