Holiday rentals in Olympia Fields

5 out of 5 average rating, 12 reviews

Suburban Haven: Cozy Escape with a Touch of Luxury

This newly updated home is the perfect place to enjoy some peace and quiet. You’ll find ample seating for your whole group, and sleeping accommodations for up to 16. Using this as a homebase, you can enjoy everything Chicagoland has to offer. This home is perfect for reunions, family getaways and vacations. You’ll find a light and airy home that is beautifully decorated and tastefully furnished, with everything you need in ready supply. Enjoy a restful stay in this beautiful suburban getaway!

4.92 out of 5 average rating, 78 reviews

Flat in Homewood

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 lovely downtown Homewood to enjoy shopping & dining or catch the train to Chicago. After a day of exploring, a king-sized sleep number bed and lush bathroom features will pamper you! A fold-down sofa creates an additional bed. Dogs are welcome! This suite has a kitchenette with a convection toaster oven, induction cooktop, and fridge!

4.99 out of 5 average rating, 659 reviews

Guest suite in Geneva

A Suite within a Cozy cottage in Geneva Illinois.

Cozy private suite in the lower level. Guests have the suite to themselves. The bathroom is adjacent to the room and is private. There is a small fridge, a coffee maker, and a microwave oven. We are in Geneva, Illinois. We are LGBTQ+friendly. Our space is ideal for shorter stays and visitors on the go . Not suitable for staycations. Quiet area. Hosts live on the upper level and guests pass through our space to get to the suite. In a bind we can accommodate a 3rd guest and a pet. Welcome.

4.76 out of 5 average rating, 33 reviews

Tiny home in Steger

Home away from home

Come stay with us! This cozy renovated home offers two bedrooms (one queen w/ensuite and one full size sleeper sofa), one bathroom with laundry room, and beautiful kitchen that waits for you. Great for travelers looking to get away from the busy life. A few blocks away from local convenience stores. 11 mins away from Starbucks or Dunkin if you need a coffee run! -Only 4.6 miles from Metra Richton Park. -40 mins from Downtown Chicago. -Midway International Airport 49 mins and Ohare 58 mins.

4.84 out of 5 average rating, 70 reviews

Flat in Homewood

Spacious and Cozy Oasis Close to Fun

Escape to our inviting 2nd-floor High-End condo, just a short 37-minute drive from the vibrant heart of Downtown Chicago, Millennium Park, and Navy Pier. Immerse yourself in the charm of our neighborhood, surrounded by custom homes, golf clubs, and family-friendly entertainment. Many dining options all within a 2-minute drive or a quick Uber ride. Large balcony with seating for six and 2 minutes from the Metra Train Station for a fast trip to Chicago. Be one of our first guests!

4.84 out of 5 average rating, 149 reviews

Flat in Hammond

Plant MOOD FREE Wi-fi, parking, washer & dryer!

LATE CHECK-IN guest are welcome!!!! PLEASE READ MY FULL AIRBNB LISTING PRIOR TO BOOKINGS!!!! This special place is close to everything, making it easy to plan your visit. • I80, 294, 94 highways/tolls, etc. • Chicago • Shopping galore • A fun array of restaurants AND A LOT OF FREE PARKING!!! I’m extremely close to MUNSTER, HIGHLAND, SCHERERVILLE, DYER and many more Indiana locations! I’m extremely close to LYNWOOD, LANSING, CALUMET CITY, and many more!

4.97 out of 5 average rating, 109 reviews

Yurt in Homewood

Glamping Yurt&RV-Game Room-Pool-Sauna-Hotub Court

Glamping Experience to the NEXT LEVEL! Opened April - Nov. Contact during off season. Mini Resort Includes: RV w/bathroom - 2 beds & sofa sleeper 20' Safari Yurt - 4 beds w/sofa sleeper Game Room w/bathroom 1 bed & sofa sleeper Gazebo w/2 twin beds Outdoor wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Fresh Eggs seasonally Mini Golf lanes Basketball, Volleyball, Pickleball court Breakfast included is 1 dozen fresh eggs!

Guest house in Merrillville

4.92 out of 5 average rating, 109 reviews

Romantic Getaway Guesthouse/ Jacuzzi/Sauna/Pool

Romantic Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse/in-law suite offers ultimate relaxation with a private entrance, spa-like 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.

4.86 out of 5 average rating, 29 reviews

Flat in Matteson

Cozy Suburban Getaway

If you’re looking for a quiet stay away from the busy city - this cozy retreat will feel just like home. We take pride in client service, cleanliness, and convenience. If you need a host that aims to please…look no further. We’re loaded with bonus amenities to make your stay easy and stress free. We’re a text message away should you have any questions. We look forward to offering you our suburban hospitality!

Townhouse in Country Club Hills

4.96 out of 5 average rating, 47 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.

5 out of 5 average rating, 3 reviews

Modern Charming Home w/Pergola & games

➜ Fully remodeled 3 beds, 2 bath home with modern finishes ➜ Spacious backyard with, pergola, seating areas, and outdoor games ➜ Smart TVs in every room ➜ Game room with pool table, ping pong and family games ➜ Large private backyard with pergola, seating areas and outdoor playgrounds.

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Popular amenities for Olympia Fields holiday rentals

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Free parking on premises

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Other great holiday rentals in Olympia Fields

4.89 out of 5 average rating, 19 reviews

Dream Stay - Modern Bungalow Near Downtown

RodieRating, 5 stars3 months ago

My family and I had a great stay at Urania’s place! The home was clean, & comfortable. Urania was very responsive and helpful throughout the stay.

4.84 out of 5 average rating, 19 reviews

Flat in Thornton

Your quiet south suburban oasis

IzzyRating, 5 stars3 weeks ago

We stayed over the weekend for a concert in Chicago, it was a perfect drive from the venue and on the way back home to Michigan! The place was a perfect getaway with great space to hangout in the living area. It was extremely clean and Tea was very helpful and reached out when we forgot belongings soon enough for us to go grab it before heading home!

4.89 out of 5 average rating, 27 reviews

Homewood Oasis

KrystalRating, 5 stars1 week ago

The house is beautiful. It’s clean and well-kept. I appreciated the washer and dryer. I also enjoyed the stove and microwave. It was my first time staying at Airbnb. Staying at a house has advantages over staying at a hotel. Ben was also very responsive and flexible with the staying arrangements.

5 out of 5 average rating, 4 reviews

Home in Tinley Park

3BR Tranquil Home in Tinley Park

LisaRating, 5 stars3 weeks ago

We stayed at Dawn's for an unexpected death in the family. comfy beds, great location

Home in Olympia Fields

4.56 out of 5 average rating, 43 reviews

Luxurious South Suburban Villa

LanceRating, 5 stars4 months ago

My team thanks you for your comfortable home, it is what the crew needs after a day working outside on a large solar field array. Whenever on an extended out of town work trip we like to stay at an Airbnb, a much better value than several rooms at hotels. Your home was roomy & comfortable, we enjoyed our stay and thank you for being a great host.

4.5 out of 5 average rating, 18 reviews

Home in Richton Park

Home away from home

TamaraRating, 5 stars1 month ago

The house was amazing—clean, spacious, and perfect for both rooming and hosting a baby shower. The kitchen was beautiful, and the huge backyard was a big plus! Delbert was very responsive and made sure everything went smoothly. The location was also great—close to local stores and the expressway, which made getting back and forth super easy. I’ll definitely book again!

4.96 out of 5 average rating, 28 reviews

Home in Frankfort

House in Frankfort quiet family neighborhood

TeresaRating, 5 stars1 week ago

Comfortable and easy to drive to while being convenient to many great places. Was great to have access to the attached 2 car garage. The fenced backyard is an excellent asset for those with children. Patio was inviting although there wasn’t a grill. Very clean, comfortable 3 bedrooms plus basement with big tv & huge couch to relax.