Location

Dates

Guests

Vacation rentals in Illinois

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

4 bedrooms·3 baths

Western Springs • Illinois

$185/ night(excl. fees & taxes)

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

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

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

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

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

Secluded | Quiet | Wooded

Hot tub lighting

So much character

Bed 1 | 2nd Floor | Queen Size

Tucked away yet convenient to restaurants, hiking and shops

Hidden Grove- Heyworth, IL

2 bedrooms·1 bath

Heyworth • Illinois

5(3 reviews)

$229 – $614/ night(excl. fees & taxes)

Motorcycle bar in the "Secret" room

Inviting living room, gas fireplace, frame smart TV

Fun basement bar! Snow cone machine, cotton candy machine

Community pool- 8 min drive away, open year round

Primary bedroom, king bed, main floor with ensuite bedroom

Galena Haven Hideaway

4 bedrooms·4½ baths

Galena • Illinois

$700/ night(excl. fees & taxes)

Lounge seating | Umbrella

Daisy Lane- Normal, IL

Daisy Lane- Normal, IL

Daisy Lane- Normal, IL

Daisy Lane- Normal, IL

Daisy Lane- Normal, IL

2 bedrooms·1½ baths

Normal • Illinois

5(14 reviews)

$984.46 USD total for 3 nights

Sep 22 – 25, 2026

Some of our many Arcades available for free play during your stay with us!

Pac-Man wall mural designed by local artist

The Pac-Man Room

Orange couch can be used to sleep on for one person

House of Arcade!

House of Games® - Play, Relax, Unwind

3 bedrooms·2½ baths

Bloomington • Illinois

$526.82 USD $511.05 USD total for 3 nights

Sep 22 – 25, 2026

Hidden Grove is a magical place. A calm, resorative space great for relaxing, disconnecting from every day stresses and connecting with loved ones.

Magical patio area featuring an easy light propane fire table and comfortable lounge seating plus edison lighting for evening chill time.

Hidden Grove- Heyworth, IL

Vaulted ceilings for a charming and unforgettable stay

Hot tub lighting

Hidden Grove- Heyworth, IL

2 bedrooms·1 bath

Heyworth • Illinois

5(20 reviews)

$812.53 USD total for 3 nights

Sep 27 – 30, 2026

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!

Movie Room, Garden Oasis in Central Manor

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!

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Enjoy the natural light, and artwork while enjoying your stay in Chicago!

Movie Room, Garden Oasis in Central Manor

3 bedrooms·2 baths

Chicago • Illinois

$196 – $1,426/ night(excl. fees & taxes)

Screened | 50" TV | Lake Views

The Ridge- Decatur, IL

Warm vaulted ceilings, huge comfortable sofa and giant TV all add to the character and calm of The Ridge living room.

Game table | Up to 6 players

The Ridge- Decatur, IL

The Ridge- Decatur, IL

2 bedrooms·2 baths

Decatur • Illinois

5(5 reviews)

$1,143.08 USD total for 3 nights

Oct 4 – 7, 2026

Set on 5 acres, peaceful and quiet area. Close to town. Great space to walk dogs or just decompress. And no shared walls with any other living space.

100% Cotton Linens

Comfortable Sofa | Padded Ottoman

Everything you need

Convenient location, quiet rural setting yet close to everything B/N has to offer

Studio 604- Bloomington, IL

0 bedrooms·1 bath

Bloomington • Illinois

5(1 review)

Mid Century Modern Vibes! Propane fireplace! Listen to records! Enjoy nature around you!

Living room space with smart TVs, radio, record player

Private Hot tub- Use year round! No views of other homes. 6 person, wonderful jets!

Queen Bedroom with attached bathroom

Memory Foam, King Bed with views of nature!

Galena Haven Tree House

2 bedrooms·2 baths

Galena • Illinois

$250 – $410/ night(excl. fees & taxes)

Hells Branch Hideaway at Apple Canyon Lake

Hells Branch Hideaway at Apple Canyon Lake

Hells Branch Hideaway at Apple Canyon Lake

4 bedrooms·3 baths

Apple Canyon Lake • Illinois

$1,620.88 USD total for 3 nights

Sep 26 – 29, 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

$1,982.02 USD total for 3 nights

Oct 19 – 22, 2026