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

$1,084.00 USD total for 3 nights

Sep 22 – 25, 2026

Elmwood Park 2 BR Condo
Elmwood Park 2 BR Condo
Elmwood Park 2 BR Condo
Elmwood Park 2 BR Condo
Elmwood Park 2 BR Condo

Elmwood Park 2 BR Condo

2 bedrooms·1 bath
Elmwood Park • Illinois
$73 – $180/ night(excl. fees & taxes)
Elmwood Park Remodeled Studio Condo
Elmwood Park Remodeled Studio Condo
Elmwood Park Remodeled Studio Condo
Elmwood Park Remodeled Studio Condo
Elmwood Park Remodeled Studio Condo

Elmwood Park Remodeled Studio Condo

1 bedroom·1 bath
Elmwood Park • Illinois
$94 – $150/ night(excl. fees & taxes)
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)

$1,001.70 USD $970.39 USD total for 3 nights

Sep 24 – 27, 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

$1,645.57 USD $1,554.23 USD total for 3 nights

Sep 24 – 27, 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)

$2,695.14 USD $2,538.05 USD total for 3 nights

Sep 24 – 27, 2026

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

$3,525.00 USD total for 3 nights

Oct 1 – 4, 2026

Budget-Friendly Stay and Free Coffee | Downtown
Budget-Friendly Stay and Free Coffee | Downtown
Budget-Friendly Stay and Free Coffee | Downtown
Budget-Friendly Stay and Free Coffee | Downtown
Budget-Friendly Stay and Free Coffee | Downtown

Budget-Friendly Stay and Free Coffee | Downtown

1 bedroom·2 baths
Chicago • Illinois
$2,000/ night(excl. fees & taxes)
Traveler’s Favorite: Private Room Near Attractions
Traveler’s Favorite: Private Room Near Attractions
Traveler’s Favorite: Private Room Near Attractions
Traveler’s Favorite: Private Room Near Attractions
Traveler’s Favorite: Private Room Near Attractions

Traveler’s Favorite: Private Room Near Attractions

1 bedroom·2 baths
Chicago • Illinois
$2,000/ night(excl. fees & taxes)
Free Coffee & Private Room - Traveler's Favorite!
Free Coffee & Private Room - Traveler's Favorite!
Free Coffee & Private Room - Traveler's Favorite!
Free Coffee & Private Room - Traveler's Favorite!
Free Coffee & Private Room - Traveler's Favorite!

Free Coffee & Private Room - Traveler's Favorite!

1 bedroom·2 baths
Chicago • Illinois
$2,000/ night(excl. fees & taxes)
TOP PICK: Solo/Group, Private Rooms, Free Coffee!
TOP PICK: Solo/Group, Private Rooms, Free Coffee!
TOP PICK: Solo/Group, Private Rooms, Free Coffee!
TOP PICK: Solo/Group, Private Rooms, Free Coffee!
TOP PICK: Solo/Group, Private Rooms, Free Coffee!

TOP PICK: Solo/Group, Private Rooms, Free Coffee!

1 bedroom·2 baths
Chicago • Illinois
$2,000/ night(excl. fees & taxes)
All Ease Private Stay |Traveler's Top Fave!!
All Ease Private Stay |Traveler's Top Fave!!
All Ease Private Stay |Traveler's Top Fave!!
All Ease Private Stay |Traveler's Top Fave!!
All Ease Private Stay |Traveler's Top Fave!!

All Ease Private Stay |Traveler's Top Fave!!

1 bedroom·2 baths
Chicago • Illinois
$2,000/ night(excl. fees & taxes)
Secure, Private, Free Wi-Fi and Coffee, Accessible
Secure, Private, Free Wi-Fi and Coffee, Accessible
Secure, Private, Free Wi-Fi and Coffee, Accessible
Secure, Private, Free Wi-Fi and Coffee, Accessible
Secure, Private, Free Wi-Fi and Coffee, Accessible

Secure, Private, Free Wi-Fi and Coffee, Accessible

1 bedroom·2 baths
Chicago • Illinois
$2,000/ night(excl. fees & taxes)
Clean & Modern • Central Location • Free Coffee!
Clean & Modern • Central Location • Free Coffee!
Clean & Modern • Central Location • Free Coffee!
Clean & Modern • Central Location • Free Coffee!
Clean & Modern • Central Location • Free Coffee!

Clean & Modern • Central Location • Free Coffee!

1 bedroom·2 baths
Chicago • Illinois
$2,000/ night(excl. fees & taxes)
Cozy lounge with fireplace, smart TV, games & sunny windows
Bright entry with natural light and easy access to covered outdoor patio
Bright, cozy living room with fireplace, TV, and plenty of seating
Bright full bath with tub/shower, warm lighting, and stylish shelf accents
Sunny, stylish living room with hardwood floors and cozy seating

Theater Nights, Game Room & Balcony Delights

3 bedrooms·1 bath
Rockford • Illinois

$626.36 USD total for 3 nights

Oct 28 – 31, 2026

Whispering Waters Riverside
Whispering Waters Riverside
Whispering Waters Riverside
Whispering Waters Riverside
Whispering Waters Riverside

Whispering Waters Riverside

1 bedroom·1 bath
Rockford • Illinois

$3,054.00 USD total for 30 nights

Sep 22 – Oct 22, 2026

Beautiful living room
Beautiful new table
Primary bedroom with memory foam king bed
Screened in porch with propane fire pit
Beautiful living room

Galena Haven Gorgeous cabin 3bdrm/3bth, hot tub, k

3 bedrooms·3 baths
Galena • Illinois
5(34 reviews)

$2,226.00 USD total for 3 nights

Oct 6 – 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)

$1,783.74 USD $1,705.13 USD total for 3 nights

Sep 22 – 25, 2026

Cozy 2 Bed/1 Bath Unit
Cozy 2 Bed/1 Bath Unit
Cozy 2 Bed/1 Bath Unit
Cozy 2 Bed/1 Bath Unit
Cozy 2 Bed/1 Bath Unit

Cozy 2 Bed/1 Bath Unit

2 bedrooms·1 bath
Peoria • Illinois

$3,600.00 USD $3,000.00 USD total for 30 nights

Sep 22 – Oct 22, 2026

Epicurean experience home
Epicurean experience home
Epicurean experience home
Epicurean experience home
Epicurean experience home

Epicurean experience home

6 bedrooms·4 baths
Chicago • Illinois

$3,600.00 USD total for 3 nights

Sep 22 – 25, 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 22 – 25, 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)
$93/ night(excl. fees & taxes)
Enjoy a peaceful evening roasting smores, enjoying the lake and just relaxing by the water.
Comfortable living room with gorgeous lake views
Bed 1 | 2nd Floor | Queen bed
Elevated deck with spectacular views
Lake Shore Cottage- Decatur, IL

Lake Shore Cottage- Decatur, IL

3 bedrooms·2½ baths
Decatur • Illinois
5(16 reviews)

$728.23 USD total for 3 nights

Sep 22 – 25, 2026

Enjoy beautiful sunsets.
Family living room with a pull out sofa, great for large families.
Pura Vida Lake Home Retreat
Beautiful water views throughout the whole house, large sliding door makes it perfect for indoor/outdoor living.
Pura Vida Lake Home Retreat

Pura Vida Lake Home Retreat

2 bedrooms·2 baths
Greenville • Illinois

$2,076.75 USD total for 3 nights

Sep 22 – 25, 2026