House holiday rentals in Logan Square

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Top-rated house rentals in Logan Square

Guests agree: these houses are highly rated for location, cleanliness and more.

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Top guest favourite
The living room features a large window allowing natural light to fill the space. A gray sofa sits beside a small glass coffee table, facing two wooden chairs. Colorful art pieces are displayed on the walls, complementing the patterned area rug.
Home in Lake View
4.95 out of 5 average rating, 370 reviews

The Roscoe House near Wrigley Field

Enjoy stylish living in the Roscoe House, an updated 1888 Victorian where wood and granite counter tops meet walnut shelves and vintage finds, mixed with original art. The house includes a library, patio, and fully stocked gourmet kitchen. *nearby train track construction was recently mentioned in 2 reviews; the city of Chicago seems to have moved on to a new section of the track, yay! If this changes we will do our best to update you!* Bringing kids? We have a pack and play with organic cotton sheets, blow up toddler bed, sound machines, high chair, baby gate, play kitchen, toys and books. FYI: There is a Craigs List scammer using our listing photos-- Beware! We love art and design and hope our home reflects that. This newly remodeled modern space is a 3 bedroom house, each with a private bathroom and flat screen TV. (3br 3 bath) There is also a queen pullout sofa if you have a larger group- we can accommodate up to 8 people. We provide all sheets, towels, and parking permits for street parking where you can usually find a parking spot within the block radius. The living room is perfect for hanging out- enjoy the 55in SmartTV /Netflix,Amazon prime accessible or read a book or play a game in our library, and cook in the fully stocked kitchen or BBQ on our patio. The home has central air throughout- so heat in the winter and A/C in the summer. All the rooms have ceiling fans for the in between seasons. Want to be out? You're a 5-10 minute walk to many great shops, restaurants and bars. We are 20 minutes to downtown via the Red line EL train, 5 minute walk to Wrigley Baseball Stadium, 7 minute walk to Southport Street where all the family restaurants and great shops are, and a 10 minute walk to Boystown. The Roscoe House is the perfect place for your stay in Chicago! Remember though, with all this great access to city fun- you will be in the city, which means you will hear the train pass behind the house (3 lots over) and if the windows are open, you might hear the neighbors. Most say that the train sounds like a nice woosh to lull you to sleep :) Permit street parking is available (we can give you a permit)**A NOTE ABOUT THE PARKING PERMITS: Be sure to enter the date and time on the sticker for every day you park. They are only good for one night, and if you do not enter the date and time in pen (careful not to smudge) you will be ticketed!!. Of course we have a laundry room and wifi. Have a baby? We have all the gear. Looking for something a little cheaper? We have another listing, equally as beautiful, just as close to the same great shops and restaurants. Minutes from the Brown line Addison stop. Copy and paste this link to view/book: http://airbnb.com/rooms/1084001 See our recent feature in Houzz! (website hidden)(phone number hidden)/list/my-houzz-eclectic-industrial-style-in-a-charming-chicago-home Living room, laundry, library hall, kitchen, patio with grill Youre always welcome to call or text us, either through the AirBnb message thread, or to our cell phones directly. We have a contractor and house manager nearby if we are not able to meet you at that moment. Walk to great shops, restaurants, and bars in less than 10 minutes. Visit Wrigley Field nearby, or explore Southport Street, which boasts family-friendly restaurants and great shops. Boystown is a 10-minute walk, too. 7 minute walk to the Belmont stop on the Redline EL train You can hear the woosh of the train as it passes behind the house. It is urban living and will lull you to sleep..... PLEASE NOTE WE DO NOT POST ON (SENSITIVE CONTENTS HIDDEN). ANY POSTING ON OTHER WEBSITES IS A SCAM, PLEASE NOTIFY US IF YOU HAVE SEEN ONE.

Top guest favourite
A spacious living area features a comfortable sofa adorned with orange and green cushions. A sleek black coffee table sits atop a striped rug. Floor-to-ceiling sheer curtains allow natural light to filter in, while an artwork hangs on a contrasting blue wall.
Home in Wicker Park
4.93 out of 5 average rating, 296 reviews

Cool Quiet Coach House, Private Access + Patio

Retreat to the brick patio of this lovingly renovated home after a long day traversing the neighborhood. The interior is an expression of creativity, greyscale walls, rustic accents, and a varied selection of art and wall hangings tie in the decor. Split Level Floor plan. 1st floor = Living, Eat in Kitchen, bedroom 1 and bathroom. 2nd Floor = 2nd bedroom , bath and an additional sleeping area and desk area. Also features a gorgeous shared yard. The entire coach house is yours!! The coach house is set back behind a 2 unit building and the yard is shared between both. We are available via text or airbnb messaging and try to respond quickly. Please reach out anytime if you need anything at all. Extra supplies, neighborhood recommendations or tips in the neighborhood. The home is located on the border of Wicker Park and Bucktown which is Chicago's original hub of cool. It is a vibrant enclave of culture and commerce, explore vintage finds, record stores, and plenty of indie shopping in this trendy part of town The 24 hour Blue Line EL train is just a 5 minute walk. Door to Door it's only 25 minutes to Millennium park. (5 min walk to the blue line, 10 min ride on the train, 10 minute walk to the Park). The neighborhood is pedestrian and bike friendly , the 606 trail is just a few blocks away also.

Guest favourite
The exterior of the home features a warm brick façade, large front windows allowing natural light to fill the interior, and inviting steps leading to a decorative front door. Lush greenery and potted plants enhance the welcoming atmosphere of the entrance.
Home in Hermosa
4.95 out of 5 average rating, 100 reviews

H&H 1896 - Spacious, Fully Stocked, & Free Parking

Built in 1896, modern restoration, & featured on HermosaChi blog “Homes built before 1900”. The exterior of this private compound includes free driveway parking for up to 6 cars, beautiful backyard garden, pergola, fire pit, basketball court, & children’s swing set. The interior sleeps up to 21 guests, consists of modern aesthetics, moody hues, home theatre, exercise room & also a kids jungle gym. Located just 20 minutes from the heart of downtown Chicago, your private urban retreat awaits!

Top guest favourite
A cozy living room features a gray sofa with decorative pillows, a round dining table with chairs, and a stone fireplace. Natural light enters through windows adorned with decorative molding, while a few bookshelves provide a space for books and decor. A colorful area rug adds warmth to the hardwood floor.
Home in Oak Park
4.98 out of 5 average rating, 191 reviews

Clean, 1 Bedroom Apt. w/ Kitchen & Parking for 4

Enjoy our historic district three-flat w/ free parking in upscale, safe Oak Park just 3 blocks to the train, easy access to Chicago. Enjoy some tranquil time in our little eco suburban farm. Check out the gardens and visit our 6 friendly chickens. This non-smoking unit with full kitchen is perfect for tourists, families, or business travelers. We require no check-out chores. Easy highway and airport access. No parties. Booking age, 25 or at least one 5 ⭐️ review. Visit profile for more units.

Top guest favourite
The living area showcases a dark blue accent wall, complemented by a modern light fixture. A cozy sectional sofa is framed by two framed artworks, while a round coffee table holds decorative items. An adjacent dining space features a light wood table surrounded by chairs and a built-in cabinet.
Home in Lincoln Park
4.97 out of 5 average rating, 159 reviews

Charming 3-BED in Lincoln Park/ Old Town & Parking

Welcome to our charming retreat in the historic Old Town Triangle/Lincoln Park district of Chicago. This conveniently located 3-bedroom apt, including office space, is nestled in the heart of a safe residential neighborhood with a 5-min walk to Brown Line and 10-min to Red Line. Within a 20-min walk, you'll find yourself at Lincoln Park Zoo, Beach, Second City, and Wells Street, immersing yourself in the vibrance of the old town. Book now to experience the best of Chicago. Parking+EV charging.

Guest favourite
A spacious living area features a vibrant orange sofa adorned with green and beige throw blankets. A stylish coffee table holds decorative items, while a large houseplant adds a touch of greenery. Natural light fills the room, highlighting the wooden staircase in the background.
Home in Avondale
4.93 out of 5 average rating, 175 reviews

BoHo House - A Chic, 1903 Chicago Workers Cottage

Welcome to BoHo House – a charming, airy bohemian gem built in 1903. This beautifully designed 3BR home is just a short walk from Chicago's popular bars, restaurants, and coffee shops. Enjoy the peaceful private fenced backyard, perfect for your pup to roam, complete with an adorable outdoor space. Host a cozy patio dinner by the fire or unwind indoors with a movie. Just 20 minutes from ORD, 10 minutes to downtown, with 800+ Mbps WiFi, free coffee and snacks, and secure 2-car garage parking!

Guest favourite
A charming raised brick ranch home with a welcoming front porch is displayed. The exterior features large windows, a wooden front door, and a neat landscaping area with greenery, enhancing the curb appeal along a tree-lined street.
Home in Logan Square
4.94 out of 5 average rating, 113 reviews

City Cottage in Logan Square-Avondale

Our two-bedroom home has been beautifully appointed for a relaxing stay. You'll have access to all the amenities of home with a private backyard space. The location is conveniently located between Avondale and Logan Square neighborhoods. It's a 14-minute walk to either the Belmont Blue Line or Logan Square Blue Line stops that take you to Downtown or O'Hare Airport. Walk to great restaurants, coffee shops, bars, music venues, vintage boutiques, Logan Square Farmers Market, and more!

Top guest favourite
A stylish living space is highlighted by a brown leather sofa and a large area rug, with natural light streaming through the window. The modern kitchen is equipped with sleek black cabinetry and stainless steel appliances. Potted plants add a touch of greenery to the setting.
Home in Wicker Park
4.97 out of 5 average rating, 272 reviews

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

Guest favourite
The living area features a stylish yellow sofa paired with two accent chairs. A round coffee table sits on a soft area rug, while large windows are dressed with sheer curtains, allowing natural light to fill the space. A decorative plant adds a touch of greenery.
Home in Avondale
4.83 out of 5 average rating, 155 reviews

The Logandale: HUGE Mid-Century Home, sleeps 15

Welcome to The Logandale! This 4 bed/3 bath mid-century modern home is ideal for families, professionals, and groups. Enjoy an open floor plan, private patio, game room, and bedrooms with memory foam mattresses. The fully-equipped kitchen, Smart TVs with Netflix, and a backyard fire pit ensure a comfortable stay. Located in the trendy Avondale/Logan Square, you're close to public transport, eateries, and attractions. Experience Chicago's best with us! 🌃🛏️🎮🔥

Top guest favourite
The exterior of the house features a modern navy blue facade with white trim and a red front door. A porch runs along the front, adorned with rocking chairs. An American flag is displayed, enhancing the welcoming character of the home amidst a green lawn and surrounding trees.
Home in Logan Square
4.91 out of 5 average rating, 136 reviews

Kid friendly 2 bedroom w/ private office

Private first-floor 2-bed apartment in hip Logan Square. Full bath, kitchen, WFH space and separate entrance. Walk to restaurants, cafes, parks, Blue Line/bus, 5 mins from bike rental/606 trail. We are kid/family friendly! We live upstairs with two young kids. Our ideal guest is comfortable with some family noise and apartment living. Cozy, convenient, and perfect for travelers seeking an authentic neighborhood stay! Please read other notes for more info!

Top guest favourite
A spacious living area features a dark leather sofa and a modern accent chair beside a circular glass coffee table. A patterned area rug in neutral tones lies on the hardwood floor, while a dining area with a round table and chairs is visible in the background.
Home in Portage Park
4.97 out of 5 average rating, 224 reviews

The Evergreen House

Relax and feel at home on the first floor apartment (completely private) of my Chicago 2-Flat. This home away from home is well stocked with anything that you might need whether you are staying for 2 nights or 2 months. There are 3 televisions with Wifi and Netflix throughout the apartment. There is a nice backyard that you are welcome to use and street parking is free. Washer and Dryer available in the basement. The highways and bus are also nearby.

Top guest favourite
A modern kitchen and dining area features sleek cabinetry and a large window allowing natural light. A glass dining table with blue chairs is positioned centrally, adjacent to stainless steel appliances and counter space. Light hardwood flooring enhances the spacious look of the room.
Home in Mayfair
4.95 out of 5 average rating, 111 reviews

Northside Chicago Getaway

This home is a classic Chicago bungalow that has been recently updated. There are some special features including whole home audio, a 75" TV with 9.1 Dolby atmosphere surround sound, a 3-person sauna, complete kitchen, fire pit out back and private parking for 2 cars. The Home is located in the Mayfair Park area of Chicago and offers a taste of the City life but also has a little space to breathe. Hope you enjoy it as much as I have over the years!

Popular amenities for house rentals in Logan Square

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Quick stats about house rentals in Logan Square

  • Total holiday rentals

    Explore 80 holiday rentals in Logan Square

  • Nightly prices starting at

    Logan Square holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 5,620 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    80 of Logan Square holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Logan Square rentals

  • 4.9 Average rating

    Logan Square stays are highly rated by guests – averaging 4.9 out of 5!

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