A gazebo surrounded by a landscaped garden with trees displaying autumn foliage.

Search Vacation Homes in Orland Park

Dates

November 2026

December 2026

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Our top choices for Orland Park vacation homes

A bedroom with a stone wall, a TV mounted on it, a bed with a white comforter, and a view of the outdoors through a window.

1. Beautifully furnished one bedroom loft located in Chicago's South side suburb

Hazel Green

Nick L.

AED 1,183 total

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with dark wood cabinets, stainless steel appliances, a granite countertop, and a small island with stools.

2. Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Lockport

Kathy L.

AED 1,641 total

includes taxes & fees

8 Dec - 9 Dec

A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

3. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Westmont

Tomas R.

AED 907 total

includes taxes & fees

9 Nov - 10 Nov

A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

4. Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Westmont

Kelly K.

AED 1,048 total

includes taxes & fees

1 Dec - 2 Dec

A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

5. Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...

Brookfield

Steve H.

AED 1,541 total

includes taxes & fees

9 Nov - 10 Nov

A staircase leading to a living area with a sofa, a coffee table, and a television.

6. Renovated 2BR Near Joliet | King Bed, Parking + Patio | Sleeps 6

Crest Hill

A dining room with a wooden table set for six, flanked by bookshelves, and a view into another room through a glass door.

7. Travelers Retreat/King Beds/Game Room/Play House

Joliet

Ken B.

AED 1,748 total

includes taxes & fees

12 Nov - 13 Nov

A modern kitchen with stainless steel appliances, a marble countertop, and grey cabinetry.

8. Modern Spacious 4BR Home Near Chicago • Sleeps 10 • Family & Pets Friendly

Westmont

ronald M.

AED 2,442 total

includes taxes & fees

9 Nov - 10 Nov

A backyard with a barbecue grill, a dining table with chairs, and a fire pit.

9. PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

Lisle

Emily W.

AED 1,043 total

includes taxes & fees

9 Nov - 10 Nov

A sunroom with white walls, wooden flooring, two blue armchairs, a small table with books, and hanging plants.

10. The Heron House, King Bed Suite, Spacious Remodeled House

Joliet

Rich D.

AED 1,404 total

includes taxes & fees

22 Nov - 23 Nov

A modern kitchen with dark cabinets, stainless steel appliances, and a patterned tile backsplash.

11. 5-minute walk to the largest old school arcade in America! Family friendly.

Brookfield

Ryan S.

AED 1,892 total

includes taxes & fees

10 Nov - 11 Nov

A living room with a gray sofa, a blue chair, a fireplace, and a ceiling fan.

12. PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!

Aurora

Scott D.

AED 1,026 total

includes taxes & fees

9 Nov - 10 Nov

(OUTDOOR SPACE) Where comfort and charm come together. Unwind in the outdoor lounge set under an inviting gazebo with twinkling lights. Stay fresh with a gentle breeze from the fan as you relax.

13. 30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious

Plainfield

Taylor E.

AED 2,126 total

includes taxes & fees

9 Nov - 10 Nov

A wooden interior hallway with a staircase, a wooden wardrobe, and a cabinet with glass doors.

14. River Park Paradise w/ Fire Pit & Chef's Kitchen

Bolingbrook

Sue B.

AED 3,013 total

includes taxes & fees

9 Nov - 10 Nov

A modern living room with a sofa set, a coffee table, and a rug.

15. Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield

Plainfield

Yolanda P.

AED 1,873 total

includes taxes & fees

9 Nov - 10 Nov

A white house with a garden featuring purple flowers and a birdbath.

16. ✽ Charming Cottage ✽ close to College/Town/Station

Wheaton

Laurie R.

AED 1,133 total

includes taxes & fees

16 Nov - 17 Nov

A modern living room with a grey sofa, a white armchair, a coffee table, and a TV. There is a kitchen area in the background with a dining table and chairs.

17. Cozy Home | King Bed | 10P | Metra |Chicago Suburb

Highland Hills

"I booked this property because I was told (before I made the reservation) that the bedroom and one of the bathrooms were on the main floor. I specifically inquired whether my mother-in-law would need to use stairs to access a bedroom and bathroom. In the words of the host, "the main living area, kitchen, two bedrooms and a full bathroom are on the main floor. Only the basement requires the use of steps ". This was not the case. The two bedrooms and a full bathroom are up a flight of 5...

Denise G.

AED 1,465 total

includes taxes & fees

18 Nov - 19 Nov

A spacious living room with a fireplace, a large sofa, a coffee table, and a TV.

18. 4BR Tudor • Wooded Lot • 10 Min to Downtown

Naperville

Alicia F.

AED 2,223 total

includes taxes & fees

6 Dec - 7 Dec

19. Vibrant House, Walk to Train, Game Room

Brookfield

Chasity D.

AED 2,361 total

includes taxes & fees

9 Nov - 10 Nov

A bunk bed with a ladder, a small table, a potted plant, and a window with blinds.

20. Vintage meets Modern 20 min from Chicago.

Calumet City

AED 1,339 total

includes taxes & fees

9 Nov - 10 Nov

View all properties

Learn more about Orland Park

Sprawling parks and nature preserves invite hikers to explore miles of scenic trails just 25 miles from Chicago's bustle. Shoppers flock to Orland Square Mall while families enjoy the Centennial Park aquatic center's slides and pools during summer months.

See all hotels in Orland Park

Top reviews in Orland Park

A hotel reception desk with a 'Welcome to the Prairie State' sign, a 'Hilton Honors' sign, and a 'Hilton Honors' plaque.

Hampton Inn Chicago Orland Park

Orland Park

10/10 Excellent

Diane

A spacious living room with a blue sectional sofa, two armchairs, a coffee table, and a patterned rug.

Homewood Suites by Hilton Orland Park

Orland Park

10/10 Excellent

Anonymous traveler

A spacious lobby with a central spiral staircase, seating areas, and a reception desk.

Quality Inn & Suites Orland Park - Chicago

Orland Hills

10/10 Excellent

Zequita

A spacious lobby with a modern design, featuring a seating area with sofas and armchairs, a staircase, and large windows providing natural light.

Wingate by Wyndham Tinley Park

Tinley Park

10/10 Excellent

Daniel

A multi-story hotel with a prominent entrance and a parking lot.

Country inn & Suites by Radisson, Bolingbrook- Romeoville, I-55

Bolingbrook

10/10 Excellent

I recently had the pleasure of staying at Country Inn & Suites in Bolingbrook, and I must say, it exceeded my expectations! The hotel has a fresh look, with modern decor that creates a welcoming atmosphere. The staff were incredibly friendly and attentive, making my stay even more enjoyable. Additionally, the rooms and common areas were nice and clean, which added to the overall comfort. I would highly recommend this hotel for anyone looking for a pleasant stay in the area!

Sarah

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

L7 CHICAGO by LOTTE HOTELS

Downtown Chicago

10/10 Excellent

Erin

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

10/10 Excellent

Jennifer

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Excellent

blerina

A modern indoor pool area with lounge chairs, a wooden table, and large windows.

Hampton Inn & Suites Chicago Medical District UIC

Near West Side

10/10 Excellent

Rashad

La Quinta Inn & Suites by Wyndham Shorewood

Joliet

10/10 Excellent

David

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

Hotel Riu Plaza Chicago

Downtown Chicago

10/10 Excellent

We chose this hotel last minute and we were nervous because there were a couple recent negative reviews. There were 4 of us in our family and couldn't find anything negative to say about the hotel. The only disappointing fact was that the rooftop bar was not open but that wasn't a big deal. Everything was very clean. I actually wiped the floor in our room with a wet, white wash cloth, it was clean! There was no hair in the bathroom from a previous guest. There was no hair in the bed from a...

Donna

A modern interior with a geometric bookshelf filled with books, a bench, and a lamp.

Arlo Chicago

Downtown Chicago

10/10 Excellent

Arlo Chicago is in the perfect location for walkable access to so many Chicago sights, excellent food (please try the Broken English Taco Pub around the corner!), bars, shopping, etc. It was also very conveniently located to access the L when we needed to get to other parts of the city! The staff was BEYOND accommodating, friendly, and helpful. The room was clean and exceeded all comfort expectations! I also highly recommend the lobby bar for a great happy hour spot!!! Everyone at this hotel...

Lina