1. USA
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  3. Portland
  4. Dock Square
  5. Winter Rental

Dock Square Winter Rentals & Holiday Homes

Discover winter rentals Dock Square - We found 354 exact matches

About Dock Square Winter Rental on SunSkiResorts

Planning a winter vacation in Dock Square? Discover 354 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Dock Square, ME 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 Dock Square start at US $901. The most popular properties in Dock Square 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 Dock Square, 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 Dock Square and unlock incredible deals.

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Frequently Asked Questions About Dock Square Winter Rentals

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

The average cost for winter rentals in Dock Square is $901 per night. SunSki has a wide list of great winter places to stay near Dock Square 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 Dock Square that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Dock Square on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Dock Square to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 354 private swimming pools or indoor pools accommodations near Dock Square along with other great amenities.

About 354 holiday rentals in Dock Square 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 Dock Square for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Dock Square with all the best amenities for your next trip.