Skip to content

Vacation rentals in Kendall County

Find and book unique accommodations on Airbnb

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 Oswego
Friendly, Clean and Quiet, Room A Queen bed
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.
$43 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

Other great vacation rentals in Kendall County

Private room in Montgomery
Private Room with Closet
$41 per night
SUPERHOST
Rental unit in Oswego
Rustic Studio Apt. 2 min drive to Downtown Oswego
$62 per night
SUPERHOST
Rental unit in Oswego
No Stairs Rustic Farmhouse APT King Beds/Fast WIFI
$107 per night
SUPERHOST
Townhouse in Yorkville
Riverfront Townhome in Downtown Yorkville
$93 per night
SUPERHOST
Home in Montgomery
Nice, Private Ranch Home
$85 per night
SUPERHOST
Rental unit in Oswego
Convenient Studio Apartment in Oswego | Fast WIFI
$71 per night
Home in Yorkville
Patriotic Cottage on the Hill
$145 per night
SUPERHOST
Townhouse in Yorkville
Beachy Vibes Sleeps 10 Near White Water Rapids
$100 per night
Guesthouse in Oswego
The Loft-Rustic Retreat and Sauna
$165 per night
SUPERHOST
Guest suite in Montgomery
STUDIO BY THE FOX RIVER/ Beautiful Basement Studio
$80 per night
SUPERHOST
Home in Oswego
Cozy 4-bedroom ranch - minutes from everything
$185 per night
Home in Oswego
Cheerful house with hot jacuzzi bathroom
$193 per night