Essex County Winter Rentals & Holiday Homes

Discover winter rentals Essex County - We found 857 exact matches

About Essex County Winter Rental on SunSkiResorts

Planning a winter vacation in Essex County? Discover 857 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Essex County, MA 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 Essex County start at $539. The most popular properties in Essex County 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 Essex County, 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 Essex County and unlock incredible deals.

Show more
Show less

Frequently Asked Questions About Essex County Winter Rentals

The average cost for winter rentals in Essex County is $539 per night. SunSki has a wide list of great winter places to stay near Essex County 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 Essex County that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Essex County on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Essex County to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 857 private swimming pools or indoor pools accommodations near Essex County along with other great amenities.

About 857 holiday rentals in Essex County 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 Essex County for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Essex County with all the best amenities for your next trip.