6 bedroom! Pool Table, Gaming Area, Firepit & More image 1
6 bedroom! Pool Table, Gaming Area, Firepit & More image 2
6 bedroom! Pool Table, Gaming Area, Firepit & More image 3
6 bedroom! Pool Table, Gaming Area, Firepit & More image 4
6 bedroom! Pool Table, Gaming Area, Firepit & More image 5

6 bedroom! Pool Table, Gaming Area, Firepit & More

6 bedrooms·3 baths
Joliet • Illinois
4.92(24 reviews)

$2,390.00 USD total for 3 nights

Nov 2 – 5, 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

Nov 3 – 9, 2026

Make smores while you relax around a cozy fire!
Everything is within easy reach for the chef of the house.
Comfortable seating for eight.
For your convenience, there are hardwired ethernet connections in select spots on the main level.
Gaze at this unique Chicago skyline, handcrafted by the artist from scraps of wood.

NEW Comfy Suburban Chicago Oasis w/ River Access!

5 bedrooms·2½ baths
Bolingbrook • Illinois
5(8 reviews)

$1,948.66 USD $1,861.81 USD total for 3 nights

Nov 3 – 6, 2026

Spacious Home with 4 Full Baths
Spacious Home with 4 Full Baths
Spacious Home with 4 Full Baths
Spacious Home with 4 Full Baths
Spacious Home with 4 Full Baths

Spacious Home with 4 Full Baths

4 bedrooms·4 baths
Willowbrook • Illinois

$1,123.00 USD total for 3 nights

Nov 3 – 6, 2026

Front of the house
Entrance to the unit
Backyard
Bedroom 1
Bedroom 1

Middle Level of the House with Working Space

2 bedrooms·1 bath
Darien • Illinois
4.73(44 reviews)

$494.76 USD total for 4 nights

Nov 3 – 7, 2026

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

$2,112.80 USD $2,007.17 USD total for 3 nights

Nov 3 – 6, 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)

$1,066.65 USD $1,024.00 USD total for 3 nights

Nov 4 – 7, 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)

$3,339.01 USD $2,838.16 USD total for 3 nights

Nov 4 – 7, 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)
Modern Oasis in Glen Ellyn
Modern Oasis in Glen Ellyn
Modern Oasis in Glen Ellyn
Modern Oasis in Glen Ellyn
Modern Oasis in Glen Ellyn

Modern Oasis in Glen Ellyn

3 bedrooms·2½ baths
Glen Ellyn • Illinois

$2,920.00 USD total for 3 nights

Nov 3 – 6, 2026

Living Room
Dining Room
Kitchen
Family Room
Family Room

Ruby’s Retreat - 4BD/3BA+Office in Western Springs

4 bedrooms·3 baths
Western Springs • Illinois

$6,336.75 USD $5,755.58 USD total for 30 nights

Aug 28 – Sep 27, 2027

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

$706.00 USD total for 3 nights

Nov 3 – 6, 2026

Cozy Home Sleeps 10 Lombard Chicago Suburb
Cozy Home Sleeps 10 Lombard Chicago Suburb
Cozy Home Sleeps 10 Lombard Chicago Suburb
Cozy Home Sleeps 10 Lombard Chicago Suburb
Cozy Home Sleeps 10 Lombard Chicago Suburb

Cozy Home Sleeps 10 Lombard Chicago Suburb

3 bedrooms·2 baths
Lombard • Illinois

$915.96 USD total for 3 nights

Nov 3 – 6, 2026

Cozy Retreat Near Oakbrook Center
Cozy Retreat Near Oakbrook Center
Cozy Retreat Near Oakbrook Center
Cozy Retreat Near Oakbrook Center
Cozy Retreat Near Oakbrook Center

Cozy Retreat Near Oakbrook Center

4 bedrooms·2 baths
Oakbrook Terrace • Illinois

$917.00 USD total for 3 nights

Nov 9 – 12, 2026

Stylish & Comfy Stay • Close to Downtown
Stylish & Comfy Stay • Close to Downtown
Stylish & Comfy Stay • Close to Downtown
Stylish & Comfy Stay • Close to Downtown
Stylish & Comfy Stay • Close to Downtown

Stylish & Comfy Stay • Close to Downtown

2 bedrooms·1 bath
Chicago • Illinois

$2,913.05 USD total for 31 nights

Nov 3 – Dec 4, 2026

Chic & Cozy Chicago Stay • Close to Downtown
Chic & Cozy Chicago Stay • Close to Downtown
Chic & Cozy Chicago Stay • Close to Downtown
Chic & Cozy Chicago Stay • Close to Downtown
Chic & Cozy Chicago Stay • Close to Downtown

Chic & Cozy Chicago Stay • Close to Downtown

3 bedrooms·1 bath
Chicago • Illinois

$3,072.70 USD total for 31 nights

Nov 3 – Dec 4, 2026

Stylish & Comfy Stay • Close to Downtown
Stylish & Comfy Stay • Close to Downtown
Stylish & Comfy Stay • Close to Downtown
Stylish & Comfy Stay • Close to Downtown
Stylish & Comfy Stay • Close to Downtown

Stylish & Comfy Stay • Close to Downtown

2 bedrooms·1 bath
Chicago • Illinois

$2,771.40 USD total for 31 nights

Jan 26 – Feb 26, 2027

Chic & Cozy Chicago Stay • Close to Downtown
Chic & Cozy Chicago Stay • Close to Downtown
Chic & Cozy Chicago Stay • Close to Downtown
Chic & Cozy Chicago Stay • Close to Downtown
Chic & Cozy Chicago Stay • Close to Downtown

Chic & Cozy Chicago Stay • Close to Downtown

3 bedrooms·1 bath
Chicago • Illinois

$2,931.05 USD total for 31 nights

Dec 8, 2026 – Jan 8, 2027

Chicago Getaway | Cozy 2BR Near Downtown
Thoughtful extras: coffee bar, games, full cookware & pet-friendly perks
Chicago Getaway | Cozy 2BR Near Downtown
Chicago Getaway | Cozy 2BR Near Downtown
Bright living space with hardwood floors and wall-mounted streaming TV

Chicago Getaway | Cozy 2BR Near Downtown

2 bedrooms·1 bath
Chicago • Illinois

$822.95 USD total for 3 nights

Nov 3 – 6, 2026

Imagine enjoying your Chicago vacation in this comfortably furnished living room, equipped with a 80-inch smart TV, you will be able to enjoy movie nights, sports games, and more with family & friends. Comes with Netflix included.
Central | BBQ Deck | Family-Friendly Pueblo Magíco
Send us a message to pair this with a SUV Rental for half off! Traveling in groups > 12? Send us a message to book our other vacation homes close by at a discount! If you send us a message, we probably will work out a deal that fits your budget! TY!
Central | BBQ Deck | Family-Friendly Pueblo Magíco
Send us a message to pair this with a SUV Rental for half off! Traveling in groups > 12? Send us a message to book our other vacation homes close by at a discount! If you send us a message, we probably will work out a deal that fits your budget! TY!

Central | BBQ Deck | Family-Friendly Pueblo Magíco

5 bedrooms·2 baths
Chicago • Illinois

$1,051.00 USD total for 3 nights

Nov 3 – 6, 2026