Holiday Rentals in Oak Park

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Oak Park holiday rentals
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Oak Park holiday rentals: compare the best deals

Best family friendly Oak Park holiday rentals

Among the 269 accommodations in Oak Park, here are the 4 best family friendly rentals

Restored Victorian 5* Locale Queen Beds W/ Parking - Oak Park
9.6 57 reviews
Oak Park
07/17 – 07/27
HK$2445/nightTotal: HK$24450 (10 )

Restored Victorian 5* Locale Queen Beds W/ Parking

1 1
apartment , Oak Park
This charming Victorian home is located in Oak Park, just 8 kilometres from downtown Chicago, offering easy access to parks, the Oak Park Conservatory and a pool/water park. The property consistently receives excellent ratings for location, cleanliness and user experience.
This three-bedroom property comfortably accommodates up to seven guests. Enjoy a blend of vintage and contemporary design with modern conveniences including a fully equipped kitchen, Wi-Fi speakers and a spacious garden with a patio, fire pit and Weber gas grill.
Pilsen 8 Min-downtown Washerdryer 2300 Square Feet - Oak Park
9.8 100 reviews
Oak Park
07/10 – 07/12
HK$6904/nightTotal: HK$13808 (2 )

Pilsen 8 Min-downtown Washerdryer 2300 Square Feet

4 14
apartment , Chicago
This apartment is situated in the trendy Pilsen neighbourhood, just 10 kilometres from the city centre and close to Chinatown, offering easy access to Chicago's attractions. The property boasts excellent user, location and cleanliness ratings.
This spacious flat has four bedrooms and two bathrooms, comfortably accommodating up to 16 guests. The apartment is fully equipped with a kitchen, air conditioning, free street parking, and high-speed Wi-Fi, ensuring a comfortable and convenient stay.
Great Location. 5min To Mccormick Place. Downtown. Chinatown - Oak Park
8.8 5 reviews
Oak Park
06/28 – 07/05
HK$2616/nightTotal: HK$18312 (7 )

Great Location. 5min To Mccormick Place. Downtown. Chinatown

3 5
apartment , Chicago
This Bridgeport, Chicago flat is situated near Chinatown, approximately 0.8 km from McCormick Place and the city centre, offering easy access to Guaranteed Rate Field.
The three-bedroom property sleeps eight, includes a full kitchen with dishwasher, in-unit laundry, and a private backyard with cornhole and barbecue facilities; long-term stays are welcome.
Bright Garden Studio - Oak Park
8.2 35 reviews
Oak Park
09/06 – 09/07
HK$2309/nightfor 1 night

Bright Garden Studio

1 2
studio , Evanston
This Evanston studio apartment, located in a quiet, family-friendly upper-middle-class neighbourhood with easy access to CTA bus and train lines for travel to Chicago attractions, offers a convenient base for exploring the city.
The 74-square-metre (approximately 796 square feet) self-catering apartment features a sophisticated open-plan design, accommodating up to four guests and boasting amenities including a Jacuzzi, garden, and parking.

Best Oak Park holiday rentals with parking

Cheerful Remodel Prime Location - Oak Park
9.8 139 reviews
Oak Park
10/11 – 10/21
HK$1576/nightTotal: HK$15760 (10 )

Cheerful Remodel Prime Location

1 2
apartment , Oak Park
This Oak Park flat is situated a short distance from the Green Line, offering easy access to Chicago city centre and is within 0.8 km of Whole Foods and Trader Joe's.
The one-bedroom, one-bathroom apartment sleeps two guests and includes parking, Wi-Fi, air conditioning, and a fully equipped kitchen; nearby attractions include Oak Park's shops and restaurants, easily accessible within a 0.8 km walk.
Exquisite Rogers Park 1 Bedroom, 1 Bath Apartment Near Evanston - Oak Park
8.2 5 reviews
Oak Park
06/25 – 07/25
HK$2765/nightTotal: HK$82950 (30 )

Exquisite Rogers Park 1 Bedroom, 1 Bath Apartment Near Evanston

1 3
apartment , Chicago
This Rogers Park flat in Chicago is situated 3.5km from Loyola University Chicago and within a reasonable driving distance of Wrigley Field and Lincoln Park Zoo.
The 93 square metre self-catering apartment sleeps two, offering a fully equipped kitchen, free Wi-Fi, private parking, and a private entrance.
Comfortable Living, Within Reach! - Oak Park
Oak Park
09/06 – 09/07
HK$7729/nightfor 1 night

Comfortable Living, Within Reach!

2 2
apartment , Oak Park
This Oak Park flat is located 8.5 kilometres from the United Centre, providing easy access to downtown Chicago landmarks within an 8.5-kilometre radius and is 9.9 kilometres from Midway International Airport.
This one-bedroom flat offers accommodation for up to 11 guests, featuring air conditioning, complimentary Wi-Fi, a fully equipped kitchen with a dishwasher and oven, and an in-unit washing machine, with parking available and pets permitted.
Designer Themed 4 Bedroom In Best Location With Patio And Fireplace - Oak Park
9.6 676 reviews
Oak Park
09/06 – 09/07
HK$10144/nightfor 1 night

Designer Themed 4 Bedroom In Best Location With Patio And Fireplace

4 2
house , Chicago
This four-bedroom holiday home is located in Chicago's Old Town district, just a short walk from Oak Street Beach and Lincoln Park Zoo, offering easy access to the city's attractions and restaurants. The property consistently receives excellent ratings for its location, cleanliness, and overall experience.
The house is spacious and comfortable, accommodating larger groups with ease. Guests can enjoy a range of amenities, including a fully equipped kitchen, a patio, a garden, a spa, a fitness centre, and a tennis court.

Frequently asked questions about holiday rentals in Oak Park

  • What should a first-time visitor not miss in Oak Park, IL?

    A first-time visitor to Oak Park should definitely check out the Frank Lloyd Wright Home and Studio. It's a must-see for architecture enthusiasts and gives you a glimpse into the life of this famous architect. You should also visit the Oak Park River Forest Museum, which tells the story of the area's history and culture.
  • What are the best Airbnb and vacation rentals in Oak Park?

    Charming Chicago-style - Vintage - Tv Nfl Pass, Modern Victorian With Old World Charm and Coachhouse In Central Op 4 Blk To L are the most popular Airbnb and vacation rentals in Oak Park among travelers.

  • Which neighborhood in Oak Park, IL should you consider for a vacation rental?

    The heart of Oak Park is the village centre, and it's a great place to stay. It's walkable to many restaurants, shops, and attractions, including the Oak Park Public Library. If you prefer a quieter neighbourhood, consider the area around the Forest Park station, which has a more residential feel.
  • What are the most popular Airbnbs in Oak Park?

  • What are the top family-friendly attractions in Oak Park, IL?

    The Oak Park Conservatory is a great spot for families, with its beautiful gardens and interactive exhibits. The park also has a playground and a splash pad. The Scoville Park is another great option, with its large green space, playground, and tennis courts.
  • What are the best vacation rentals with a pool in Oak Park?

  • When is the best time to book a vacation rental in Oak Park, IL?

    The best time to book a vacation rental in Oak Park is during the shoulder seasons, which are spring and autumn. The weather is pleasant, and the crowds are smaller. You'll find good deals on accommodation during these periods.
  • What are the best rentals for families and kids in Oak Park?

  • What are the best budget-friendly activities in Oak Park, IL?

    Oak Park has many free or low-cost activities, such as visiting the Oak Park Public Library, taking a walk or cycle along the Des Plaines River Trail, or enjoying a picnic in one of the many parks. The village also has a number of free concerts and events throughout the year.
  • What are the best rentals or Airbnbs with a jacuzzi in Oak Park?

  • What are the best restaurants with local dishes in Oak Park, IL?

    Oak Park has a vibrant culinary scene, with many restaurants serving local and regional dishes. Some of the best include Maya Del Sol, which serves Mexican cuisine, and the Oak Park Brewing Company, which serves craft beers and pub fare.
  • What are the best walking or cycling routes in Oak Park, IL?

    Oak Park has a network of walking and cycling paths, including the Des Plaines River Trail, which runs along the river for over 100 km. The village also has a number of parks and green spaces, which are great for a leisurely stroll or bike ride.
  • Are there pet-friendly attractions in Oak Park, IL?

    Many of Oak Park's parks and green spaces are pet-friendly, including Scoville Park and the Oak Park Conservatory. You can also find dog-friendly restaurants and cafes in the village.
  • What are the benefits of choosing a vacation rental in Oak Park, IL?

    Vacation rentals in Oak Park offer more space and privacy than hotels, and they are often located in more residential areas. They can also be a more affordable option, especially for families or groups.
  • What are the top sports attractions and facilities in Oak Park, IL?

    Oak Park is home to the Oak Park and River Forest High School, which has a number of athletic facilities, including a football stadium, a baseball field, and a swimming pool. The village also has a number of parks and green spaces with tennis courts, basketball courts, and playgrounds.

Destinations nearby

Best Oak Park holiday rentals with a balcony

Fantastic Home In Wicker Park - Oak Park
10 162 reviews
Oak Park
10/11 – 10/21
HK$13722/nightTotal: HK$137220 (10 )

Fantastic Home In Wicker Park

5 2
apartment , Chicago
This five-bedroom apartment is conveniently located in Wicker Park, just a short walk from the trendy shops, bars, and restaurants of this popular Chicago neighbourhood. The property has received excellent ratings for its location, cleanliness, and overall experience, making it a great choice for travellers.
The spacious home has three living areas, a dedicated dining space, and 12 beds, making it ideal for large groups or families. The apartment offers modern amenities, including a fully equipped kitchen, washer and dryer, secure parking, a terrace, and a garden, ensuring a comfortable and enjoyable stay.
Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms - Oak Park
9.6 383 reviews
Oak Park
06/28 – 07/05
HK$14235/nightTotal: HK$99645 (7 )

Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms

4 5
apartment , Chicago
This apartment is located in Wrigleyville, just steps away from Wrigley Field, a lively area with a bustling atmosphere. It has excellent user, location and cleanliness ratings.
The flat accommodates up to 9 guests in four bedrooms, ideal for families or groups. It offers a fully equipped kitchen, two bathrooms, a terrace, a garden, and a fireplace, plus a washer and dryer, Smart TVs, and a Keurig coffee maker.
Elegant Retreat In Historic Oak Park - Oak Park
Oak Park
10/11 – 10/21
HK$3199/nightTotal: HK$31990 (10 )

Elegant Retreat In Historic Oak Park

2 2
apartment , Oak Park
This recently refurbished two-bedroom, two-bathroom flat is situated in Oak Park, providing convenient access to local shops, cafes, and parks, with public transport links to Chicago.
Spanning 93 square meters, this accommodation for four includes a fully equipped kitchen, air conditioning, a terrace, spa, and parking, with paid laundry facilities available in the building and nearby opportunities for swimming, cycling, and hiking.
Norwood Park/edison Park! Workstation & In-unit Laundry! 2nd Floor Apt - Oak Park
Oak Park
06/25 – 07/25
HK$3346/nightTotal: HK$100380 (30 )

Norwood Park/edison Park! Workstation & In-unit Laundry! 2nd Floor Apt

2 3
apartment , Chicago
This two-bedroom flat is situated in the Norwood Park/Edison Park neighbourhood of Chicago, a quiet area located 12 kilometres from Loyola University Chicago and 15 kilometres from Wrigley Field.
The 85 square metre property can accommodate up to four guests and features a fully equipped kitchen, a patio, a garden, and outdoor play equipment, ideal for families with children.

Best Oak Park holiday rentals with air conditioning

The Urban Oasis - Oak Park
Oak Park
07/17 – 07/27
HK$1627/nightTotal: HK$16270 (10 )

The Urban Oasis

1 1
apartment , Chicago (IL)
Apartment rental. You will be in Chicago (IL).
Services and facilities include a dish washer, a fridge and an iron. Take advantage of the air conditioning in this apartment!
7b 3ba Private Unit In Lincoln Park Near Wrigley - Oak Park
9.8 135 reviews
Oak Park
07/10 – 07/12
HK$15478/nightTotal: HK$30956 (2 )

7b 3ba Private Unit In Lincoln Park Near Wrigley

7 14
apartment , Chicago
This seven-bedroom, three-bathroom Lincoln Park duplex in Chicago offers convenient access to Lincoln Park itself and Chicago's attractions, though precise distances aren't specified.
Sleeping fourteen guests, this spacious two-storey property features a fully equipped kitchen with outdoor grill, fast Wi-Fi, and free overnight street parking for two cars; additional paid parking is available nearby.
The Evergreen House - Oak Park
9.9 227 reviews
Oak Park
06/28 – 07/05
HK$2115/nightTotal: HK$14805 (7 )

The Evergreen House

1 5
apartment , Chicago
This first-floor flat is located in a quiet residential area of Chicago, just a short distance from the city centre and within easy reach of public transport. The apartment has consistently received excellent ratings from previous guests for its cleanliness, location and overall experience.
The flat is ideal for families or groups of up to 5 people, with two bedrooms and one bathroom. It comes with a well-equipped kitchen, multiple TVs with access to Netflix, free street parking, a private backyard and a washer and dryer in the basement.
Six-bedrooms In Wrigleyville - Oak Park
9.5 4 reviews
Oak Park
07/10 – 07/12
HK$24270/nightTotal: HK$48540 (2 )

Six-bedrooms In Wrigleyville

1 14
apartment , Chicago
This Wrigleyville apartment rental sleeps up to 16 guests and is situated near Wrigley Field in Chicago's North Side, offering easy access to Wrigleyville's restaurants and bars.
The six-bedroom, two-bathroom property features two combined apartments with spacious living areas, a shared back deck, parking permits available upon request, and includes all necessary amenities such as a fully equipped kitchen and air conditioning.
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