Sister Bay Condo Rentals - Vacation Rentals in Roscoe Village

Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood From US $354
         

Bright and Cozy 1BR Apartment in Logan Square! From US $112
         

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Wrigleyville Inn From US $531
         

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10.0 (23 Reviews)
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4BR Old Town Chicago Loft | Walk to Wells St From US $949
         

10.0 (120 Reviews)
Apartment
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Unique Chicago Penthouse Loft - Amazing Deal & Location From US $393
         

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

10.0 (38 Reviews)
House
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  • Pet Friendly
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field From US $615
         

10.0 (113 Reviews)
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  • Pet Friendly

Luxury Places to Stay in Roscoe Village

Over 1942+ Luxury Places to Stay in or Near Roscoe Village
Wrigley 4BR Home, Sleeps 10 From US $3,786
         

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: The Wolcott : Modern Elegance at Its Finest From US $3,557
         

9.4 (14 Reviews)
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  • Designated Smoking Area
Wrigley 4BR Home, Sleeps 10, Firepit From US $2,628
         

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Stunning 5BR Home in Heart of Chicago with 2 Rooftops From US $2,234
         

Top-Rated Vacation Rentals with a Pool in Roscoe Village

Over 65+ Top-Rated Vacation Rentals with a Pool in or Near Roscoe Village
Uptown Gem From US $117
         

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10.0 (12 Reviews)
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Cozy Family 3BR Oasis: Park, Private Yard, & BBQ! From US $361
         

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

9.8 (40 Reviews)
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Foundry Unmatched Skyline Views at Lincoln Park From US $1,691
         

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9.4 (15 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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  • Pool

Pet-Friendly Vacation Rentals in Roscoe Village

Over 760+ Pet-Friendly Vacation Rentals in or Near Roscoe Village
Roscoe Village- Only steps to cute shops & dining! Sleeps 4-6 From US $314
         

10.0 (96 Reviews)
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  • Pet Friendly
Chicago Quick Stay From US $130
         

6.3 (47 Reviews)
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  • Air Conditioner
  • Pet Friendly
  • Internet
The Villa Toscana From US $103
         

7.8 (636 Reviews)
Bed & Breakfast
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The Avondale Lower Level From US $251
         

9.6 (60 Reviews)
Apartment
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  • Pet Friendly
Wrigley Field/Lakeview -Entire Home- Large Groups! From US $753
         

9.8 (89 Reviews)
House
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  • Pet Friendly
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)
Condo
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Stylish, Inviting 2-BR near Logan Square and Wrigley Field From US $247
         

10.0 (73 Reviews)
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  • Pet Friendly

Large Vacation Homes & Villas in Roscoe Village

Over 272+ Large Vacation Homes & Villas in or Near Roscoe Village
Magic Factory Loft 3East 4 Bd/4 Ba Families Groups From US $1,129
         

10.0 (106 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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5 Bedroom Wrigleyville experience right by stadium From US $903
         

10.0 (63 Reviews)
Apartment
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Chicago Bootlegger House Sleeps 11-22 with 3 parking spots From US $873
         

10.0 (48 Reviews)
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  • Pet Friendly

Wheelchair Accessible Vacation Homes in Roscoe Village

Over 250+ Wheelchair Accessible Vacation Homes in or Near Roscoe Village
Spacious 4BR Central Apartment w/Skyline Views From US $465
         

10.0 (12 Reviews)
Apartment
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  • Pet Friendly
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Ray's Bucktown Bed and Breakfast From US $271
         

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9.5 (161 Reviews)
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Villa D' Citta From US $242
         

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9.4 (115 Reviews)
Bed & Breakfast
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The Cornerstone - Designer 4BR Flat in Bucktown/WP From US $1,000
         

10.0 (11 Reviews)
Apartment
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  • TV
  • Wheelchair Accessible
Modern & Bright Chicago City Escape From US $388
         

10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Chic apartment in marvelous Chicago with WiFi, AC From US $267
         

10.0 (10 Reviews)
Apartment
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Game Day Stay Steps to Wrigley + Garage From US $625
         

10.0 (4 Reviews)
Apartment
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  • Pet Friendly
Modern 1 King City Escape From US $1,013
         

10.0 (3 Reviews)
Apartment
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  • Pet Friendly
  • TV

Roscoe Village Vacation Rentals and Airbnb Places to Stay Under $200

Over 635+ Roscoe Village Vacation Rentals and Airbnb Places to Stay Under $200
Wicker Park 1-BR Walk to Train & Grocery Easy Downtown Access From US $187
         

10.0 (8 Reviews)
Apartment
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  • Pet Friendly
Ray's Bucktown B&B From US $178
         

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9.8 (394 Reviews)
Bed & Breakfast
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  • Balcony/Terrace
Cozy 1 Bedroom Apt near Logan Sq Chicago From US $200
         

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

10.0 (2 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety

Instantly Bookable Vacation Homes in Roscoe Village

Over 1031+ Instantly Bookable Vacation Homes in or Near Roscoe Village
Wrigley Field Home Run 4 Bedroom, 2 Bathroom From US $1,083
         

9.6 (20 Reviews)
Condo
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1BR Well-Equipped Apartment From US $186
         

New
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Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms From US $1,944
         

9.0 (15 Reviews)
Condo
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  • Child Friendly
Wrigley Field All Star Suite 3 Bedrooms 2 Bath From US $958
         

9.4 (22 Reviews)
Condo
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  • TV
  • Security/Safety
Great Location-Beautiful Friendly Andersonville Neighborhood From US $293
         

Cozy Nest in Chicago's Vibrant Lincoln Square From US $394
         

10.0 (74 Reviews)
Apartment
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  • Parking
  • TV

About Roscoe Village Vacation Rentals

With more than 1951 Roscoe Village 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 Roscoe Village.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Sisterbaycondorentals Roscoe Village, 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 Roscoe Village. Places to stay near Roscoe Village are 785.46 ft² on average, with prices averaging $461 a night.

Sisterbaycondorentals makes it easy and safe to find and compare vacation rentals in Roscoe Village 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 Roscoe Village

Type Count
Holiday Apartments 1322
Vacation Homes 329
Hotels with Suites 79
B&B 24
Hostels 5
Cottages 2
Others 2
Cabin Rentals 1
Resorts 1

Use these Quick Filters to Find a Vacation Rental in Roscoe Village

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 Roscoe Village.

Weather in Roscoe Village

View the weather forecast for Roscoe Village before booking your Roscoe Village 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

Roscoe Village Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Roscoe Village?
How many vacation rentals are available in Roscoe Village?

Currently, the total number of properties listed in 2026 is over 1951 in the Roscoe Village area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Roscoe Village.