Holiday houses in Riverdale

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Top-rated holiday rentals in Riverdale

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Superhost
A cozy living area features a gray couch adorned with blue and green cushions. A round coffee table sits in front of a flat-screen television. Wall art depicting tranquil landscapes enhances the space, while a wall clock indicates the time.
Guest suite in Chicago
4.86 out of 5 average rating, 114 reviews

Comfortable and Cozy Suite in Quiet Neighborhood

Are you coming to town to visit family, friends or for business? This cozy, clean, comfortable & 420 friendly suite has all you need to escape your everyday. Look no further! This one-bedroom suite is perfect for 1-3 people, small families, or individuals. If you're visiting family or friends and want your personal space or are in town for business and need a comfy bed, wifi, and office space, then this place was designed for you. Kick back and relax in this calm, stylish, 420 friendly space.

Guest favourite
A vibrant garden area is filled with a variety of lush green plants and colorful flowers. Stone elements lead to a small water feature, surrounded by dense foliage. The peaceful setting offers a natural retreat, inviting exploration or relaxation.
Apartment in Homewood
4.92 out of 5 average rating, 95 reviews

Charming Garden Apartment

Make yourself at home in a charming apartment with all the amenities! Lose yourself birding or reading a book surrounded by lush gardens. Take a short walk to lovely downtown Homewood to enjoy shopping & dining or catch the train to Chicago. After a day of exploring, a king-sized sleep number bed and lush bathroom features will pamper you! A fold-down sofa creates an additional bed. Dogs are welcome! This suite has a kitchenette with a convection toaster oven, induction cooktop, and fridge!

Guest favourite
A modern kitchen features sleek white cabinetry and stainless steel appliances. A central island serves as a dining space, complemented by two navy blue stools with gold accents. Pendant lights provide illumination, enhancing the contemporary feel of the room.
Home in Chicago
4.88 out of 5 average rating, 162 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

Guest favourite
A welcoming entrance is framed by a well-maintained garden pathway leading to a wooden door with a decorative awning. Potted plants and colorful flowers on either side enhance the entry, creating an inviting first impression.
Apartment in Chatham
4.91 out of 5 average rating, 89 reviews

Carol’s Guesthouse: Your Needs Are Covered!

Hello Travelers! My name is Carol, and I welcome you to enjoy a stay at my guesthouse located in a nice middle class Chatham neighborhood on Chicago’s Southside. The 1st Floor apartment is air conditioned and spacious. It has a living room, dining room, bathroom, two bedrooms and a kitchen. There is a queen bed in each bedroom. The kitchen is fully stocked for your cooking needs. Enjoy aTV in the livingroom and the two bedrooms. Reservations are limited to 4 guests.

Guest favourite
A spacious living area features a comfortable sofa and a grand piano, complemented by a decorative area rug on polished wooden floors. A window allows natural light to illuminate the room, and a small bookshelf adds a touch of warmth. A small dog with a scarf rests nearby.
Home in Homewood
4.93 out of 5 average rating, 103 reviews

Boulderstrewn: Historic Homewood home

Charming and historic Sears Catalog House on 2/3 acre wooded lot. Less than 10 minute walk to shops and restaurants in downtown Homewood to Metra rail (and Amtrak) station with express service to Hyde Park and University of Chicago (less than a half hour) and Chicago's 3 magnificent downtown waterfront stations (~40 minutes). Fire pit in yard can be used to enjoy summer nights. No cable, but several digital antenna channels available as well as Netflix, XBox and DVDs.

Guest favourite
A well-lit living area is furnished with a black couch and two floral accent chairs. A light area rug sits under a glass coffee table. A work desk with a chair is positioned beside a large window, allowing natural light to fill the space.
Home in Homewood
4.87 out of 5 average rating, 52 reviews

The executive suite

Live the high life in this stylish executive suite, never get cold feet with heated floors throughout. 75” tv in living room, 58” in each bedroom, work from home with fast internet and dedicated work desk. Located in a super quiet neighborhood. Very safe as well. Enjoy your home away from home. Close to fine dining, and brand new casino coming. be downtown Chicago in minutes with a quick Metra train ride minutes from this home. And please, no smoking or parties.

Guest favourite
A cozy living area is displayed with a pair of beige sofas, accented by decorative pillows. Framed wall art complements the decor. A soft rug is positioned on the wooden floor, while a lampshade on a side table adds subtle illumination.
Home in Blue Island
4.82 out of 5 average rating, 215 reviews

Warm and comfortable inviting Suburban home !

160 year old land mark community, Framed cedar bevel siding 2 story home, front porch , 10 ft high ceilings, kitchen canned lighting home. 6 feet fence In closed yard, whole house water filtration system , Quite neighborhood with sidewalks . 19 miles to downtown Chicago , Metra train station and bus route, in walking distance . driving to the city of Chicago 5 minutes to major expressways . Host is willing to be available for any and all information 24/7.

Top Guest favourite
The kitchen area is equipped with modern stainless steel appliances, including a refrigerator and stove. A wooden table with two place settings is set beside a gray couch. A doorway leads to a laundry area with washer and dryer units.
Guest suite in Chicago
5 out of 5 average rating, 11 reviews

Guest Suite w/Private Entrance Beverly Basement

Great location. recently rehabbed. Space: This is a new guest suite in the basement of my home. The suite is equipped with a full kitchen featuring high-quality appliances. The suite includes a large bathroom, a bedroom with a new queen-size mattress, and a washer and dryer onsite. The suite offers a peaceful and comfortable place to stay. A 2 block walk will get you to the commuter train, Subway sandwiches, an Italian deli, CVS Pharmacy, and Starbucks.

The exterior of a single-story house is shown, featuring a beige vinyl siding and a distinctive peaked roof. A welcoming entryway is highlighted by a glass-paneled door. The front yard includes a well-maintained flower bed with various plants and a pathway leading to the entrance.
Home in Riverdale
4.64 out of 5 average rating, 39 reviews

Cozy 3Bed Home in Friendly South Chicago Suburbs

Welcome to our clean and comfy home located in a warm, family neighborhood, perfectly nestled between Chicago and northern Indiana. This upgraded and cost-effective 3-bedroom, 1-bath house offers everything you need for a comfortable and efficient stay. Get the best value for your money without compromising on comfort or amenities. Our home is ideal for families, business travelers, or small groups looking for a convenient and affordable place to stay.

Top Guest favourite
A cozy living area is featured with two large windows allowing natural light to fill the space. A hanging chair adds a unique touch, while a dark sofa and a coffee table sit on a patterned rug. A television is positioned on a stand nearby.
Apartment in Blue Island
4.94 out of 5 average rating, 310 reviews

Charming Unique 2 Bdrm Apartment in Victorian Home

My place is close to the excitement and culture of the beautiful city of Chicago. It is a short walk to Metra trains with a 25 minute ride downtown. You’ll love my place because of the diverse, comfortable, quiet, tree lined neighborhood where you can relax and feel secure. It is close to expressways, golf courses and a local park with walking path. The apartment is not available to guests without previous positive reviews.

Superhost
An outdoor seating area is set up with six cushioned chairs arranged around a central glass table. A patterned area rug adds color, while a fire pit is positioned nearby, creating a cozy ambiance for gatherings.
Home in Calumet Park
4.77 out of 5 average rating, 107 reviews

My quaint little escape

Cozy and clean. Keep it simple at this peaceful and centrally-located place. Moments from 1-57 and 1-94 expressways. plenty of eateries, 2 grocery stores, parks and more. Take a moment to sit in the yard and grill or light the fire pit and relax. Just a quiet, cozy, quaint little home, available for you to come and relax for business or pleasure.

Superhost
A cozy living area features a gray sofa adorned with decorative pillows, flanked by two lamps on white side tables. A set of colorful chairs is positioned around a small coffee table. Natural light enters through large windows, creating a bright and inviting space.
Apartment in Chicago
4.81 out of 5 average rating, 113 reviews

Ultra Modern Beverly Suite

This stylish place to stay is perfect for any event. 420 friendly. Come and let us pamper you. Come and enjoy are tree lined community in the historical Beverly area. This Suite has all the latest amentities and beautifully furnished. The whole group will be comfortable in this spacious and unique space.

Popular amenities for Riverdale holiday rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Riverdale