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House vacation 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.

Home in Chicago

4.92 out of 5 average rating, 250 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 Naperville

4.92 out of 5 average rating, 109 reviews

California King Bed | Fast Wi-Fi | 75" Smart TV

Our 3bd, 2.5ba house is perfect for a group of friends or family looking for a clean, modern place in a wonderful, quiet neighborhood. Built w/ cathedral ceilings, there is plenty of space for 10 people to sleep comfortably (6 beds & several comfy couches), as well as 3 smart TVs (w/ complimentary Hulu & Disney+), an indoor fireplace, a gas grill & large yard (including outdoor games), a desk space, & more. Enjoy close access to main roads & large stores (Costco, Walmart, hardware stores, etc.)!

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

Home in Chicago

4.85 out of 5 average rating, 85 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 Elgin

4.94 out of 5 average rating, 141 reviews

My Lagoon - 3 br Entire SF home Sleeps 8. King Bed

Welcome to your lagoon. An entire single family house boasting 3 bedrooms with a King bed, 2 queens and a Sofa bed. A true home away from home freshly renovated with tasteful modern coziness. 2 car garage w/ plenty of driveway space for 4 more. You are 25 mins from O'Hare Airport, 35 from the Epic Chicago Dwntwn. Stay Local? Plenty to do ! 10 mins to Now arena, 10 mins to Woodfield Mall, mins away is Villa Olivia, Arboretum, Main Event and more. Short Term, Keyless entry make yourself at home.

Home in Elmhurst

4.85 out of 5 average rating, 13 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.

Home in Plainfield

4.96 out of 5 average rating, 47 reviews

WATER FRONT LUXURY HOME WILL FEEL LIKE A RESORT!

LUXURY HOME WITH A SPECTACULAR VIEW OF THE WATER. EXECUTIVE BRICK HOME WITH BRAZILIAN CHERRY-HARD WOOD FLOORS. FLOOR TO CEILING WINDOWS IN FAMILY ROOM WITH 14' CEILINGS/DECORATIVE BRICK FIREPLACE. GOURMET KITCHEN W/ MAPLE CABINETS/GRANITE & SS APPS/EATING ISLAND. SUNROOM WITH BEAUTIFUL VIEW OF POND. LUXURY MASTER SUITE W/ LUXURY BATH. FULL FINISHED BASEMENT WITH 9' FOOT CEILINGS INC FULL BATH & BED. TRANQUIL BRICK PAVER PATIO. (Plus 100-acre park, paths, soccer & baseball fields, & more).

Home in Highland Park

4.95 out of 5 average rating, 21 reviews

The Sunset Manor - Luxe Mansion for Serene retreat

Welcome to Sunset Manor, a 6-bed, 4.5-bath haven of elegance. The grand foyer sets the tone for luxury, leading to open-concept living spaces adorned with stylish furnishings. Entertainment thrives with a dedicated theatre room for cinematic experiences & a sleek bar area to unwind. Nestled in a serene location, Sunset Manor is ideal for family vacations, friend reunions, or corporate retreats. Book your stay for luxury, convenience, & tranquility. Your unforgettable escape begins here.

Home in Chicago

4.91 out of 5 average rating, 172 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!

Home in Algonquin

4.85 out of 5 average rating, 52 reviews

The River House Sauna/Kayaks/Hot Tub/Fire Pit

The newly remodeled water front 4 bd 2 bath home is within walking distance of Algonquin’s fabulous "Old Town District", restaurants, pubs and entertainment. Likewise, the gorgeously landscaped River Park is a short stroll away, giving one much to see and do. The residence feature a beautiful kitchen; large dining area adjoins the kitchen as does a brightly sun shined living room complete with big glass doors overlooking the water. A picturesque living for both work and play awaits!

Home in Homewood

4.91 out of 5 average rating, 118 reviews

Peaceful & Private Hot Tub Vacation Home Getaway

A Rare gem 💎in the heart of Homewood. This Quaint 2-bedroom remodeled home is charming, sophisticated and discrete. It is minutes away from the Metra station, golf course and downtown Homewood shops. The energy is very calm and quiet ☯️. This is the home away from home where details are everything and the pictures do not capture the essence of this luxurious space. Experience the love, the joy and the peace that continues to leave its mark. Peace and Love - Michael and KP💞

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Popular amenities for Northwest Side house rentals

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House rentals with a pool

Home in Highland Park

4.91 out of 5 average rating, 141 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Home in Munster

5 out of 5 average rating, 9 reviews

Munster hide away

Home in Bloomingdale

4.95 out of 5 average rating, 38 reviews

Whole House with a Hot Tub!

Home in Schaumburg

4.86 out of 5 average rating, 14 reviews

Schaumburg Oasis with a Pool and Hidden Garden

Home in Gary

4.81 out of 5 average rating, 226 reviews

Oasis , Near Beach, Hard Rock and Dunes

Home in Plainfield

4.93 out of 5 average rating, 75 reviews

Beautiful Spanish style Home (w/inground pool)

Home in Lake Forest

4.9 out of 5 average rating, 63 reviews

Beautiful 137 Year Old Farm Home (3night min)

Weekly house rentals

Home in Chicago

4.93 out of 5 average rating, 263 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

Home in Lansing

4.81 out of 5 average rating, 107 reviews

Hello 2025! -2bd/1bath Cozy Home

Home in Chicago

4.86 out of 5 average rating, 220 reviews

The Avondale Guesthouse

Home in Streamwood

4.98 out of 5 average rating, 42 reviews

Suburban Serenity~Grill, Fire pit, Big yard~

Home in Whiting

4.83 out of 5 average rating, 144 reviews

The Spa of Downtown Whiting

Home in Chicago

4.94 out of 5 average rating, 180 reviews

Wrigleyville Greystone

Home in Justice

4.94 out of 5 average rating, 220 reviews

3 Kng, 1 Qn, 1 Full, 3AirBd|Basktbll Crt|FreePrkin

Home in Winfield

4.98 out of 5 average rating, 153 reviews

Cozy, Clean & Well-Stocked Home!

Private house rentals

Home in Lake Zurich

4.76 out of 5 average rating, 37 reviews

Comfortable 4 bedroom home with indoor fireplace

Home in Aurora

4.94 out of 5 average rating, 32 reviews

Spacious family friendly home away from home

Home in Chicago

4.94 out of 5 average rating, 16 reviews

Warm bungalow in New City

Home in Bolingbrook

4.73 out of 5 average rating, 22 reviews

Serenity King|7 min -> Hwy & Mall|Backyard

Home in Chicago

4.95 out of 5 average rating, 39 reviews

Gorgeous and Luxurious 3 BR Home

Home in Chicago

4.87 out of 5 average rating, 47 reviews

Grand Victorian Mansion in Austin Area

Home in Blue Island

4.81 out of 5 average rating, 183 reviews

Warm and comfortable inviting Suburban home !

Home in Chicago Ridge

4.94 out of 5 average rating, 109 reviews

Quiet cul-de-sac with huge fenced in backyard

Destinations to explore