Discover winter rentals Essex - We found 98 exact matches
About Essex Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Essex, IL perfect for your winter retreat or seasonal escape. Our listings encompass hotels, private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, ensuring travelers find their ideal accommodation. Vacation Cottage's winter vacation homes boast premier amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you're seeking to escape the snow or embrace it, Vacation Cottage facilitates your connection to the finest cabins, bungalows, lodges, rent-by-owner homes, and the best accommodations in both sunny retreats and ski resorts. Vacation Cottage ensures your winter getaway becomes an unforgettable experience.
Vacation Cottage presents luxury options for travelers seeking to rent a place in Essex. To access these benefits and book your winter vacation home, simply utilize the Vacation Cottage filter option. Enter your travel dates, refine your search with filters for property type and amenities, then choose from our extensive list of exceptional winter vacation rentals hassle-free. Our interactive map further enhances your experience, allowing you to explore destinations worldwide or within Essex and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Essex Winter Rentals
What are the top rated Winter Rentals in Essex?
There are a lot of options in Essex. If you plan on staying in the Essex area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Essex:
- Gorgeous historic mansion on UChicago campus. Renovation with original detail.
- The Hyde Park Haven
- Gorgeous 4BDR in Chicago/15mins from DWTN Brand New!
- Cozy & Near Downtown, Hyde Park & the Metra
- Modern Townhome in the Heart of Hyde Park
- Luxe Loft vibe –4BR/3BA Apt– King Suite-11 minutes from downtown-Families-Groups
- Luxe Loft vibe with King Suite - 4BR 3Ba
- Beautiful 4 bedroom 2 bathroom apartment near everything
- Bedroom with private full bathroom, linen and towels are provided.
- Modern 3-bedroom 2.5 Bathroom house with Garage Parking and experienced host.
How much does it cost to rent a place to stay near Essex in the wintertime?
The average cost for winter rentals in Essex is $311 per night. Vacation Cottage has a wide list of great winter places to stay near Essex that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Essex that allow pets?
Yes, here are the top cottage/chalet rentals in Essex that allow you to bring your pet or dog:
- Fantastic 4-bedroom house 12 minutes away from downtown Chicago
- Beautiful 4 bedroom 2 bathroom apartment near everything
- Sophy Hyde Park
- Cozy & Near Downtown, Hyde Park & the Metra
See all pet-friendly vacation rentals in Essex on Vacation Cottage
Do you have any winter rentals in Essex that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Essex to find what works for you.
Are there winter accommodations in Essex that have indoor swimming pools?
As of 2025, the data from Vacation Cottage shows that there are over 98 private swimming pools or indoor pools accommodations near Essex along with other great amenities.
Do any winter holiday rentals in Essex have hot tubs?
About 98 holiday rentals in Essex boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Essex?
Yes, there are many luxury places to stay in Essex for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Essex with all the best amenities for your next trip.
