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House vacation rentals in Near North Side

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Top-rated house rentals in Near North Side

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Top guest favorite

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

4.92 out of 5 average rating, 291 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.

An outdoor space is showcased featuring a hot tub under a pergola with string lights, providing a relaxed ambiance. Comfortable seating is arranged around a firepit table, complemented by a gas grill visible in the background.

Home in Bridgeport

4.95 out of 5 average rating, 142 reviews

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard with exceptional landscaping. The property has a car port in back which allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! NO CHORES! Please reach out with any questions you may have before booking Hot tub 5-6 Person Spa

Top guest favorite

A spacious kitchen features sleek black countertops and a large central island. Stainless steel appliances include a refrigerator and a gas range. Natural light enters through the windows, illuminating decorative plants and kitchen essentials arranged on shelves.

Home in North Side

4.98 out of 5 average rating, 113 reviews

Flat in Lincoln Park 2-Flat Central to Everything

Historic, newly renovated flat in the heart of Lincoln Park, with garage! A block from the famous Blues club "Kingston Mines". Close to great bars and restaurants, including Alinea, the only restaurant in Chicago awarded 3 Michelin Stars. A mile to Lincoln Park Zoo, less than 1-1/2 miles to the lake. Beautiful yard (shared with lower unit) has gas grill, patio, deck, and a garage space. Enjoy the Lincoln Park area in this unique home that offers everything you need for your holiday in Chicago.

A private outdoor patio is surrounded by wooden fencing, featuring a glowing sofa and two chairs placed on a patterned rug. A small table holds a plant, while greenery adds a natural touch to the tranquil setting, under a colorful sky at dusk.

Home in North Park

4.96 out of 5 average rating, 186 reviews

Chicago River House -BBQ Oasis now open!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

A cozy sleeping area features two sets of full over full bunk beds against a light wall, each topped with white bedding. A round mirror hangs above a simple desk, and two accent chairs provide additional seating around a circular wooden coffee table.

Home in Old Town

4.94 out of 5 average rating, 124 reviews

Luxury SOHO Styled Two-Level Townhouse | Old Town

NEWLY CONSTRUCTED TOWNHOUSE IN THE HEART OF OLD TOWN! This private luxury townhouse (duplex) is perfectly located in vibrant Old Town-surrounded by nightlife, restaurants, cultural attractions, and is only a 5 min walk to the beach, steps from Lincoln Park, and next to Second City. This 2,800 square foot townhouse features 13 foot ceilings, open floorplan, private patio, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between.

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, 149 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.

Top guest favorite

A fenced backyard features a circular arrangement of wooden lounge chairs centered around a propane fire pit, creating a cozy gathering space. Twinkling string lights hang above, illuminating a bistro table with two blue chairs. Lush green grass surrounds the stone patio area.

4.98 out of 5 average rating, 169 reviews

Retro Modern Bungalow | fire pit | free parking

Experience the city in style at our Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Top guest favorite

A cozy living area features a light gray sofa with decorative pillows, alongside a wooden dining table and four stools at the breakfast bar. The kitchen is partially visible, showcasing stainless steel appliances and dark mahogany paneling.

Home in Lake View

4.98 out of 5 average rating, 280 reviews

Wrigleyville Southport Studio

This Wrigleyville studio is the best of urban living combined with a tranquil retreat. With vintage, mahogany paneled walls and a comfy king size bed this apartment has everything! Free coffee, tea, snacks and dedicated work space. The Southport Corridor is blocks away with restaurants, bars and shopping. Free street parking and 4 blocks to El/ Brown/Purple/ Red line trains. Wrigley Field, Metro and Vic is 4 blocks away. This garden studio is the perfect retreat in the heart of Chicago!

Top guest favorite

A spacious living room features a decorative fireplace and large bay windows that allow natural light to fill the space. Comfortable seating options include a light-colored armchair and couch, complemented by a glass coffee table and a colorful area rug.

Home in West Loop

4.98 out of 5 average rating, 365 reviews

Cozy garden apartment historic Jackson Bvld.

Just a short walk to the United Center our cozy 1 bdrm garden apt is located on Historic Jackson Blvd's tree lined st. Stop back & warm up by the fireplace before heading out to near by shopping & restaurants. Less than an hour from Midway or O'Hare. Walking distance to Randolph St. Restaurant Row, Little Italy, Greek Town, Union Pk, Fulton Warehouse Dist, Rush Hospital and UIC. A quick train/bus to The Loop, Theater Dist, Mag Mile, Wicker Pk. Free, convenient street pkg.

Top guest favorite

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, 267 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).

An open living area features a light-colored sofa facing a modern fireplace and a flat-screen television. A dining table with chairs is positioned nearby, while a staircase leads to the upper levels. Balanced lighting highlights the neutral tones and spacious layout.

Home in Lincoln Park

4.82 out of 5 average rating, 253 reviews

Spacious Luxury Townhouse - Old Town

Historic 3 bedroom home in Old Town! Comfortably sleeps 6, and access to 3 levels of living space. The massive rain shower in the master bath is my favorite part, but there's plenty of luxury here to enjoy. Plus, we're right in the heart of Old Town, just steps from all of the shops and restaurants on Wells Street, and a 5 minute walk to the Sedgwick Brown/Purple line stop - you can be in the Loop in 20 minutes! Book today!

The living area features a spacious sectional sofa with red accent pillows, positioned near a large arched window that offers views of the private outdoor space. A round dining table and colorful rug add a cheerful touch, while a flat-screen TV is mounted nearby.

Home in Humboldt Park

4.97 out of 5 average rating, 140 reviews

Cozy/Spacious WFH Family Friendly w Permit Parking

Bright first-floor private apartment with free parking passes for permit-only street parking. Enjoy the wide-open windows, a private outdoor space, and two bathtubs for ultimate relaxation. Cook for yourself in the fully-equipped kitchen or explore some of the amazing restaurants nearby. Family/baby friendly with included highchair, pack n' play, crib, baby monitor, and more!

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Popular amenities for Near North Side house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Fulton Market

4.67 out of 5 average rating, 18 reviews

Chic Fulton Market Oasis + Curated Comfort & Style

The exterior of a mid-century modern ranch home is displayed, featuring a flat roof and a large, contemporary garage door. Lush greenery surrounds the entrance, complemented by a well-maintained lawn. The driveway provides ample space for parking, enhancing accessibility.

Luxury fenced in modern ranch

Home in Elmhurst

New place to stay

Elmhurst Luxury 4BR w/ Pool, Fenced Yard, Downtown

A sunny backyard features a round in-ground pool surrounded by lush green grass and vibrant flower pots. The house showcases a two-story design with a balcony and large windows, providing views of the serene outdoor space and nearby landscaping.

Home in Des Plaines

5 out of 5 average rating, 11 reviews

Rosemont 4BD2BA house with Pool

An open-concept living area showcases a spacious, modern white sectional sofa with accent pillows. A glass coffee table sits atop a patterned rug. The dining area features a round table for six, illuminated by warm lighting, with a view of the kitchen in the background.

Home in Elmhurst

4.14 out of 5 average rating, 7 reviews

Lucky #7 w/ Gym

An inviting living area features a large flat-screen television mounted on a light-coloured unit. Two couches, one in neutral tones and another in deep blue, surround a circular marble-top coffee table. Exposed brick walls and natural wood accents add texture, while large windows provide natural light.

Home in Lake View

4.85 out of 5 average rating, 65 reviews

Luxury Loft with Private Pool and Movie Theater

Weekly house rentals

A spacious living area is illuminated by natural light, featuring large windows that frame views of greenery outside. A modern sofa and armchair sit around a round coffee table, while a sleek fireplace adds warmth to the elegant decor.

Home in Gold Coast

4.95 out of 5 average rating, 44 reviews

Gold Coast Home|Rooftop |PoolTable |Parking |Views

A spacious living room is furnished with two comfortable sofas and a wooden coffee table. A large black-and-white cityscape photograph is displayed on the wall. Natural light fills the room through windows, highlighting the polished wood floors and decorative ceiling. A dining area is visible in the background.

Home in Lake View

4.9 out of 5 average rating, 158 reviews

Spacious Two Story Luxurious Home w/Outdoor Deck!

Two white Adirondack chairs are positioned on a grassy area, complementing the inviting façade of the home. Flower boxes filled with vibrant flowers adorn the windows, and natural light creates a warm atmosphere, highlighting the exterior's textures.

Home in Old Town Triangle

4.99 out of 5 average rating, 70 reviews

Old Town Cosmopolitan Four Bedroom, Four Bath

A modern kitchen featuring stainless steel appliances, including a refrigerator and gas range. A spacious island with white marble countertop is surrounded by light-colored chairs. Above, stylish pendant lights provide ample illumination, while the open layout invites natural light from adjacent glass doors.

Home in West Town

4.94 out of 5 average rating, 87 reviews

NEW! 3BR/2.5B Duplex in Noble Sq

A spacious living area features a blend of warm wall colors and modern decor. Comfortable seating includes a light-colored sofa and a wooden chair. A fireplace is highlighted on one wall, accompanied by a ceiling fan and natural light from large windows.

Home in River West

4.85 out of 5 average rating, 327 reviews

Lux Urban 3BR/3BA Duplex + Parking!

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, 164 reviews

BoHo House - A Chic, 1903 Chicago Workers Cottage

An expansive rooftop patio is showcased, featuring woven outdoor couches with blue cushions arranged around a glass-top table. The city skyline is prominently visible, with notable buildings punctuating the clear blue sky, complemented by touches of lush greenery.

Home in Near North Side

4.99 out of 5 average rating, 79 reviews

Private Downtown Retreat with Rooftop Oasis

An elegant 1890 Greystone building is presented, showcasing a symmetrical façade with decorative stonework. A tiered front staircase leads to a charming entryway, flanked by well-maintained landscaping. Large windows enhance natural light, while a vibrant green shrub adds a touch of color to the exterior.

Home in Chicago

4.94 out of 5 average rating, 113 reviews

Beautiful Chicago Greystone

Private house rentals

The spacious living area features a modern sectional sofa adorned with textured throws. A stylish coffee table is positioned atop a plush area rug. The room is complemented by a sleek dining table set for six and adorned with decorative accents, blending comfort and elegance.

Home in Ukrainian Village

4.94 out of 5 average rating, 65 reviews

Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design

Top guest favorite

A bright dining area features a long wooden table surrounded by six blue chairs. A modern chandelier hangs above, illuminating the space. In the background, a staircase leads to the upper level, while a cozy living area is visible, providing an open and inviting layout.

Home in Wicker Park

4.98 out of 5 average rating, 44 reviews

Large Wicker Park 6bd 4ba w/Parking-Steps to CTA

A stylish living area features a black leather chesterfield sofa adorned with plush white pillows. A glass coffee table rests on a decorative area rug, while elegant chandeliers hang from the ceiling. The backdrop reveals an open kitchen with cabinetry, enhancing the room's sophistication.

Home in Old Town Triangle

4.98 out of 5 average rating, 86 reviews

Opulent 3bdr2bth Old Town Luxury + Parking prmts

Home in Old Town Triangle

5 out of 5 average rating, 22 reviews

4 BR • Theater Room • Gym • Walk to Lincoln Park!

The inviting living area features two red armchairs facing a coffee table and a decorative metallic side table. A fireplace is centered beneath a large flat-screen TV. A plush area rug lies across a marble floor, and shelves are arranged with various decorative items.

Home in Old Town

4.75 out of 5 average rating, 4 reviews

Luxury 4BR 4-Story Chicago Villa |Prime Gold Coast

An inviting dining area is complemented by a wooden table surrounded by six dark chairs. A large mirror reflects natural light from the windows, while contemporary artwork adorns the walls. A cozy seating area with a green sofa is visible in the background.

Home in Ranch Triangle

4.88 out of 5 average rating, 93 reviews

Sophisticated Twnhm in Prestigious S. Lincoln Park

A spacious dining area features a marble-topped table surrounded by dark leather chairs. The room opens to a cozy seating area with a plush sofa, vibrant green chairs, and large windows allowing ample natural light. Decorative elements include a floral centerpiece and wall art.

Home in Gold Coast

4.86 out of 5 average rating, 22 reviews

Spectacular Gilded Age Gold Coast Mansion w/Deck

Top guest favorite

The brick exterior of the three-story home features large windows that provide natural light, framed by dark accents. A set of stairs leads to the black front door, showcasing a modern design. The surrounding area includes concrete walkways and mature trees.

Home in Wrigleyville

4.99 out of 5 average rating, 83 reviews

Wrigleyville Single Family

Quick stats about house rentals in Near North Side

Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ331 before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace

Destinations to explore