Location

Dates

Guests

Vacation rentals in Darien, Illinois, United States

Fab space for the whole group!

Fully stocked chef's kitchen

MFL 3 East

4 bedrooms·4 baths

Chicago • Illinois

4.99(93 reviews)

$3,160.34 USD $2,715.91 USD total for 3 nights

Sep 7 – 10, 2026

2BD/1 BA with summer patio in quiet Roscoe Village

2BD/1 BA with summer patio in quiet Roscoe Village

2BD/1 BA with summer patio in quiet Roscoe Village

2BD/1 BA with summer patio in quiet Roscoe Village

2BD/1 BA with summer patio in quiet Roscoe Village

2BD/1 BA with summer patio in quiet Roscoe Village

2 bedrooms·1 bath

Chicago • Illinois

4.97(98 reviews)

$763.56 USD total for 3 nights

Sep 21 – 24, 2026

4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 bedrooms·2 baths

Chicago • Illinois

$2,495.47 USD total for 3 nights

Sep 7 – 10, 2026

Charming Getaway in Homewood Near Chicago

Spacious Living Room, opened up to the Dining Room

Modern Fully Stocked Kitchen

Upstairs Living Room, off the Master Bedroom

Private workspace

Charming Getaway in Homewood Near Chicago

3 bedrooms·1½ baths

Homewood • Illinois

$777.00 USD total for 3 nights

Sep 7 – 10, 2026

Walk to Downtown! 6-Bedroom Home

Walk to Downtown! 6-Bedroom Home

Walk to Downtown! 6-Bedroom Home

Walk to Downtown! 6-Bedroom Home

Walk to Downtown! 6-Bedroom Home

Walk to Downtown! 6-Bedroom Home

6 bedrooms·3 baths

St. Charles • Illinois

$1,011.00 USD total for 3 nights

Sep 7 – 10, 2026

Arlington Heights Home

Arlington Heights Home

Arlington Heights Home

Arlington Heights Home

Arlington Heights Home

Arlington Heights Home

1 bedroom·1 bath

Arlington Heights • Illinois

$806.76 USD total for 3 nights

Sep 7 – 10, 2026

Cute 2 br with King and Queen

Cute 2 br with King and Queen

Cute 2 br with King and Queen

Cute 2 br with King and Queen

Cute 2 br with King and Queen

Cute 2 br with King and Queen

2 bedrooms·1 bath

Park Forest • Illinois

4.95(20 reviews)

$119 – $199/ night(excl. fees & taxes)

Workspace in the living room

Ashland

3 bedrooms·1 bath

Chicago • Illinois

Wind down under the cozy lighting at the end of your day. Relax in the hot tub or gather around the fire table.

Regulation size pickleball court with Sport Court surface is only shared with guests who book the Guest Quarters.

The LED lights on the corn hole boards can make playing in the evening more adventurous.

Warning! Playing these games may cause competitive natures to rise and may lead to tears and belly aches from too much laughing.

View down from the top of the stairs.Caution! Top step is more shallow than other steps.

Deer Run Log Cabin

3 bedrooms·2 baths

Yorkville • Illinois

$1,543.01 USD $1,459.86 USD total for 3 nights

Sep 7 – 10, 2026

Private deck with fire table, seating, BBQ grill, hot tub, and glowing café lights—perfect for relaxing nights outdoors.

The onsite pickleball court has a Sport Court surface and is shared with the guests in the Cabin. Deer frequently pass by the court.

Relax by the fire table in the gazebo.

The corn hole boards have LED lighting that make playing at dusk more exciting.

Shared Space: Bond and laugh over some board games.

Deer Run Guest Quarters

1 bedroom·1 bath

Yorkville • Illinois

5(1 review)

$998.28 USD $967.10 USD total for 3 nights

Sep 7 – 10, 2026

Regulation size pickleball court with Sport Court surface on site!

Unwind on the deck under the cafe lights or around the fire pit.

There is plenty of comfortable seating so everyone in your group can have a seat without crowding each other. There are even throw blankets and pillows for additional comfort.

Relax in the 7-person hot tub under the cafe lights at night.

Everyone in your group can sit around the table together as it seats up to 12 people. There are also 2 additional seats at the kitchen island..

Deer Run Lodge

4 bedrooms·3 baths

Yorkville • Illinois

5(1 review)

$2,688.30 USD $2,531.76 USD total for 3 nights

Sep 7 – 10, 2026

Chicago Lakefront · Fire Pit Patio · Beach Across image 1

Chicago Lakefront · Fire Pit Patio · Beach Across image 2

To the right: two plush couches and a large window. Opposite you: a mounted TV and a table with four chairs. To the right of the table is a corner desk with a lamp. A large rug anchors the center floor. Simple, clear, and easy to navigate.

Chicago Lakefront · Fire Pit Patio · Beach Across image 4

Chicago Lakefront · Fire Pit Patio · Beach Across image 5

Chicago Lakefront · Fire Pit Patio · Beach Across

1 bedroom·1 bath

Chicago • Illinois

5(1 review)

$447.00 USD $357.60 USD total for 3 nights

Sep 7 – 10, 2026

Master Bedroom 2nd floor

1500Main EVANSTON

1500Main EVANSTON

2 bedrooms·1½ baths

Evanston • Illinois

5(166 reviews)

$1,140.42 USD total for 4 nights

Nov 1 – 5, 2026

Free cancellation

Living Room with 65" TV

Living Room with 65" TV

Indoor Swim Spa

Charming Garden Retreat

5 bedrooms·3½ baths

Evanston • Illinois

$4,583.78 USD total for 3 nights

Sep 7 – 10, 2026

Family&Pet Friendly-No Stairs-Kingbeds-Peaceful. image 1

Gather, dine and unwind. Kids are welcome at the table too!

Cook , connect and savor meals ina space where modern kitchen meets no fuss chilling.

Dream in king sized comfort, along with the convenience of an ensuite

Unpack without having to reach for the floor with the luggage racks. Connect your laptop to the provided monitor for work with a corner desk and ergonomic chair.

Single-Family Home. Fully Furnished

3 bedrooms·2 baths

Minooka • Illinois

5(16 reviews)

$1,935.00 USD total for 6 nights

Sep 7 – 13, 2026

Master Bedroom Second Floor

Family Room First Floor open to Loft Second Floor two story family room with skylights

Master Bedroom Second Floor

Kitchen First Floor

Beautiful spacious gem Oasis Manor 6 BR 4 1/2 BA

6 bedrooms·4 baths

East Dundee • Illinois

5(9 reviews)

$800 – $835/ night(excl. fees & taxes)