Holiday rentals in Flossmoor

4.89 out of 5 average rating, 18 reviews

Flat in Homewood

Basement Apartment

Clean, quiet, and comfortable space in this garden apartment with beautiful view in all seasons. Acre property backs up to nature preserve with lakes and walking trails. Downtown Homewood is a short walk, with numerous shops and restaurants. The village and park district host many farmers markets, fests, and activities year-round. Homewood voted one of the most livable cities in the country within walking distance to train. Downtown Chicago 40-minute train ride. Located just south of I-80.

Guest house in Valparaiso

4.98 out of 5 average rating, 103 reviews

Unique Dome Retreat by Indiana Dunes w/ Lake View

Escape to our Valparaiso Lakeside Retreat with king bed, lake views, unique dome experience, fire pit, grill & hot tub, all near Indiana Dunes National Park, Valparaiso University & 4 local parks! Experience a nature getaway at our newly renovated lake guest house on the ground level of our home with keyless entry & unique outdoor amenities, ideal for friend groups, small families, business travelers & couples. 10 min - downtown Valparaiso. Book now to experience this unique tranquil retreat.

4.93 out of 5 average rating, 15 reviews

Charming & Cozy Getaway - A Heroic Stay Awaits!

Welcome to our snug and inviting home nestled in the heart of the Chicago suburbs! Perfect for a relaxing getaway, this cozy space offers everything you need for a comfortable stay. Enjoy a fully stocked kitchen, along with an in-unit washer and dryer for your convenience. We've made sure to provide plenty of linens, ensuring you have a cozy retreat to come home to after a day of exploring. Whether you're here for business or leisure, this home offers the perfect balance of comfort and warmth!

4.96 out of 5 average rating, 195 reviews

Farm stay in De Motte

Cozy barn loft on organic vegetable farm

Find peace and restoration in this beautiful barn loft at Perkins' Good Earth Farm. The loft has a bedroom, separate shower and toilet spaces, work area, sitting room, kitchen space, and heating/cooling fresh air system. Located above our farm store, the loft provides privacy for you while giving you access to fresh fruits & veggies, locally sourced meats, homemade soups & salads from our farm kitchen, and so much more. You can also walk our farm trails, visit the veggies, or enjoy a campfire.

4.91 out of 5 average rating, 91 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!

5 out of 5 average rating, 12 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!

4.92 out of 5 average rating, 65 reviews

Charming Homewood Away from Home

Keep it simple at this peaceful and centrally-located place. Cozy and Charming brick ranch nested on a quiet street. Minutes from the metra line taking you to downtown Chicago or visit the neighborhood shopping in downtown Homewood. No smoking and no parties. We are unable to accommodate a party of any size because of our agreement with our neighbors. Driveway is narrow. Limit 2 cars. No extra guest without notice. Extremely strict neighbors! We follow all cancellation rules.

4.8 out of 5 average rating, 84 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!

4.96 out of 5 average rating, 24 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.

4.98 out of 5 average rating, 120 reviews

Yurt in Homewood

Glamping Yurt&RV Gaming Room Pool/Hotub/Court more

GLAMPING FUN! April - mid Nov RV w/bathroom - 2 beds 20' Safari Yurt - 4 beds Gaming Room w/bathroom queen & sofa sleeper Xbox Series X & PS5 Gazebo w/2 twin beds (seasonal) Outdoor wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Fresh Eggs (seasonal) mini golf 3-n-1 Court; Event Yurt add on $180 up to 15 additional non/overnight guest Contact me for Fall/Winter Glamping no more than 10

4.86 out of 5 average rating, 36 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!