Middletown Winter Rentals & Holiday Homes

Discover winter rentals Middletown - We found 19 exact matches

About Middletown Winter Rental on SunSkiResorts

Planning a winter vacation in Middletown? Discover 19 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Middletown, CT 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 Middletown start at US $346. The most popular properties in Middletown 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 Middletown, 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 Middletown and unlock incredible deals.

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Frequently Asked Questions About Middletown Winter Rentals

The average cost for winter rentals in Middletown is $346 per night. SunSki has a wide list of great winter places to stay near Middletown 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 Middletown that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Middletown on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Middletown to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 19 private swimming pools or indoor pools accommodations near Middletown along with other great amenities.

About 19 holiday rentals in Middletown 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 Middletown for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Middletown with all the best amenities for your next trip.