Top Cottages in Kendall County in 2026

A cityscape with a bridge over a river, a historic building with arches, and modern high-rise buildings.

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Our top choices for Kendall County cottages

Westmont Home w/ Hot Tub! Walk to Metra Station

Westmont

"Very upset with the communication of this rental. I booked this rental for a weekend getaway with the family. I received an email a couple of days ahead of the booking reminding me of my trip and that I was all set. Then on check in day, I realized that I needed the check in information. I sent a message through the app to the renter. The response was "it may take a few days for the property to get back with you" so I called the number on the response. The operator then tried to look up my...

Rick

Ottawa Cabin: Hot Tub, Wraparound Deck, Games

Ottawa

Peaceful Warrenville Home: 1 Mi to Herrick Lake!

Warrenville

House, 1 Queen Bed (Huck Finn) | Exterior

Huck Finn #26

Ottawa

House, 1 Queen Bed (Captain's Quarters) | Exterior

Captain`s Quarters - 179 Leeward Way, Cottage #6

Ottawa

Home w/ Office + Yard: 25 Mi to Downtown Chicago!

Glen Ellyn

Rural Seneca House w/ Yard Near I-80

Seneca

Maria

Private Plainfield Retreat w/ Gas Grill + Patio

Plainfield

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Top Kendall County Hotel Reviews

Hilton Chicago/Oak Brook Hills Resort & Conference Center

8/10 Good

"La chica que atiende la cafeteria , es muy grosera y pesada la forma como trata alos clientes , estoy sorprendida de sigue todabia ahi , el lugar es limpio todas las veces que hemos estado ahi lo hemos pasado exelente ."