Oak Park vacation rentals
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Top-rated vacation rentals in Oak Park
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Guest suite in Oak Park
4.89 out of 5 average rating, 394 reviewsEntire upstairs in Arts and Crafts Oak Park home
You have the use of the entire upstairs (with a separate, lockable private entrance) and bicycles. With two bedrooms, bathroom and a common area with a futon, table, fridge, microwave, coffee maker and kettle, it is flexible for individuals, couples, families or small groups. Free overnight parking. We're a quick walk to the CTA Blue line, coffee shops and restaurants, parks, musical venues, the Oak Park Arts District, and a quick drive to downtown. Our home is cozy, in a friendly neighborhood.
Dec 4 – 11
Apartment in Oak Park
4.79 out of 5 average rating, 164 reviewsCozy modern unit w/ easy access to downtown Chi
Enjoy a newly remodeled two bedroom basement unit in the historic Oak Park suburb of Chicago. This unit is within walking distance to local cafes, amazing restaurants, ice cream shops, and a grocery store to meet your needs. Explore the nearby Frank Lloyd Wright district and the birthplace of Ernest Hemingway. Walk 2 blocks to the train leading to all neighborhoods of Chicago, or simply enjoy a relaxing stay in the cozy apartment. Easy access to nearby airports. Pets welcome with additional fee.
Jun 19 – 26
Home in Berwyn
4.92 out of 5 average rating, 232 reviewsPrivate apartment with retro vibe
Gunderson Getaway is a cosy one BR apartment with some retro style touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus sofa & extra single bed available. EASY free street parking right by unit. Quick drive to City. Convenient to both airports, United Center and walk to Fitzgerald’s Club. Near Blue Line, restaurants, groceries, great bakery. NO smoking, candles or glitter! Pets MUST be pre-approved and never left alone.
Sep 3 – 10
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Oak Park vacation rentals
Other great vacation rentals in Oak Park
Apartment in Forest Park
4.83 out of 5 average rating, 161 reviewsCozy & Convenient Oak Park incl parking / transit
Jun 14 – 21
Apartment in Oak Park
4.95 out of 5 average rating, 154 reviewsA quiet stay while you are away
Jan 13 – 20
Apartment in Berwyn
4.86 out of 5 average rating, 132 reviewsThe Green Bungalow: Charming 1-BR apt. with patio
Jun 3 – 10
Apartment in Oak Park
4.88 out of 5 average rating, 103 reviewsStunning 2bd 1bath w/free parking, W/D & fireplace
Jul 14 – 21
Apartment in Oak Park
4.91 out of 5 average rating, 167 reviewsLarge sunny 3BR apt. in downtown Oak Park
Sep 25 – Oct 2
Guest suite in Oak Park
4.82 out of 5 average rating, 149 reviewsPrivate 2 BR Oak Park Garden Apt
Jul 14 – 21
Apartment in Oak Park
4.87 out of 5 average rating, 146 reviewsSmall But Mighty 700 Sqft Cottage Apt (1BR/1BA)
Apr 19 – 26
Apartment in Berwyn
4.92 out of 5 average rating, 144 reviewsFriendly Rock ’n’ Roll Retreat
Feb 13 – 20
Apartment in Forest Park
4.96 out of 5 average rating, 226 reviewsMid-Century Charm. Near Chicago. Low Cleaning Fee!
Aug 23 – 30
Apartment in Forest Park
4.95 out of 5 average rating, 129 reviewsLarge, modern 2 bedroom in heart of Forest Park
Nov 4 – 11
Apartment in Berwyn
4.99 out of 5 average rating, 248 reviewsBerwyn Betty Apartment
Feb 17 – 24
Apartment in Cicero
4.98 out of 5 average rating, 190 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
Oct 19 – 26
Other great vacation rentals in Oak Park
Apartment in Forest Park
4.99 out of 5 average rating, 85 reviewsSunny 1 bedroom apartment 1 block from restaurants
Feb 19 – 26
Apartment in Oak Park
5.0 out of 5 average rating, 63 reviewsCheerful Oak Park Apartment
Sep 12 – 19
Guesthouse in Oak Park
4.94 out of 5 average rating, 70 reviewsO'Malley Oasis!
Jun 24 – Jul 1
Apartment in Oak Park
4.96 out of 5 average rating, 27 reviews2BR/2BA Oak Park Gem - Ideal Comfort
Jun 18 – 25
Apartment in Forest Park
4.96 out of 5 average rating, 76 reviews1 bedroom garden apartment in Forest Park
Jan 10 – 17
Apartment in Forest Park
4.93 out of 5 average rating, 75 reviewsHome away from home upstairs.
Oct 28 – Nov 4
Apartment in Forest Park
4.93 out of 5 average rating, 42 reviewsEnjoy the Chicago | Modern 2 Bedroom Apartment
Apr 17 – 24
Guesthouse in Oak Park
4.9 out of 5 average rating, 62 reviewsSunny Coach House in Historic Oak Park
Jul 6 – 13
Apartment in Oak Park
5.0 out of 5 average rating, 4 reviewsCozy Hideaway Mins From Downtown Chicago/Suburbs
Apr 24 – May 1
Apartment in Oak Park
4.91 out of 5 average rating, 11 reviewsGorgeous/Quiet/Apt/Free Parking/FirePit/Close 2 DT
May 5 – 12
Apartment in Oak Park
5.0 out of 5 average rating, 17 reviewsThe Artist's Loft - Oak Park
Dec 10 – 17
Home in Oak Park
4.97 out of 5 average rating, 63 reviewsClean, Comfy Duplex with Kitchen & Free Parking
Apr 29 – May 4
Quick stats about vacation rentals in Oak Park
Total rentals | 320 properties |
---|---|
Wifi availability | 310 properties include access to wifi |
Rentals with dedicated workspaces | 170 properties have a dedicated workspace |
Pet-friendly rentals | 70 properties allow pets |
Family-friendly rentals | 140 properties are a good fit for families |
Total number of reviews | 16K reviews |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Oak Park?
Four-legged friends are welcome in Oak Park. Choose from more than 70 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Oak Park?
Yes! Work meets play with ease at over 170 vacation rentals in Oak Park featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly vacation rentals in Oak Park?
Oak Park has more than 140 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do guesthouse rentals in Oak Park have air conditioning?
Absolutely! We offer over 10 guesthouse rentals with air conditioning in Oak Park. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in condo rentals in Oak Park?
Experience the best of Oak Park with our condo rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Oak Park have wireless internet?
Absolutely! We offer over 130 house rentals with wireless internet in Oak Park. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Oak Park have a gym?
Absolutely! We offer over 10 apartment rentals with a gym in Oak Park. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Oak Park have a bbq area?
Absolutely! We offer over 10 apartment rentals with a bbq area in Oak Park. Enjoy a tailored experience with all the comforts you desire.
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