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Compare 579 Vacation Homes in Oak Park with updated reviews, rates, and availability.

Cozy Midway Home
Exterior detail
Cozy Midway Home
2.0 star property
10.0 out of 10, Exceptional, (12)
"This was a perfect little house to stay for our weekend trip! "
Cozy Midway Home
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
First floor living room with leather couch, smart cable TV, and Alexa speaker.
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
10.0 out of 10, Exceptional, (118)
"We were a group of 20 family members coming from all over the country for a wedding just a few blocks away. There was room for everyone, plus hairdryers, ironing board, iron, etc. needed to prepare for the big day. Target and Aldi, train station, and several coffee shops and restaurants, and parks within close walking distance made this the perfect location. Everyone loved staying here. We had good weather for porch sitting, and gathering outside after dark. Very helpful and available hosts too ...
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
Lincoln Park Living - Suite 2!
Living Room / Dining Room
Lincoln Park Living - Suite 2!
10.0 out of 10, Exceptional, (17)
"Very convenient. Spacious and comfortable condo."
Lincoln Park Living - Suite 2!
Great 3 bedroom rental unit near Logan Square
Interior
Great 3 bedroom rental unit near Logan Square
9.4 out of 10, Exceptional, (21)
"The property was perfect for me and my buddies for a football weekend!"
Great 3 bedroom rental unit near Logan Square
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Interior
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
Terrace/patio
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
9.8 out of 10, Exceptional, (13)
"Before and throughout the trip the hosts were very responsive and helpful. We fully booked the house and there was plenty of room for us in the common areas and backyard. The neighborhood around also has an excellent coffee shop, bar, and food areas within walking distance. Next time I bring a group to the Bridgeport area I’ll definitely try to book this property again "
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
7.4 out of 10, Good, (3)
"As good as advertised. Plenty of room for our group. Definitely recommend. "
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
Charming 3-bedroom house with AC and WiFi in serene Des Plaines near O’Hare
Living area
Charming 3-bedroom house with AC and WiFi in serene Des Plaines near O’Hare
2.0 star property
6.8 out of 10, (3)
"Perfect for our family weekend getaway! "
The price is AED 753
AED 1,183 total
includes taxes & fees
25 Nov - 26 Nov
Charming 3-bedroom house with AC and WiFi in serene Des Plaines near O’Hare
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
Interior
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
10.0 out of 10, Exceptional, (32)
"We had a great time staying here for a family trip. Plenty of space for games, cooking, sleeping, talking. We only used a fraction of what was available. When we had trouble figuring out heating system, host was very responsive. "
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐
Living area
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐
9.8 out of 10, Exceptional, (6)
"This is a very nice property. The only thing I caution is that it’s a 3rd floor walk up (actually on the 4th floor because there is nothing on the ground floor). "
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐
Wicker Park Entire House, Private Yard and Parking!
Interior
Wicker Park Entire House, Private Yard and Parking!
10.0 out of 10, Exceptional, (7)
"Walking distance to the best pastries you will ever eat (Mindys) and the best Ramen you will ever eat (Oii Star). Walking distance to the best line (Blue Line). Place was great, location was great! "
Wicker Park Entire House, Private Yard and Parking!
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Living area
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (81)
"Overall a great place to stay. Location is really great. You can walk to all of Old Town. Well equipped property. As the only member of our group that drove, was nice to have a garage! "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Room
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
9.6 out of 10, Exceptional, (79)
"This Old Town property was an excellent base for walking exploration of Lincoln Park (Saturday Farmer's Market was fantastic!) and Old Town itself (lively, with very good food, residential neighborhoods, shops, and entertainment), and had easy access to CTA trains to the Loop, Riverwalk, Millennium Park, and much more, had we had time. 7 adults (seniors) spent four nights, and found the four bedrooms, four bathrooms, large fully-equipped kitchen, and living/dining room/patio provided plenty of...
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Spacious 5 BR / King Size Beds + Private Parking!
Living Room
Spacious 5 BR / King Size Beds + Private Parking!
9.6 out of 10, Exceptional, (8)
"My coworkers and I came to Chicago for a conference and this was the perfect place to stay for it. The rooms were well separated so noise didn't travel between them, and the house was clean and comfortable. The host was extremely accommodating, and it was only a short distance from downtown Chicago."
Spacious 5 BR / King Size Beds + Private Parking!
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
Home Decor,Furniture,Indoors,Living Room,Table
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
9.2 out of 10, Wonderful, (7)
"The house was good, plenty of space. The steps were hard to get up and down but the upstairs was a nice space. House had a bit of a musty odor and the windows could use a cleaning. One night while watching a movie, we received a text stating we were had a loud party and to keep it down. They must have big brother watching us as the only party going on that night was in the movie. Overall the house was close to the city but in a nice Neiborhood. Having a fenced yard with off street parking...
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
Breathtaking home close to Schaumburg, Chicago
Exterior
Breathtaking home close to Schaumburg, Chicago
9.8 out of 10, Exceptional, (43)
"Great house in a great locations. Beautiful backyard with ample room and swing set for the kids. The rooms are big with very comfortable beds. Love the house. "
Breathtaking home close to Schaumburg, Chicago
Chicago-burb -Medinah -1 King and 1 Queen beds
Living area
Chicago-burb -Medinah -1 King and 1 Queen beds
9.4 out of 10, Exceptional, (15)
"Nice and quiet neighborhood. Host was great! Highly recommended!!"
Chicago-burb -Medinah -1 King and 1 Queen beds
Great location-King beds-Kids playroom
Huge and beautiful family room with access to outdoor patio
Great location-King beds-Kids playroom
10.0 out of 10, Exceptional, (17)
"We did enjoy our stay in this beautiful home. We had everything we needed to be comfortable. The location was perfect fou our needs."
Great location-King beds-Kids playroom
5 minutes from Midway Int'l Airport Single Family Home.
Family Room
5 minutes from Midway Int'l Airport Single Family Home.
9.2 out of 10, Wonderful, (5)
"Good area super easy process "
5 minutes from Midway Int'l Airport Single Family Home.
"Charming 3-Bedroom Home
Bathroom
"Charming 3-Bedroom Home
10.0 out of 10, Exceptional, (2)
"Just beautiful!"
"Charming 3-Bedroom Home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Oak Park

Chic Suite/Mins to L Train /Laundry/Free Parking
Room
Chic Suite/Mins to L Train /Laundry/Free Parking
9.6 out of 10, Exceptional, (35)
"Had a great stay! Thank you!"
Chic Suite/Mins to L Train /Laundry/Free Parking
Cozy modern unit w/ easy access to downtown Chi
Living area
Cozy modern unit w/ easy access to downtown Chi
9.4 out of 10, Exceptional, (34)
"Clean, exactly as described and reasonably priced. Also a great location to access public transit & lots of restaurants nearby. Had a great stay!"
Cozy modern unit w/ easy access to downtown Chi
Sentral Michigan Avenue
Garden
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (592)
"Great stay. Will stay again!"
The price is AED 396
AED 573 total
includes taxes & fees
24 Nov - 25 Nov
Sentral Michigan Avenue
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.