Trippy Mates - Vacation Rentals in Roscoe Village

Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood From US $238
         

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

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New
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Wrigleyville Inn From US $531
         

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10.0 (21 Reviews)
House
  • Air Conditioner
  • Parking
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Magic Factory Loft 2East 4 Bd/3 Ba Families Groups From US $822
         

10.0 (119 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld! From US $195
         

10.0 (38 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field From US $593
         

10.0 (111 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Roscoe Village

Over 1823+ Luxury Places to Stay in or Near Roscoe Village
Wrigley 4BR Home, Sleeps 10 From US $4,986
         

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: The Wolcott : Modern Elegance at Its Finest From US $3,480
         

Top-Rated Vacation Rentals with a Pool in Roscoe Village

Over 67+ 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)
Apartment
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Lincoln Park Getaway: Skyline Views & Luxury From US $433
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • TV
Prime Lincoln Park Views + Modern Amenities Await From US $420
         

Unique Chicago Penthouse Loft - Amazing Deal & Location From US $418
         

Historic 1920s Private Bungalow Near Logan Square! From US $371
         

9.8 (40 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Roscoe Village

Over 696+ Pet-Friendly Vacation Rentals in or Near Roscoe Village
The Avondale Lower Level From US $132
         

9.6 (55 Reviews)
Apartment
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  • Parking
  • Pet Friendly
Chicago Quick Stay From US $130
         

6.3 (47 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Internet
The Villa Toscana From US $70
         

7.8 (622 Reviews)
Bed & Breakfast
  • Parking
  • Pet Friendly
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Wrigley Field/Lakeview -Entire Home- Large Groups! From US $762
         

10.0 (85 Reviews)
House
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  • Parking
  • Pet Friendly
NEW LUXURY PENTHOUSE CONDO From US $399
         

10.0 (200 Reviews)
Condo
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  • Parking
  • Pet Friendly
NEW LUXURY CONDO WITH PATIO DECK From US $293
         

10.0 (190 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Stylish, Inviting 2-BR near Logan Square and Wrigley Field From US $187
         

10.0 (66 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Roscoe Village

Over 251+ Large Vacation Homes & Villas in or Near Roscoe Village
Magic Factory Loft 3East 4 Bd/4 Ba Families Groups From US $1,119
         

10.0 (106 Reviews)
Apartment
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  • Parking
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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 $811
         

10.0 (60 Reviews)
Apartment
  • Air Conditioner
  • Parking
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Chicago Bootlegger House Sleeps 11-22 with 3 parking spots From US $732
         

10.0 (47 Reviews)
House
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  • Parking
  • Pet Friendly
Entire house 1 city block from Wrigley Field. From US $1,234
         

10.0 (24 Reviews)
House
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  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Roscoe Village

Over 243+ Wheelchair Accessible Vacation Homes in or Near Roscoe Village
Spacious 4BR Central Apartment w/Skyline Views From US $402
         

10.0 (7 Reviews)
Apartment
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  • TV
  • Wheelchair Accessible
Ray's Bucktown Bed and Breakfast From US $271
         

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9.3 (172 Reviews)
Bed & Breakfast
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  • Parking
  • Pet Friendly
Villa D' Citta From US $242
         

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9.4 (111 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Modern & Bright Chicago City Escape From US $231
         

10.0 (6 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
2BR City Loft Sweeping Glass Views From US $851
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
1BR City Loft With Modern Glass Views From US $209
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Game Day Stay Steps to Wrigley + Garage From US $516
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
New, Modern 1BR Lux City Escape From US $195
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Roscoe Village Varoom and Airbnb Places to Stay Under $200

Over 723+ Roscoe Village Varoom and Airbnb Places to Stay Under $200
Family-friendly, stylish Chicago Apartment in Logan Square From US $179
         

Stylish 2BR stunner in unbeatable location From US $194
         

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10.0 (3 Reviews)
Apartment
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  • Pet Friendly
Ray's Bucktown B&B From US $178
         

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9.8 (382 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Balcony/Terrace
North Center King Bed Walkable Highly Rated NEWYEARS WEEK AVAILABLE From US $193
         

Light and bright 3BD duplex in Avondale, Chicago From US $190
         

10.0 (27 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Roscoe Village

Over 975+ Instantly Bookable Vacation Homes in or Near Roscoe Village
Wrigley Field Home Run 4 Bedroom, 2 Bathroom From US $1,095
         

9.6 (19 Reviews)
Condo
  • Balcony/Terrace
  • Security/Safety
  • Fireplace/Heating
1BR Well-Equipped Apartment From US $186
         

New
Apartment
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  • Pet Friendly
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Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms From US $1,095
         

9.0 (14 Reviews)
Condo
  • Balcony/Terrace
  • Security/Safety
  • Child Friendly
Wrigley Field All Star Suite 3 Bedrooms 2 Bath From US $954
         

9.4 (22 Reviews)
Condo
  • Air Conditioner
  • TV
  • Security/Safety
Great Location-Beautiful Friendly Andersonville Neighborhood From US $257
         

Cozy Nest in Chicago's Vibrant Lincoln Square From US $294
         

10.0 (70 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

About Roscoe Village Vacation Rentals

With more than 1832 Roscoe Village vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Trippymates 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 Trippymates 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 761.88 ft² on average, with prices averaging $406 a night.

Trippymates 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 1231
Vacation Homes 314
Hotels with Suites 78
B&B 25
Hostels 4
Cottages 2
Others 2
Cabin Rentals 1
Resorts 1

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

Pro Tip: Trippymates makes it easy to compare the best listings on Trippymates homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Trippymates 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