Bridgeport Winter Rentals & Holiday Homes

Discover winter rentals Bridgeport - We found 33 exact matches

About Bridgeport Winter Rental on SunSkiResorts

Planning a winter vacation in Bridgeport? Discover 33 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Bridgeport 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 Bridgeport start at US $120. The most popular properties in Bridgeport 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 Bridgeport, 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 Bridgeport and unlock incredible deals.

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Frequently Asked Questions About Bridgeport Winter Rentals

The average cost for winter rentals in Bridgeport is $120 per night. SunSki has a wide list of great winter places to stay near Bridgeport 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 Bridgeport that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Bridgeport on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Bridgeport to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 33 private swimming pools or indoor pools accommodations near Bridgeport along with other great amenities.

About 33 holiday rentals in Bridgeport 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 Bridgeport for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Bridgeport with all the best amenities for your next trip.