Vacation rentals in Kendall County

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Top-rated vacation rentals in Kendall County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest suite in Oswego

1 Bed w/ Full Kitchen A Mile From Downtown Oswego

Enjoy a stay within walking distance of 3 parks and about a mile from downtown Oswego and its quaint shopping area. Nestled in the middle of a great neighborhood, you'll feel safe and be able to enjoy a quick getaway or an extended stay. If you're interested in visiting Chicago, we're close enough for day trips to the city (about 45 miles) but far enough to save some money. You'll definitely have a great time here!

$70 per night

SUPERHOST

Private room in Montgomery

Private Room with Closet

Private room located in Montgomery. Close to shopping and many restaurants located on Route 34. 1.5 mile walk to the Fox River and several trails. This is a bi-level home I have owned for over four years. I have recently married and welcomed a baby boy into my life. My husband and I both have experience with short term rentals and have been hosting on Airbnb for over a year.

$42 per night

SUPERHOST

Private room in Oswego

King size bed, Large Room, Quiet, Clean

There is a walking trail behind the house that goes to the city park that has a playground, skate park, basketball courts, volleyball courts, softball fields, and a splash park in the summer.

$48 per night

SUPERHOST