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Holiday rentals in Olympia Fields

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Top-rated holiday rentals in Olympia Fields

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A private outdoor gazebo houses a spacious jacuzzi, accompanied by soft lighting and a view of the surrounding greenery. Nearby, a wooden deck features a dining area with a table and chairs, inviting relaxation in a peaceful setting.
Guest house in Merrillville
4.92 out of 5 average rating, 175 reviews

Couples Getaway, Jacuzzi, Sauna, Pool

Couples Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse suite is attached to the main house but completely private—you’ll have your own private entrance for total seclusion. Enjoy spa-like relaxation with a jacuzzi, sauna, pool access, and a fully equipped gym. Perfect for honeymoons, anniversaries, or weekend escapes, our space blends comfort, privacy, and elegance for an unforgettable stay.

Guest favourite
An open living space is highlighted by a stone fireplace and a large television mounted above it. A comfortable sectional sofa surrounds a round coffee table, while natural light fills the room through large windows. A dining area can be seen in the background.
Home in Homewood
5 out of 5 average rating, 15 reviews

Fore! Peace & Love @ Golf House

Welcome to "The Golf House"! Our 4-bed, 3-bath home sleeps 8 people comfortably and, features an open living space with a stunning golf course view, a full kitchen, and a huge deck. Enjoy natural sunlight or the stars through the skylight both in the master bedroom and bathroom. The home has hardwood floors, and TVs in each bedroom. Plus, a heated meditation room for relaxation. Ideal for families, women retreats, networking events etc. Experience luxury and tranquility right by the greens!

Guest favourite
A vibrant garden area is filled with a variety of lush green plants and colorful flowers. Stone elements lead to a small water feature, surrounded by dense foliage. The peaceful setting offers a natural retreat, inviting exploration or relaxation.
Flat in Homewood
4.93 out of 5 average rating, 111 reviews

Charming Garden Apartment

Make yourself at home in a charming apartment with all the amenities! Lose yourself birding or reading a book surrounded by lush gardens. Take a short walk to downtown Homewood to enjoy shopping & dining or catch the train to Chicago. 🏳️‍🌈 BLM Safe space! After a day of exploring, a king-sized sleep number bed & lush bathroom features will pamper you! A fold-down sofa creates an additional bed. Dogs welcome! This suite has a kitchenette with a convection toaster oven & induction cooktop.

Top guest favourite
A modern farmhouse is showcased, featuring a covered front porch with comfortable seating. Lush greenery surrounds the entrance and a small outdoor seating area with a table and chairs is visible. The structure is complemented by large windows that invite natural light.
Home in Crown Point
4.97 out of 5 average rating, 116 reviews

Quiet Farmhouse Retreat

Looking for a tranquil farmhouse destination? Get away at Wadsworth Acres- a Scottish Highland hobby farm! This modern farmhouse is the perfect space to relax. Complete with a very spacious primary suite, large eat-in kitchen, exercise room, and space to play outside- you’ll never have to leave! Enjoy your morning coffee with breathtaking farm sunrises on the patio and evenings in the hammocks.Peaceful escape just 5 minutes from the highway, 10 from historical downtown, 35 from the Dunes!

Guest favourite
A modern kitchen features sleek white cabinetry and stainless steel appliances. A central island serves as a dining space, complemented by two navy blue stools with gold accents. Pendant lights provide illumination, enhancing the contemporary feel of the room.
Home in Chicago
4.88 out of 5 average rating, 171 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

Top guest favourite
A spacious living area features a corner sectional sofa with soft cushioning and a cozy throw. Large windows provide natural light and city views. A simple coffee table sits in front, with light-colored carpet underfoot, enhancing the comfortable atmosphere.
Flat in Aurora
4.98 out of 5 average rating, 242 reviews

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

Guest favourite
A spacious living area features a comfortable sofa and a grand piano, complemented by a decorative area rug on polished wooden floors. A window allows natural light to illuminate the room, and a small bookshelf adds a touch of warmth. A small dog with a scarf rests nearby.
Home in Homewood
4.93 out of 5 average rating, 107 reviews

Boulderstrewn: Historic Homewood home

Charming and historic Sears Catalog House on 2/3 acre wooded lot. Less than 10 minute walk to shops and restaurants in downtown Homewood to Metra rail (and Amtrak) station with express service to Hyde Park and University of Chicago (less than a half hour) and Chicago's 3 magnificent downtown waterfront stations (~40 minutes). Fire pit in yard can be used to enjoy summer nights. No cable, but several digital antenna channels available as well as Netflix, XBox and DVDs.

Guest favourite
A spacious living area is presented, featuring a large gray sofa and a low coffee table. A wall-mounted TV sits on a wooden stand, complemented by a patterned area rug. Dining furniture is visible in the background, with natural light filtering through large windows.
Home in Homewood
4.97 out of 5 average rating, 30 reviews

Our Homewood Home

Hi. We want to thank you for considering staying at our home in Homewood. We set this home up for us to use when we are in Chicago as a family for business or pleasure. We live out of state and needed a comfortable and quiet home where we and our 4 kids could stay for extended periods of time. This home is in a very quiet neighborhood, with amazing neighbors and a very large backyard. We hope you will enjoy it as much as we do. Scan the QR code for virtual tour.

Guest favourite
Home in Matteson
4.85 out of 5 average rating, 66 reviews

Private Oasis with Spacious Backyard

Welcome to your private oasis! - Spacious open concept upstairs with kitchen, living room, dining area, three bedrooms, and one bathroom. - Cozy downstairs living room with a wood-burning fireplace and lounge area. - Expansive backyard featuring BBQ grill, fire pit, and direct access to Butterfield Creek. - Large two-car garage and abundant parking space for guests. - Relax in nature on 1.5 acres while being minutes away from shopping and dining.

Top guest favourite
A charming single-story home is surrounded by lush greenery and colorful landscaping. The house features a light exterior with dark shutters and a welcoming front porch. A small tree adds a splash of color to the neatly manicured lawn.
Home in Munster
4.95 out of 5 average rating, 132 reviews

Cozy three bedroom home in Munster , Indiana.

Plan your next escape to Indiana or Illinois and stay in this beautifully renovated and thoughtfully appointed 3 bedroom and 1 bath home. Located in the quiet and safe suburb of Munster, Indiana, the property is just a 3 minute, easy access to the I-94 Highway. Exciting Downtown Chicago is just 30 minutes away! Walk to Riverside Park and take in the scenic view while enjoying a morning croissant and coffee from one of the quaint neighbourhood cafés.

Top guest favourite
Double doors open to a bright living area featuring a leather sofa and a light-colored armchair. A coffee table is placed on a soft area rug, while lamps provide soft illumination. A ceiling fan hangs above, and large windows allow natural light to fill the space.
Home in Manteno
4.98 out of 5 average rating, 240 reviews

Updated, bright, and modern, 3 bedroom home.

You will be comfortable in this newly remodeled three bedroom, two bathroom home. ✶ 6.7Miles to Olivet Nazarene University ✶ 8.4Miles to Riverside Medical ✶ 11Miles to Kankakee River State Park ✶ 43Miles to Midway Airport The home FEATURES: *Safe, quiet, walkable neighborhood *3 Bedroom; 1 King, 1 Queen, 2 twin beds *Spacious fully equipped kitchen with coffee station *Washing Machine, Dryer & Dishwasher * Fast Wi-Fi

Top guest favourite
A bright living area features a large area rug with intricate patterns centered on a coffee table. Two sofas in contrasting colors—blue and orange—offer ample seating. A wall adorned with artistic lettering adds character, while the window dressed with floral curtains allows natural light to fill the space.
Townhouse in Country Club Hills
4.96 out of 5 average rating, 69 reviews

Luv Happii House

Truly enjoy home away from home at the Luv Happii House, a Charming, vintage style canna friendly townhouse. Perfect for a weekend getaway, business trip, work from home alternative, content creation, or cozy home base while exploring everything Chicago and the South Suburbs of Chicago have to offer including nearby The Credit Union 1 Amphitheater and Tinley Park Convention Center.

Popular amenities for Olympia Fields holiday rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Olympia Fields