Location

Dates

Guests

Vacation rentals in Illinois

The Farmhouse at Red River Farms

The Farmhouse at Red River Farms

The Farmhouse at Red River Farms

The Farmhouse at Red River Farms

The Farmhouse at Red River Farms

The Farmhouse at Red River Farms

4 bedrooms·2 baths

Eureka • Illinois

$870.00 USD total for 3 nights

Nov 6 – 9, 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

Nov 6 – 12, 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)

Fab space for the whole group!

Fully stocked chef's kitchen

MFL 3 East

4 bedrooms·4 baths

Chicago • Illinois

4.99(93 reviews)

$3,175.10 USD $2,729.89 USD total for 3 nights

Nov 6 – 9, 2026

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Rockford Cascade Getaway

5 bedrooms·3 baths

Rockford • Illinois

5(25 reviews)

$1,239.75 USD total for 3 nights

Nov 6 – 9, 2026

Front Room / Library

Front Room / Library

Our Murphy Home

3 bedrooms·1 bath

Murphysboro • Illinois

5(66 reviews)

$621.00 USD total for 3 nights

Nov 15 – 18, 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)

Bright and inviting living room with a spacious sectional sofa, perfect for relaxing after a day of exploring Chicago. Floor-to-ceiling mirrored walls create an open, airy feel, while large windows fill the space with natural light.

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Hand-painted vine and fruit mural along the upper wall near the ceiling, adding a distinctive decorative accent to the space.

3BR Vintage Apt • Back Yard• Walk to McKinley Park

3BR Vintage Apt • Back Yard• Walk to McKinley Park

3 bedrooms·1 bath

Chicago • Illinois

4.92(25 reviews)

$646.25 USD total for 3 nights

Nov 8 – 11, 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)

$1,019.15 USD total for 3 nights

Nov 6 – 9, 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

Nov 6 – 9, 2026

Private entrance to Cottage

Peaceful surroundings on 150+ year old farm

Entrance to the Cottage

An Instagram dream

Queen bed in bedroom 1- now with A/C in room

The Cottage at Rendleman Orchards

2 bedrooms·1 bath

Alto Pass • Illinois

5(6 reviews)

$577.67 USD total for 3 nights

Nov 15 – 18, 2026

Welcome to Green Acres!

Main floor layout

Fire pit with seating

Dining room and kitchen

Cozy outdoor space

Green Acres

3 bedrooms·3 baths

Carbondale • Illinois

5(1 review)

$1,030.33 USD $929.27 USD total for 3 nights

Nov 15 – 18, 2026

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Waterfront Cottage/sauna/kayaks/firepit/dock

1 bedroom·1 bath

Fox River Grove • Illinois

4.88(40 reviews)

$855.00 USD total for 3 nights

Nov 6 – 9, 2026

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

$2,090.00 USD total for 5 nights

Nov 6 – 11, 2026

Safe, Walkable Streets! 1/2 mile to downtown

Color Me Home

2 bedrooms·1 bath

Marion • Illinois

$2,903.04 USD total for 28 nights

Nov 6 – Dec 4, 2026

All 3 Cabins at Sunrise Hill

All 3 Cabins at Sunrise Hill

All 3 Cabins at Sunrise Hill

All 3 Cabins at Sunrise Hill

All 3 Cabins at Sunrise Hill

All 3 Cabins at Sunrise Hill

5 bedrooms·3 baths

Makanda • Illinois

$2,267.62 USD total for 3 nights

Nov 29 – Dec 2, 2026

3 Lake homes on private drive

Chairs and umbrella by serene lake.

A cozy backyard with a fire pit surrounded by chairs, perfect for gathering and enjoying outdoor warmth and relaxation.

Dock with slide

Playground for kids on site

The Sunset Drive Houses

11 bedrooms·7½ baths

Marion • Illinois

$3,644.03 USD total for 3 nights

Nov 8 – 11, 2026

Living room with fireplace

Front view of the cabin

Elm Cabin 2

1 bedroom·1 bath

Carbondale • Illinois

5(6 reviews)

$1,091.78 USD total for 3 nights

Nov 10 – 13, 2026

Directly above Seasonings Bistro

Large open windows with eastern light

4 seats at the dining room table and 4 breakfast bar seats

4 seats at the breakfast bar

All new appliances in the kitchen

Rado's Hideaway

2 bedrooms·2 baths

Marion • Illinois

$776.35 USD total for 3 nights

Nov 8 – 11, 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 6 – 9, 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)

$3,389.15 USD $2,880.78 USD total for 3 nights

Nov 6 – 9, 2026

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

$79 – $796/ night(excl. fees & taxes)

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

$925.16 USD total for 3 nights

Nov 6 – 9, 2026

Workspace in the living room

Ashland

3 bedrooms·1 bath

Chicago • Illinois