Location

Dates

Guests

Vacation rentals in Illinois, United States

Luxurious Remodeled 1BR Condo

Luxurious Remodeled 1BR Condo

Luxurious Remodeled 1BR Condo

Luxurious Remodeled 1BR Condo

Luxurious Remodeled 1BR Condo

Luxurious Remodeled 1BR Condo

1 bedroom·1 bath

Chicago • Illinois

$938.45 USD total for 3 nights

Nov 6 – 9, 2026

Workspace in the living room

Ashland

3 bedrooms·1 bath

Chicago • Illinois

Peach Tree Inn Unit 5

Wecome to Peach Tree Inn

Re-imaged bank building in Cobden, IL

2 hot tubs on the patio for the 5 suites. Each hot tub seats 4-6 people comfortably.

Peach Tree Inn Unit 5

Peach Tree Inn Unit 5

1 bedroom·1 bath

Cobden • Illinois

$615.26 USD total for 3 nights

Nov 6 – 9, 2026

Songbird Lane Cabin

Songbird Lane Cabin

Songbird Lane Cabin

Songbird Lane Cabin

Songbird Lane Cabin

Songbird Lane Cabin

1 bedroom·2½ baths

Goreville • Illinois

$1,111.81 USD total for 3 nights

Nov 24 – 27, 2026

Bring the pickle ball set! Nice flat space

View from the water

"The Classic" on Country Club

The Classic

3 bedrooms·3 baths

Marion • Illinois

5(5 reviews)

$1,036.42 USD total for 3 nights

Nov 6 – 9, 2026

Tulipwood Cabin

Living room with fireplace and TV

Dining area table and chairs

Tulipwood Cabin 3

1 bedroom·1 bath

Carbondale • Illinois

5(6 reviews)

$912.19 USD total for 3 nights

Nov 8 – 11, 2026

Additional view of outdoor area

Covered hot tub

Seating around the fire pit

Ample seating for all

Front view of home

Sunset Ridge

3 bedrooms·2 baths

Carbondale • Illinois

5(1 review)

$911.93 USD total for 3 nights

Nov 8 – 11, 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 6 – 9, 2026

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

4 bedrooms·3 baths

Western Springs • Illinois

$6,506.85 USD $5,908.67 USD total for 30 nights

Aug 28 – Sep 27, 2027

Private Stay w/Free Coffee | Best Stay in Chicago

Private Stay w/Free Coffee | Best Stay in Chicago

Private Stay w/Free Coffee | Best Stay in Chicago

Private Stay w/Free Coffee | Best Stay in Chicago

Private Stay w/Free Coffee | Best Stay in Chicago

Private Stay w/Free Coffee | Best Stay in Chicago

1 bedroom·2 baths

Chicago • Illinois

$552.34 USD total for 3 nights

Nov 6 – 9, 2026

Best Private Room in Downtown | Free Coffee

Best Private Room in Downtown | Free Coffee

Best Private Room in Downtown | Free Coffee

Best Private Room in Downtown | Free Coffee

Best Private Room in Downtown | Free Coffee

Best Private Room in Downtown | Free Coffee

1 bedroom·2 baths

Chicago • Illinois

$8,607.15 USD total for 3 nights

Aug 28 – 31, 2027

Shawnee Apple Shack

Shawnee Apple Shack

Shawnee Apple Shack

Shawnee Apple Shack

Shawnee Apple Shack

Shawnee Apple Shack

1 bedroom·1 bath

Simpson • Illinois

5(1 review)

$697.13 USD total for 3 nights

Nov 9 – 12, 2026

View of the night sky from the dome

Natural light throughout

View of the hot tub

Welcome to the Glamping Dome!

Fire pit with seating

Shawnee Hills Glamping

1 bedroom·1 bath

Simpson • Illinois

5(7 reviews)

$1,061.34 USD total for 3 nights

Nov 8 – 11, 2026

King bed with room darkening shades

Wheelchair ramp to the entrance

Wecome to Peach Tree Inn

Wheel chair accessible vanity

Peach Tree Inn Unit 1

1 bedroom·1 bath

Cobden • Illinois

$615.26 USD total for 3 nights

Nov 6 – 9, 2026

Wecome to Peach Tree Inn

Re-imaged bank building in Cobden, IL

2 hot tubs on the patio for the 5 suites. Each hot tub seats 4-6 people comfortably.

Microwave, sink and coffee station in the lobby.

Peach Tree Inn Unit 2

1 bedroom·1 bath

Cobden • Illinois

$615.26 USD total for 3 nights

Nov 6 – 9, 2026

2 hot tubs on the patio for the 5 suites. Each hot tub seats 4-6 people comfortably.

Peach Tree Inn Unit 3

Wecome to Peach Tree Inn

Re-imaged bank building in Cobden, IL

Microwave, sink and coffee station in the lobby.

Peach Tree Inn Unit 3

1 bedroom·1 bath

Cobden • Illinois

$615.26 USD total for 3 nights

Nov 6 – 9, 2026

Microwave, sink and coffee station in the lobby.

Re-imaged bank building in Cobden, IL

Wecome to Peach Tree Inn

2 hot tubs on the patio for the 5 suites. Each hot tub seats 4-6 people comfortably.

Peach Tree Inn Unit 4

Peach Tree Inn Unit 4

1 bedroom·1 bath

Cobden • Illinois

$615.26 USD total for 3 nights

Nov 6 – 9, 2026

Own private lobby

Conversational seating for you to mix and mingle with other suite guests.

Bring your crew!

King bed with room darkening shades

Room for everyone in your group- all to yourselves

Peach Tree Inn- All Suites

5 bedrooms·5 baths

Cobden • Illinois

$2,345.82 USD total for 3 nights

Nov 6 – 9, 2026

Deck with lighting

Breathtaking views from the cabin

Deck with table and chairs plus a grill

The White Oak Cabin at Sunrise Hill

2 bedrooms·1 bath

Makanda • Illinois

5(1 review)

$1,315.37 USD total for 3 nights

Nov 12 – 15, 2026

Your outdoor dream escape

Smokeless firepit surrounded by natural rock and landscape

Hot tub overlooking woods and wildlife

King bed with own heating/air unit

Shawnee Creek Cottage

1 bedroom·1 bath

Tunnel Hill • Illinois

5(1 review)

$656.27 USD total for 3 nights

Nov 30 – Dec 3, 2026

Gram's Cabin at Bald Knob

Gram's Cabin at Bald Knob

Bald Knob Cross is 4 minutes away- 1.8 miles

Gram's Cabin at Bald Knob

Gram's Cabin at Bald Knob

Gram's Cabin at Bald Knob

2 bedrooms·2 baths

Alto Pass • Illinois

5(1 review)

$891.32 USD total for 3 nights

Nov 7 – 10, 2026

Unique craftsman custom home on Lake of Egypt

Outdoor space ready for you

Dock with seating

Lake toys ready for you

Fire pit for the whole family

Lotus Lodge

3 bedrooms·4½ baths

Goreville • Illinois

5(3 reviews)

$1,693.42 USD total for 3 nights

Nov 6 – 9, 2026

Dining for all 10!

Large kitchen and gas stove

Aerial of short walk to dock

Asphalt drive and room for a boat trailer

Pharaoh's Retreat

4 bedrooms·3 baths

Creal Springs • Illinois

5(1 review)

$1,404.47 USD total for 3 nights

Nov 8 – 11, 2026

Main Level Living room

Main Level Living room

Welcome to Timber & Tide

Gather- a dining space for everyone.

Timber and Tide

4 bedrooms·2½ baths

Goreville • Illinois

5(1 review)

$1,985.77 USD total for 3 nights

Nov 9 – 12, 2026