Holiday rentals 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 $13 SGD 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 & child-friendly amenities
Pet-friendly holiday rentals
Find 80 rentals that welcome pets
Rentals with dedicated workspaces
160 properties have a dedicated workspace
Wifi availability
290 of Oak Park holiday rentals include wifi access
Popular amenities for guests
Guests love Monthly stays, Gym and BBQ grill 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.
Sunny Jumbo Studio
Bright and sunny Oak Park jumbo garden studio, steps from cute downtown, train to Chicago, and amazing local tourist destinations- like the Hemingway Home and the Wright Studio. This welcoming studio was completely rehabbed and updated. We put a lot of care into designing a relaxing apartment with all the amenities. The main room features a king-sized bed, office nook, and fully stocked entertainment area, with games, books, and a TV. The spacious kitchen and luxurious bathroom are brand new!
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Cheerful Remodel Prime Location
Relax in this newly remodeled and beautifully decorated apartment while recharging from a long day of sightseeing in the big city! We are a block from the Green Line train to downtown! With a 5 minute walk to Whole Foods, Trader Joes, and downtown Oak Park, you can't get a better location than this! Pets are welcome on a case-by-case basis, please mention your pet in your inquiry so we can learn more about them prior to approval and be sure to register them when you select number of guests.
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Oak Park cozy carriage house-lovely, walkable area
Our comfortable, stylish retreat has everything you need to relax and recharge. Whether you are visiting to explore all that beautiful Oak Park and downtown Chicago offer or desire a peaceful space to work. -> Quiet, walkable street near popular cafes, restaurants, taverns, parks, historic homes -> Steps from the "L" Blue Line Oak Park station -> Stocked w/ snacks + gourmet coffee/tea set-up (grinder, AeroPress, and Keurig) -> Onsite off-street parking -> A/C + heat -> garden sitting area
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A Pleasant Stay in Oak Park
Welcome to our bright and peaceful townhouse in Oak Park, IL! Just steps from the vibrant Oak Park Arts District, you'll be close to the area’s best shops and restaurants. Recently renovated from top to bottom, the home features high-quality materials and a clean, modern style that beautifully honors its vintage charm. Located in a residential neighborhood step to the train, downtown Oak Park and 15 minutes to Chicago. We offer a calm and stylish space where guests can relax and unwind.
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Space & Style Duplex Near Downtown w/Parking
2024 Gut rehab! Spacious w/A+ location! 1 of 2 apts in a two flat. King bed! W/D! This unit = Main floor + finished bsmnt. 3 bdrms + 2.5 baths. Steps to FLW Home. 20 min to downtown Chicago. Walk to dining + train. Open living/dining/kitchen/sunroom. Powder room. Primary w/king + ensuite. 2nd bedroom w/queen + 3rd bedroom w/2 double beds, walk-in closet. 2nd full bath + work/gameroom. Coffee bar, pantry. Private entry/deck. Driveway parking. Upstairs apt not included in this listing.
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Guest Favorite Stay in Oak Park| In Unit Laundry
2nd-floor unit with elevator access. Older building with radiant heat managed by the building. Includes an all-in-one electric washer and dryer. Welcome to your stylish Oak Park retreat! This newly remodeled 2BR/2BA apartment blends modern comfort with historic charm. Enjoy a bright space with a full kitchen, cozy living area, and designer touches. Walk to shops, cafes, and parks, or use nearby transit for easy access to Chicago. Perfect for families, friends, or business stays.
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Top floor of Historic Oak Park Home /2 Car Garage
Secluded but never isolated; 3 blocks from the L-line, next door to Hemingway's birthplace, surrounded by dozens of Frank Lloyd Wright homes, 30 min from the Loop, MDW and ORD, makes this location an ideal platform for the cultural explorer. Experience an ambiance that supports the work-from-home Urban Professional, combining it with a multibedroom layout designed to accommodate family and friends. Gig-speed internet supports sophisticated professional and gaming applications.
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Studio Apartment in Oak Park
Nestled in Oak Park's historic district, this charming studio apartment is within walking distance of cafes, shops, restaurants, a movie theater, and the CTA/Metra for city and suburban excursions. Featuring a comfortable queen-sized bed, a newly updated full bathroom, and a kitchenette, it sits mere steps from Ernest Hemingway's childhood home and a few blocks from Frank Lloyd Wright's residence and studio. Enjoy the serenity of this historic home and its hidden garden oasis.
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Modern NEW Deluxe Studio in Oak Park
Enjoy a stylish experience at this centrally-located studio In charming Oak Park. Tourist-friendly and trendy downtown Oak Park has a buzzing restaurant district, great cafes, and an assortment of excellent storefronts, including vintage shops, boutique toy stores, mom-and-pop bookstores, and a variety of spas and salons to choose from. Parks in this world-class suburb are everywhere. Views from the unit are fabulous. This deluxe studio has it all.
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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.
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Restored Mid-Century 4 Square
A group up to four will enjoy easy access to everything from our centrally located getaway. This extra large 4 room 1 bedroom + 3 season porch with swing is the ideal retreat after a day of working or sightseeing around Chicago. This one bedroom, king suite with sofa sleeper, encompasses the first floor of the building. There are 7 stairs to get into the unit. Off street parking on the driveway is included.
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Bright & Spacious Victorian-FREE PKG walk to train
This historic Queen Anne home built in 1889 is in the heart of Oak Park. Walk to all tourist attractions, public transportation that takes you directly to downtown Chicago, great restaurants, boutiques and grocery stores. It’s the perfect base for exploring Oak Park and Chicago. We kindly ask that you read our full listing description and our house rules prior to booking.
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Popular amenities for Oak Park holiday rentals
Other great holiday rentals in Oak Park
Historic Hotspot: Downtown Oak Park w/parking spot
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3BR/1BA With Private Garage, Near Train & Shops
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Architect-Designed 2BR Oak Park Flat
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2nd Floor Apartment in the Heart of Oak Park
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Explore Oak Park & Chicago
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OakPark Gem. Family-Friendly Getaway near Downtown
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Serene 1-Bedroom Suite in Oak Park (Free Parking!)
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Studio Mins Walk to DT OAK PARK
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When is the best time to visit Oak Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $123 SGD | $131 SGD | $146 SGD | $150 SGD | $184 SGD | $193 SGD | $181 SGD | $179 SGD | $154 SGD | $152 SGD | $141 SGD | $132 SGD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°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
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- Navy Pier
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- University of Chicago
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- Loyola University Chicago
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