What are the top rated Cottage Rentals in North Side?

There are a lot of options in North Side. If you plan on staying in the North Side area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in North Side: <a href="/property/the-sono-chicago/EP-12913775" class="class="static-page-link"">The Sono Chicago</a> <a href="/property/roscoe-village-inn-guesthouse-walk-to-chicago-s-wrigley-field/HA-321708795" class="class="static-page-link"">Roscoe Village Inn -Guesthouse - Walk to Chicago&#39;s Wrigley Field</a> <a href="/property/single-family-home-sleeps-8-lincoln-park-lakeview/HA-321885106" class="class="static-page-link"">Single Family Home! Sleeps 8 Lincoln Park/Lakeview</a> <a href="/property/lakeview-lincolnpark-2br-1ba-updated-vintage-apartment-in-walkable-neighborhood/HA-121343481" class="class="static-page-link"">Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood</a> <a href="/property/amazing-lincoln-park-rowhouse-perfect-for-groups-reunions-and-cubs-games/HA-321704920" class="class="static-page-link"">Amazing Lincoln Park Rowhouse - Perfect for Groups, Reunions and Cubs Games!</a> <a href="/property/north-center-modern-safe-family-friendly-solar-powered-apartment/HA-3211885535" class="class="static-page-link"">North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment</a> <a href="/property/wrigleyville-condo-sleeps-10-1-2-block-from-wrigley-field/HA-1214194027" class="class="static-page-link"">Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field</a> <a href="/property/dramatic-wrigley-loft-private-rooftop-center-of-wrigley-ranked-guest-favorite/HA-3211159084" class="class="static-page-link"">Dramatic Wrigley Loft +PRIVATE Rooftop, Center of Wrigley, Ranked GUEST FAVORITE</a> <a href="/property/roscoe-village-only-steps-to-cute-shops-dining-sleeps-4-6/HA-321429436" class="class="static-page-link"">Roscoe Village- Only steps to cute shops &amp; dining! Sleeps 4-6</a> <a href="/property/trendy-2br-apartment-in-logan-square/HA-3211952396" class="class="static-page-link"">Trendy 2BR Apartment in Logan Square!</a>

How much does it cost to rent a cottage in North Side?

The average cost for a cottage rental in North Side is $196 per night. Familyfriendlyvillas has a wide list of great cottages near North Side that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in North Side that allow pets?

Yes, here are the top cottage rentals in North Side that allow you to bring your pet: Private Cozy Cottage House in Lincoln Park w/Porch Classic Workers Cottage in Vibrant Bucktown Chicago. Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood Bright and Cozy 1BR Apartment in Logan Square! The Sono Chicago The Bucktown House - Heart of Bucktown/Wicker Park, 10 Min Uber to Downtown <a href="/all/usa/illinois/north-side" class="class="static-page-link"">See all pet-friendly vacation rentals in North Side on Familyfriendlyvillas</a>

Do you have any rental cottages in North Side that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in North Side to find one that works for you.

Are there quality cottages in North Side that have indoor swimming pools?

As of 2026, the data from Familyfriendlyvillas shows that there are Over 2 private swimming pools or cottages with indoor pools in the North Side area along with other great amenities.

North Side Cottage Rentals By Owner

Private Cozy Cottage House in Lincoln Park w/Porch

From US $157

10.0 (1 Review)

Cottage

Private Cozy Cottage House in Lincoln Park w/Porch

Air Conditioner
TV
Balcony/Terrace

North Side Cottage Rentals & Holiday Homes

Find the best cottages in North Side - We found 2 exact matches

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