Compare Cottages, Resorts, & Rentals in North Side, Illinois, USA
About North Side Vacation Rentals
There are over 1174 amazing vacation rentals available in North Side. Choose from a variety of options including villas, hotels, and other rental properties. Explore a vast selection of luxury amenities at unbeatable prices, providing you with the ideal spot for your next getaway. Life is Better at the Cottage with Vacation Cottage, where you can discover fantastic stays in North Side.
Vacation Cottage offers numerous last-minute deals on villas, hotels, and rentals, both near you and across the globe. Whether you need accommodations for a group or event, such as a hotel or vacation rental (including cabins and private luxury villas), let us assist you. With Vacation Cottage in North Side, you can easily compare options from multiple suppliers with just a click to find the perfect price point, amenities, and style of stay for you. Whether you're seeking group discounts, private pools, hot tubs, pet-friendly options, or spacious master suite bedrooms with open-air showers, you can find it all with Vacation Cottage vacation rentals, resorts, and Airbnb-style properties in North Side. The average size of places to stay near North Side is approximately 846.72 ft², with prices averaging US $443 per night.
Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in North Side. Prices listed often feature discounts compared to rack rates. Simply search for your destination and secure your ideal place to stay today.
Find Vacation Cottage Rentals in these Cities and Neighborhoods North Side, IL
Frequently Asked Questions About North Side?
What are the top cottages, summer homes, and lake houses in North Side?
- The Sono Chicago
- Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
- Single Family Home! Sleeps 8 Lincoln Park/Lakeview
- Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
- Amazing Lincoln Park Rowhouse - Perfect for Groups, Reunions and Cubs Games!
- North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
- Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
- Dramatic Wrigley Loft +PRIVATE Rooftop, Center of Wrigley, Ranked GUEST FAVORITE
- Roscoe Village- Only steps to cute shops & dining! Sleeps 4-6
- Trendy 2BR Apartment in Logan Square!
How many rentals, hotels, or resorts are available in North Side?
Vacation Cottage consistently updates its selection, offering a blend of new options alongside well-established accommodations in prime locations. Currently, there are over 1174 properties listed by Vacation Cottage in the North Side area for the year 2026, with this number increasing daily. By aggregating listings from various websites and travel providers, Vacation Cottage ensures a diverse array of choices for the best luxury stays in North Side.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Rental Cottages and Private Getaways in Chicago, Illinois | 1547 |
| Near North Side Rental Cottages and Private Getaways in Chicago, Illinois | 618 |
| River North Rental Cottages and Private Getaways in Chicago, Illinois | 331 |
| West Town Rental Cottages and Private Getaways in Chicago, Illinois | 307 |
| Lakeview Rental Cottages and Private Getaways in Chicago, Illinois | 267 |
| Lincoln Park Rental Cottages and Private Getaways in Chicago, Illinois | 155 |
| Logan Square Rental Cottages and Private Getaways in Chicago, Illinois | 88 |
| Lake View East Rental Cottages and Private Getaways in Chicago, Illinois | 79 |
| North Center Rental Cottages and Private Getaways in Chicago, Illinois | 69 |
| Old Town Rental Cottages and Private Getaways in Chicago, Illinois | 59 |
| Irving Park Rental Cottages and Private Getaways in Chicago, Illinois | 57 |
| Avondale Rental Cottages and Private Getaways in Chicago, Illinois | 55 |
| Wrigleyville Rental Cottages and Private Getaways in Chicago, Illinois | 49 |
| Wicker Park Rental Cottages and Private Getaways in Chicago, Illinois | 47 |
| Gold Coast Rental Cottages and Private Getaways in Chicago, Illinois | 37 |
| Uptown Rental Cottages and Private Getaways in Chicago, Illinois | 35 |
