Vacation rentals in Flossmoor

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Top-rated vacation rentals in Flossmoor

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

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Superhost

Apartment in Homewood

4.89 out of 5 average rating, 18 reviews

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 favorite

Home in Homewood

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!

Top guest favorite

Farm stay in De Motte

4.96 out of 5 average rating, 195 reviews

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.

Guest favorite

Apartment in Homewood

4.91 out of 5 average rating, 91 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 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!

Guest favorite

Home in Homewood

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!

Guest favorite

Home in Homewood

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.

Guest favorite

Apartment in Hammond

4.85 out of 5 average rating, 161 reviews

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!

Top guest favorite

Yurt in Homewood

4.98 out of 5 average rating, 120 reviews

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

Superhost

Apartment in Matteson

4.86 out of 5 average rating, 36 reviews

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!

Top guest favorite

Townhouse in Country Club Hills

4.96 out of 5 average rating, 56 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.

Guest favorite

Home in Homewood

5 out of 5 average rating, 6 reviews

Spruce Sanctuary

Welcome to this cozy, family-friendly 3BR home in the heart of Homewood, IL! Sleeps up to 8 with a brand-new kitchen, central heat & AC and fast WiFi -- ideal for work-from-home stays. Enjoy the fully fenced yard, perfect for kids and pets. Free driveway and street parking. Just minutes from parks, restaurants, and shopping. A perfect blend of comfort, convenience, and charm!

Top guest favorite

Home in Homewood

5 out of 5 average rating, 15 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.