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

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184 Best Vacation Rentals in Roseland (Starting from $79)

Fully Equipped Cozy 4/5 BR
Fully Equipped Cozy 4/5 BR
Apartment
Chicago, IL, USA
1.8k from Roseland center

Apartments, Accommodations, Pools, Lodgings, Hot tubs, Places to stay, Family

4 Bedrooms10 Guests
5.4

Review score

29 reviews

$284
Average price / night
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Cozy 2 bedroom single residence near the Historical Beverly Hills community
Cozy 2 bedroom single residence near the Historical Beverly Hills community
House
Chicago, IL, 60628, United States
1.4k from Roseland center

AC, Heater, Internet, Kitchen, No Smoking

2 Bedrooms4 Guests
New to Booking
$142
Average price / night
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Entire Guest 1bedroom with private entrance
Entire Guest 1bedroom with private entrance
House
Chicago, IL, USA
2.2k from Roseland center

Air Conditioner, Internet, Parking, Child Friendly

1 Bedroom3 Guests
New to Booking
$132
Average price / night
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1 Block to Red Line Station: Walkable Chicago Home
1 Block to Red Line Station: Walkable Chicago Home
House
Chicago, IL, 60619, United States
1.7k from Roseland center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Kitchen, Living Area

6 Bedrooms8 Guests
New to Booking
$144
Average price / night
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Beautiful 4 bedroom 2 bathroom apartment near everything
Beautiful 4 bedroom 2 bathroom apartment near everything
Apartment
Chicago, IL, USA
4.1k from Roseland center

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

4 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$250
Average price / night
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Modern \"Blast From The Past\" A Real Retreat 3Bedroom Unit
Modern \"Blast From The Past\" A Real Retreat 3Bedroom Unit
Apartment
Chicago, IL, 60628, United States
1.7k from Roseland center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Toys

4 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$220
Average price / night
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New Luxurious 5BD-2BA Home-FREE WINE-2CAR Parking
New Luxurious 5BD-2BA Home-FREE WINE-2CAR Parking
Apartment
Chicago, IL, USA
4.6k from Roseland center

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

5 Bedrooms10 Guests
8.7

Fabulous

3 reviews

$464
Average price / night
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Wonderful 4-bedroom house with AC in charming Chicago
Wonderful 4-bedroom house with AC in charming Chicago
House
Chicago, IL, 60643, United States
1.9k from Roseland center

AC, Internet, No Smoking

4 Bedrooms8 Guests
New to Booking
$381
Average price / night
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Comfortable & Relaxing Charming 3BR unit
Comfortable & Relaxing Charming 3BR unit
Apartment
Chicago, IL, USA
4.7k from Roseland center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Self-catering

3 Bedrooms7 Guests
7.7

Good

4 reviews

$213
Average price / night
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Chic Retreat, Chic Retreat \"Your Urban Getaway\"
Chic Retreat, Chic Retreat \"Your Urban Getaway\"
Apartment
Chicago, IL, 60619, United States
2.0k from Roseland center

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

3 Bedrooms9 Guests
6.0

Review score

4 reviews

$419
Average price / night
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2 Mi to Calumet Park and Beach Windy City Escape!
2 Mi to Calumet Park and Beach Windy City Escape!
House
Chicago, IL, USA
5.0k from Roseland center

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

3 Bedrooms8 Guests
New to Booking
$354
Average price / night
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Home in the Historic Town of Pullman
Home in the Historic Town of Pullman
House
Chicago, IL, 60628, United States
2.4k from Roseland center

AC, Free Parking, Heater, Internet, Kitchen, No Smoking

4 Bedrooms4 Guests
New to Booking
$170
Average price / night
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Gorgeous 5 BR Gem with Games
Gorgeous 5 BR Gem with Games
House
Chicago, IL, USA
5.5k from Roseland center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Family

5 Bedrooms16 Guests
New to Booking
$367
Average price / night
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Upscale Chatham Home Perfect for Families & Groups
Upscale Chatham Home Perfect for Families & Groups
House
Chicago, IL, 60619, United States
2.5k from Roseland center

AC, Barbecue, Fireplace, Heater, Internet, Microwave, TV

4 Bedrooms10 Guests
New to Booking
$491
Average price / night
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Bluenile
Bluenile
Apartment
Chicago, IL, USA
5.6k from Roseland center

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

6 Bedrooms14 Guests
New to Booking
$252
Average price / night
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This is a totally new rehab
This is a totally new rehab
House
Chicago, IL, 60619, United States
2.5k from Roseland center

AC, Free Parking, Heater, Hot Tub, Internet, Kitchen, Microwave, No Smoking, TV

5 Bedrooms10 Guests
5.8

Review score

6 reviews

$413
Average price / night
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Chicago Home Near Navy Pier & Shedd Aquarium!
Chicago Home Near Navy Pier & Shedd Aquarium!
House
Chicago, IL, 60619-7436, United States
2.5k from Roseland center

AC, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking, TV, Washer

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$236
Average price / night
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Chicago Apt 3 Mi to Lake Michigan!
Chicago Apt 3 Mi to Lake Michigan!
Apartment
Chicago, IL, USA
6.1k from Roseland center

Apartments, Accommodations, Parking, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$79
Average price / night
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Beautiful home near WhiteSox Stadium and Downtown Chicago.
Beautiful home near WhiteSox Stadium and Downtown Chicago.
House
Chicago, IL, 60619, United States
2.8k from Roseland center

AC, Heater, Internet, Kitchen, No Smoking, Patio, TV

3 Bedrooms10 Guests
New to Booking
$283
Average price / night
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Beautiful Big 3 bedroom Quiet Apt near downtown
Beautiful Big 3 bedroom Quiet Apt near downtown
Apartment
Chicago, IL, USA
6.2k from Roseland center

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

5 Bedrooms8 Guests
8.7

Fabulous

20 reviews

$259
Average price / night
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Private Basement Suite-Completely separate from the rest of the house
Private Basement Suite-Completely separate from the rest of the house
House
Chicago, IL, 60619, United States
2.8k from Roseland center

AC, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, No Smoking, TV

1 Bedroom2 Guests
New to Booking
$123
Average price / night
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Beautiful and Spacious Home near Beverly area
Beautiful and Spacious Home near Beverly area
House
Chicago, IL, 60643, United States
2.9k from Roseland center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Microwave

4 Bedrooms6 Guests
New to Booking
$191
Average price / night
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Luxury 2-Bedroom Home with Themed Rooms & Private Party Space
Luxury 2-Bedroom Home with Themed Rooms & Private Party Space
House
Chicago, IL, 60643, United States
2.9k from Roseland center

Pet Friendly, Smoking

2 Bedrooms6 Guests
New to Booking
$201
Average price / night
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Charming 4-bedroom house with WiFi and AC in amazing Chicago
Charming 4-bedroom house with WiFi and AC in amazing Chicago
House
Chicago, IL, 60620, United States
2.9k from Roseland center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
9.0

Fabulous

2 reviews

$679
Average price / night
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Chicago Furnished 2-bedroom apartment with free WiFi & heated bathroom floors!
Chicago Furnished 2-bedroom apartment with free WiFi & heated bathroom floors!
Apartment
Chicago, IL, 60643, United States
3.1k from Roseland center

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

2 Bedrooms1 Guest
New to Booking
$127
Average price / night
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20 mins to downtown or Indiana
20 mins to downtown or Indiana
Apartment
Chicago, IL, 60619, United States
3.2k from Roseland center

AC, Dryer, Heater, Internet, Laundry, Washer

2 Bedrooms6 Guests
New to Booking
$114
Average price / night
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Luxury 3-Bedroom Home with Themed Rooms & Private Party Space
Luxury 3-Bedroom Home with Themed Rooms & Private Party Space
House
Chicago, IL, 60643, United States
3.2k from Roseland center

Dryer, Heater, Internet, Kitchen, Laundry, Microwave, TV, Washer

3 Bedrooms10 Guests
New to Booking
$301
Average price / night
Check Availability

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 Roseland.

Stay Near Roseland's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Roseland Vacation Rentals on the Map

Frequently Asked Questions

You can explore 184 verified vacation rentals in Roseland. 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 Roseland vary depending on the season, property size, and location. Rates typically start from around $79 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 Roseland 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 Roseland welcome pets. Currently, 27 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 Roseland often include amenities such as Fireplace/Heating, Internet, and Bedding/Linens. 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.