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Holiday houses in Oak Park

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Quick stats about holiday rentals in Oak Park

  • Total holiday rentals

    Explore 300 holiday rentals in Oak Park

  • Nightly prices starting at

    Oak Park holiday rentals start at $18 NZD per night before taxes and fees

  • Verified guest reviews

    Over 22,070 verified reviews to help you choose

  • Family-friendly holiday rentals

    150 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 80 rentals that welcome pets

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wi-Fi availability

    290 of Oak Park holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Monthly stays, Gym and BBQ across Oak Park rentals

  • 4.7 Average rating

    Oak Park stays receive an average rating of 4.7 out of 5 from guests

Top-rated holiday rentals in Oak Park

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Apartment in Oak Park

Oak Park Space+Style Duplex Parking+Walk to Train

A warm, curated home with two floors of living space. Perfect for families with kids, groups of friends and multi-generational living. The main floor + finished basement total 3 bdrms + 2.5 baths. Primary suite is on the main floor. Two secondary bedrooms are on the lower w/ a full bath. 20 min to downtown Chicago. Walk to dining + train+ FLW Home. Open living/dining/kitchen/sunroom. Remote work space. Coffee bar. Private entry/deck. Driveway parking. Central AC. Upstairs apartment is separate.

5.0 out of 5 average rating, 104 reviews
Top Guest favourite
The living room is bright and spacious, featuring a comfortable seating area with a sofa and two armchairs. A coffee table is centered on a plush area rug, while natural light enters through multiple windows adorned with light curtains. Decorative artwork complements the warm color scheme.
Apartment in Oak Park

SuperHost and Super Location Central OP

4.98 Star Superhost rating for this ideal Centrally-located, light, bright, spacious 2 bedroom 1 bath 2nd floor unit in a beautifully updated vintage building! Central air and forced air heat, hardwood floors throughout. Wonderful floor plan to enjoy your stay while you are "in", Near public transportation when you want to "be on the go"! Designated work space, high speed WIFI and 1 parking space on premises. Deck off the kitchen.. Keyless access. 1 King/ 1 Queen bed.Owner lives on the 1st floor

4.98 out of 5 average rating, 149 reviews
Top Guest favourite
Apartment in Oak Park

Serene 1-Bedroom Suite in Oak Park (Free Parking!)

This serene, one-bedroom unit is nestled beneath our cozy Oak Park bungalow, with free off-street parking, strong Wi-Fi, and within walking distance of the Chicago Blue Line, which can take you into the city or to O'Hare. We are just 8 miles west of downtown to Chicago. Full of natural light and thoughtfully furnished with a kitchenette, coffee nook, large-screen TV, and dedicated workspace, this private unit is a comfortable retreat perfect for solo travelers or couples seeking a quiet stay.

4.98 out of 5 average rating, 85 reviews
Superhost
A spacious living area is highlighted by a black sofa facing a light-colored coffee table. A vibrant area rug adds color underfoot. The walls are adorned with colorful vinyl records and framed artwork, while original woodwork details frame the open layout leading to the dining area.
Apartment in Oak Park

Rockin' 2Bed steps to shops/food/train

This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving

4.87 out of 5 average rating, 795 reviews
Guest favourite
Apartment in Oak Park

3BR/1BA With Private Garage, Near Train & Shops

Experience the comfort of our spacious, modern apartment in Oak Park's Historic Gunderson District. Walk to parks, the train station, restaurants, cafés, and local shops in this vibrant, walkable neighborhood. The home features 3 bedrooms with queen-size beds, 1 full bathroom, a cozy living area, and an air mattress available upon request. Enjoy high-speed Wi-Fi, a fully equipped kitchen, in-unit laundry, private garage parking, and easy access to downtown Chicago in just 15–20 minutes.

5.0 out of 5 average rating, 8 reviews
Top Guest favourite
Home in Oak Park

Coach House•Theater•Parking•6 minute Walk to FLW

Welcome to our fully stocked 2BR Coach House in Oak Park! This thoughtfully designed home offers free parking, central AC/heat, in-unit laundry, fast Wi-Fi, a private backyard, and more. Unwind in the board game and arcade room or relax in the theater room equipped with a 75” TV with complementary snacks and drinks. Perfect for families, couples, remote workers, or friends seeking a private, comfortable home base with easy access to downtown Chicago and all Oak Park offers.

5.0 out of 5 average rating, 43 reviews
Guest favourite
Apartment in Oak Park

Wonderful 1BR Retreat with Balcony in Oak Park

3rd-floor unit with elevator access and a balcony. This stylish 1BR/1BA apartment offers the perfect blend of comfort and practicality. Enjoy a fully equipped kitchen, a cozy yet spacious living area, and sleek, contemporary finishes throughout. Guests also have access to building amenities, including a fully equipped gym and a rooftop with beautiful views. Just 15 minutes from Chicago, it’s an ideal home base for a relaxing and convenient stay.

4.9 out of 5 average rating, 21 reviews
Top Guest favourite
A charming Victorian home is showcased, featuring a front porch with wide steps leading to a door framed by lush greenery. The exterior is painted in a crisp white, complemented by dark accents on the windows. A manicured lawn adds to the inviting landscape.
Home in Oak Park

Oak Park Victorian by FLW Studio

Discover historic charm in our updated 4-bedroom Victorian home in the iconic Frank Lloyd Wright district. Comfortably sleeps 8. Features a fully equipped kitchen, dedicated workspace, and modern amenities. Perfectly located for exploring local gems on foot or a quick 15-min drive to downtown Chicago. Enjoy private parking and easy access to public transit. Ideal for families and groups seeking a stylish, central retreat.

4.96 out of 5 average rating, 148 reviews
Top Guest favourite
A historic Queen Anne home features a distinctive turret and a wraparound porch, surrounded by lush greenery. The exterior showcases a blend of siding and masonry with intricate architectural details reflective of its 1889 origins.
Apartment in Oak Park

Victorian Charm in Historic Oak Park Free Parking

This historic Queen Anne home built in 1889 is in the heart of Oak Park. Centrally located and within walking distance to all tourist attractions, public transportation, great restaurants, boutiques and grocery stores. It’s the perfect base for exploring Oak Park and Chicago Perfect for long-term stays. We kindly ask that you read our full listing description and our house rules prior to booking.

4.98 out of 5 average rating, 278 reviews
Luxe
Condo in Oak Park

Architect-Designed 3BR Oak Park Flat

Experience historic Oak Park in our beautifully renovated 3-bedroom apartment. Blending 1920s charm with modern luxury, this space comfortably fits families or groups. Features a dedicated workspace, new kitchen, and a shared roof deck. Located steps from the Green Line, offering a quick, direct ride to downtown Chicago. Perfect for exploring both Oak Park's cultural gems and the Windy City.

5.0 out of 5 average rating, 18 reviews
Guest favourite
A light-filled living room showcases a comfortable sofa adorned with various cushions, complemented by a stylish coffee table. Large windows with black blinds overlook the street, while a decorative rug adds warmth to the hardwood flooring. A chair and lamp create a cozy reading nook.
Apartment in Oak Park

Urban oasis in Oak Park

Steps to all of Oak Park and next to the train to downtown. Your cool and centrally-located apartment is near everything that Oak Park and Forest Park have to offer: cafes, great restaurants, shopping, parks, yoga studios, Frank Lloyd Wright, Hemingway District and so much more! Best location in Oak Park on a quiet, tree lined street but super close to restaurants, cafes and shopping!

4.83 out of 5 average rating, 58 reviews
Top Guest favourite
A cozy living area features a light-colored sofa and a soft lounge chair, positioned around a low table. Natural light enters through large windows adorned with sheer curtains, illuminating the wood flooring and a colorful area rug.
Townhouse in Oak Park

Lovely Central Oak Park TH w/parking & on Green el

Great central Oak Park location, close to everything including dining, Green Line, Metra, and OPRF High School. Enjoy farm fresh produce, eggs, and cheese or pick up some famous Farmers Market Donuts from the Oak Park Farmers Market just steps out your front door every Saturday May-October. Free (driveway) parking for one car. Backyard & deck space off the kitchen.

4.98 out of 5 average rating, 247 reviews

Popular amenities for Oak Park holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Stay near Oak Park's top sights

Frank Lloyd Wright Home and Studio

243 locals recommend

Ernest Hemingway Birthplace

108 locals recommend

Fitzgerald's

94 locals recommend

Oak Park Conservatory

58 locals recommend

Unity Temple

37 locals recommend

Pleasant Home

30 locals recommend

Other great holiday rentals in Oak Park

Top Guest favourite
Decorative elements are displayed on a mantel, featuring two sculptural figures crafted from textured metal. A collection of books about Oak Park is arranged alongside dried floral arrangements, adding to the aesthetic appeal of the space.
Apartment in Oak Park

Historic Hotspot: Downtown Oak Park w/parking spot

4.97 out of 5 average rating, 96 reviews
Guest favourite
A stylish studio features a spacious bed adorned with colorful pillows. A cozy seating area with a dark sofa is positioned near large windows that allow natural light to fill the room. A small dining table with chairs sits beside the sofa, enhancing the open layout.
Apartment in Oak Park

Modern NEW Deluxe Studio in Oak Park

4.92 out of 5 average rating, 64 reviews
Top Guest favourite
A blue Victorian-style house is framed by a lush green lawn and several trees. The structure features a prominent gabled roof and a welcoming porch with steps leading to the entrance. Surrounding foliage adds to the home's charm.
Apartment in Oak Park

Large 2 BR Apt in FLW Historic Dist. in Oak Park!

4.95 out of 5 average rating, 39 reviews
Top Guest favourite
A living area features a cozy orange sofa and two gray armchairs set around a round coffee table. Natural light enters through large windows dressed in floral curtains, while a colorful area rug adds warmth to the space.
Apartment in Oak Park

Large sunny 3BR apt. in downtown Oak Park

4.92 out of 5 average rating, 209 reviews
Top Guest favourite
A charming house is framed by a lush garden filled with various shrubs and flowering plants. The exterior features a mix of wood siding and prominent windows, while a white picket fence lines the front yard, enhancing the home's inviting presence.
Guest suite in Oak Park

Entire upstairs in Arts and Crafts Oak Park home

4.91 out of 5 average rating, 543 reviews
Top Guest favourite
A spacious living area features a light-colored sectional sofa facing a large flat-screen television mounted on the wall. Natural light enters through a nearby doorway, illuminating the hardwood flooring and highlighting the room's high ceilings.
Home in Oak Park

The Maple Place

4.93 out of 5 average rating, 56 reviews
Top Guest favourite
Home in Oak Park

Oak Park Two Flat Oasis

4.92 out of 5 average rating, 25 reviews
Top Guest favourite
Apartment in Oak Park

Comfortable & Easy

5.0 out of 5 average rating, 13 reviews

When is the best time to visit Oak Park?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$170 NZD$180 NZD$202 NZD$207 NZD$255 NZD$267 NZD$249 NZD$248 NZD$212 NZD$210 NZD$194 NZD$182 NZD
Avg. temp-3°C-1°C4°C10°C16°C22°C25°C24°C20°C13°C6°C0°C

Frequently Asked Questions

  • What are the best places to stay in Oak Park?

    Stays near downtown Oak Park are often recommended for easy access to dining, shopping, and transit. Neighborhoods close to parks or historic districts have a quieter ambiance and blend community with convenience.

  • What are the best things to do in Oak Park with kids?

    Families often explore interactive exhibits at the Children’s Museum, play in Scoville Park, or visit local libraries for storytime. Many parks have playgrounds, and seasonal events provide hands-on activities for children.

  • What are some of the best things to do in Oak Park?

    Discover Oak Park’s historic architecture, visit local museums, and attend community theater or art shows. Independent shops, farmers markets, and neighborhood parks add variety to daily adventures.

  • How is the weather in Oak Park?

    Oak Park has cold winters around 19–33°F (-7–0°C), while summers bring warmer afternoons near 68–85°F (20–29°C). Spring and autumn have milder temperatures and occasional rain, so packing layers is helpful.

  • When is the best time to visit Oak Park?

    Late spring through early fall is often recommended, with warmer temperatures and outdoor festivals. Winter has lower temperatures, so pack accordingly if you plan to visit during colder months.

  • What are the best places to visit in Oak Park?

    Explore the Frank Lloyd Wright Home and Studio, the Ernest Hemingway Birthplace Museum, and Scoville Park for a glimpse of local history. Art galleries and cultural centers around downtown highlight Oak Park’s creative roots.

  • What are some hiking trails in Oak Park?

    Oak Park has tree-lined walking paths in local parks, such as Austin Gardens and Lindberg Park. Trail enthusiasts often explore nature preserves around the area or venture into nearby forested spaces for varied experiences.

  • What are some family activities we can do in Oak Park?

    Families can explore parks with playgrounds, join events at the local library, or visit interactive museum spaces. Community centers and seasonal festivals provide hands-on fun for all ages.

  • What are some of the best day trip ideas from Oak Park?

    Nearby areas have cultural museums, nature preserves, and lakeshore parks that are often recommended for day trips. Chicago's downtown, with its theaters and riverfront walks, is a frequently suggested destination for visitors.

  • Are there any pet friendly accommodations available in Oak Park?

    Several Oak Park vacation rentals welcome pets, especially houses and ground-floor apartments near green spaces. Local parks such as Lindberg Park make outings with your dog convenient.

  • What are some local tips for visiting Oak Park?

    Consider exploring Oak Park by foot or bicycle to appreciate historic architecture and murals. Locals suggest sampling small businesses, packing layers for unpredictable weather, and checking out neighborhood events to connect with the community.

  • What is Oak Park known for?

    Oak Park is known for its historic architecture, including several Frank Lloyd Wright-designed homes, its literary heritage linked to Ernest Hemingway, and vibrant community arts. The area has diverse eateries and independent shops.

  • What are the best hidden gems to explore in Oak Park?

    Oak Park has lesser-known murals and community gardens that locals often highlight. Small galleries, independent bookshops, and historic alleys near the arts district offer quiet places to explore.

  • What are the best foods to try in Oak Park?

    Oak Park has a mix of locally rooted cuisines, with pizza, classic Chicago-style hot dogs, and diverse vegetarian dishes frequently suggested. Independent bakeries, global eateries, and seasonal farmers market fare round out the food scene.

  • What should I bring for a trip to Oak Park?

    Pack versatile layers, as temperatures range from around 19°F (-7°C) in winter to 85°F (29°C) in summer. Comfortable shoes are helpful for walking through historic districts and parks, and a reusable water bottle suits busy days out.

  • What is the nightlife in Oak Park like?

    Oak Park has neighborhood bars, music venues, café lounges, and spots with occasional live performances. The scene is relaxed, with locals gathering for casual dining, craft drinks, and community events.

  • What are the most popular events or festivals in Oak Park?

    Oak Park hosts seasonal festivals, including an arts-focused event often recommended in summer and community celebrations around Labor Day weekend. Local farmers markets and neighborhood block parties are also frequently suggested.

  • Are there family friendly vacation rentals in Oak Park?

    Oak Park has a variety of family-friendly vacation rentals, including apartments and houses near parks and schools. Many hosts include amenities such as play spaces, high chairs, and board games.

Destinations to explore