Holiday Rentals in Oak Park
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Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Neighbourhood
Distance from
5 km
124 rentals in Oak Park.
Heart of Oak Park, train ride to downtown Chicago. WIFI & Cable Included!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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Oak Park 3 Bed Beauty/Close2Chicago/Sleeps 1-8 Guests
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
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Oak Park Home
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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Logan Square 2 BR/1 BA-modern, near METRA
Condo/Apartment in North Side, Logan Square
2 bedrooms
1 bathroom
Sleeps 4
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Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Cozy, Comfortable and Convenient apartment. Close to everything!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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A quiet stay while you are away
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Vintage Greystone in historic Oak Park walking distance to restaurants and shops
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
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Bright & Clean Apt in Front of Lovely Park!
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
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Spacious 3-bedroom, 2-bath condo, free parking/Oak Park
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 7
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Sunny Jumbo Studio in the Heart of Oak Park
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Elegantly decorated spacious 4 bedroom, 5 bathroom home in historic Oak Park
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 9
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Cozy modern unit w/ easy access to downtown Chi
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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Comfortable home in historic Oak Park- open For Thanksgiving and Christmas!!!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Vintage Greystone in walking distance to restaurants and shops.
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Cozy Apt with Fireplace in Frank Lloyd Historic District
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Top floor of Historic Oak Park Home / 2 Car Grge
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
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1BR Apartment - Walk to Shops - Downtown OAK PARK
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
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Oak Park Beauty Sleeps 1 to 8 Guests
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
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Charming Oak Park Home w/ Private Fire Pit!
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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Greystone, 3500 sq ft, Rooftop Access, Sleeps 16
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 16
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LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!
Holiday Rental House in North Side, Logan Square
2 bedrooms
1 bathroom
Sleeps 6
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Family-friendly, stylish Chicago Apartment in Logan Square
Condo/Apartment in North Side, Logan Square
3 bedrooms
1 bathroom
Sleeps 7
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Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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Quiet, family getaway. Puppers welcome!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Calm and Serene - Downtown Oak Park, Pets OK
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Oak Park House - 11 Mi From Downtown Chicago!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Art Deco Suite; Time Travelers Retreat
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 7
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Modern 3-Bed Stay w/ Firepit, 15 Minutes to Downtown
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
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Clean & Cozy entire 3 bedroom unit 7 miles from downtown
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 7
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Home away from home. Perfect for remote workers.
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Chicago Modern Condo- Perfect for family time or a good time in Chicago.
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
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Chic, spacious 3bed, 2 bath home
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
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CPS3 Logan Square Corner 3BR Apt Walkable to Highlights
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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LA1 3-BR Gem with Parking and In-Unit Laundry
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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LA3 3BR Comfy Apt in Logan Square
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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Chicago Vacation Rental ~ 7 Miles to Downtown
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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Brand new private 2 bedroom unit
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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FREE PARKING! Desirable Logan Square Location with Modern Touches and Beautiful
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
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Cozy 2 Bedroom on a Quite Street
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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Condo
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Vintage/Modern Hideaway in Logan Square
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
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Lux Chicago Home- 6 bd 4 ba- 2 car garage. 25 mins to downtown.
Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 2
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Quiet Chicago Townhome - 7 Mi to Downtown!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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KING LOVELY SPACE
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
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3710 W Diversey · Lovely Logan Square 2 Bedroom
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Charming 3 beds 2 baths close to Chicago city walk to trains SLEEP 6
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
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Oak Park Bungalow
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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ENTIRE CLEAN MODERN 2 BEDROOM APARTMENT HAVEN /GARAGE PARKING
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Showing results 1-50 of 124
Frequently Asked Questions about Oak Park
- Yes, here are some popular holiday rentals in Oak Park that have a pool:See all holiday rentals with a pool in Oak Park on Tripadvisor
- Yes, here are some popular holiday rentals in Oak Park that have internet access:See all holiday rentals in Oak Park on Tripadvisor
- Some of the most popular kid friendly rentals in Oak Park are:See all kid friendly holiday rentals in Oak Park on Tripadvisor