Rent a cabin in Highwood, IL

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Highwood, IL

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Popular cabins

Charming Ranch-style Cottage

Moraine Township, Highland Park, IL

10 guests

From 
$74
/hr
4 hr min

North Shore Designer Home with Natural Light + Outdoor Living (Film/Photo)

Highland Park, IL

4.9 (14)

25 guests

From 
$200
/hr
4 hr min

Secluded Mansion in Riverwoods

Riverwoods, IL

5.0 (3)

30 guests

From 
$300
/hr
3 hr min

Architect Designed & Owned 1960s Built Mid-Century Modern Custom Contemporary Home

Moraine Township, Highland Park, IL

5.0 (2)

50 guests

From 
$325
/hr
2 hr min

Amazing Farmhouse with pool on sprawling 5 acre green space

West Deerfield Township, Bannockburn, IL

25 guests

From 
$165
/hr
4 hr min

Seasonal Serenity: A Professionally, Seasonally, Decorated Single Family Home Illuminated by Natural Light

Highland Park, IL

5.0 (10)

20 guests

From 
$100
/hr
2 hr min

Midcentury Modern on the River

Vernon Township, Riverwoods, IL

5.0 (4)

120 guests

From 
$200
/hr
5 hr min

Charming Country Stay Surrounded by Jungle, Steps from a Lake

New Trier Township, northfield, IL

5.0 (1)

70 guests

From 
$150
/hr
2 hr min

Charming English Cottage

Evanston, IL

5.0 (12)

40 guests

From 
$250
/hr
4 hr min

Sun-Drenched Designer Colonial with Modern Luxury Upgrades

Evanston, IL

5.0 (1)

15 guests

From 
$125
/hr
4 hr min

Spacious Home in Barrington

Ela Township, Deer Park, IL

5.0 (1)

63 guests

From 
$150
/hr
2 hr min

Rustic Retreat

Zion Township, IL

20 guests

From 
$125
/hr
3 hr min

"Versatile Jefferson Park Recording Studio with Warehouse and Workshop | Vintage 1950s Vibe—Perfect for Photography, Video, Audio Recording, and Performance. Acoustically Treated Interview & Podcast Space."

Albany Park, Chicago, IL

5.0 (2)

12 guests

From 
$100
/hr
3 hr min

Suburban Traditional Updated Spacious Home

Winston Knolls, Hoffman Estates, IL

20 guests

From 
$200
/hr
4 hr min

Beautiful lake side property for a perfect photo shoot with amazingly colorful sunsets.

Venetian Village, Lake Villa, IL

5.0 (2)

50 guests

From 
$75
/hr
2 hr min

3614 W Irving Park Space for Events

Irving Park, Chicago, IL

50 guests

From 
$75
/hr
4 hr min

Historic & Moody Cocktail Lounge + Massive 8,000 Sq Ft Patio in Uptown

Uptown, Chicago, IL

35 guests

From 
$200
/hr
4 hr min

Lakeview Lux

Lake View, Chicago, IL

5.0 (4)

25 guests

From 
$160
/hr
4 hr min

Timber Loft in Chicago

West Town, Chicago, IL

4 guests

From 
$150
/hr
2 hr min

Vibrant and Vintage Historical Home

Lincoln Park, Chicago, IL

5.0 (1)

6 guests

From 
$250
/hr
3 hr min

Charming Urban Chicago Apartment | Cozy, Stylish & Versatile Space in Little Village

Little Village, Chicago, IL

8 guests

From 
$59
/hr
2 hr min

Two Level, Chic, Upscale, Rustic Studio With Plenty Of Natural Lighting But Also Intimate Coverings To Accommodate Any Event

THE CAMBRIDGE, Chicago, IL

50 guests

From 
$150
/hr
2 hr min

The Barrel House – Industrial, Rustic, and Highly Customizable Backdrop

Humboldt Park, Chicago, IL

250 guests

From 
$500
/hr
4 hr min

Secluded , Traditional Contemporary Split Level hone built in 1975. Completely updated, and on a tree lined acre.

Milton Township, Glen Ellyn, IL

25 guests

From 
$200
/hr
4 hr min

River Forest Mid-Century Modern Ranch (10 miles outside Downtown Chicago)

River Forest, IL

5.0 (6)

60 guests

From 
$250
/hr
2 hr min

Modern Production Home in Pilsen w/ Parking

Lower West Side, chicago, IL

5.0 (18)

10 guests

From 
$150
/hr
5 hr min

Rustic Mix

Garfield Park, Chicago, IL

8 guests

From 
$125
/hr
4 hr min

Roff Home: Award-Winning Historic 1868 Victorian Italianate Home + Grounds

Lake View, Chicago, IL

5.0 (21)

40 guests

From 
$99
/hr
4 hr min

El Motel Tres in Logan Square

Logan Square, Chicago, IL

5.0 (1)

30 guests

From 
$200
/hr
4 hr min

Vintage Funky Farmhouse, Barn & Garden

Oak Park Township, IL

5.0 (17)

20 guests

From 
$175
/hr
3 hr min

A bespoke private villa with on-site speakeasy, theater and bistro.

Bucktown, Chicago, IL

99 guests

From 
$350
/hr
2 hr min

A Rustic “Intimate space with infinite vibes” tucked away in the Bronzville area and just 10 minutes from downtown

South Side, Chicago, IL

5.0 (1)

50 guests

From 
$150
/hr
4 hr min

Artsy Urban Historic House

Oak Park Township, IL

4.7 (3)

20 guests

From 
$90
/hr
2 hr min

Logan Square Coach House with a Beautiful Garden

Avondale, Chicago, IL

4.5 (2)

50 guests

From 
$100
/hr
4 hr min

Urban Jungle Apartment in Former Mansion

Near North Side, Chicago, IL

5.0 (9)

15 guests

From 
$75
/hr
4 hr min

Urban, loft space, creative space, industrial, farm house, rustic

South Side, Chicago, IL

25 guests

From 
$85
/hr
2 hr min

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Nearby locations

Highland Park, IL
Bannockburn, IL
Deerfield, IL
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Wheeling, IL
Buffalo Grove, IL
Wilmette, IL
Updated October 25, 2026Our data is refreshed in real time using booking trends, verified guest reviews, and direct partner updates — with additional quality checks from our team.