House vacation rentals in Skokie

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Top-rated house rentals in Skokie

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Top guest favorite

The living area features a cozy sofa and a patterned armchair, complemented by a glass coffee table. A television is positioned in one corner. Large windows invite natural light, while floor-to-ceiling curtains offer privacy. A potted plant adds a touch of greenery.

Home in Wilmette

4.97 out of 5 average rating, 153 reviews

Unique porcelain-enamel paneled "Lustron" home

This rare modern post war home has a style all its own. Created by Carl Strandlund in Columbus Ohio, it consisted of prefabricated porcelain enamel covered panels inside and out making it durable and easy to clean. Easing the postwar housing shortage and its maintenance free design were its selling points. Great care has been taken to reflect its true character so enjoy the well thought out floor plan and huge yard. Close to Northwestern, Gilson park beach, and downtown Chicago via car or train.

Top guest favorite

A well-maintained gray exterior with white trim is presented. Surrounded by a wooden fence, the yard features a grassy area and is shaded by trees. A sunny sky with scattered clouds adds to the inviting ambiance of the outdoor space.

Home in Evanston

5 out of 5 average rating, 106 reviews

Larimer Park Carriage House

Charming, historic carriage house only a few short blocks from Evanston's best shopping, restaurants and beaches. Home offers 2 bedrooms each with private ensuite bathrooms. Larger bedroom has king size bed and bathroom with large shower. Second bedroom has queen bed and shower/tub combo. Open layout on main floor with huge sectional sofa, 4-person dining table, and fully equipped kitchen with dishwasher. Laundry in home + parking space! Nestled in historic neighborhood next to Larimer Park

Top guest favorite

The cozy living room is designed with soft seating arrangements and a wooden coffee table at the center. Natural light flows through nearby windows, enhancing the inviting atmosphere. A chandelier and wall mirror add character, while decorative accents on the table provide visual interest.

Home in Highland Park

4.97 out of 5 average rating, 121 reviews

Charming Ranch-Style Cottage

Escape the hustle and bustle of the city in this relaxing, cozy, cottage that is a few blocks away from downtown Highland Park and Highwood, with great restaurants, bars and coffee shops. It is perfect for single travelers, couples, or a small family. We are grateful for the amazing Airbnb hosts across the globe, who opened their homes to us, and made our trips so memorable. So when we bought our own home, it was only right that we would return the favor and open our home to fellow adventurers

Guest favorite

An outdoor area features a partially enclosed space highlighted by warm wood paneling and a large window. A grill is positioned against the wall, with a concrete floor leading toward a well-lit interior visible through glass doors.

Home in North Park

4.96 out of 5 average rating, 173 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

Guest favorite

Home in Avondale

4.94 out of 5 average rating, 148 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!

Top guest favorite

A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.

Home in Berwyn

4.99 out of 5 average rating, 146 reviews

Retro Modern Bungalow | fire pit | free parking

Experience the city in style at 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] back yard. Enjoy central HVAC, hi-speed 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

The modern kitchen showcases sleek white cabinetry and a spacious island topped with a white marble surface. Stainless steel appliances, including a gas stove and a refrigerator, are complemented by glass-front cabinets displaying elegant dishware. Soft blue lighting highlights the room's contemporary design.

Home in Portage Park

4.97 out of 5 average rating, 117 reviews

Ultra Modern, 2800 SQ Ft, Outdoor Gazebo Sleeps 14

Treat yourself to this Chicago getaway with 14 of your friends & family. Be inspired to create culinary delights in our celebrated 5 stars outdoor kitchen. Reboot & relax in each of our thoughtfully designed powered by SOLAR ENERGY throughout. After a memorable night in OR an adventurous night out you will ask yourselves, 'Why don't we do this more often?' 15 mins to Downtown, O’Hare airport, West Loop. 20 mins to Lakeview, Wrigleyville, Boystown, Logan Square, Bucktown & Wicker Park.

Superhost

The exterior of a single-story home is framed by lush green grass and dark mulch landscaping. A welcoming pathway leads to the front door, adorned with a seasonal wreath. A large tree provides shade, and a white fence marks the boundary of the yard.

Home in Naperville

4.85 out of 5 average rating, 126 reviews

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!

Guest favorite

A stylish living area features a comfortable blue couch adorned with decorative pillows. A glass coffee table sits atop an area rug, surrounded by an array of colorful artwork on the walls. A cozy sleeping area is visible in the background, draped with vibrant blankets.

Home in Evanston

4.87 out of 5 average rating, 151 reviews

SW Evanston Private, Stylish, Spacious Suite

Comfort and convenience abound in this stylish suburban suite! Mid-century and vintage motif meets modern touches and style. Guests have the entire basement, with a private bedroom, bathroom, huge living space, and a private entrance in a quiet house on a beautiful treelined street. Backyard access, coffee, easy street parking. Walking distance to parks and public transportation, a short drive to downtown Evanston and the lakefront, easy access to Chicago, Northwestern. Loyola, Skokie.

Guest favorite

A well-lit sleeping area is featuring two spacious beds with crisp white bedding. A dresser is positioned nearby, and a round mirror is mounted on the wall, reflecting natural light from a window. A bold blue accent wall adds a pop of color to the room.

Home in Oak Park

4.97 out of 5 average rating, 116 reviews

Garden Unit, King & Queen, Kitchenette & Parking

Our comfy, recently remodeled garden unit is 3 blocks to the train with free parking in upscale, safe, walkable Oak Park. Enjoy some time in our little urban farm. Check out the gardens and visit our 4 friendly hens. This non-smoking studio with a kitchenette is perfect for tourists, families, or business travelers. We require no check-out chores. Easy highway and airport access. No parties, 4 guests max allowed. Minimum age to book is 25. Visit my profile for additional units

Top guest favorite

A welcoming living area is presented with a mix of plush seating, including a white chair and a vibrant orange sofa. A wooden shelving unit displays decorative items and books. Soft lighting enhances the wooden floor, while light streams through large windows dressed with sheer coverings.

Home in Lincoln Square

4.98 out of 5 average rating, 115 reviews

Entire first floor in Lincoln Square!

First floor of a restored 1903 Victorian in Lincoln Square. The home is spacious with high ceilings throughout and a very open feel. You'll have the whole 1st-floor with access to the backyard with chairs & fire pit. Two bedrooms and an office with additional sleeping options (ask me!). Large dining room & eat-in kitchen. Brand new kitchen & huge new bath! Many short-term rentals in this area are third-floor walk-ups. Make your life easier and stay on the first floor!

Guest favorite

The exterior of a restored Victorian house is presented, featuring a striking red front door and large windows that invite natural light. A welcoming porch is adorned with seating, surrounded by meticulously landscaped greenery and plants, creating an engaging atmosphere.

Home in East Rogers Park

4.98 out of 5 average rating, 99 reviews

Victorian House in Heart of Rogers Park

Newly restored Victorian house giving you a touch of Chicago's history with modern comfort. Feel at home away from home with fully equipped kitchen, entire house, and outdoor spaces with beautifully landscaped garden for lounging, grilling, and chilling. Large screen TV in living room and TVs in each bedroom. Fast Wi-Fi throughout the house. Walking distance to public transit, restaurants, bars, beach and shopping. Designated parking. #TheCatalpa