Photo by Jess Rigdon

Roscoe Village holiday lettings

We found 266 holiday rentals — enter your dates for availability

Discover a selection of 8 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:14 Nov - 21 Nov
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Find out more about Roscoe Village

Find out more about Roscoe Village

Why visit Roscoe Village

  • Family-Friendly Activities: Roscoe Village boasts a variety of attractions suitable for families, ensuring fun for all ages.
  • Outdoor Adventures: The area is perfect for outdoor enthusiasts, with numerous parks and recreational activities available.
  • Charming Local Culture: Enjoy the vibrant atmosphere with trendy cafes and boutiques that reflect the neighbourhood's unique character.
  • Picturesque Old Town: Explore the nearby Old Town, known for its romantic ambiance and scenic views.
  • Diverse Accommodation Options: Choose from delightful guesthouses, inviting inns, or stylish apartments for a comfortable stay.

Popular types of accommodation around Roscoe Village

If you're pondering the ideal accommodation for your stay in Roscoe Village, look no further. Our range of options includes charming guesthouses, inviting inns, and well-appointed apartments. Whether you're seeking a private vacation home or a stylish condo, Roscoe Village has something for everyone. Explore our selection of short-term rentals and enjoy a delightful getaway with all the comforts of home.

  • Apartments: The top choice for visitors in Roscoe Village, offering spacious living areas and convenient amenities for a comfortable stay.
  • Houses: A fantastic option for families or groups, providing a homely atmosphere with privacy and flexibility.
  • Condos: A popular selection that combines modern design with communal facilities, ideal for short or extended stays.
  • Cottages: A quaint and charming retreat, perfect for those seeking a cosy and intimate getaway.**

Top attractions near Roscoe Village

Roscoe Village is an excellent choice for families and those seeking outdoor activities. Visitors can enjoy a variety of attractions, including beaches, urban parks, and modern universities, all of which provide rich cultural experiences. Whether you're travelling with loved ones or looking for sports activities, Roscoe Village offers something for everyone to enjoy during their stay.

  • Michigan Avenue: A bustling thoroughfare renowned for its vibrant city atmosphere, Michigan Avenue is lined with high-end shops, iconic architecture, and dining options, making it a must-visit for urban enthusiasts.
  • Chicago Riverwalk: This picturesque waterfront promenade offers a perfect family-friendly environment, ideal for leisurely strolls, dining, and enjoying outdoor activities along the scenic Chicago River.
  • Loyola University Chicago: A modern institution set against a backdrop of urban charm, Loyola University features beautiful campus grounds and a lively atmosphere, attracting visitors with its engaging community and events.

Things to do recommended for couples

For a delightful couple's getaway in Roscoe Village, enjoy a lively concert at the Aragon Ballroom or Lincoln Hall, both just 1.2km away. For a romantic dinner, head to the Historic Michael Jordan Restaurant, located 3.1km away, offering a lovely atmosphere and delicious cuisine.

Things to do recommended for families

During your family holiday in Roscoe Village, explore the iconic Wrigley Field, just 1.2km away, for a sporty atmosphere. Enjoy wellness at Hamlin Park, a mere 311m from your base, or relax at the stunning Northerly Island Natural Area, located 4.3km away.

Things to do recommended for groups

Experience a delightful evening at Vic Theatre, just 1.2km from Roscoe Village, where entertainment and culture flourish. For laughs, head to Second City, 1.9km away, perfect for family fun. Don't miss shopping at 900 North Michigan Shops, 2.5km away, offering business and entertainment vibes.

What do I need to keep in mind when booking a vacation around Roscoe Village

If you're travelling with a group, family, pets, or seeking extended stays, be sure to apply the appropriate filters to meet your needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Roscoe Village with a group: Think about how many bedrooms you’ll require, along with features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily apply filters for these options and many more on Vrbo.
  • Traveling to Roscoe Village with young kids: Travelling with young children can present its challenges. It’s essential to prioritize their comfort and safety, as well as to seek out suitable amenities, like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Roscoe Village: For many, a family holiday wouldn't feel complete without their four-legged companion. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Roscoe Village: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Roscoe Village

Roscoe Village, a charming neighbourhood in Chicago, offers a delightful blend of family-friendly activities and vibrant local culture. Perfect for outdoor enthusiasts and sports lovers, you'll find trendy cafes and boutiques lining the streets. Nearby, explore the picturesque Old Town with its romantic atmosphere and scenic views. With its great location and friendly locals, Roscoe Village is an ideal base for experiencing the best of urban life and family-oriented fun.

  • Chicago: Chicago is a vibrant metropolis located a mere 3.1km from Roscoe Village, offering a plethora of experiences for families and outdoor enthusiasts alike. Renowned for its iconic skyline and rich cultural scene, visitors can indulge in retail therapy at its many shopping districts or catch a thrilling game at one of the famed sports stadiums. The city's attractions, including educational venues, provide a well-rounded travel experience, making it a prime destination for both leisure and exploration.
  • Downtown Chicago: Just 3.1km from Roscoe Village, Downtown Chicago serves as the bustling heart of the city. This neighbourhood is perfect for families and city lovers, featuring an array of shopping areas and world-class theatres that showcase everything from Broadway hits to local performances. The proximity to major landmarks, including sports facilities and vibrant tourist precincts, ensures that visitors are never short of things to do and see, offering an unforgettable urban adventure.
  • North Center: Located a mere 186m from Roscoe Village, North Center is a charming neighbourhood that caters to sports enthusiasts and families seeking outdoor activities. With its urban parks and local theatres hosting music concerts, this area provides a delightful blend of leisure and entertainment. The nearby stadiums add to the excitement, making North Center a fantastic spot for those looking to immerse themselves in local culture and community spirit.

Best time to go to Roscoe Village

If you're planning a trip to Roscoe Village, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudyAverageSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyAverageSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageSlightly Low
April46.0°F (7.8°C)Light RainMostly SunnySlightly HighAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnySlightly HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighSlightly High
August73.0°F (22.8°C)Light RainMostly SunnyAverageSlightly High
September67.1°F (19.5°C)Light RainMostly SunnyAverageAverage
October54.9°F (12.7°C)Light RainMostly SunnySlightly LowAverage
November42.3°F (5.7°C)Light RainMostly SunnySlightly LowAverage
December33.1°F (0.6°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to cut costs on your next getaway? It might be worth being flexible with your travel dates, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that suits your budget, make use of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform for you to craft new journeys, keep your plans on track, or review and arrange your bookings. Your saved or reserved properties are neatly categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental 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. Vrbo has holiday rentals 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 rental 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 Vrbo holiday rentals 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 rental. Enter your Roscoe Village travel dates to view your available options on Vrbo. Did someone just say "private pool"? Use the filters to choose the features and amenities you want in your rental.
Are there pet-friendly holiday rentals in Roscoe Village?
Yes. You'll have your pick of 10 holiday rentals that cater to pets in Roscoe Village. Many of our pet-friendly holiday rentals 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 Vrbo.
What are popular rental amenities in Roscoe Village?
Some of the most popular rental 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, Vrbo holiday properties have the best amenities for fun and relaxation with the people you love.
Are there large group holiday rentals in Roscoe Village?
With seven Roscoe Village holiday rentals 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, Vrbo will help you book the ideal space to match the occasion.
Are there holiday rentals 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 rentals. 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 rentals 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 Vrbo.
Are there holiday rentals with WiFi in Roscoe Village?
You'll have a choice of three holiday rentals 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 Vrbo.
How can I find holiday rentals with air conditioning in Roscoe Village?
Roscoe Village has nine holiday rentals where you can relax in air-conditioned comfort. To find a property on Vrbo 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 rental in Roscoe Village?
You should check with the Roscoe Village holiday rental you'd like on Vrbo as the age limit varies. However, it's typically 16, 18 or 21.
How long can I rent a holiday rental 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.

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