Vacation Rentals in Roscoe Village, IL: Compare 10+ Sites & Save

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2085 Best Vacation Rentals in Roscoe Village (Starting from $78)

The Roscoe Village Guesthouse
The Roscoe Village Guesthouse
Apartment
Chicago, IL, USA
0.1k from Roscoe Village center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Family, Self-catering

3 Bedrooms6 Guests
9.7

Exceptional

8 reviews

$360
Average price / night
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Urban Oasis in Roscoe Village! Pet friendly and family friendly!
Urban Oasis in Roscoe Village! Pet friendly and family friendly!
Apartment
Chicago, IL, 60618, United States
0.2k from Roscoe Village center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms8 Guests
9.8

Exceptional

10 reviews

$485
Average price / night
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Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Apartment
Chicago, IL, 60618, United States
0.2k from Roscoe Village center

AC, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
9.8

Exceptional

152 reviews

$344
Average price / night
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Roscoe Village Family Hideaway
Roscoe Village Family Hideaway
House
Chicago, IL, USA
0.5k from Roscoe Village center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

4 Bedrooms13 Guests
9.0

Fabulous

1 reviews

$795
Average price / night
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The Roscoe Village Brownstone\n
The Roscoe Village Brownstone\n
Apartment
Chicago, IL, 60618, United States
0.2k from Roscoe Village center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms4 Guests
9.8

Exceptional

28 reviews

$415
Average price / night
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FRONTDESK Modern 2 BR Apt with Lake View
FRONTDESK Modern 2 BR Apt with Lake View
Apartment
Chicago, IL, USA
0.7k from Roscoe Village center

Air Conditioner, Internet, Parking

2 Bedrooms4 Guests
7.7

Good

3 reviews

$99
Average price / night
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Modern 2BR in Roscoe/Wrigley with Free Street Parking walk to Paulina Brown-line
Modern 2BR in Roscoe/Wrigley with Free Street Parking walk to Paulina Brown-line
House
Chicago, IL, 60657, United States
0.3k from Roscoe Village center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$138
Average price / night
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FRONTDESK Revamped 1 BR Apt with Laundry and Lake View
FRONTDESK Revamped 1 BR Apt with Laundry and Lake View
Apartment
Chicago, IL, USA
0.7k from Roscoe Village center

Internet, Air Conditioner

1 Bedroom2 Guests
5.5

Review score

4 reviews

$78
Average price / night
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Urban Oasis in Roscoe Village
Urban Oasis in Roscoe Village
Apartment
Chicago, IL, 60618, United States
0.3k from Roscoe Village center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms8 Guests
New to Booking
$231
Average price / night
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Vibrant 1BR Apartment in Roscoe Village - Marshfield N3
Vibrant 1BR Apartment in Roscoe Village - Marshfield N3
Apartment
Chicago, IL, USA
0.8k from Roscoe Village center

Air Conditioner, Parking, Internet, Pet Friendly, Guest Services, Security/Safety, Child Friendly

1 Bedroom2 Guests
7.4

Good

5 reviews

$366
Average price / night
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Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
Apartment
Chicago, IL, 60618, United States
0.3k from Roscoe Village center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

201 reviews

$285
Average price / night
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Conveniently Located 1BR Apartment - Marshfield E2
Conveniently Located 1BR Apartment - Marshfield E2
Apartment
Chicago, IL, USA
0.8k from Roscoe Village center

Internet, Pet Friendly, Guest Services, Security/Safety, Child Friendly

1 Bedroom2 Guests
1.0

Review score

1 reviews

$367
Average price / night
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Roscoe Village- Only steps to cute shops & dining! Sleeps 4-6
Roscoe Village- Only steps to cute shops & dining! Sleeps 4-6
Apartment
Chicago, IL, 60618, United States
0.3k from Roscoe Village center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
10.0

Exceptional

96 reviews

$314
Average price / night
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Chic 1BR Apt Close to Everything - Marshfield E3
Chic 1BR Apt Close to Everything - Marshfield E3
Apartment
Chicago, IL, USA
0.8k from Roscoe Village center

Apartments, Accommodations, Pet-friendly, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
4.0

Review score

3 reviews

$299
Average price / night
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Luxury duplex home in Roscoe Village/Wrigley Field with Free Steet Parking
Luxury duplex home in Roscoe Village/Wrigley Field with Free Steet Parking
House
Chicago, IL, 60657, United States
0.3k from Roscoe Village center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms7 Guests
10.0

Exceptional

30 reviews

$555
Average price / night
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1BR Fully Equipped & Central - Belmont rep
1BR Fully Equipped & Central - Belmont rep
Apartment
Chicago, IL, USA
0.9k from Roscoe Village center

Apartments, Cheap, Accommodations, Pet-friendly, Lodgings, Places to stay

2 Bedrooms2 Guests
8.1

Very Good

7 reviews

$304
Average price / night
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2BR Enticing Apt in Chicago near Restaurants - Belmont A2 A4 rep
2BR Enticing Apt in Chicago near Restaurants - Belmont A2 A4 rep
Apartment
Chicago, IL, USA
0.9k from Roscoe Village center

Internet, Fireplace/Heating, Security/Safety, Guest Services, Pet Friendly, Child Friendly

2 Bedrooms4 Guests
5.5

Review score

2 reviews

$438
Average price / night
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Prime 4 BR Sleeps 13, Chef Kitchen, 8 Blks to Wrigley, 15min Train to Mag Mile
Prime 4 BR Sleeps 13, Chef Kitchen, 8 Blks to Wrigley, 15min Train to Mag Mile
House
Chicago, IL, 60657, United States
0.4k from Roscoe Village center

AC, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms13 Guests
9.8

Exceptional

25 reviews

$1126
Average price / night
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Wrigley 2BR, 1BA with Free Parking
Wrigley 2BR, 1BA with Free Parking
Apartment
Chicago, IL, USA
1.0k from Roscoe Village center

Air Conditioner, Balcony/Terrace, Breakfast, Parking, Fireplace/Heating, Internet, Sports/Activities

2 Bedrooms6 Guests
9.0

Fabulous

2 reviews

$618
Average price / night
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Warm Modern 2BR • Walkable Roscoe Village
Warm Modern 2BR • Walkable Roscoe Village
Apartment
Chicago, IL, 60618, United States
0.5k from Roscoe Village center

AC, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, TV

2 Bedrooms4 Guests
New to Booking
$130
Average price / night
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The Broasis at Wrigley
The Broasis at Wrigley
Apartment
Chicago, IL, 60613, United States
0.7k from Roscoe Village center

AC, Balcony, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$861
Average price / night
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The Grand Vic: Large 5BD/3BA Home +Garage\n
The Grand Vic: Large 5BD/3BA Home +Garage\n
Apartment
Chicago, IL, 60613, United States
0.7k from Roscoe Village center

AC, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms12 Guests
10.0

Exceptional

8 reviews

$786
Average price / night
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Spacious 3BR/2BA North Center Gem - 10-Min Walk to Brown Line - Fast Wi-Fi
Spacious 3BR/2BA North Center Gem - 10-Min Walk to Brown Line - Fast Wi-Fi
Apartment
Chicago, IL, 60618, United States
0.7k from Roscoe Village center

AC, Balcony, Crib, Dryer, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$575
Average price / night
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Cozy Lakeview apartment near Train Station
Cozy Lakeview apartment near Train Station
Apartment
Chicago, IL, 60657, United States
0.7k from Roscoe Village center

AC, Arcade, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$171
Average price / night
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Large 2-Bedroom w/ Huge Roofdeck view of Skyline
Large 2-Bedroom w/ Huge Roofdeck view of Skyline
Apartment
Chicago, IL, 60618, United States
0.8k from Roscoe Village center

AC, Balcony, Barbecue, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
9.4

Superb

6 reviews

$414
Average price / night
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Clean & Equipped 1BR Apt
Clean & Equipped 1BR Apt
Apartment
Chicago, IL, 60657, United States
0.8k from Roscoe Village center

Dryer, Heater, Internet, Kitchen, Laundry, No Smoking, TV, Washer

1 Bedroom2 Guests
9.2

Superb

60 reviews

$175
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Roscoe Village.

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Frequently Asked Questions

You can explore 2085 verified vacation rentals in Roscoe Village. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Roscoe Village vary depending on the season, property size, and location. Rates typically start from around $78 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Roscoe Village include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Roscoe Village welcome pets. Currently, 42 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Roscoe Village often include amenities such as Fireplace/Heating, Wellness Facilities, and Internet. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.