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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, 165 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.

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

4.95 out of 5 average rating, 177 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 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.

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

4.91 out of 5 average rating, 295 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!

Top guest favorite

The exterior of the house features a modern navy blue facade with white trim and a red front door. A porch runs along the front, adorned with rocking chairs. An American flag is displayed, enhancing the welcoming character of the home amidst a green lawn and surrounding trees.

Home in Logan Square

4.91 out of 5 average rating, 121 reviews

Kid friendly 2 bedroom w/ private office

Come enjoy a hip trip to Logan Square, Chicago! Minutes from local bars, restaurants, parks, the bike trail, and public transit, our toddler friendly, 2 bedroom 1st floor apartment has all you need! Cozy bedrooms and brightly lit common spaces make our space inviting and relaxing. Enjoy a private dedicated work from home space with large windows and tons of light. A front porch swing is also great for a morning cup of coffee or adult beverage wind down. We can't wait to host you!

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, 133 reviews

Walkable, Near Chicago, Sleeps 4, Free Parking

Our Oak Park, 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 6 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. Booking age, 25 or at least one 5 ⭐️ review. Visit profile for more units.

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, 122 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, 209 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, 109 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 cozy living area showcases a brown leather sofa adorned with decorative cushions. A round glass coffee table rests on a patterned rug, complementing the hardwood flooring. Framed artwork decorates the wall, while natural light enters through nearby windows.

Home in Logan Square

4.98 out of 5 average rating, 123 reviews

The Hamlin in Logan Square 4BR/2BA w/Parking!

Welcome to The Hamlin House in Logan Square! Enjoy four bedrooms, two full bathrooms and complimentary two-car garage parking during your stay. This home is perfect for both family and group vacations in Chicago. Logan Square is a thriving neighborhood filled with amazing art, restaurants and architecture. The neighborhood provides easy access to downtown while avoiding downtown hotel pricing for larger groups.

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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

4.81 out of 5 average rating, 21 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 living room is presented with light wooden flooring and a soothing grey wall. Two red sofas are arranged for seating, facing a wall-mounted television. Natural light filters through two textured window shades, and a lamp stands beside the furnishings, adding to the room's cozy layout.

Home in Schaumburg

4.74 out of 5 average rating, 23 reviews

Spacious 3 Floor Townhome

An expansive outdoor space showcases a landscaped backyard with an in-ground pool, surrounded by a protective fence. Loungers are positioned around the pool, and a covered seating area is visible, providing shaded relaxation options. Nearby, a well-maintained lawn extends into the background.

Home in Plainfield

4.77 out of 5 average rating, 47 reviews

30 mins to CHI_3 Kings_BBQ Grill_Spacious_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

A spacious backyard is illuminated by soft evening light, showcasing a lush green lawn framed by well-maintained gardens. Multiple seating areas are visible, including a hammock, lounge chairs, and patio furniture. A large tree offers shade, while a pool is partially seen beyond the greenery.

Home in Schaumburg

4.94 out of 5 average rating, 34 reviews

Schaumburg Oasis:Private Pool & Enchanted Garden

Weekly house rentals

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

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

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 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 |

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

Top guest favorite

A two-story brick home features a welcoming front porch with a stoop and entrance framed by tall windows. Lush greenery and vibrant flower beds add color to the exterior, enhancing the inviting presence of the residence.

Home in Chicago

4.97 out of 5 average rating, 29 reviews

Big house in the BEST Location!

A cozy living room features four plush purple chairs arranged around a circular table. A modern television is mounted above a white brick fireplace, complemented by bookshelves filled with various items. A large potted plant adds a touch of greenery, enhancing the warm atmosphere.

4.85 out of 5 average rating, 68 reviews

A Comfortable Stay While You are Away in Oak Park

A cozy outdoor seating area is showcased under a large canopy, illuminated by string lights. The space is furnished with multiple woven chairs and tables, surrounded by a grassy area and wooden fencing, providing a serene spot for relaxation.

Home in Oak Park

4.93 out of 5 average rating, 60 reviews

Oak Park 3000 sq ft, sleeps 16

Private house rentals

Top guest favorite

A spacious living area features a large sectional sofa arranged around a circular coffee table. A television is positioned on a media stand, and natural light enhances the room through a large arched window, complemented by decorative plants and neutral-colored accents.

Home in Elmhurst

4.95 out of 5 average rating, 39 reviews

Premier 5BR/3BA Modern Retreat with King Suite!

Top guest favorite

A bright living room features a mix of comfortable seating with a tan leather sofa and two light-colored armchairs. A wooden coffee table sits center stage, complemented by decorative items. Large windows allow natural light to flow in, enhancing the cozy atmosphere.

Home in Northbrook

4.97 out of 5 average rating, 77 reviews

*King bed *Outdoor Living *Sought-After Area

Top guest favorite

A cozy bedroom showcases a spacious bed adorned with colorful floral and patterned pillows. Green nightstands are positioned on either side, complemented by wall-mounted lamps. Dark curtains frame a window that offers a view of the outdoors, adding to the inviting decor.

Home in Clarendon Hills

4.98 out of 5 average rating, 45 reviews

3 Bedroom+Office*Huge Sofa*Chic Decor*Garden*5 TVs

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!

A comfortable living area is highlighted by a blue sofa, accompanied by a decorative throw pillow featuring the Chicago flag. A coffee table with books and magazines sits in front of the sofa. An array of city-themed artwork adorns the wall, while a television is mounted nearby.

4.86 out of 5 average rating, 51 reviews

Berwyn Bungalow

A dining area is shown featuring a wooden table set for four with woven placemats. Brown leather chairs complement the modern aesthetic. A ceiling fan hangs above, and a mounted television is visible on the wall. Light enters through the windows, illuminating the space.

Home in Maywood

4.93 out of 5 average rating, 14 reviews

Charming Home Close to Loyola, Zoo & Chicagoland

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

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

4.89 out of 5 average rating, 35 reviews

Bliss in Brookfield- 5BR, 3BA

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

Destinations to explore