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House vacation rentals in Oak Park

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Top-rated house rentals in Oak Park

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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

4.98 out of 5 average rating, 164 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 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.

4.98 out of 5 average rating, 156 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] 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.

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

4.95 out of 5 average rating, 176 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

Top guest favorite

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, 171 reviews

Walkable, 1st Flr Flat, Kitchen, Parking, Sleeps 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 favorite

A spacious living area showcases a comfortable gray sectional sofa and a reclining chair. A contemporary coffee table rests on an area rug with floral patterns. A mounted TV is visible alongside a wooden credenza featuring a coffee maker and supplies, enhancing the functionality of the space.

Home in Forest Park

4.98 out of 5 average rating, 125 reviews

NEW Gather in spacious 3 bedroom 2 bath home

CA relief: if IL is an option for temporarary housing, please reach out! I have 4 properties I will do whatever I can. Introducing Mohr Cottage in the heart of Forest Park. Spacious & recently updated 3 bedroom 2 full bath 2 story home is perfect for families or large groups looking space & comfort. Quiet residential neighborhood, blocks from restaurants, shops, coffee. Dogs welcome. Near public transportation, easy access to expressway to downtown Chicago. STRICT Non-smoking property.

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

4.98 out of 5 average rating, 120 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.

A comfortable sleeping area features a spacious bed adorned with a decorative pillow displaying a tree branch design in earthy tones. Soft lighting from two bedside lamps provides a warm glow, while a piece of framed art hangs above the bed against a muted green wall.

Home in Forest Park

4.9 out of 5 average rating, 292 reviews

Charming dog friendly 2-Bath Bungalow Near Chicago

Steps from the cobblestone streets of Forest Park into our cheery bungalow, perfect for artistic souls and business travelers alike. Inside is a design savvy mix of mid-century furniture, comfy beds, and art from around the globe. Built in 1908, it boasts modern amenities you desire without sacrificing vintage charm. Minutes away from local shops, restaurants. Just off I-290, Blue Line CTA, 20. min drive to ORD, Midway & Downtown Chicago. Plus we’re dog-friendly-- bring up to 2 pups!

A modern kitchen features an island with seating for two and stainless steel appliances. White cabinetry contrasts with a dark backsplash, while large windows allow natural light to illuminate the workspace. The clean design promotes a functional and inviting cooking area.

Home in Elmhurst

4.97 out of 5 average rating, 121 reviews

Elmhurst NEW - Super Clean Modern Farmhouse!

Not your average Air BNB!!! 🏡 Newly renovated - CLEAN modern farmhouse in a great location! ✨ ✅Pet Friendly! 🐕 ✅15 min from O'hare. ✈ ✅25 min to Downtown Chicago 🏦 ✅Close to Grocery, restaurants, coffee, shopping, golf, expressways, down town Elmhurst ,Train and Oakbrook and Fashion Outlet Mall. ✅3 great sized bedrooms, 2 living area sofas converts into sleepers ✅Smart TV in family room and Master. ✅ Back patio with dining and seating ✅Large fenced in yard.

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, 256 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).

Top guest favorite

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

4.98 out of 5 average rating, 208 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.

An open concept living and dining area features a blue sectional sofa paired with a round coffee table on a patterned rug. A sleek TV stand displays a scenic image. A dining table with black chairs and a chandelier is visible in the background, enhancing the space.

Home in Brookfield

4.89 out of 5 average rating, 108 reviews

The Brookfield Breakaway w/ Game Room

This stylish place to stay is perfect for group trips. This split level home has an open concept living room and dining room combo. The gorgeous kitchen has exceptional attention to detail. There are three bedrooms and one bathroom upstairs. Downstairs you’ll find a master suite equipped with its own living space and en suite bathroom. Relax outside on our sectional and enjoy BBQ time with your loved ones. There’s enough space for everyone to enjoy.

Top guest favorite

A welcoming living room is highlighted by a comfortable sectional sofa with decorative pillows. A patterned area rug covers the hardwood floor, and a reading nook features a unique egg chair. Artwork adorns the walls, complemented by greenery from potted plants.

Home in Lombard

4.99 out of 5 average rating, 119 reviews

Modern Boho house in Lombard 7 min to Metra

Kick back and relax in this calm, stylish space. Visiting family in Chicagoland area? Traveling for work? Lombard is centrally located 30 min to everywhere! The house is only 6 min to Oakbrook Shopping and Business Center and upscale shopping and fabulous restaurants like RH with rooftop restaurant, 8 min to Yorktown Shopping Center. Whatever your travel purpose is, we will be happy to host you! Welcome home!

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Popular amenities for Oak Park house rentals

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living area is characterized by a plush gray sofa and a round coffee table. Decorative wall elements and a vibrant red holiday tree enhance the modern decor. Soft lighting is provided by a statement chandelier hanging from the ceiling.

Home in Glen Ellyn

4.8 out of 5 average rating, 20 reviews

Pardizes Suites

A swimming pool is seen surrounded by a white fence, with colorful pool floats inviting fun. Sunlight reflects off the clear blue water, and lush green trees provide a natural backdrop. A patterned mat lies at the edge, enhancing the relaxing atmosphere.

Home in Glen Ellyn

4.95 out of 5 average rating, 20 reviews

Glen Ellyn Home

A spacious living area is showcased with large floor-to-ceiling windows, offering panoramic city views. The room features a sleek sofa and a vibrant green chair, complemented by a round wooden coffee table. A dining area is visible in the background, along with a modern kitchen layout.

Home in West Loop

4.63 out of 5 average rating, 16 reviews

Foodies!Best Dining & Nightlife Steps Away|TheBoho

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, 7 reviews

Rosemont 4BD2BA house with Pool

A spacious basement game area features a classic pool table with a vibrant green felt surface, complemented by cues and an arranged set of colored balls. Nearby, a seating area with leather couches and an arcade machine is visible along the wooden-paneled wall.

Home in Bloomingdale

4.91 out of 5 average rating, 57 reviews

Now Open: Heated Pool with Entire House

Home in Riverwoods

Riverwoods Nature Retreat

Home in The Loop

4.88 out of 5 average rating, 58 reviews

Downtown 2BR: Unique Amenities, Ideal for Tourism

A spacious living area features a large projector screen displaying a vibrant image. Comfortable seating surrounds a modern electric fireplace, while a potted plant and decorative artwork add subtle touches to the space. Natural light is invited through nearby sliding glass doors.

Home in Logan Square

5 out of 5 average rating, 10 reviews

LUXURY - Movie Theater + Spa House

Weekly house rentals

A spacious living room is illuminated by natural light from two large windows. A large sectional sofa with a throw blanket and decorative pillows provides comfortable seating. A wall-mounted TV displays various applications. A small area rug and potted plant complete the cozy atmosphere.

Home in Oak Park

4.83 out of 5 average rating, 6 reviews

Modern 2BR Gem Oak park+Free parking nearby train

A single-story house with a well-maintained front yard, featuring a manicured lawn and flowerbed. Large windows are framed by a stone facade, while a cement walkway leads to the entrance. The surrounding area includes neighboring homes, enhancing the sense of community.

Home in Westchester

5 out of 5 average rating, 12 reviews

Canterbury Haven

A welcoming entrance features a chandelier that casts soft light over the space. Intricately detailed wood accents frame the door and windows, which allow natural light to fill the area. A decorative painting stands on an easel, enhancing the classic ambiance.

Home in Oak Park

4.76 out of 5 average rating, 25 reviews

Luxe Downtown Historic Victorian, A+ Location

Top guest favorite

A modern kitchen is viewed from a doorway, featuring white cabinetry and a spacious island with seating. Natural light filters through the windows, highlighting the sleek countertops and decor. A warm area rug adds texture to the hardwood floor, creating a welcoming atmosphere.

Home in Forest Park

4.97 out of 5 average rating, 34 reviews

Walk to Oak Park From Our Large Sun-Soaked Home!

The exterior of a historic house features a two-story facade with a gabled roof and large windows on the first level. Lush greenery surrounds the property, creating a welcoming atmosphere and enhancing the home’s charm.

Home in Oak Park

5 out of 5 average rating, 6 reviews

3 Parking Spaces 8 Bedrooms 3 Full Bath

Top guest favorite

The open living area features a spacious sectional sofa facing a modern stone fireplace. A wall-mounted smart TV is visible above the fireplace, while a kitchen island with bar seating is positioned nearby. Natural light enters through windows, enhancing the neutral decor.

5 out of 5 average rating, 25 reviews

Casa 22 | Luxury Modern House for 6 | 3 Bed,2 Bath

Top guest favorite

A single-story brick home with a well-maintained front yard features green shrubs and a neat pathway leading to the entrance. Large windows allow natural light to illuminate the interior, while a tree provides shade near the entrance.

Home in Brookfield

4.97 out of 5 average rating, 37 reviews

Cozy Home in Brookfield

The exterior of a European custom-built home is showcased, featuring a charming brick façade and a distinctive curved entryway. Elegant windows are framed with decorative stone accents. A well-maintained lawn with seasonal foliage surrounds the home, highlighting its vintage architectural details.

4.92 out of 5 average rating, 24 reviews

European Custom Built Home 2 Bedrooms

Private house rentals

Top guest favorite

A charming sitting area features a round table adorned with a lace tablecloth, surrounded by vintage dining chairs. The room is illuminated by a standing lamp and natural light streaming through a lace-covered window. Antique decor, including framed artwork and a wooden cabinet, decorates the walls.

4.93 out of 5 average rating, 28 reviews

5BR Historic Family Home: Unique & Cozy w/ Parking

The bathroom features a sleek design with light grey tile flooring and patterned wall accents. A bathtub is partially obscured by a white shower curtain, and a dark vanity with a marble countertop is visible. Two bath mats provide comfort underfoot.

Home in Melrose Park

4.93 out of 5 average rating, 15 reviews

A ranch home within the outskirts of Chicago

Top guest favorite

A spacious living area showcases wooden floors and a green accent wall. Natural light streams through multiple windows adorned with dark frames. Comfortable seating includes a gray sofa with colorful throw pillows, and a wooden coffee table occupies the center. A glimpse of a dining area is visible in the background.

Home in Andersonville

4.95 out of 5 average rating, 22 reviews

Charming 3bd Bungalow In Vibrant Andersonville

A spacious dining area is highlighted by a large wooden table surrounded by light-colored upholstered chairs. The walls are painted a calming blue, complemented by large windows that allow natural light to fill the room. Elegant curtains frame the windows, adding a touch of softness.

Home in Brookfield

4.91 out of 5 average rating, 33 reviews

Bliss in Brookfield- 5BR, 3BA

The exterior of a charming two-story home is featured, surrounded by well-maintained landscaping. A pathway made of pavers leads to the front entrance, framed by vibrant green shrubs and trees. The house showcases a gabled roof with dormer windows and yellow front door.

4.87 out of 5 average rating, 97 reviews

Luxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |

Top guest favorite

A modern living room is equipped with two comfortable sofas and a stylish coffee table. A large TV is mounted above a white brick fireplace. Soft lighting complements the space, enhanced by a unique hanging chair and a small workspace with a chair.

Home in Des Plaines

4.98 out of 5 average rating, 61 reviews

5 Star Luxury Stay Near Chicago O'hare Airport,

A comfortable living area is featured with a sectional sofa adorned in cream and blue hues. Natural light floods in through two large windows, framed by soft curtains. A light wooden coffee table anchors the space, accompanied by a vibrant blue armchair and decorative plant arrangements.

Home in Oak Park

5 out of 5 average rating, 3 reviews

New! 5bd/2bth sleeps 11 with 3 private parking

A modern living area features a coffered ceiling and polished hardwood floors. A round dining table with stylish chairs is set against a backdrop of framed artwork. A cozy seating area showcases a gray sofa, while a fireplace adds warmth. A doorway leads to the entrance.

Home in Humboldt Park

4.99 out of 5 average rating, 71 reviews

5 BR | Rooftop | 6 Spa Baths |Sleep 16 | Near Loop

Quick stats about house rentals in Oak Park

Total rentals
130 properties
Total number of reviews
4.3K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Wifi availability
130 properties include access to wifi

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