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Oak Park Holiday Homes

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    $223 Average
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    Don't let other travellers get your favourite Oak Park area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 19 Rentals in Oak Park
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    Historic Chicago Style Bungalow Business Ready1 / 25
    (2)Excellent
    Oak Park
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Oak Park
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Oak Park
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    Oak Park
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    • Grill
    • Terrace
    • Balcony
    • Private Garden
    • Wi-Fi
    • Patio
    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
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    Condo
    Oak Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Oak Park
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    Amenities & Details
    • Balcony
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • 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
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    Oak Park
    4 Bedrooms, 2 Bathrooms, Sleeps 1 Quick View
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Washer
    • Housekeeping Included
    • Satellite TV
    • Private Garden
    • 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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 1
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    Oak Park
    3 Bedrooms, 1 Bathroom, Sleeps 9 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Housekeeping Included
    • Grill
    • Patio
    • Washer
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Oak Park
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Balcony
    • Terrace
    • Patio
    • Private Garden
    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
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    The following rentals are within 25 kilometres of Oak Park.
    Lombard
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Eclectic furniture, comfortable beds, large yard, 25 minutes to down town Chicago, walking distance to shopping, restaurants and grocery. Large all weather room seats 18. There is only one other house on the block and it is a dead end street so very quiet, adorned by large trees, there is also...
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    Location Information
    Lombard, DuPage County 60148
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Forest Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Forest Park, Illinois 60130
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Evanston
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    Amenities & Details
    • Private Garden
    • Internet Access
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Pinewoods Retreat is home to a small artist community including musicians, painters and acrobats. Here you will find an eclectic yet quiet escape from the fast paced city. We take great pride in the peaceful environment that we have created here and welcome you to share in our retreat. Please...
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    Location Information
    Evanston, Illinois 60203
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 3
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    Burr Ridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Grill
    • DVD Player
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Patio
    Suitability
    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 4,000 square feet of beautifully-appointed living space and a large yard on 5 well-groomed...
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    Location Information
    Burr Ridge, DuPage County 60517
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Wilmette
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Patio
    • Grill
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Contemporary 3 BR Townhouse with granite-countertop kitchen and a peaceful, private backyard in the safe and beautiful Wilmette neighborhood. Walk to Walgreens, Fresh Mart, and many shops & restaurants. Just 1 min. to 94 Highway Lake Ave. Exit, 10 min. to Lake Michigan & Botanic Garden, and 20 min....
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    Location Information
    Wilmette, Illinois 60091
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Des Plaines
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Central Heating
    • Balcony
    • Housekeeping Included
    • DVD Player
    • Terrace
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very Clean and Large 2 bed, 1 bath apartment 20 minutes north of downtown Chicago. and 10 minutes from O'Hare Airport. 1st floor, one king bed, two twin beds. Large fully equipped kitchen and Free parking, WiFi, Roku TV, DVD, Wii and Laundry on site (fee). Always fresh towels and linens for...
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    Location Information
    Des Plaines, Illinois 60016
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    River Grove
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Satellite TV
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is partially SHARED and a few blocks from the Metra Station as well as buses. You’ll love this place because of the location, the ambiance, and the outdoors space. It is good for couples, solo adventurers, and business travelers. River Grove community is nice and quiet, just that perfect...
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    River Grove, Illinois 60171
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The Davis House, Landmarked 1892 Farm House1 / 35
    (7)Very good
    Glen Ellyn
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Satellite TV
    • Washer
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 June 2015
    We gathered at The Davis House for a family reunion and to celebrate my husband’s 80 birthday. My daughter, husband and two small children were very comfortable in the bedroom...
    Reviewed 3 December 2012
    My mom died peacefully and we needed a place to gather our family, grieve, eat, and just be together. It was truly last minute, and the owner, Will, made it happen (he wasn't...
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    About this property
    The Davis Victorian Farm house is an 1892 landmark home. It is located in beautiful Glen Ellyn, known for its quaint down town and Vintage Homes. We are also minutes away from Wheaton, home of Wheaton College. The Davis House is located on a very quiet cul-de-sac. Set back from Davis Terrace, its...
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    Location Information
    Glen Ellyn, DuPage County 60137
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Downers Grove
    6 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Washer
    • Patio
    • Parking
    • Satellite TV
    • Grill
    Suitability
    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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    Location Information
    Downers Grove, DuPage County 60516
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 15
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    Lombard
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • DVD Player
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My place is 30 minutes from downtown Chicago. Located 8 minutes from Oakbrook Center Mall and 15 min from Wheaton College. Plenty of restaurants and dining and family-friendly activities nearby. Large backyard and deck that's great for pets and entertaining! This cozy house gets tons of sunlight...
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    Location Information
    Lombard, DuPage County 60148
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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