Roscoe Village holiday rentals
We found 290 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:25 Dec - 1 Jan

Exceptional
(113 reviews)
Wrigley Field/Lakeview -Entire Home- Large Groups!
Chicago
AU$7,619
for 7 nights, 1 home
AU$1,088 per night
includes taxes & fees

Exceptional
(57 reviews)
Cozy two bedroom close to Wrigley Field
Chicago
AU$4,833
for 7 nights, 1 apartment
AU$690 per night
includes taxes & fees

Exceptional
(192 reviews)
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Chicago
AU$8,423
for 7 nights, 1 home
AU$1,203 per night
includes taxes & fees

Exceptional
(9 reviews)
Elite 4BR Art Deco suite. Garage included.
Chicago
AU$10,645
for 7 nights, 1 apartment
AU$1,521 per night
includes taxes & fees

Exceptional
(35 reviews)
Lincoln Park Charm Near Everything + On site Parking Spot Included
Chicago
AU$8,661
for 7 nights, 1 apartment
AU$1,237 per night
includes taxes & fees

Exceptional
(38 reviews)
Cozy 2-Bedroom Apartment | Close to Wrigley
Chicago
AU$4,094
for 7 nights, 1 apartment
AU$585 per night
includes taxes & fees

Exceptional
(21 reviews)
Chicago Bear Den
Chicago
AU$2,447
for 7 nights, 1 apartment
AU$350 per night
includes taxes & fees

Exceptional
(10 reviews)
3BR Art Deco retreat with garage.
Chicago
AU$9,899
for 7 nights, 1 apartment
AU$1,414 per night
includes taxes & fees

Wonderful
(14 reviews)
Expertly designed 2BR Art Deco sanctuary.
Chicago
AU$4,367
for 7 nights, 1 apartment
AU$624 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

Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
Sleeps 4 · 2 bedrooms

Roscoe Village- Only steps to cute shops & dining! Sleeps 4-6
Sleeps 6 · 2 bedrooms · 1 bathroom

Prime 4 BR Sleeps 13, Chef Kitchen, 8 Blks to Wrigley, 15min Train to Mag Mile
Sleeps 13 · 4 bedrooms · 3 bathrooms

Urban Oasis in Roscoe Village! Pet friendly and family friendly!
Sleeps 8 · 3 bedrooms · 2 bathrooms

Wrigleyville Suites
Sleeps 10 · 3 bedrooms

Large 2-Bedroom w/ Huge Roofdeck view of Skyline
Sleeps 4 · 2 bedrooms · 2 bathrooms
- 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 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.
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.
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.
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 Stayz.
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.
Are all fees included in the Roscoe Village holiday homes prices shown on Stayz?
Stayz 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.
Are there any Roscoe Village holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Roscoe Village holiday homes?
You can find great discounts on holiday homes in Roscoe Village on Stayz, 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.
Can I change or cancel my Roscoe Village holiday home booking on Stayz?
To find Roscoe Village holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Roscoe Village?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Roscoe Village holiday home?
Book your Roscoe Village holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Roscoe Village?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Roscoe Village to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
More holiday ideas
- Aurora Historical Museum Holiday Rentals
- Hutchinson Street Historic District Holiday Rentals
- Yorkville Holiday Rentals
- Gold Pyramid House Holiday Rentals
- 875 North Michigan Avenue Holiday Rentals
- Fox Lake Holiday Rentals
- Chicago Architecture Foundation Holiday Rentals
- Mccormick Place Holiday Rentals
- Cog Hill Golf & Country Club Holiday Rentals
- Albany Park Holiday Rentals
- Forest Lake Holiday Rentals
- Lake Catherine Holiday Rentals
- Hyde Park Holiday Rentals
- Chicago Holiday Rentals
- Lake Barrington Holiday Rentals
- Inverness Holiday Rentals
- Country Club Hills Holiday Rentals
- Naperville Holiday Rentals
- Old Town Triangle Holiday Rentals
- One Superior Place Holiday Rentals
- Chicago Holiday Rentals
- Lincoln Park Holiday Rentals
- Pilsen Holiday Rentals
- Lakeview Holiday Rentals
- Downtown Chicago Holiday Rentals
- Baha'i House of Worship Holiday Rentals
- Wrigleyville Holiday Rentals
- House rentals in Chicago
