What are the top rated Winter Rentals in Roscoe Village?

There are a lot of options in Roscoe Village. If you plan on staying in the Roscoe Village area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Roscoe Village: NEW LUXURY PENTHOUSE CONDO NEW LUXURY CONDO WITH PATIO DECK Dramatic Wrigley Loft +PRIVATE Rooftop, Center of Wrigley, Ranked GUEST FAVORITE Stunning Lincoln Park Single-Family House with Fantastic Game Room Spacious 3 bedroom in ideal Roscoe village location The Bucktown House - Heart of Bucktown/Wicker Park, 10 Min Uber to Downtown Classic Chicago 2 Flat transformed into a Parisian plant lovers paradise Luxury Two-Level Townhouse | Patio | Lincoln Park Modern, Cozy & Chic 2 BR/1BA Apartment in Lincoln Square/Ravenswood, Chicago, IL Stunning 4-Bed 4-Bath Home - Prime Location OHare & Downtown

How much does it cost to rent a place to stay near Roscoe Village in the wintertime?

The average cost for winter rentals in Roscoe Village is $499 per night. Cabinns.com has a wide list of great winter places to stay near Roscoe Village that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Are there any winter cottages/chalets in Roscoe Village that allow pets?

Yes, here are the top cottage/chalet rentals in Roscoe Village that allow you to bring your pet or dog: Chic 3-Bedroom Condo in Lakeview Central. Private Rooftop, City & Ballpark Views Uptown Gem Wrigleyville Inn Furnished 2-Bed, 1.5-Bath Home – Old Irving Park – Perfect for Longer Stays! See all pet-friendly vacation rentals in Roscoe Village on Cabinns.com

Do you have any winter rentals in Roscoe Village that are suitable for families?

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Roscoe Village to find what works for you.

Are there winter accommodations in Roscoe Village that have indoor swimming pools?

As of 2025, the data from Cabinns.com shows that there are over 390 private swimming pools or indoor pools accommodations near Roscoe Village along with other great amenities.

Do any winter holiday rentals in Roscoe Village have hot tubs?

About 390 holiday rentals in Roscoe Village boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include: Roscoe Village Rentals with hot tub

Are there luxury winter rentals in Roscoe Village?

Yes, there are many luxury places to stay in Roscoe Village for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Roscoe Village with all the best amenities for your next trip.