Photo by Jess Rigdon
Roscoe Village holiday rentals
We found 274 holiday rentals — enter your dates for availability
Discover a selection of 11 apartments and other holiday rentals in Roscoe Village that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the best amenities for spending time at your holiday home, which might include Wi-Fi and a pool. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Roscoe Village
Showing deals for:3 Oct - 10 Oct
Image gallery for Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!
Chicago, IL
7% off
Price is AU$9,835
AU$9,835
AU$1,405 per night
includes taxes & fees
Image gallery for 2-bedroom apartment just 2 minutes drive to Wrigley Field
9.49.4 out of 10 rating
Exceptional
(27 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
9% off
Price is AU$2,971
AU$2,971
AU$424 per night
includes taxes & fees
Image gallery for Spacious 3 bedroom in ideal Roscoe village location
1010 out of 10 rating
Exceptional
(45 reviews)
Spacious 3 bedroom in ideal Roscoe village location
Chicago, IL
7% off
Price is AU$2,946
AU$2,946
AU$421 per night
includes taxes & fees
Image gallery for Eddy House, Roscoe Village Haven
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Eddy House, Roscoe Village Haven
Chicago, IL
12% off
Price is AU$12,042
AU$12,042
AU$1,720 per night
includes taxes & fees
Image gallery for Perfect weekend getaway 2BR 2BA Apartment near Wrigley Field
1010 out of 10 rating
Exceptional
(43 reviews)
Perfect weekend getaway 2BR 2BA Apartment near Wrigley Field
Chicago, IL
7% off
Price is AU$3,717
AU$3,717
AU$531 per night
includes taxes & fees
Image gallery for The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence
9.69.6 out of 10 rating
Exceptional
(166 reviews)
The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence
Chicago, IL
17% off
Price is AU$5,631
AU$5,631
AU$804 per night
includes taxes & fees
Image gallery for Chic and Spacious Bi-level 3BD in Bucktown!
1010 out of 10 rating
Exceptional
(6 reviews)
Chic and Spacious Bi-level 3BD in Bucktown!
Chicago, IL
7% off
Price is AU$5,260
AU$5,260
AU$751 per night
includes taxes & fees
Image gallery for PRISTINE PREMIER LUXURY 3-STORY GREYSTONE HOME! ABSOLUTELY NO PARTIES!
1010 out of 10 rating
Exceptional
(51 reviews)
PRISTINE PREMIER LUXURY 3-STORY GREYSTONE HOME! ABSOLUTELY NO PARTIES!
Chicago, IL
8% off
Price is AU$16,067
AU$16,067
AU$2,295 per night
includes taxes & fees
Image gallery for The Irving Park Hideaway – Prime Location w/ Patio & Parking!
1010 out of 10 rating
Exceptional
(18 reviews)
The Irving Park Hideaway – Prime Location w/ Patio & Parking!
Chicago, IL
7% off
Price is AU$4,441
AU$4,441
AU$634 per night
includes taxes & fees
Image gallery for Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!
9.49.4 out of 10 rating
Exceptional
(40 reviews)
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!
Chicago, IL
13% off
Price is AU$14,009
AU$14,009
AU$2,001 per night
includes taxes & fees
Image gallery for Unique Chicago Penthouse Loft - Amazing Deal & Location
9.89.8 out of 10 rating
Exceptional
(95 reviews)
Unique Chicago Penthouse Loft - Amazing Deal & Location
Chicago, IL
11% off
Price is AU$5,156
AU$5,156
AU$737 per night
includes taxes & fees
Image gallery for Modern 4 Bedroom Apt Next to Park&Pool | Lakeview
9.89.8 out of 10 rating
Exceptional
(60 reviews)
Modern 4 Bedroom Apt Next to Park&Pool | Lakeview
Chicago, IL
10% off
Price is AU$4,724
AU$4,724
AU$675 per night
includes taxes & fees
Image gallery for Gather Together & WFH in Piece of Chicago History
1010 out of 10 rating
Exceptional
(8 reviews)
Gather Together & WFH in Piece of Chicago History
Chicago, IL
14% off
Price is AU$7,707
AU$7,707
AU$1,101 per night
includes taxes & fees
Image gallery for Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
9.89.8 out of 10 rating
Exceptional
(138 reviews)
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Chicago, IL
7% off
Price is AU$4,082
AU$4,082
AU$583 per night
includes taxes & fees
Image gallery for The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!
9.89.8 out of 10 rating
Exceptional
(78 reviews)
The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!
Chicago, IL
18% off
Price is AU$7,096
AU$7,096
AU$1,014 per night
includes taxes & fees
Image gallery for Wrigleyville Jungle House w/ game room basement party room for large groups!
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Wrigleyville Jungle House w/ game room basement party room for large groups!
Chicago, IL
8% off
Price is AU$13,997
AU$13,997
AU$2,000 per night
includes taxes & fees
Image gallery for The Wrigleyville Garden- 200 Steps to Wrigley - Super Clean!
9.89.8 out of 10 rating
Exceptional
(65 reviews)
The Wrigleyville Garden- 200 Steps to Wrigley - Super Clean!
Chicago, IL
17% off
Price is AU$4,631
AU$4,631
AU$662 per night
includes taxes & fees
Image gallery for Charming|Comfortable|1BR|Lincoln Square
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Charming|Comfortable|1BR|Lincoln Square
Chicago, IL
7% off
Price is AU$3,799
AU$3,799
AU$543 per night
includes taxes & fees
Image gallery for Stylish, Inviting 2-BR near Logan Square and Wrigley Field
1010 out of 10 rating
Exceptional
(54 reviews)
Stylish, Inviting 2-BR near Logan Square and Wrigley Field
Chicago, IL
7% off
Price is AU$2,648
AU$2,648
AU$378 per night
includes taxes & fees
Image gallery for 3BR Modern Condo near Wrigley/Dwtn +Free Parking
9.49.4 out of 10 rating
Exceptional
(30 reviews)
3BR Modern Condo near Wrigley/Dwtn +Free Parking
Chicago, IL
7% off
Price is AU$5,505
AU$5,505
AU$786 per night
includes taxes & fees
Image gallery for Vintage Wrigleyville Apartment + Free Parking
1010 out of 10 rating
Exceptional
(41 reviews)
Vintage Wrigleyville Apartment + Free Parking
Chicago, IL
11% off
Price is AU$5,347
AU$5,347
AU$764 per night
includes taxes & fees
Image gallery for 2 New Construction Suites Same Place
9.49.4 out of 10 rating
Exceptional
(21 reviews)
2 New Construction Suites Same Place
Chicago, IL
15% off
Price is AU$8,825
AU$8,825
AU$1,261 per night
includes taxes & fees
Image gallery for Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
1010 out of 10 rating
Exceptional
(146 reviews)
Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
Chicago, IL
22% off
Price is AU$2,811
AU$2,811
AU$402 per night
includes taxes & fees
Image gallery for Walk to Wrigley Field/Monthly Discounts Available
9.69.6 out of 10 rating
Exceptional
(147 reviews)
Walk to Wrigley Field/Monthly Discounts Available
Chicago, IL
15% off
Price is AU$3,570
AU$3,570
AU$510 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Roscoe Village
Showing deals for: 1 Oct - 4 Oct
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Sleeps 6 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
138 reviews(138 reviews)
The current price is AU$1,822
AU$1,822
for 3 nights, 1 room
AU$607 per night
includes taxes & fees
The Roscoe Village Brownstone
Sleeps 4 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
21 reviews(21 reviews)
The current price is AU$2,073
AU$2,073
for 3 nights, 1 apartment
AU$691 per night
includes taxes & fees
Modern 4 Bedroom Apt Next to Park&Pool | Lakeview
Sleeps 8 · 4 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
60 reviews(60 reviews)
The current price is AU$2,529
AU$2,529
for 3 nights, 1 apartment
AU$843 per night
includes taxes & fees
Luxury duplex home in Roscoe Village/Wrigley Field with Free Steet Parking
Sleeps 7 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
The current price is AU$2,286
AU$2,286
for 3 nights, 1 home
AU$762 per night
includes taxes & fees
Urban Oasis in Roscoe Village! Pet friendly and family friendly!
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
The current price is AU$2,812
AU$2,812
for 3 nights, 1 apartment
AU$937 per night
includes taxes & fees
Roscoe Village- Only steps to cute shops & dining! Sleeps 4-6
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
90 reviews(90 reviews)
The current price is AU$1,584
AU$1,584
for 3 nights, 1 apartment
AU$528 per night
includes taxes & fees
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday home accommodation in Roscoe Village?
According to our research, apartments are the most sought-after type of holiday property in Roscoe Village. But as you know, everyone's idea of an epic stay differs. Stayz has holiday homes of all shapes, sizes and budgets, and we'll help you locate the best fit for your needs.
How much does it cost to rent a holiday home in Roscoe Village?
Season, property type and length of stay are some things that can determine the price of a holiday home. Simply click on your travel dates to find the ultimate escape. From comfy cabins to sprawling luxury villas, all Stayz holiday homes offer unbeatable value.
How much does it cost to rent a beach house in Roscoe Village?
When you travel and the style and size of the property will influence how much you'll pay for your beachside holiday home. Enter your Roscoe Village travel dates to view your available options on Stayz. Did someone just say "private pool"? Use the filters to choose the features and amenities you want in your home.
Are there pet-friendly holiday homes in Roscoe Village?
Yes. You'll have your pick of 10 holiday homes that cater to pets in Roscoe Village. Many of our pet-friendly holiday homes even have a backyard for your four-legged fur baby to have fun in, complimentary treats, doggie beds and proximity to parks or green space. Apply the "Pets allowed" filter to find your pawfect place on Stayz.
What are popular home amenities in Roscoe Village?
Some of the most popular home amenities people are searching for in Roscoe Village include a barbecue grill, a garden and a fireplace. Whether you're travelling with family, pals or even pets, Stayz holiday properties have the best amenities for fun and relaxation with the people you love.
Are there large group holiday homes in Roscoe Village?
With seven Roscoe Village holiday homes that can sleep five or more people, you can invite a few extra family members or friends along. Whether you're planning an informal gathering or a special event, Stayz will help you book the ideal space to match the occasion.
Are there holiday homes in Roscoe Village that welcome kids?
Gather the whole crew for a fun-packed adventure in Roscoe Village at one of our 10 family-friendly holiday homes. A lot of these stays come with amenities that are ideally suited to getaways with children, like laundries, living rooms and outdoor spaces. Simply click on the "Properties good for families" filter and select your favourite.
What are the top attractions for families in Roscoe Village?
Keep the kids occupied at these top family-friendly attractions in Roscoe Village:
- Navy Pier
- Chicago Riverwalk
- Shedd Aquarium
Can I find two-bedroom holiday homes in Roscoe Village?
Roscoe Village has five two-bedroom holiday properties that you can choose from. Go for a holiday home with all the comfort and space you want at a price that won't break the bank on Stayz.
Are there holiday homes with WiFi in Roscoe Village?
You'll have a choice of three holiday homes with WiFi in Roscoe Village. If you want to disconnect from daily life on your holiday, but still need to be connected to the internet, these getaways have just what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Roscoe Village?
Roscoe Village has nine holiday homes where you can relax in air-conditioned comfort. To find a property on Stayz with this perk, choose your travel dates and use the filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Roscoe Village?
You should check with the Roscoe Village holiday home you'd like on Stayz as the age limit varies. However, it's typically 16, 18 or 21.
How long can I rent a holiday home in Roscoe Village for?
The amount of time you can book a Roscoe Village holiday home for depends on the property. Just tap in your travel dates to browse options that offer long-term stays. They have all you need to make your extended break more enjoyable and comfortable, such as kitchens and yards. Some holiday homes might also offer weekly or monthly discounts, so you can stay longer for less money.