Search Vacation Homes in Orland Park

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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 486 Vacation Homes in Orland Park with updated reviews, rates, and availability.

Luxury Home Away From Your Home
Fridge, microwave, oven, stovetop

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (118)
"Perfect for what we were looking for!"
Luxury Home Away From Your Home
Charming 3-bedroom house in marvelous Ukrainian village Chicago
Living area

Charming 3-bedroom house in marvelous Ukrainian village Chicago

6.0 out of 10, (1)
"We enjoyed our stay, especially the location of the neighborhood."
Charming 3-bedroom house in marvelous Ukrainian village Chicago
Cozy 3-bedroom house in family-oriented Melrose Park.
Interior

Cozy 3-bedroom house in family-oriented Melrose Park.

10.0 out of 10, Exceptional, (12)
"This is a great place and very pet friendly. Only negatives were lack of hashtags (only one in the home), no hair dryer when it advertised it had one, and no TV in any of the bedrooms. The home was clean, spacious, fireplace and hot tub are a great bonus."
Cozy 3-bedroom house in family-oriented Melrose Park.
✽ Charming Cottage ✽ close to College/Town/Station
Outdoor dining

✽ Charming Cottage ✽ close to College/Town/Station

10.0 out of 10, Exceptional, (43)
"Just the cutest place!"
The price is AED 624
AED 1,069 total
includes taxes & fees
18 Jun - 19 Jun
✽ Charming Cottage ✽ close to College/Town/Station
Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick
Smart TV, fireplace

Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick

Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick
Charming 3-bedroom in awesome Chicago with AC, WiFi
Private kitchen

Charming 3-bedroom in awesome Chicago with AC, WiFi

2.0 out of 10, (2)
"The property has only one bathroom, but the online listing claimed it has two bathrooms, which is completely false. There were six of us, all adults, and hence we wanted a property that sleeps six with two bathrooms. If we had wanted a one bathroom there were plenty of other options that cost less from the online listing. We chose this property because of the two bathrooms in consideration of the ladies in the family. We were cheated! The world has gotten crazier because of unscrupulous...
Charming 3-bedroom in awesome Chicago with AC, WiFi
Comfy Cozy 2BR Home Away from Home
Property grounds

Comfy Cozy 2BR Home Away from Home

10.0 out of 10, Exceptional, (10)
"The place are amazing… "
Comfy Cozy 2BR Home Away from Home
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Fridge, microwave, oven, stovetop

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

9.8 out of 10, Exceptional, (13)
"We enjoyed our stay"
The price is AED 1,030
AED 1,949 total
includes taxes & fees
23 Jun - 24 Jun
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Relaxing Oak Park Home
Fridge, microwave, oven, stovetop

Relaxing Oak Park Home

9.8 out of 10, Exceptional, (77)
"Kitchen, dining room, living room, bathroom, and bedrooms were all spacious and well-appointed. Beds were comfortable. House was warm and cozy. "
Relaxing Oak Park Home
Wicker Park 6bd/4ba, Steps from CTA, Parking Incl by AllSet Turnover
TV

Wicker Park 6bd/4ba, Steps from CTA, Parking Incl by AllSet Turnover

9.0 out of 10, Wonderful, (6)
"Very convenient to the Metra blue line, lots of bars and restaurants in the neighborhood. "
Wicker Park 6bd/4ba, Steps from CTA, Parking Incl by AllSet Turnover
3BR w/ Large Yard + Near Mall | LCP Collection
Fridge, microwave, oven, stovetop

3BR w/ Large Yard + Near Mall | LCP Collection

9.6 out of 10, Exceptional, (4)
"Everything was clean and in good shape and the beds were very comfortable "
The price is AED 874
AED 2,038 total
includes taxes & fees
3 Jun - 4 Jun
3BR w/ Large Yard + Near Mall | LCP Collection
Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!
Private kitchen

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

7.0 out of 10, Good, (2)
"The space - number of rooms and bathrooms - was great for a big group. We were able to sleep multiple families comfortably with no issues getting ready with the number of bathrooms. There was plenty of free street parking close, so we also didn't have any problems finding parking for all our cars. Some more specific instructions on how to use the key pad (to enter and lock) would be helpful, but otherwise no complaints! I would recommend this Vrbo! "
Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!
3-bedroom building in lovely Westchester with AC, WiFi. Enjoy your stay
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

3-bedroom building in lovely Westchester with AC, WiFi. Enjoy your stay

6.0 out of 10, (1)
"We had a couple of challenges but the host was very attentive. Plenty of room and property was clean. "
3-bedroom building in lovely Westchester with AC, WiFi. Enjoy your stay
Spacious Deck & Balcony, Game Area, Garage
Private kitchen

Spacious Deck & Balcony, Game Area, Garage

9.6 out of 10, Exceptional, (11)
"We had a great stay! Thank you for hosting us!"
The price is AED 629
AED 1,745 total
includes taxes & fees
3 Jun - 4 Jun
Spacious Deck & Balcony, Game Area, Garage
3-bedroom hillside property in woods with fireplace and lake view
Smart TV, fireplace

3-bedroom hillside property in woods with fireplace and lake view

6.0 out of 10, (1)
"Was nice and secluded. Driveway is very steep. Not all windows had curtains. Kitchen is pretty tiny. "
The price is AED 1,058
AED 1,361 total
includes taxes & fees
3 Jun - 4 Jun
3-bedroom hillside property in woods with fireplace and lake view
Relaxing hot and beautiful 4 bed, 2 baths in peaceful area
Private kitchen

Relaxing hot and beautiful 4 bed, 2 baths in peaceful area

Relaxing hot and beautiful 4 bed, 2 baths in peaceful area
Charming ModernRetro Home!
Smart TV

Charming ModernRetro Home!

9.2 out of 10, Wonderful, (18)
"Brittany was absolutely amazing. Her home was gorgeous and cozy. Served our needs exact. We will be coming back! "
Charming ModernRetro Home!
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
Pool

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

9.2 out of 10, Wonderful, (47)
"We had a lovely Christmas at this gorgeous apartment. Everything was as advertised and the location was perfect for our first visit to Chicago. "
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
Chic 3bed 2bath Home with free parking close to United Center
Exterior

Chic 3bed 2bath Home with free parking close to United Center

10.0 out of 10, Exceptional, (12)
"We were in town for a Bears game and this was a great place to relax and hang out with family. Good location"
The price is AED 918
AED 1,698 total
includes taxes & fees
4 Jun - 5 Jun
Chic 3bed 2bath Home with free parking close to United Center
Updated Forest Park 3 BR Bungalow
Fridge, microwave, oven, stovetop

Updated Forest Park 3 BR Bungalow

10.0 out of 10, Exceptional, (104)
"This Forest Park bungalow was perfect for our ladies weekend. It is clean, comfortable, updated, charming, well stocked with supplies, has off-street parking, and is convenient to the city. I highly recommend this lovely home."
Updated Forest Park 3 BR Bungalow
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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