Roscoe Village holiday lettings

We found 303 holiday rentals — enter your dates for availability

Discover a selection of 10 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.

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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 in Roscoe Village?
In Roscoe Village, holiday houses are the most popular type of holiday rental, with around 20 available throughout the area. These properties typically offer spacious living environments, featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces great for relaxation. Many also include amenities such as BBQ grills and private gardens, making them ideal for families or groups looking to enjoy a cozy feel while exploring the charming neighbourhood. Additionally, there are about 12 apartments available, which provide a cozier alternative with comfortable living areas and essential amenities, suiting those seeking a more compact stay.
Are there any beach house rentals in Roscoe Village?
In Roscoe Village, there are beach house rentals available, offering a great experience for those looking to enjoy a lakeside retreat. While Roscoe Village is primarily a residential neighbourhood, visitors can find charming properties that provide a comfortable stay. These rentals typically feature spacious living areas, fully equipped kitchens, and outdoor spaces where guests can relax and enjoy the surroundings. The proximity to the nearby lakefront parks allows for easy access to recreational activities such as walking, cycling, and picnicking.
How much does it cost to rent a holiday home in Roscoe Village?
Prices for holiday rentals in Roscoe Village vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Roscoe Village to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Roscoe Village holiday house rentals?
You can find great discounts on house rentals in Roscoe Village on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Roscoe Village?
In Roscoe Village, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature blenders for those who enjoy smoothies or other blended drinks. Onsite parking is commonly available, providing convenience for travellers with vehicles. Air conditioning is a standard amenity, ensuring comfort during warmer months. Additionally, you can expect coffee and tea makers in most rentals, superb for enjoying a hot beverage in the morning or after a day of exploring the charming neighbourhood.
Can I find family house rentals in Roscoe Village?
In Roscoe Village, several family-friendly homes are available, making it an excellent choice for those travelling with children. This charming neighbourhood is known for its tree-lined streets and close-knit community vibe. Many properties feature spacious living areas, full kitchens for preparing family meals, and outdoor spaces where kids can enjoy the fresh air. Some homes may also have amenities like game rooms or backyard patios, providing ample space for relaxation and entertainment.

Visitors can explore nearby attractions such as the picturesque parks and local shops along Roscoe Street. The area is also conveniently located near the vibrant culture of Chicago, allowing for easy day trips to museums, theatres, and other family-friendly activities.
Are there any Roscoe Village holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Roscoe Village with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I book pet-friendly holiday rentals in Roscoe Village?
In Roscoe Village, there are several pet-friendly holiday rentals available for those travelling with their furry companions. Visitors can expect a variety of amenities in these properties, including spacious living areas, fully equipped kitchens, and outdoor spaces where pets can enjoy the fresh air. Many rentals in this charming neighbourhood are designed with comfort in mind, often featuring modern furnishings and convenient access to local parks.

Roscoe Village is known for its quaint streets and friendly atmosphere, making it an ideal spot for pet owners. Nearby parks provide opportunities for leisurely walks and playtime, ensuring that both you and your pet can enjoy the outdoors.
Can I find long-stay holiday rentals in Roscoe Village?
A long-stay holiday rental in Roscoe Village is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Roscoe Village for a holiday rental?
The best time to visit Roscoe Village for a holiday rental is during the summer months of June to August, with July being the most popular month. This vibrant season attracts families and tourists eager to explore the charming streets of Roscoe Village, where they can enjoy a variety of outdoor activities, local festivals, and delightful dining experiences. The warm weather, typically ranging from 20 to 30 degrees Celsius, creates a great backdrop for leisurely walks along the scenic riverfront and visits to the quaint shops.

In addition to the pleasant climate, summer offers a lively option, as visitors flock to the area to partake in community events and immerse themselves in the local culture. The abundance of outdoor dining options allows for relaxing meals with friends and family while basking in the sunshine.

For those seeking a more budget-friendly experience, consider planning your trip in November. This month falls outside the high tourist season, offering a quieter environment to appreciate the beauty of Roscoe Village. The crisp autumn air provides an excellent opportunity for peaceful strolls and enjoying the stunning fall colours in the surrounding nature.

Ultimately, your ideal time to visit Roscoe Village will depend on whether you prefer the lively summer atmosphere filled with activities or the serene charm of the quieter shoulder months.
Are there any remote work holiday rentals in Roscoe Village?
In Roscoe Village, Illinois, there are numerous remote work-friendly holiday rentals available, with around 32 options to choose from. This charming neighbourhood boasts a vibrant community atmosphere and easy access to local parks, cafés, and shops, making it an appealing choice for those looking to balance work and leisure.

Many of the holiday rentals in the area come equipped with essential amenities for remote work, such as complimentary Wi-Fi and designated workspace areas. Some properties also allow for events to be hosted, adding flexibility for those who may need to conduct meetings or gatherings during their stay.

The nearby attractions, including the picturesque Roscoe Village shops and the scenic riverfront, provide excellent opportunities for relaxation after a productive day. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Roscoe Village holiday rental?
Book your Roscoe Village holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Roscoe Village, Illinois, United States of America?
In Roscoe Village, visitors can enjoy a charming blend of local attractions that reflect the neighbourhood's unique character. The area is known for its picturesque tree-lined streets and vibrant community atmosphere, making it great for leisurely strolls. The Roscoe Village Neighbourhood Association often hosts events that highlight local artisans and businesses.

One of the focal points is the well-loved Roscoe Village Park, which features playgrounds and green space, ideal for families and outdoor enthusiasts. Additionally, the area is home to a variety of quaint shops, cafes, and restaurants offering a taste of local cuisine and culture.

Nearby, the historic Southport Corridor provides further shopping and dining options while maintaining a friendly, community-oriented feel.
Can I change or cancel my Roscoe Village home rental booking on Vrbo?
To find Roscoe Village holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Roscoe Village holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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