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House holiday rentals in Northwest Side

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Top-rated house rentals in Northwest Side

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Home in Chicago

4.87 out of 5 average rating, 127 reviews

Soak Up Mid-Century Style in Wrigleyville and Boystown

This is an architecturally significant (3-bedroom 3.5-bathroom) home by noted Las Vegas architect Homer Rissman. We are located in the heart of East Lakeview, just half a block from Lake Michigan and Lincoln Park, and blocks away from Wrigley Field and Boystown. Smart TVs (with Netflix, Hulu, Amazon Prime) are located in the shared main level TV lounge, and also the lower level lounge. Entire home I like in-person check-in but full privacy is offered You will receive a link with detailed instructions within 24 hours of your check-in. If you have a U.S. mobile number, you will also receive a text message FULL DISCLOSURE: If you haven't used a lockbox (or don't know how to), self-check-in isn't for you. Your check-in should be in person. Lakeview is home to two of the most vibrant sports, nightlife, and theater scenes in Chicago: Wrigleyville and Boystown. Explore souvenir shops and casual eateries by day, and hop from bar to bar along Clark, Addison, and Sheffield Avenues by night. You walk to Treasure Island (half block), Jewel Osco (2 minutes), Whole Foods (4 minutes), Lakeview Athletic Club (4 minutes), XSports Fitness (5 minutes), Walgreens (3 blocks), bars and restaurants aound the corner. Close to multiple buses on Lake Shore Drive. Grab a bus to downtown in 15 minutes You will have to climb one flight of stairs for all bedrooms Street parking is free on the east side of Broadway. The west side requires 383 permits. Please, read the signs.

Guest favourite

Home in Chicago

4.92 out of 5 average rating, 258 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.

Home in Highland Park

5 out of 5 average rating, 28 reviews

Sanctuary on the Ravine

Take it easy at this unique and tranquil get away, walking distance to Ravinia and Beaches 3 Blocks.This historic, beautifully decorated and well maintained home has a lovely, peaceful & serene setting. Multiple indoor and outdoor seating arrangements. Fully stocked kitchen that opens to family room looking out onto several multilevel brick patios and a quiet, private ravine. The extra large living room has a down feathered sectional couch that seats up to 10 people. No parties or gatherings

Guest favourite

Home in Chicago

4.86 out of 5 average rating, 90 reviews

California Cottage/4br prime location Logan Square

Incredible location in Logan Square! Walking distance from dozens of restaurants, breweries, bars, nightlife, the square, the farmers’ market and much more. Free street parking in front. 2 blocks from 90/94 and close to the blue line train which goes to many of Chicago’s iconic neighborhoods, downtown, and directly to O’ Hare airport. Beautiful house with high ceilings on the 1st floor. Lovely kitchen with nice appliances. 2 cozy bedrooms upstairs. One with a queen and the other has 3 twins.

Home in Carol Stream

4.57 out of 5 average rating, 23 reviews

Amazing Summer Pool Awaits You!

Vacation, Staycation or Business, you will love your stay at this beautiful paradise with heated pool and tri-level entertainment deck equipped with grill and outside seating and gazebo! Semi-secluded backyard, walking distance to bike path, playground, skate park, walking trails, restaurants and even the gym! Relax on the magnificent deck while watching the sunset This home is pet free and smoke free. Pool is available May-Sept. WiFi is available throughout and Smart TV in the family room.

Guest favourite

Home in Elmhurst

4.82 out of 5 average rating, 17 reviews

Enamored in Elmhurst

Have fun with the whole family at this beautifully renovated house with and open floor plan, fully stocked kitchen, 4 bedrooms, 2 bathrooms with smart tv's in all the bedrooms and quick reliable wifi for all to enjoy. Home is located only minutes from the highways, enjoy the deck right off the living room and overlooking a private yard . House also has a fully finished basement with 2 of the bedrooms, a full bathroom and a theater room with a sectional sleeper sofa if more space is needed.

Guest favourite

Home in Chicago

4.91 out of 5 average rating, 174 reviews

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Say "WOW" in this top floor, IMMACULATE SPACIOUS with cozy FIREPLACE + ROOFTOP overlooking skyline! Open 2-story layout w/7 bed options, 3 bathrooms, private rooftop with skyline. Luxury flooring, soaring high ceilings, fully-stocked kitchen + huge island, keyless entry, 2 HD TVs, & outdoor grill. Perfect for SPECIAL OCCASIONS! Next to all Wrigley bars & restaurants. Train to Downtown <12 mins. Private parking for rent. As a "GUEST FAVORITE" we boast >1220 5-star reviews across listings!

Guest favourite

Home in Oak Park

5 out of 5 average rating, 8 reviews

Downtown Oak Park LUXE Home | 3 Bedrooms, 2 Baths

Enjoy the comfort & luxury of this large, cozy and stylish 3-bedroom property located in Oak Park's historic district. Just a few steps from iconic sites like the Frank Lloyd Wright Studio and the Ernest Hemingway Birthplace Museum, this contemporary oasis is within walking distance of Oak Park’s vibrant downtown and public transit. This special home is brand new and meticulously clean! it is close to everything, making it easy to plan your visit. Party is not allowed in the house.

Guest favourite

Home in Chicago

5 out of 5 average rating, 9 reviews

Alluring Avondale Abode

Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

Guest favourite

Home in Naperville

4.87 out of 5 average rating, 128 reviews

Home away from home

Perfect location, walk/bike to downtown area/ High Speed Wifi throughout the house / 2 King size beds one Queen bed /Newly remodeled / Huge back yard / Brand new appliances / Space for your car in a garage or plenty of parking on long driveway/ Outside porch with seating / Pet friendly - no deposit or any other charge. This is my first house ever listed I will add to the describtion more, after people will notice more things, too many to list.

Guest favourite

Home in Addison

4.96 out of 5 average rating, 72 reviews

Home in Unincorporated Addison. RV & Pet Friendly

Your family will be close to everything when you stay at this centrally-located place. This house is extremely family friendly. It has 4 bedrooms and three baths. It has been recently remodeled inside and out. The yard is close to 3/4 acres and has a kids playground and firepit. The driveway is long and can park a long RV if needed. This is a quiet location. Fully Fenced in Yard with lights all around the house. Very safe location.

Guest favourite

Home in Schaumburg

4.88 out of 5 average rating, 100 reviews

InstaWorthy! Modern Gem, Perfect Family Getaway-Pe

Have fun with the whole family at this stylish place! - Minutes away from Woodfield Mall, Legoland Waterworks Indoor Water Park, Golf, Outdoors, and more! - Private Driveway - Blazing Fast 1GB internet speed - 60 4K Smart TV w/ Roku Live TV - Pack n Play, High Chair, Stroller - Stocked Kitchen with Coffee and Waffle Bar! - Outdoor Patio Area w/ games - Working Desk Area. - Firepit, Corn Hole, Pool Table - King Size Bed in Main

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Popular amenities for house rentals in Northwest Side

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Chicago

5 out of 5 average rating, 6 reviews

Luxury Condo Downtown Chicago

Home in Bartlett

4.63 out of 5 average rating, 24 reviews

Fully Furnished Executive Home, Lux Amenities

Home in Plainfield

4.81 out of 5 average rating, 36 reviews

30 mins to CHI* 3 Kings *Fireplace *W/D* Workspace

Guest favourite

Home in Bloomingdale

4.95 out of 5 average rating, 43 reviews

Whole House with a Hot Tub!

Guest favourite

Home in Schaumburg

4.87 out of 5 average rating, 15 reviews

Schaumburg Oasis with a Pool and Hidden Garden

Guest favourite

Home in Chicago

4.87 out of 5 average rating, 53 reviews

Luxury Cabin in Lakeview

Weekly house rentals

Guest favourite

Home in Chicago

4.92 out of 5 average rating, 271 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

Guest favourite

Home in Glen Ellyn

4.92 out of 5 average rating, 140 reviews

Home in Glen Ellyn

Guest favourite

Home in Chicago

4.97 out of 5 average rating, 31 reviews

Wicker Park 6bd/4ba, Steps from Cta, Parking Incl

Guest favourite

Home in Chicago

4.86 out of 5 average rating, 221 reviews

The Avondale Guesthouse

Home in Whiting

4.84 out of 5 average rating, 146 reviews

The Spa of Downtown Whiting

Guest favourite

Home in Chicago

4.95 out of 5 average rating, 182 reviews

Wrigleyville Greystone

Guest favourite

Home in Chicago

4.96 out of 5 average rating, 209 reviews

Paradise on the Park

Guest favourite

Home in Winfield

4.98 out of 5 average rating, 158 reviews

Cozy, Clean & Well-Stocked Home!

Private house rentals

Home in Oak Park

5 out of 5 average rating, 4 reviews

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath

Guest favourite

Home in Chicago

4.94 out of 5 average rating, 16 reviews

Warm bungalow in New City

Guest favourite

Home in Chicago

4.95 out of 5 average rating, 39 reviews

Gorgeous and Luxurious 3 BR Home

Home in Chicago

4.88 out of 5 average rating, 48 reviews

Grand Victorian Mansion in Austin Area

Home in Blue Island

4.81 out of 5 average rating, 188 reviews

Warm and comfortable inviting Suburban home !

Guest favourite

Home in Chicago Ridge

4.93 out of 5 average rating, 113 reviews

Quiet cul-de-sac with huge fenced in backyard

Home in Chicago

4.84 out of 5 average rating, 491 reviews

*ENTIRE CITY HOUSE/PARKING - 3 MIN WALK TO TRAIN

Guest favourite

Home in Chicago

4.93 out of 5 average rating, 27 reviews

A serene haven perfect for the whole family!

Destinations to explore