Roscoe Village vacation rentals

We found 304 vacation rentals — enter your dates for availability

Discover a selection of 10 apartments and other vacation rentals in Roscoe Village that are perfect for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation rentals have the amenities you need and want for your stay, which might include cable TV and a washer and dryer. No matter what you're looking for, you'll find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

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Find out more about Roscoe Village

Why visit Roscoe Village

  • Charming Streets: Stroll through picturesque streets lined with quaint shops and eateries, showcasing the neighborhood's unique character.
  • Family-Friendly Activities: Enjoy a variety of family-oriented attractions, ensuring fun for visitors of all ages.
  • Scenic Parks: Relax in beautiful parks that provide a perfect escape from the urban hustle and bustle.
  • Cultural Immersion: Dive into the vibrant local culture with events, art, and community gatherings.
  • Convenient Accommodations: Choose from cozy apartments and stylish condos to make your stay comfortable and enjoyable.

Popular types of accommodation around Roscoe Village

If you're exploring vacation rentals in Roscoe Village, you're in for a treat. The most popular options include cozy apartments, spacious houses, and stylish condos. Whether you're seeking a charming Roscoe Village guesthouse with a welcoming living room or a modern apartment on Roscoe Street with air conditioning, we have a variety of choices to ensure your stay is comfortable and enjoyable.

  • Apartments: The top choice for vacation rentals in Roscoe Village, offering a range of amenities and convenient locations for a comfortable stay.
  • Houses: A popular option for families or groups seeking spacious accommodations with a personal touch.
  • Condos: Ideal for those looking for modern living spaces with access to shared facilities and community vibes.
  • Cottages: A charming retreat option, perfect for a cozy getaway while enjoying the local scenery.**

Top attractions near Roscoe Village

Roscoe Village offers a delightful blend of family-friendly activities and urban charm, making it perfect for city-themed vacations. Explore local attractions like parks, beaches, and iconic skyscrapers, all while immersing yourself in the vibrant culture. Whether you're traveling with family or seeking a unique city experience, Roscoe Village has something for everyone. Don't miss the opportunity to discover the hidden gems of this charming neighborhood during your visit.

  • Michigan Avenue: A vibrant street known for its bustling atmosphere, featuring high-end shops, dining options, and iconic architecture. It’s the perfect place to experience the city’s energy and indulge in retail therapy.
  • Chicago Riverwalk: A scenic waterfront path ideal for families and outdoor enthusiasts. Stroll along the river, enjoy restaurants, and take in stunning views of the city skyline while soaking up the lively atmosphere.
  • 875 North Michigan Avenue: An impressive skyscraper offering breathtaking city views. Visit the observation deck for a unique perspective of Chicago’s architectural beauty, and explore nearby attractions.

Things to do recommended for couples

For a romantic getaway in Roscoe Village, consider visiting Chevy Chase Country Club or Ravinia Green Country Club, both 19 miles away. Enjoy the luxurious ambiance, perfect for couples looking to unwind and create lasting memories amidst beautiful surroundings.

Things to do recommended for families

Families visiting Roscoe Village can explore the charming streets filled with local shops and eateries, enjoy a day at the nearby Lincoln Park Zoo, and participate in hands-on activities at the Chicago Children's Museum, ensuring a fun and memorable experience for all ages.

Things to do recommended for groups

Explore the charming streets of Roscoe Village with a guided walking tour, savor delicious bites at local eateries, or enjoy a fun-filled evening at a nearby comedy club. Don't miss the chance to unwind in the lush parks perfect for group picnics and outdoor games.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Roscoe Village with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all of these options, and more, on Vrbo.
  • Traveling to Roscoe Village with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions can really enhance your experience.
  • Taking your pets with you to Roscoe Village: For many families, a vacation wouldn’t feel complete without their furry companion. If that resonates with you, consider exploring Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer amenities like feeding bowls and beds, ensuring that every member of your family feels at home.
  • Planning for a long term stay visiting Roscoe Village: If you're searching for vacation rentals offering discounts for stays of a month or longer, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Roscoe Village

Roscoe Village offers a delightful blend of family-friendly vibes and urban charm, making it an ideal base for your Chicago vacation. Explore the picturesque streets lined with quaint shops and eateries, or venture into nearby neighborhoods like Old Town and Downtown Chicago for a taste of city life. Whether you're enjoying the scenic parks or immersing yourself in the local culture, Roscoe Village and its surroundings promise a memorable experience for every traveler.

  • Chicago: As a vibrant metropolis, Chicago is a must-visit destination for tourists. Located in the heart of the Midwest, Roscoe Village is nestled within this bustling city. Travelers are drawn to Chicago for its diverse family-friendly attractions and outdoor experiences. You can enjoy a day of shopping in the Magnificent Mile, catch a concert at the United Center, or enjoy a theater performance in the Loop. Notable landmarks such as the iconic Wrigley Field, Millennium Park, and the Art Institute of Chicago are just a short trip away, offering a rich tapestry of culture, art, and sports.
  • Downtown Chicago: Just 5 miles from Roscoe Village, Downtown Chicago is the city's energetic core. This lively neighborhood is perfect for families and those seeking the quintessential city experience. Here, you can explore a wide array of shopping options, from high-end boutiques to local favorites. Enjoy a thrilling game at the United Center or take in a show at one of the renowned theaters. Key attractions include the famous Navy Pier, Grant Park, and the bustling tourist precinct, making Downtown Chicago a must-visit on your itinerary.
  • North Center: A mere 0.3 miles from Roscoe Village, North Center is a charming neighborhood known for its family-friendly atmosphere and vibrant cultural scene. This area is perfect for those interested in theater, music concerts, and educational experiences. Visitors can explore local parks such as the picturesque River Park or catch a show at the acclaimed Apollo Theater. With its close proximity to Roscoe Village, North Center offers an inviting escape filled with unique dining options, local shops, and a strong sense of community.

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 a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate significantly. Furthermore, extending your stay can often lead to substantial savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers an easy way to plan your travel. You can create new trips, resume your previous plans, or organize your itinerary all in one place. You’ll be able to see the properties you’ve saved or booked, sorted into categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Roscoe Village?
In Roscoe Village, vacation houses and apartments are both quite popular, with several options available in this charming neighborhood. The vacation houses typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and private outdoor areas, making them ideal for families or groups. On the other hand, the apartments tend to offer a cozy and convenient stay, often including modern amenities like comfortable living spaces and kitchens for preparing meals.
How much does it cost to rent a vacation home in Roscoe Village?
Prices for vacation 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 vacation 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, making it easy for guests to prepare meals during their stay. Many properties also come with a blender for those who enjoy smoothies or other blended drinks. Onsite parking is typically available, providing convenience for travelers with vehicles. Air conditioning is a common feature, ensuring comfort during warmer months. Additionally, many rentals offer coffee and tea makers, allowing guests to enjoy a warm beverage at their leisure.
Can I find family house rentals in Roscoe Village?
In Roscoe Village, visitors will discover several family-friendly house rentals that cater to groups of all sizes. The neighborhood is known for its charming tree-lined streets and proximity to local parks, making it an ideal spot for families. Many of these homes offer spacious living areas, fully equipped kitchens great for preparing family meals, and outdoor spaces where children can play.

Additionally, amenities such as Wi-Fi and air conditioning ensure a comfortable stay. Families can also enjoy nearby attractions, including parks with playgrounds and walking trails, providing plenty of options for outdoor activities.
Are there any Roscoe Village vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Roscoe Village with parking available—perfect for families or travelers 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 vacation rentals in Roscoe Village?
In Roscoe Village, travelers can find several pet-friendly vacation rentals that cater to a variety of needs. This charming neighborhood is known for its tree-lined streets and proximity to parks, making it an excellent choice for those traveling with pets. Many of the vacation homes offer modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy some fresh air.

The nearby Roscoe Village Dog Park provides a fantastic spot for pets to socialize and play, ensuring that furry companions have a great time during their stay. Additionally, the neighborhood features pet-friendly cafes and local shops, which enhance the overall experience for both travelers and their pets.
Can I find long-stay vacation rentals in Roscoe Village?
A long-stay vacation rental in Roscoe Village is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Roscoe Village for a vacation rental?
The peak season for visiting Roscoe Village is during the vibrant summer months of June through August, with July being the most popular time. During this period, travelers flock to the village to enjoy the warm weather and partake in a variety of outdoor activities, from exploring the charming shops to strolling along the scenic riverfront. The atmosphere is lively, making it an ideal time for families and friends looking to create memorable experiences together.

Temperatures in July typically range from the mid-60s to the low 80s Fahrenheit, providing a comfortable environment for sightseeing and outdoor adventures. Visitors can take part in the local culture, enjoying events and festivals that showcase the unique heritage of Roscoe Village.

For those seeking a more budget-friendly option, consider planning your trip in November. In this season, this month offers a quieter atmosphere great for leisurely exploration. You can enjoy the beauty of the village in fall, with fewer crowds and the chance to appreciate the local history and architecture at a more relaxed pace.

Ultimately, the best time to book a vacation rental in Roscoe Village depends on your preferences—whether you thrive in the bustling summer atmosphere or prefer the calm and charm of the shoulder months.
Are there any remote work vacation rentals in Roscoe Village?
In Roscoe Village, Illinois, there are several remote work vacation rentals available, making it an excellent option for those looking to combine work and leisure. Many of these properties come equipped with essential amenities such as reliable Wi-Fi, dedicated desk spaces, and comfortable chairs to create a productive work environment. Travelers can expect cozy accommodations that often include private rooms, kitchen facilities for meal preparation, and ample living space to unwind after a workday.

The neighborhood itself is known for its charming tree-lined streets and proximity to various local attractions, including parks and quaint shops. This makes it convenient for remote workers to enjoy a break and explore the vibrant community. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Roscoe Village vacation rental?
Book your Roscoe Village vacation 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 vacation 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 and amenities. The neighborhood is known for its picturesque tree-lined streets and a strong sense of community, making it a pleasant area to explore on foot. One of the highlights is the Roscoe Village Dog Park, which provides a great spot for pet owners to relax and socialize their furry friends.

The area also features boutique shops and a variety of dining options along Roscoe Street, where visitors can find everything from cozy cafes to fine dining establishments. Additionally, the nearby Chicago River offers opportunities for scenic walks and biking along the waterfront. Just a short distance away, the expansive Wrigley Field provides a chance to catch a baseball game and experience the vibrant setting during the season.
Can I change or cancel my Roscoe Village home rental booking on Vrbo?
To find Roscoe Village vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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