Rent The Cottages - Vacation Rentals in Oak Park

Relaxing Oak Park Home From US $240
         

9.8 (85 Reviews)
House
  • Air Conditioner
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Lovely Oak Park Apt - Easy Access to Downtown! From US $136
         

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4.3 (3 Reviews)
Apartment
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  • Wheelchair Accessible
  • Child Friendly
Historic Oak Park Home From US $270
         

10.0 (5 Reviews)
Apartment
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Modern Victorian Vibes ❤️ | Character & Charm From US $504
         

10.0 (26 Reviews)
House
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Comfy Bed/Free Parking&Wifi/NearHosp/ORD/MDW/DT From US $130
         

10.0 (15 Reviews)
Apartment
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Vintage Urban Retreat From US $455
         

10.0 (12 Reviews)
House
  • Air Conditioner
  • Security/Safety
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Luxury Places to Stay in Oak Park

Over 188+ Luxury Places to Stay in or Near Oak Park
Spacious Comfy 2BR Near HighwayTrain Station From US $4,500
         

New
Apartment
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  • Pet Friendly
Modern Victorian With Old World Charm From US $2,569
         

10.0 (1 Review)
Apartment
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Oak Park 3000 sq ft, sleep 16 From US $1,349
         

10.0 (6 Reviews)
House
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Stunning Modern & Spacious Sleeps 16 in Forest Park From US $1,131
         

10.0 (4 Reviews)
House
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  • TV
  • Balcony/Terrace
Chic 3bed 2bath Home with free parking close to United Center From US $682
         

9.8 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Oak Park

Over 1+ Top-Rated Vacation Rentals with a Pool in or Near Oak Park

Pet-Friendly Vacation Rentals in Oak Park

Over 68+ Pet-Friendly Vacation Rentals in or Near Oak Park
8 Mi to Chicago Oak Park Home with Fenced Backyard! From US $195
         

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7.7 (3 Reviews)
House
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  • Pet Friendly
  • Accessibility
Spacious, lovely 2bed 1bath with free parking From US $369
         

9.8 (18 Reviews)
Apartment
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  • Parking
  • Pet Friendly
Downtown Oak Park/Fast WIFI/Free Parking/Victorian Home/Sleeps 6 From US $205
         

9.6 (28 Reviews)
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  • Pet Friendly
A Pleasant Stay From US $180
         

9.6 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Oak Park, IL, entire house, short walk to train. From US $168
         

9.4 (21 Reviews)
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  • Pet Friendly
Cozy modern unit w/easy access to downtown Chi From US $140
         

9.2 (50 Reviews)
Apartment
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  • Parking
  • Pet Friendly
Charming Oak Park 4BD/3.5BA and 2 Private Parking by AllSet Turnover From US $317
         

See More Pet-Friendly Vacation Rentals in Oak Park on PetFriendly.io

Large Vacation Homes & Villas in Oak Park

Over 17+ Large Vacation Homes & Villas in or Near Oak Park
Harvey House Bed & Breakfast From US $307
         

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9.8 (39 Reviews)
Bed & Breakfast
  • Air Conditioner
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  • Balcony/Terrace
Top floor of Historic Oak Park Villa/Grge: 2Cars From US $453
         

10.0 (5 Reviews)
Apartment
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Spacious 4BR Home in Oak Park From US $394
         

New
House
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  • Pet Friendly
Spacious Home Base for Families and Groups
New
From US $375
         

New
House
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  • Pet Friendly
INSTA-WORTHY Loft+Condo, FREE Parking, Near Downtown Chicago From US $200
         

9.6 (8 Reviews)
Condo
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  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Oak Park

Over 13+ Wheelchair Accessible Vacation Homes in or Near Oak Park
Carleton of Oak Park From US $184
         

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8.3 (172 Reviews)
Hotel
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  • Wheelchair Accessible
Carleton of Oak Park From US $151
         

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9.2 (1023 Reviews)
Hotel
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Rooftop Access with Views and Gym - LCP Collection From US $388
         

8.6 (14 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV

Oak Park Varoom and Airbnb Places to Stay Under $200

Over 70+ Oak Park Varoom and Airbnb Places to Stay Under $200
Historic Oak Park Residence From US $187
         

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9.8 (6 Reviews)
Apartment
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Holiday Inn Express and Suites Chicago West Oak Park by IHG From US $129
         

New
Hotel
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  • Accessibility
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Chic Retreat, 2 Queen Beds, FREE PARKING, Walk to Train From US $186
         

10.0 (2 Reviews)
Apartment
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Newly Built, Bright Garden Studio in Oak Park. From US $184
         

10.0 (2 Reviews)
Apartment
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  • TV
  • Balcony/Terrace
Sunny Coach House in Historic Oak Park From US $128
         

9.8 (68 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG From US $150
         

Modern Deluxe Studio Suite in lovely Oak Park! From US $142
         

9.6 (5 Reviews)
Apartment
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Instantly Bookable Vacation Homes in Oak Park

Over 71+ Instantly Bookable Vacation Homes in or Near Oak Park
Elevated & Elegant 4 BD 2BA apartment 25 min to downtown From US $610
         

New
Apartment
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Walking Distance to everything. From US $255
         

10.0 (11 Reviews)
Apartment
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  • TV
  • Balcony/Terrace
The Oak Park Loft, Including Garage From US $280
         

10.0 (10 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
A quiet stay while you are away From US $244
         

9.8 (32 Reviews)
House
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  • Parking
  • TV
Spacious Oak Park Home, 11 Mi to Downtown Chicago! From US $323
         

Oak Park Home w/Grill - 5 Mi to Garfield Park! From US $305
         

9.8 (18 Reviews)
House
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About Oak Park Vacation Rentals

With more than 197 Oak Park vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rentthecottages and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Oak Park.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Rentthecottages Oak Park, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Oak Park. Places to stay near Oak Park are 840.81 ft² on average, with prices averaging $307 a night.

Rentthecottages makes it easy and safe to find and compare vacation rentals in Oak Park with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Oak Park

Type Count
Holiday Apartments 128
Vacation Homes 58
Hotels with Suites 4
B&B 2

Use these Quick Filters to Find a Vacation Rental in Oak Park

Pro Tip: Rentthecottages makes it easy to compare the best listings on Rentthecottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Rentthecottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Oak Park.

Weather in Oak Park

View the weather forecast for Oak Park before booking your Oak Park Vacation Rentals to confirm your best time to go.

December - February
High 46°F       Low 20°F
March - May
High 68°F       Low 32°F
June - August
High 83°F       Low 62°F
September - November
High 80°F       Low 33°F