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Holiday homes in Oak Park You’ll Love (Page 2)

Top-Rated Oak Park Holiday homes for Every Budget and Style!

Looking for a holiday home in Oak Park (Illinois)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $51.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Oak Park.

We found 52 Holiday-homes in Oak Park and the surrounding area (within 20 miles)

Spacious Ukrainian Village Retreat in Chicago, USA

Spacious Ukrainian Village Retreat

Holiday home in Chicago near Oak Park, Illinois , 2148 West Chicago
Spacious Ukrainian Village Retreat offers accommodations in Chicago, 2.9 miles from Water Tower Chicago and 3.1 miles from Chicago Museum of Contempor...
  • Parking
  • Pets allowed
  • Fitness centre

Passable 2 Reviews 5.5

from $57.00 Show details »

Oak Park Home with Fire Pit - 5 Mi to Garfield Park! in Oak Park, USA

Oak Park Home with Fire Pit - 5 Mi to Ga...

Holiday home in Oak Park, Illinois
Oak Park Home with Fire Pit - 5 Mi to Garfield Park! offers accommodations in Oak Park, 11 miles from Union Station and 11 miles from Willis Tower.
  • Parking

Fabulous 1 Reviews 9.0

from $283.71 Show details »

Spacious Oak Park Home, 11 Mi to Downtown Chicago! in Oak Park, USA

Spacious Oak Park Home, 11 Mi to Downtow...

Holiday home in Oak Park, Illinois
Spacious Oak Park Home, 11 Mi to Downtown Chicago! offers accommodations in Oak Park, 8.9 miles from United Center and 10 miles from Lincoln Park Zoo.
  • Parking

Fabulous 7 Reviews 9.0

from $345.33 Show details »

Hidden East Village Gem in Chicago, USA

Hidden East Village Gem

Holiday home in Chicago near Oak Park, Illinois , 869 N Marshfield Ave
1.6 miles from United Center in Chicago, Hidden East Village Gem provides accommodations with access to a hot tub.
  • Family rooms

Good 2 Reviews 7.0

from $96.00 Show details »

Cozy & comfy w/free parking & W/D in Oak Park, USA

Cozy & comfy w/free parking & W/D

Holiday home in Oak Park, Illinois , 822 Belleforte Avenue
Cozy & comfy w/free parking & W/D is located in Oak Park, just 9.2 miles from United Center and 9.4 miles from Water Tower Chicago.
  • Parking
  • Pets allowed

no reviews

from $90.00 Show details »

Chicago New 2BR Home w 3 Beds and HighSpeed Internet in Chicago, USA

Chicago New 2BR Home w 3 Beds and HighSp...

Holiday home in Chicago near Oak Park, Illinois , West Potomac Avenue 1731
Chicago New 2BR Home w 3 Beds and HighSpeed Internet offers accommodations in Chicago, 2.7 miles from Water Tower Chicago and 2.8 miles from Chicago M...
  • Parking

Good 4 Reviews 7.8

from $59.00 Show details »

Stunning 5BR Home in Heart of Chicago with 2 Rooftops in Chicago, USA

Stunning 5BR Home in Heart of Chicago wi...

Holiday home in Chicago near Oak Park, Illinois , 1307 North Bell Avenue
Stunning 5BR Home in Heart of Chicago with 2 Rooftops is located in Chicago, just 3.4 miles from Lincoln Park Zoo and 3.6 miles from Water Tower Chica...

Exceptional 2 Reviews 10.0

from $396.06 Show details »

Steel and Sky in Chicago, USA

Steel and Sky

Holiday home in Chicago near Oak Park, Illinois , 1358 North Campbell Avenue
Steel and Sky offers accommodations in Chicago, 2.5 miles from United Center and 3.6 miles from Lincoln Park Zoo.
  • Parking
  • Pets allowed

no reviews

from $1.440.48 Show details »

Luxury Retreat with Home Theater in Chicago, USA

Luxury Retreat with Home Theater

Holiday home in Chicago near Oak Park, Illinois , West Beach Avenue 1621
Luxury Retreat with Home Theater offers accommodations in Chicago, 2.2 miles from United Center and 2.5 miles from Lincoln Park Zoo.
  • Parking

Exceptional 2 Reviews 10.0

from $456.73 Show details »

Luxe SFH Bucktown Retreat with Garage Parking in Chicago, USA

Luxe SFH Bucktown Retreat with Garage Pa...

Holiday home in Chicago near Oak Park, Illinois , 1629 N Rockwell S
Providing a garden, Luxe SFH Bucktown Retreat with Garage Parking offers accommodations in Chicago.
  • Parking
  • Pets allowed

Exceptional 1 Reviews 10.0

from $1.168.39 Show details »

Historic Chicago Bungalow about 12 Mi to Downtown in Chicago, USA

Historic Chicago Bungalow about 12 Mi to...

Holiday home in Chicago near Oak Park, Illinois
Historic Chicago Bungalow about 12 Mi to Downtown is located in Chicago, just 10 miles from Wrigley Field and 10 miles from Water Tower Chicago.
  • Parking
  • Pets allowed

no reviews

from $55.00 Show details »

5BR 5BA Architectural Estate-Theatre Gym Rooftop in Chicago, USA

5BR 5BA Architectural Estate-Theatre Gym...

Holiday home in Chicago near Oak Park, Illinois , 1856 North Fairfield Avenue
5BR 5BA Architectural Estate-Theatre Gym Rooftop is located in Chicago, just 3.3 miles from Lincoln Park Zoo and 3.4 miles from United Center.
  • Parking
  • Fitness centre

Fabulous 3 Reviews 8.7

from $53.00 Show details »

MAGNIFICENT NEW Home w/8 Beds & Free Parking in Chicago, USA

MAGNIFICENT NEW Home w/8 Beds & Free Par...

Holiday home in Chicago near Oak Park, Illinois , 2019 North Bingham Street
MAGNIFICENT NEW Home w/8 Beds & Free Parking offers accommodations in Chicago, 3.9 miles from Wrigley Field and 4 miles from Water Tower Chicago.
  • Parking

Exceptional 16 Reviews 9.5

from $74.00 Show details »

Top Rated Luxury 2BR Condo Historic Location in Elmwood Park, USA

Top Rated Luxury 2BR Condo Historic Loca...

Holiday home in Elmwood Park near Oak Park, Illinois , 2434 North 78th Avenue, Unit 2W, Elmwood Park, IL 60707
Top Rated Luxury 2BR Condo Historic Location offers accommodations in Elmwood Park, 9.1 miles from United Center and 10 miles from Lincoln Park Zoo.
  • Pets allowed

no reviews

from $61.00 Show details »

Luxury King Sleep Number Historic Location in Elmwood Park, USA

Luxury King Sleep Number Historic Locati...

Holiday home in Elmwood Park near Oak Park, Illinois , 2434 North 78th Avenue, Unit GE, Elmwood Park , IL, 60707
Luxury King Sleep Number Historic Location is located in Elmwood Park, just 9.1 miles from United Center and 10 miles from Lincoln Park Zoo.
  • Pets allowed

no reviews

from $54.00 Show details »

Luxury Artistic Condo Historic Location in Elmwood Park, USA

Luxury Artistic Condo Historic Location

Holiday home in Elmwood Park near Oak Park, Illinois , 2434 North 78th Avenue, Unit 2E, Elmwood Park, IL 60707
Luxury Artistic Condo Historic Location is located in Elmwood Park, just 9.1 miles from United Center and 10 miles from Lincoln Park Zoo.
  • Pets allowed

no reviews

from $84.00 Show details »

90s Condo Family Friendly in Elmwood Park, USA

90s Condo Family Friendly

Holiday home in Elmwood Park near Oak Park, Illinois , 2434 North 78th Avenue, Unit 1W, Elmwood Park, IL 60707
90s Condo Family Friendly offers accommodations in Elmwood Park, 10 miles from Wrigley Field and 11 miles from 360 Chicago.
  • Pets allowed

no reviews

from $87.00 Show details »

Logan Square Oasis in Chicago, USA

Logan Square Oasis

Holiday home in Chicago near Oak Park, Illinois , 2508 N Spaulding Ave
Logan Square Oasis offers accommodations in Chicago, 4.2 miles from Wrigley Field and 4.6 miles from United Center.
  • Pets allowed

Exceptional 2 Reviews 10.0

from $79.00 Show details »

The Logandale: HUGE Mid-Century Home, sleeps 15 in Chicago, USA

The Logandale: HUGE Mid-Century Home, sl...

Holiday home in Chicago near Oak Park, Illinois , 2920 North Gresham Avenue
The Logandale: HUGE Mid-Century Home, sleeps 15 offers accommodations in Chicago, 4.6 miles from Lincoln Park Zoo and 5.1 miles from United Center.
  • Parking
  • Family rooms
  • Kids' outdoor play equipment

Fabulous 6 Reviews 9.0

from $243.33 Show details »

The Avondale Guesthouse in Chicago, USA

The Avondale Guesthouse

Holiday home in Chicago near Oak Park, Illinois , 2973 North Elston Avenue
The Avondale Guesthouse is a recently renovated vacation home in Chicago where guests can make the most of the garden and barbecue facilities.
  • Parking
  • Family rooms

Exceptional 126 Reviews 9.6

from $115.86 Show details »

Charming Elmwood Park Retreat in Elmwood Park, USA

Charming Elmwood Park Retreat

Holiday home in Elmwood Park near Oak Park, Illinois , 7920 West Fletcher Street
Charming Elmwood Park Retreat is located in Elmwood Park, just 10 miles from Lincoln Park Zoo and 10 miles from United Center.
  • Parking
  • Pets allowed

Exceptional 1 Reviews 10.0

from $425.94 Show details »

3BR Gym Workspace Chicago Condo in Chicago, USA

3BR Gym Workspace Chicago Condo

Holiday home in Chicago near Oak Park, Illinois , 3656 North Osage Avenue Unit 2
3BR Gym Workspace Chicago Condo is located in Chicago, just 10 miles from Wrigley Field and 11 miles from Lincoln Park Zoo.
  • Pets allowed
  • Fitness centre

no reviews

from $315.00 Show details »

New Modern 3BR, Gym, Workspace, Quiet Location in Chicago, USA

New Modern 3BR, Gym, Workspace, Quiet Lo...

Holiday home in Chicago near Oak Park, Illinois , 3656 N Osage Ave unit 3, Chicago, IL 60634, USA
New Modern 3BR, Gym, Workspace, Quiet Location is located in Chicago, just 10 miles from Wrigley Field and 11 miles from Lincoln Park Zoo.
  • Pets allowed
  • Fitness centre

Superb 3 Reviews 9.3

from $323.67 Show details »

Windy City Getaway - 3BR 2BA Chicago Townhouse home in Chicago, USA

Windy City Getaway - 3BR 2BA Chicago Tow...

Holiday home in Chicago near Oak Park, Illinois
Windy City Getaway - 3BR 2BA Chicago Townhouse home is located in Chicago, just 5 miles from Wrigley Field and 6.1 miles from Lincoln Park Zoo.
  • Parking

Exceptional 2 Reviews 9.5

from $307.60 Show details »

Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub in Chicago, USA

Historic Home with Outdoor Hot Tub Near...

Holiday home in Chicago near Oak Park, Illinois , 3742 N. Keeler Avenue, Chicago,
A recently renovated vacation home, Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub offers accommodations in Chicago.
  • Parking
  • Family rooms
  • Kids' outdoor play equipment

Superb 8 Reviews 9.4

from $63.00 Show details »

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