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Homewood Vacation Rentals

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    Don't let other travelers get your favorite Homewood area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 26 Rentals in Homewood
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    Homewood
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    The following rentals are within 25 miles of Homewood.
    Dyer, IN
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Beautiful Home near Chicago, IL1 / 15
    (1)Very good
    Tinley Park
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Forest Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Spacious 1 bedroom suite with a big screen TV, a super comfy bed & the convenience of cooking your own meals (oven, frig & microwave in your kitchen). Located on a wonderfully quiet residential block, very close to public trans and expressway. Downtown Chicago & O'Hare airport are one train ride...
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    Forest Park, Illinois 60130
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Historic Chicago Style Bungalow Business Ready1 / 25
    (3)Very good
    Oak Park
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Yard
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    Pet friendly
    Kid friendly
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    Reviewed August 21, 2017
    Lovely updated home in a lovely area...close to drive into Chicago or take the train..nice big screen tv...
    Reviewed June 6, 2017
    The house was great very modern and clean good location. The location was great not far from downtown.
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    About this property
    Oak Park Duplex. This charming Oak Park Duplex offers a quiet relaxing environment to unwind after a busy day of site seeing in Chicago or enjoying the historic beauty of Oak Park. The home has been divided into two units. The top two floors (Duplex) are the rental space above a garden...
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    Oak Park, Illinois 60304
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Gary, IN
    4 Bedrooms, 4 Bathrooms, Sleeps 19 Quick View
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    • Waterfront
    • Sauna
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *If booking 3 to 6 nights, system-generated quote is NOT accurate. Nightly rate after 2nd night is discounted; please inquire. This 5-Star luxury oasis, only 40 minutes from Chicago, is a private, secluded, spa-quality, ultimate beachfront getaway right on the Indiana Dunes National Lakeshore. The...
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    Gary, Indiana 46403
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 19
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    NEW! 3BR Burr Ridge House on 5 Manicured Acres!1 / 24
    (1)Very good
    Burr Ridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Internet Access
    • Cable/satellite TV
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you’re seeking the perfect spot for your business retreat or family gathering, look no further than this 3-bedroom, 2-bathroom vacation rental house in Burr Ridge! With accommodations for 6 throughout approximately 4,000 square feet of beautifully-appointed living space and a large yard on 5...
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    Burr Ridge, Illinois 60517
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Downers Grove
    6 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 5000 square foot classic Colonial home is located in a private cul-de-sac on an acre of picturesque greens, trees, perennial garden and in ground pool. Its western suburban Chicago location is minutes from major expressways and Metra making quick and easy access to all Chicagoland has to...
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    Downers Grove, DuPage County 60516
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 15
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    Gary, IN
    6 Bedrooms, 5 Bathrooms, Sleeps 30 Quick View
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    • Patio
    • Hot Tub
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *If booking 2 or more nights, system-generated quote is NOT accurate. *Nightly rate after 2nd night is deeply discounted, please inquire. Indiana's first and ONLY Luxury Elite Property as recognized by Andrew Harper, LLC. Completed in June, 2016, Villa Santorini, only 40 minutes from Chicago,...
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    Gary, Indiana 46403
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 30
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    Highland, IN
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautifully furnished home offers everything you need for a week or two of self-indulgence. Located in the prestigious Highlands Reserve Golf Community, this wonderful 4 bedroom 2 bathroom home comprises of two queen bedrooms and two twin bedrooms capable of sleeping up to 9 people...
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    Highland, Indiana 46322
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Oak Park Beauty Sleeps 1 to 8 Guests1 / 14
    (1)Excellent
    Oak Park
    3 Bedrooms, 1 Bathroom, Sleeps 9 Quick View
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    • Wi-Fi
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    • Housekeeping Included
    • Grill
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    • Washer
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We enjoyed our one-night stay at the house. The hosts were wonderful, the house was immaculately clean, everything was provided for. Plenty of linens and blankets, the kitchen...
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    About this property
    Come relax in OAK PARK (OP) after a long day of shopping on Michigan Avenue, sightseeing in Chicago, or family gatherings. Just 10 minutes from downtown Chicago, Oak Park, and our flat offers the best of both worlds at a price you can afford. Just blocks from 2 train lines to Chicago. Pristine,...
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    Oak Park, Illinois 60302
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 9
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    Condo
    Oak Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    When traveling and looking for an upscale location. Oak Park offer a great traveler great food, entertainment, relaxing environment. Safe and a wide array of guided tours, Frank Lloyd Widget homes is just the start. My condo has two room with king bed half bath master bedroom, 2 bedroom has queen...
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    Oak Park, Illinois 60302
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Oak Park
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Private Yard
    • Secure Parking
    • Wi-Fi
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This house is simply beautiful on a tree lined street located in the Historic District of Oak Park. This home is spacious, comfortable, with nice art pieces, bright and clean. Central air conditioning. Huge privacy fenced yard with a trampoline and grill, patio. 10 minutes from downtown Chicago,...
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    Oak Park, Illinois 60302
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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    Gary, IN
    6 Bedrooms, 5 Bathrooms, Sleeps 29 Quick View
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    Amenities & Details
    • Sauna
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Waterfront
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *If booking 3 to 6 nights, system-generated quote is NOT accurate. *Nightly rate after 2nd night is much lower; please inquire This 5-Star luxury oasis, only 40 minutes from Chicago, is a private, secluded, spa-quality, ultimate beachfront getaway right on the Indiana Dunes National Lakeshore. The...
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    Location Information
    Gary, Indiana 46403
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 29
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    Oak Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Eclectic Artists Flat Close2Chicago & Fitzgerald's Live Music Club Located near the Oak Park Arts District, this living space is located on the second floor of a brick home. The flat is colorful and filled with art with an eclectic ambiance. Very large rooms and spacious bathroom. 1.5 Baths. A...
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    Location Information
    Oak Park, Illinois 60304
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Forest Park
    4 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Central Heating
    • Grill
    • Terrace
    • DVD Player
    • Balcony
    • Housekeeping Included
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming private apartment in the heart of Forest Park! Perfect mix of cozy, chic, & antique! Long term or a quick weekend away! Ideal for couples, solo adventurers, business travelers, families, big groups, even pets! Four bedrooms, spacious living area, beautiful backyard garden with seating for...
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    Location Information
    Forest Park, Illinois 60130
    Condo/Apartment - 4 Bedrooms, 1 Bathroom, Sleeps 5
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    Gary, IN
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Balcony
    • Terrace
    • Private Yard
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great for walking and hiking in the dunes and on the beach. Watch the woods from the screened in front porch. Great wood stove . 5 minute walk from semi-private Lake Michigan beach and 45 minutes from downtown Chicago. The house, is built into dunes so most of the living space is on second floor...
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    Gary, Indiana 46403
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Crete
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    • Internet Access
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** 1-night stays acceptable. Please reach out to Evolve for more information. ** Pack your bags for the wonders of the great Midwest and book your stay at this quaint 3-bedroom, 1-bathroom Crete vacation rental apartment! With sleeping space for 8, charming amenities, an extensive backyard and...
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    Crete, Illinois 60417
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Humphrey Homestay - Yellow Room, Bed 11 / 7
    (1)Excellent
    Oak Park
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    • Balcony
    • Wi-Fi
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 4, 2017
    If you are looking for an accommodation in Chicago, I recommend you the Humphrey Homestay located in the west of the city. You will settle in Oak Park, a wealthy village marking...
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    About this property
    Located just west of Chicago - Oak Park is a historic neighborhood 30 minutes from downtown. Humphrey Homestay provides a residence for international students or medical students completing rotations in the Chicagoland area. We provide home cooked meals, all utilities including high speed wifi, in...
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    Location Information
    Oak Park, Illinois 60302
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    Gary, IN
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Waterfront
    • Hot Tub
    • Patio
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *If booking 3 to 6 nights, system-generated quote is NOT accurate. *Nightly rate after 2nd night is much lower; please inquire Guesthouse is right on the Indiana Dunes National Lakeshore, only 40 minutes from Chicago, and has a private deck with unspoiled views of Lake Michigan and beautiful...
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    Gary, Indiana 46403
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Oak Park
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    • Grill
    • Terrace
    • Balcony
    • Private Yard
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just west of Chicago - Oak Park is a historic neighborhood 30 minutes from downtown. Humphrey Homestay provides a residence for international students or medical students completing rotations in the Chicagoland area. We provide home cooked meals, all utilities including high speed wifi, in...
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    Location Information
    Oak Park, Illinois 60302
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    Oak Park
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    • Balcony
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Private Yard
    • Terrace
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just west of Chicago - Oak Park is a historic neighborhood 30 minutes from downtown. Humphrey Homestay provides a residence for international students or medical students completing rotations in the Chicagoland area. We provide home cooked meals, all utilities including high speed wifi, in...
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    Location Information
    Oak Park, Illinois 60302
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    Oak Park
    4 Bedrooms, 2 Bathrooms, Sleeps 1 Quick View
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    • Wi-Fi
    • Grill
    • Washer
    • Housekeeping Included
    • Cable/satellite TV
    • Private Yard
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just west of Chicago - Oak Park is a historic neighborhood 30 minutes from downtown. Humphrey Homestay provides a residence for international students or medical students completing rotations in the Chicagoland area. We provide home cooked meals, all utilities including high speed wifi, in...
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    Oak Park, Illinois 60302
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 1
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    Oak Park
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    - Safe and quiet residential area by the Oak Park Arts District - Many art shops, two cafes, Italian restaurant and family-friendly activities all within walking distance. - Space is master bedroom on the 2nd floor - Free parking on premise - 15-20 mins Chicago Loop/Downtown by car - 2 mins walk to...
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    Oak Park, Illinois 60304
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Oak Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Beautiful Oak Park, IL home of Earnest Hemingway and Frank Lloyd Wright. We boast beautiful homes, superb restaurants, shops and we are next door to Chicago a world class city!! Welcome to my home where you will find comfortable beds, refreshments, conversation and a warm feeling of being...
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    Oak Park, Illinois 60302
    Private Room - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Oak Park
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    • Grill
    • Wi-Fi
    • Balcony
    • Terrace
    • Patio
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just west of Chicago - Oak Park is a historic neighborhood 30 minutes from downtown. Humphrey Homestay provides a residence for international students or medical students completing rotations in the Chicagoland area. We provide home cooked meals, all utilities including high speed wifi, in...
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    Location Information
    Oak Park, Illinois 60302
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 1
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