Location

Dates

Guests

Vacation rentals in Illinois

Rockford Cascade Getaway image 1

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Rockford Cascade Getaway

5 bedrooms·3 baths

Rockford • Illinois

5(25 reviews)

$1,009.75 USD total for 3 nights

Sep 22 – 25, 2026

Step into serenity at our welcoming retreat. Follow detailed check-in directions to unlock the smart lock for secure access. Relax in the cozy living room with a 30" Smart TV and a collection of board games. Outside, unwind in the serene backyard.

Discover local gems in our custom guidebook. Outside, find tranquility in the serene backyard oasis. Entertain in the lower-level living room, complete with a 55" Smart TV, kitchenette, and study desk. The sofa can also be used for sleeping space.

Unwind in our inviting sanctuary. Seamless check-in with detailed instructions and a smart lock. Cozy up in the relaxing living room, equipped with a 30" Smart TV and a selection of board games. Step outside to a tranquil backyard with a pergola.

Step into tranquility with seamless check-in and a smart lock. Explore local treasures with our custom guidebook. Outside, unwind in the serene backyard oasis, complete with a pergola, fire-pit, outdoor gas grill, and picnic table dining.

Discover local gems in our custom guidebook. Outside, find tranquility in the serene backyard oasis. Entertain in the lower-level living room, complete with a 55" Smart TV, kitchenette, and study desk. The sofa can also be used for sleeping space.

Artistic Stay near Hyde Park: 2 Living, Courtyard

3 bedrooms·2½ baths

Chicago • Illinois

5(92 reviews)

$924.00 USD total for 3 nights

Oct 4 – 7, 2026

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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 22 – 28, 2026

Large Cozy 3BR near UChicago Medical Midway Museum

Main bedroom from desk area

Second bedroom -- a headboard has been added (didn't get a picture of that yet).

Third bedroom, desk and closet

Large Cozy 3BR near UChicago Medical Midway Museum

3 bedrooms·1 bath

Chicago • Illinois

5(8 reviews)

$349/ night(excl. fees & taxes)

Front Room / Library

Front Room / Library

Our Murphy Home

3 bedrooms·1 bath

Murphysboro • Illinois

5(65 reviews)

$621.00 USD total for 3 nights

Sep 27 – 30, 2026

Cozy Bluebird Haven - Cozy & Clean near I-57

Cozy Bluebird Haven - Cozy & Clean near I-57

Cozy Bluebird Haven - Cozy & Clean near I-57

Cozy Bluebird Haven - Cozy & Clean near I-57

Cozy Bluebird Haven - Cozy & Clean near I-57

Cozy Bluebird Haven - Cozy & Clean near I-57

3 bedrooms·1 bath

Marion • Illinois

5(5 reviews)

$816.41 USD total for 3 nights

Sep 22 – 25, 2026

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Spacious family home, Hot tub

6 bedrooms·4 baths

Rockford • Illinois

5(7 reviews)

$3,100.00 USD total for 3 nights

Sep 27 – 30, 2026

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Waterfront Cottage/sauna/kayaks/firepit/dock

1 bedroom·1 bath

Fox River Grove • Illinois

4.88(40 reviews)

$220 – $250/ night(excl. fees & taxes)

Apartment with breathtaking 360 degree views

Apartment with breathtaking 360 degree views

Apartment with breathtaking 360 degree views

Apartment with breathtaking 360 degree views

Apartment with breathtaking 360 degree views

Apartment with breathtaking 360 degree views

3 bedrooms·3 baths

Chicago • Illinois

$418/ night(excl. fees & taxes)

Workspace in the living room

Ashland

3 bedrooms·1 bath

Chicago • Illinois

Cozy private deck with cushioned seating and a stylish fire table

Prime Chicago base—minutes to Mag Mile, Navy Pier, parks & airports.

Bright living room with recliners, fireplace, TV, and abundant natural light

Spa-style jetted soaking tub for a relaxing, luxurious stay

Cozy fire table patio with wine—perfect for relaxing evening nights

Chicago Oasis | Spa Bath, Patio & Fireplace

1 bedroom·1 bath

Chicago • Illinois

$149 – $642/ night(excl. fees & taxes)

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The Kozy Keep! 1500 Sq.ft. - Sleeps 8!

2 bedrooms·2 baths

Olney • Illinois

4.86(56 reviews)

$465.00 USD total for 3 nights

Sep 22 – 25, 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

$1,195.00 USD total for 3 nights

Oct 10 – 13, 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

$1,584.00 USD total for 3 nights

Sep 29 – Oct 2, 2026

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

4 bedrooms·3 baths

Western Springs • Illinois

$185/ night(excl. fees & taxes)

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

$1,189.00 USD total for 3 nights

Oct 5 – 8, 2026

Modern Boho Entire Home in Glen Ellyn

Modern Boho Entire Home in Glen Ellyn

Modern Boho Entire Home in Glen Ellyn

Modern Boho Entire Home in Glen Ellyn

Modern Boho Entire Home in Glen Ellyn

Modern Boho Entire Home in Glen Ellyn

4 bedrooms·2 baths

Glen Ellyn • Illinois

$1,214.00 USD total for 3 nights

Sep 28 – Oct 1, 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

$1,084.00 USD total for 3 nights

Sep 22 – 25, 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)

$1,001.70 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

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