Hermosa Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Hermosa, Chicago, Illinois, USA

New Mid-Century Gem in Avondale - 2BR - Office - Free Parking
Apartment
Mid-Century Gem in Avondale - 2BR - Office - Free Parking
From US $247 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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Well-Appointed Cozy Portage Park Apt, Dogs, Kids, Free Parking, 420 Compliant
Apartment
Well-Appointed Cozy Portage Park Apt, Dogs, Kids, Free Parking, 420 Compliant
From US $107 per night
|
10.0 (10 Reviews)
3 Bedrooms 10 Guests
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Ray's Bucktown B&B
Bed & Breakfast
Ray's Bucktown B&B
From US $202 per night
|
9.8 (370 Reviews)
1 Bedroom 2 Guests
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The Logandale: HUGE Mid-Century Home, sleeps 15
House
The Logandale: HUGE Mid-Century Home, sleeps 15
From US $484 per night
|
10.0 (4 Reviews)
4 Bedrooms 15 Guests
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Chicago Avenue Inn
House
Chicago Avenue Inn
From US $132 per night
7.0 (90 Reviews)
1 Bedroom 2 Guests
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The Robey, Chicago, a Member of Design Hotels
Hotel
The Robey, Chicago, a Member of Design Hotels
From US $263 per night
|
9.2 (948 Reviews)
1 Bedroom 2 Guests
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Perfect Location Across from Park & Train Station
House
Perfect Location Across from Park & Train Station
From US $734 per night
|
10.0 (1 Review)
5 Bedrooms 13 Guests
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Pulaski Point Properties
Apartment
Pulaski Point Properties
From US $189 per night
|
9.8 (32 Reviews)
3 Bedrooms 6 Guests
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New Charming Garden Flat w/King Bed
House
Charming Garden Flat w/King Bed
From US $181 per night
New
2 Bedrooms 2 Guests
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Irving Park updated vintage top unit 2-flat
Apartment
Irving Park updated vintage top unit 2-flat
From US $320 per night
|
9.8 (31 Reviews)
2 Bedrooms 6 Guests
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New Artsy Chicago - 1BR/1BATH
Condo
Artsy Chicago - 1BR/1BATH
From US $163 per night
New
1 Bedroom 4 Guests
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The Avondale Attic
Apartment
The Avondale Attic
From US $120 per night
|
9.8 (12 Reviews)
1 Bedroom 4 Guests
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NEW LUXURY PENTHOUSE CONDO
Condo
NEW LUXURY PENTHOUSE CONDO
From US $385 per night
10.0 (189 Reviews)
2 Bedrooms 9 Guests
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Chic & Fully Furnished 2BR Apartment - Roscoe 1
Apartment
Chic & Fully Furnished 2BR Apartment - Roscoe 1
From US $345 per night
|
9.7 (3 Reviews)
2 Bedrooms 4 Guests
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NEW LUXURY CONDO WITH PATIO DECK
Condo
NEW LUXURY CONDO WITH PATIO DECK
From US $304 per night
10.0 (180 Reviews)
1 Bedroom 5 Guests
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The Avondale Guesthouse
House
The Avondale Guesthouse
From US $283 per night
|
9.5 (131 Reviews)
3 Bedrooms 6 Guests
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Bucktown Private Condo
Apartment
Bucktown Private Condo
From US $151 per night
9.5 (23 Reviews)
2 Bedrooms 4 Guests
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Trendy 2BR Apartment in Logan Square!
Apartment
Trendy 2BR Apartment in Logan Square!
From US $233 per night
10.0 (84 Reviews)
2 Bedrooms 5 Guests
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Modern & Furnished 2BR Apt with In-unit Laundry - Sunnyside 2E
Apartment
Modern & Furnished 2BR Apt with In-unit Laundry - Sunnyside 2E
From US $350 per night
9.5 (4 Reviews)
2 Bedrooms 4 Guests
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Stylish, Inviting 2-BR near Logan Square and Wrigley Field
Apartment
Stylish, Inviting 2-BR near Logan Square and Wrigley Field
From US $222 per night
10.0 (61 Reviews)
2 Bedrooms 4 Guests
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Ray's Bucktown Bed and Breakfast
Bed & Breakfast
Ray's Bucktown Bed and Breakfast
From US $271 per night
|
9.4 (202 Reviews)
11 Bedrooms 31 Guests
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Entire Below Level Studio w/Private Sauna
Apartment
Entire Below Level Studio w/Private Sauna
From US $203 per night
10.0 (54 Reviews)
1 Bedroom 3 Guests
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Boho Bliss - 1Br, 1Bath w/Patio!
Apartment
Boho Bliss - 1Br, 1Bath w/Patio!
From US $149 per night
9.2 (17 Reviews)
1 Bedroom 4 Guests
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Stylish and Cute 2BR Apartment Near Wrigley!
Apartment
Stylish and Cute 2BR Apartment Near Wrigley!
From US $276 per night
10.0 (45 Reviews)
2 Bedrooms 4 Guests
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UrbanEden Loft Apartment
Apartment
UrbanEden Loft Apartment
From US $103 per night
9.2 (5 Reviews)
2 Bedrooms 4 Guests
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MAGNIFICENT NEW Home w/8 Beds & Free Parking
House
MAGNIFICENT NEW Home w/8 Beds & Free Parking
From US $900 per night
|
9.1 (6 Reviews)
4 Bedrooms 15 Guests
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LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!
House
LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!
From US $185 per night
10.0 (38 Reviews)
2 Bedrooms 6 Guests
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Modern 2 Bedroom in Avondale
Apartment
Modern 2 Bedroom in Avondale
From US $309 per night
|
9.0 (27 Reviews)
2 Bedrooms 4 Guests
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Bright and Cozy 1BR Apartment in Logan Square!
Apartment
Bright and Cozy 1BR Apartment in Logan Square!
From US $142 per night
10.0 (36 Reviews)
1 Bedroom 2 Guests
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Wicker Park 2BR Modern Apartment DV3
Apartment
Wicker Park 2BR Modern Apartment DV3
From US $396 per night
9.0 (18 Reviews)
2 Bedrooms 5 Guests
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8 MILES FROM DOWNTOWN CHICAGO!
Apartment
8 MILES FROM DOWNTOWN CHICAGO!
From US $238 per night
10.0 (35 Reviews)
2 Bedrooms 4 Guests
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3BR Spacious Apartment with In-Unit Laundry - Kedzie 3F
Apartment
3BR Spacious Apartment with In-Unit Laundry - Kedzie 3F
From US $831 per night
|
9.0 (4 Reviews)
3 Bedrooms 6 Guests
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❤️ Stylish and Cozy 2BR in Logan Square!
Apartment
❤️ Stylish and Cozy 2BR in Logan Square!
From US $191 per night
10.0 (35 Reviews)
2 Bedrooms 4 Guests
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Cozy Vintage Chicago Apartment near Downtown
Apartment
Cozy Vintage Chicago Apartment near Downtown
From US $202 per night
10.0 (25 Reviews)
1 Bedroom 4 Guests
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Bucktown Private Condo
Condo
Bucktown Private Condo
From US $379 per night
10.0 (11 Reviews)
2 Bedrooms 4 Guests
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Bucktown Condo Just Two Blocks from the L by AllSet Turnover
Condo
Bucktown Condo Just Two Blocks from the L by AllSet Turnover
From US $219 per night
10.0 (11 Reviews)
2 Bedrooms 4 Guests
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Modern 2-bedroom townhome in Chicago with private patio
House
Modern 2-bedroom townhome in Chicago with private patio
From US $401 per night
10.0 (1 Review)
2 Bedrooms 9 Guests
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2BR Stylish Apartment in Avondale close to Shops - Roscoe 1W
Apartment
2BR Stylish Apartment in Avondale close to Shops - Roscoe 1W
From US $243 per night
9.0 (3 Reviews)
2 Bedrooms 4 Guests
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The Hotel at Midtown
Hotel
The Hotel at Midtown
From US $320 per night
|
9.0 (784 Reviews)
1 Bedroom 2 Guests
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2BR, Sleeps7 Coffee Station, Backyard w/Grill
Apartment
2BR, Sleeps7 Coffee Station, Backyard w/Grill
From US $395 per night
10.0 (1 Review)
2 Bedrooms 7 Guests
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8BR | Kids Room, Game Room, Gym & Theater
House
8BR | Kids Room, Game Room, Gym & Theater
From US $1,294 per night
New
8 Bedrooms 18 Guests
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Logan Square Coach House
House
Logan Square Coach House
From US $186 per night
|
8.7 (20 Reviews)
1 Bedroom 4 Guests
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Chic|Comfy|Renovated1Bd1Ba Perfect for Couples
Apartment
Chic|Comfy|Renovated1Bd1Ba Perfect for Couples
From US $293 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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Red Robin Rentals - Wicker Park
Apartment
Red Robin Rentals - Wicker Park
From US $308 per night
|
8.7 (15 Reviews)
3 Bedrooms 10 Guests
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2BR City Loft Sweeping Glass Views
Apartment
2BR City Loft Sweeping Glass Views
From US $282 per night
10.0 (1 Review)
2 Bedrooms 6 Guests
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Walk to Train l Near attractions and ORD l Free Parking l Patio
Apartment
Walk to Train l Near attractions and ORD l Free Parking l Patio
From US $133 per night
8.7 (3 Reviews)
2 Bedrooms 4 Guests
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Beautiful 1st floor apartment.
Apartment
Beautiful 1st floor apartment.
From US $243 per night
10.0 (1 Review)
2 Bedrooms 5 Guests
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Vibrant 1BR Apartment close to Dining - Cullom B3
Apartment
Vibrant 1BR Apartment close to Dining - Cullom B3
From US $298 per night
8.3 (3 Reviews)
1 Bedroom 2 Guests
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Quiet, family getaway. Puppers welcome!
House
Quiet, family getaway. Puppers welcome!
From US $239 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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Cozy & Modern 3BR Apartment - Division 201W 301W REP
Apartment
Cozy & Modern 3BR Apartment - Division 201W 301W REP
From US $808 per night
|
8.1 (34 Reviews)
3 Bedrooms 6 Guests
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1BR City Loft With Modern Glass Views
Apartment
1BR City Loft With Modern Glass Views
From US $230 per night
10.0 (1 Review)
1 Bedroom 4 Guests
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Wicker Park 2BR Modern Apartment DV3
Apartment
Wicker Park 2BR Modern Apartment DV3
From US $400 per night
|
8.0 (1 Review)
2 Bedrooms 5 Guests
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Chic & Fully Furnished 2BR Apt!
Apartment
Chic & Fully Furnished 2BR Apt!
From US $218 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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Chic Studio in Heart of Chicago
Apartment
Chic Studio in Heart of Chicago
From US $217 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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A Hidden Gem, approx 15 mins to downtown Chicago!
House
A Hidden Gem, approx 15 mins to downtown Chicago!
From US $95 per night
7.8 (25 Reviews)
1 Bedroom 2 Guests
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Harmonious 2BR Apartment
Apartment
Harmonious 2BR Apartment
From US $215 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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3BR Apt in Logan Square Walkable to Highlights - Central Park S6
Apartment
3BR Apt in Logan Square Walkable to Highlights - Central Park S6
From US $679 per night
7.8 (19 Reviews)
3 Bedrooms 6 Guests
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Sunny & Stylish 2BR S
Apartment
Sunny & Stylish 2BR S
From US $213 per night
10.0 (1 Review)
2 Bedrooms 3 Guests
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Lively 3BR Apt in Chicago - Milwaukee N3
Apartment
Lively 3BR Apt in Chicago - Milwaukee N3
From US $656 per night
7.7 (3 Reviews)
3 Bedrooms 6 Guests
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About Hermosa Vacation Rentals

With more than 727 Hermosa vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Hermosa.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Hermosa, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Hermosa. Places to stay near Hermosa are 739.93 ft² on average, with prices averaging US $321 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Hermosa with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Other Places to Stay in Hermosa, IL


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Frequently Asked Questions About Hermosa?

What are the top vacation rentals in Hermosa?

How many Rentbyowner vacation rentals are available in Hermosa?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 727 in the Hermosa area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Hermosa. 

Nearby Neighborhood (1)

Neighborhood Property Count
Logan Square Vacation Rentals in Chicago, Illinois 81

There are 727 Hermosa, IL Vacation Rentals

Recently Booked Vacation Rentals Near Hermosa