Vacation rentals in Homewood

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Top-rated vacation rentals in Homewood

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

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Top guest favorite
A cozy bedroom space features a queen-sized bed adorned with a colorful patterned blanket. Two bedside lamps provide soft lighting. A large window offers views of the outdoors, while wooden walls enhance the rustic charm of the loft.
Farm stay in De Motte
4.96 out of 5 average rating, 217 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.

Top guest favorite
A natural pathway leads to a charming safari yurt, adorned with greenery and decorative elements. A wooden archway introduces the entrance, while a nearby barrel sauna complements the serene outdoor setting, surrounded by trees and mulch landscaping.
Yurt in Homewood
4.98 out of 5 average rating, 125 reviews

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

GLAMPING FUN April - Nov Winter Glamping sleeps 8 RV, Gazebo & Safari Yurt closed. Includes heated event yurt, Game room, and Hot Tub in Winter. No additional fee for event yurt in winter for 8 guest. RV w/bathroom - 2 beds 20' Safari Yurt - 4 beds Game Room w/bathroom queen & sofa sleeper Gazebo 2 twin beds 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

Guest favorite
A well-appointed bedroom features a spacious bed adorned with a soft blush and white blanket. A bedside lamp and decorative elements are present. Natural light filters through a window dressed with sheer curtains, creating a cozy ambiance. A small chair complements the interior design.
Apartment in Hammond
4.85 out of 5 average rating, 167 reviews

1Plant MOOD FREE Wi-Fi Parking Washer/Dryer

PLEASE READ THE ENTIRE LISTING BEFORE BOOKING! LATE CHECKINS WELCOME! Enjoy FREE Washer/Dryer Full Kitchen + MORE! 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 Illinois locations!

Guest favorite
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.
Apartment in Homewood
4.92 out of 5 average rating, 100 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!

Top guest favorite
Home in Munster
4.95 out of 5 average rating, 107 reviews

Entire home: Private, Cozy Oasis in a Quiet Locale

30 minute drive from Chicago's Grant Park. Near Little Calumet and Monon trails. Appeals to nature enthusiasts, cyclists, remote workers and brewery aficionados. This 2 bedroom, 1 bathroom retreat offers comfort and convenience. Full kitchen, private backyard and comfortable living space. 3 casinos, 6 breweries: 3 Floyds, 18th Street, Fuzzyline, Byway, New Oberpfalz & Wildrose within 7 to 20 min drive. Early check-ins offered/subject to availability. Feel free to inquire on availability.

Guest favorite
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, 166 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 favorite
A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.
Home in Berwyn
4.98 out of 5 average rating, 183 reviews

Retro Modern Bungalow | free parking | fire pit

Experience the city in style at Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Guest favorite
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, 104 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 favorite
A cozy living area is displayed with a pair of beige sofas, accented by decorative pillows. Framed wall art complements the decor. A soft rug is positioned on the wooden floor, while a lampshade on a side table adds subtle illumination.
Home in Blue Island
4.82 out of 5 average rating, 217 reviews

Warm and comfortable inviting Suburban home !

160 year old land mark community, Framed cedar bevel siding 2 story home, front porch , 10 ft high ceilings, kitchen canned lighting home. 6 feet fence In closed yard, whole house water filtration system , Quite neighborhood with sidewalks . 19 miles to downtown Chicago , Metra train station and bus route, in walking distance . driving to the city of Chicago 5 minutes to major expressways . Host is willing to be available for any and all information 24/7.

Guest favorite
An open-concept living area showcases a dark leather sofa and recliner, complemented by a green coffee table. The kitchen features dark cabinetry and stainless steel appliances. A bookshelf stands against the wall, and natural light is provided by large windows with light curtains.
Home in Schererville
4.93 out of 5 average rating, 69 reviews

Luxury Home in Schererville-garage use included!

Located close to downtown, this spacious, new-construction, family-friendly home is the perfect getaway! Near unique shops, parks, restaurants, and local activities, there is plenty to do and see! A 45 minute drive to Chicago or a 45 minute drive to the beautiful beaches of Lake Michigan will add more fun things to do while visiting. Enjoy the comforts of modern living with a spacious 3-bedroom, 2.5 bath, 2-story home with numerous amenities and features.

Top guest favorite
The exterior of a private guest house is shown, featuring a detached two-story structure. A driveway leads to a garage with a white door, while a wooden staircase ascends to the entryway. The surrounding area includes greenery and paved walkways.
Guest suite in Crown Point
4.94 out of 5 average rating, 259 reviews

IT'S THE WRIGHT PLACE

Private guest house newly remodeled. One bedroom queen bed, bath w/shower, full kitchen stocked, including microwave and Keurig coffee maker pods included, family room TV, and WIFI. No matter if you are in town for work, sport competition, family or just vacationing we offer all the comforts of home. Air Mattress available upon request. Please treat as your own home, follow all house rules. No party or gatherings. This is a no smoking home.

Top guest favorite
A cozy living area is featured with two large windows allowing natural light to fill the space. A hanging chair adds a unique touch, while a dark sofa and a coffee table sit on a patterned rug. A television is positioned on a stand nearby.
Apartment in Blue Island
4.94 out of 5 average rating, 310 reviews

Charming Unique 2 Bdrm Apartment in Victorian Home

My place is close to the excitement and culture of the beautiful city of Chicago. It is a short walk to Metra trains with a 25 minute ride downtown. You’ll love my place because of the diverse, comfortable, quiet, tree lined neighborhood where you can relax and feel secure. It is close to expressways, golf courses and a local park with walking path. The apartment is not available to guests without previous positive reviews.

Popular amenities for Homewood vacation rentals

When is the best time to visit Homewood?

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Avg. priceﺩ.ﺇ793ﺩ.ﺇ738ﺩ.ﺇ672ﺩ.ﺇ668ﺩ.ﺇ793ﺩ.ﺇ790ﺩ.ﺇ738ﺩ.ﺇ749ﺩ.ﺇ602ﺩ.ﺇ793ﺩ.ﺇ793ﺩ.ﺇ892
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Frequently Asked Questions

  • How much does it cost to stay in house rentals in Homewood?

    Experience the best of Homewood with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly vacation rentals in Homewood?

    Homewood has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in Homewood?

    Four-legged friends are welcome in Homewood. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Homewood?

    Yes! Work meets play with ease at over 20 vacation rentals in Homewood featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • What are the most popular amenities for House Rentals in Homewood?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with wifi, over 30 homes with free parking, over 30 homes with air conditioning, over 30 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Homewood have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in Homewood. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Homewood have free parking?

    Absolutely! We offer over 30 house rentals with free parking in Homewood. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Homewood have a kitchen?

    Absolutely! We offer over 30 house rentals with a kitchen in Homewood. Enjoy a tailored experience with all the comforts you desire.

  • Where should I stay in Homewood?

    Make yourself at home in Homewood by choosing from our most frequently booked neighborhoods. We have over 170 vacation rentals in Homewood, over 100 vacation rentals in Flossmoor, and over 100 vacation rentals in East Hazel Crest.

  • Do house rentals in Homewood have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Homewood. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Homewood

  • Total vacation rentals

    Explore 40 vacation rentals in Homewood

  • Nightly prices starting at

    Homewood vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

  • Verified guest reviews

    Over 1,160 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Homewood vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Homewood rentals

  • 4.7 Average rating

    Homewood stays receive an average rating of 4.7 out of 5 from guests

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