Sister Bay Condo Rentals - Vacation Rentals in Hermosa

LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld! From US $195
         

10.0 (38 Reviews)
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Bright and Cozy 1BR Apartment in Logan Square! From US $112
         

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Ray's Bucktown B&B From US $178
         

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9.8 (394 Reviews)
Bed & Breakfast
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Modern Logan Square Luxury: 5 bedroom - sleeps 16! From US $953
         

9.8 (53 Reviews)
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The Avondale Lower Level From US $251
         

9.6 (60 Reviews)
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NEW LUXURY PENTHOUSE CONDO From US $611
         

10.0 (207 Reviews)
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NEW LUXURY CONDO WITH PATIO DECK From US $392
         

10.0 (193 Reviews)
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Luxury Places to Stay in Hermosa

Over 864+ Luxury Places to Stay in or Near Hermosa
Stunning 5BR Home in Heart of Chicago with 2 Rooftops From US $2,234
         

Greystone, 3500 sq ft, Rooftop Access, Sleeps 16 From US $1,493
         

10.0 (2 Reviews)
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Sleeps 22 Modern Multi-Unit Gym Workspaces From US $1,466
         

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Top-Rated Vacation Rentals with a Pool in Hermosa

Over 19+ Top-Rated Vacation Rentals with a Pool in or Near Hermosa
Quiet Area - Revamped Basement From US $279
         

10.0 (1 Review)
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iKlektik House/Robin From US $225
         

10.0 (1 Review)
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Cozy Family 3BR Oasis: Park, Private Yard, & BBQ! From US $361
         

9.8 (41 Reviews)
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Historic 1920s Private Bungalow Near Logan Square! From US $482
         

9.8 (40 Reviews)
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The Robey, Chicago, a Member of Design Hotels From US $214
         

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9.2 (1002 Reviews)
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The Hotel at Midtown From US $305
         

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9.0 (853 Reviews)
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The Hotel & Athletic Club at Midtown From US $1,255
         

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8.9 (182 Reviews)
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The Robey, Chicago, a Member of Design Hotels From US $423
         

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8.6 (293 Reviews)
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Pet-Friendly Vacation Rentals in Hermosa

Over 341+ Pet-Friendly Vacation Rentals in or Near Hermosa
Beautiful Roscoe Village/Hamlin Park 4 bed 3 bath. From US $691
         

10.0 (21 Reviews)
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Tranquil Library 2brm 1bath private eclectic apt at Solar Lodge From US $400
         

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10.0 (2 Reviews)
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Lynx606 From US $238
         

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BoHo House - A Chic, 1903 Chicago Workers Cottage From US $641
         

10.0 (19 Reviews)
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Bright Upper-Level 3BR Chicago King Walkable From US $511
         

10.0 (18 Reviews)
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NEW, clean & sunny, 2bd, private deck, 15min to Wrigley! From US $247
         

10.0 (12 Reviews)
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Vital Urban: Spa Inspired Retreat From US $617
         

10.0 (11 Reviews)
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Modern & Bright Chicago City Escape From US $388
         

10.0 (11 Reviews)
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  • Pet Friendly
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See More Pet-Friendly Vacation Rentals in Hermosa on PetFriendly.io

Large Vacation Homes & Villas in Hermosa

Over 127+ Large Vacation Homes & Villas in or Near Hermosa
NEW! Large/Beautiful Home with 6BDS/4BTH + Garage! From US $811
         

10.0 (9 Reviews)
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The Logandale: HUGE Mid-Century Home, sleeps 15 From US $484
         

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10.0 (4 Reviews)
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Queen Beds, EV Charging, Near Train: Luxury Stay From US $846
         

10.0 (8 Reviews)
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Beautiful duplex in the heart of bucktown. From US $579
         

10.0 (6 Reviews)
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Modern, Luxe, House 20mins to Downtown, Private Rooftop, 2car Garage From US $917
         

Designer Apt, Billiards, Private Patio, 1 Parking From US $613
         

10.0 (4 Reviews)
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Wheelchair Accessible Vacation Homes in Hermosa

Over 41+ Wheelchair Accessible Vacation Homes in or Near Hermosa
Ray's Bucktown Bed and Breakfast From US $271
         

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9.5 (161 Reviews)
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The Cornerstone - Designer 4BR Flat in Bucktown/WP From US $1,000
         

10.0 (11 Reviews)
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  • Wheelchair Accessible
Modern 1 King City Escape From US $1,013
         

10.0 (3 Reviews)
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2BR City Suite w/Amazing Glass Views From US $1,148
         

10.0 (2 Reviews)
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2BR City Loft Sweeping Glass Views From US $456
         

9.8 (9 Reviews)
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1BR City Loft With Modern Glass Views From US $278
         

9.4 (6 Reviews)
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New, Modern 1 King City Escape From US $306
         

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Hermosa Vacation Rentals and Airbnb Places to Stay Under $200

Over 309+ Hermosa Vacation Rentals and Airbnb Places to Stay Under $200
Stylish Garden-Level 2BR: Quiet Neighborhood From US $132
         

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10.0 (2 Reviews)
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Chicago Avenue Inn From US $149
         

7.0 (101 Reviews)
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King Comfort apartment, Quiet, Clean, AC & WiFi From US $138
         

10.0 (5 Reviews)
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Cozy 1 Bedroom Apt near Logan Sq Chicago From US $200
         

10.0 (2 Reviews)
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Warm & Stylish 2BR Apt From US $191
         

10.0 (2 Reviews)
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The Avondale Attic From US $82
         

10.0 (2 Reviews)
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Instantly Bookable Vacation Homes in Hermosa

Over 440+ Instantly Bookable Vacation Homes in or Near Hermosa
Entire Below Level Studio w/Private Sauna From US $296
         

10.0 (69 Reviews)
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Family-friendly, stylish Chicago Apartment in Logan Square From US $336
         

Elevated & Elegant 4 BD 2BA apartment 25 min to downtown From US $610
         

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2 Mi to Logan Square: Pet-Friendly Urban Oasis! From US $275
         

10.0 (7 Reviews)
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About Hermosa Vacation Rentals

With more than 873 Hermosa vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Sisterbaycondorentals 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 a rental property in Hermosa.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Sisterbaycondorentals Hermosa, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner 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, and other popular Airbnb-style properties in Hermosa. Places to stay near Hermosa are 786.58 ft² on average, with prices averaging $355 a night.

Sisterbaycondorentals 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.

Top Rental Accommodation Types in Hermosa

Type Count
Holiday Apartments 600
Vacation Homes 205
Hotels with Suites 12
B&B 3
Cottages 1
Hostels 1
Resorts 1

Use these Quick Filters to Find a Vacation Rental in Hermosa

Pro Tip: Sisterbaycondorentals makes it easy to compare the best listings on Sisterbaycondorentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Sisterbaycondorentals homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Hermosa.

Weather in Hermosa

View the weather forecast for Hermosa before booking your Hermosa Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Other Places to Stay Near Hermosa, IL


Hermosa Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Hermosa?
How many vacation rentals are available in Hermosa?

Currently, the total number of properties listed in 2026 is over 873 in the Hermosa area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Hermosa.