Holiday houses in Glenwood

The Ashlin House.

Stay at our family-friendly home on a quiet, cobblestone street on vacation or business. We've recently repainted the exterior and painted the master BR. Walking distance to quaint Downtown Whiting , Lake Michigan, Whihala Beach & Lakefront trails. The Horseshoe Casino, Wolf Lake & Pavilion, Hammond Sportsplex, Calumet College, PNW, IUN, U of Chicago, BP, & golf courses are a short drive. See Chicago's Skyline at Lakefront Park. Chicago's attractions & Hard Rock Casino are < 30 mins away.

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!

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.

Charming Homewood Away from Home

Keep it simple at this cozy, charming brick ranch tucked away on a quiet, friendly street. Just minutes from the Metra line for an easy ride into downtown Chicago, and close to all the great local shopping and dining in downtown Homewood. House Guidelines: • No smoking, no parties, no large gatherings • Be mindful of neighbors • Narrow driveway, limit 2 cars • No extra guests without notice • Pets are welcome, but must be added to your reservation • We have a moderate cancellation policy

Fun game-room suite with hot tub & optional Yurt

Activities includes: PS5 Disc w/TV Xbox Series X w/TV Outdoor heated Jacuzzi 27' above ground pool Pool and Air hockey table Arcade machine with 12 games Life Size Connect 4 Board games Basketball machine Electric fire place Queen & full size beds Full size sofa pull out sleeper Gazebo with two twin beds (seasonal) Fresh Eggs with chickens seasonal Gas Grill-propane included Romantic Robe for 2 (in colder months must request) Event Yurt add on $225 up to 25 additional guest

Homewood Oasis

Welcome to our Homewood Oasis, where relaxation meets family fun! As former residents of this charming town, we know the importance of a comfortable and enjoyable stay when coming back to visit. Our Airbnb is more than just a place to sleep; it's a carefully curated space designed for families like yours. As hosts who've experienced the need for a home away from home, we've put our heart into making this space welcoming and enjoyable for you. We look forward to hosting you!

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.

4BR/2BA Family Home + Fenced Backyard

Step into elegance at our beautifully furnished home. With a stylish interior and all the amenities you need, this is the perfect spot to unwind. The open living space is great for relaxing or entertaining, while the comfortable bedroom promises a restful night’s sleep. Enjoy the convenience of being close to local attractions while still enjoying the serenity of a quiet neighborhood. Ideal for travelers seeking both comfort and style.

Cottage Feel 2 bedroom Home!

Welcome to your home away from home! Relax and unwind in this cozy, peaceful space that’s thoughtfully maintained to make your stay comfortable and stress-free. While this isn’t a luxury home, it’s clean, inviting, and equipped with everything you need for a pleasant visit. Conveniently located in the south suburbs of Illinois, you’ll be just minutes from great restaurants, shopping, parks, entertainment, and major highways.

Quiet Oasis: Cozy, Private, Fenced Yard & Office

Private, pet-friendly 2-bedroom single-level retreat near Chicago, ideal for 4 guests + infant. Features a dedicated remote workspace with 413 Mbps Wi-Fi, fully equipped kitchen, and a spacious private backyard with a gas grill. Perfect for remote workers, cycling enthusiasts, and brewery lovers, offering easy access to nature trails, 6 local breweries, and casinos. Enjoy a quiet escape just 30 minutes from the city.

Two Bedroom Apartment Walk to Metra

Cozy private lower-level apartment in Homewood, just a 5-min walk to the Metra for easy access to Chicago. Features 2 bedrooms (king & queen), pullout sofa, 2 full baths, and seating for 6. Enjoy a backyard fire pit and full front driveway parking. Walk to a playground, with a skate park across the street and the casino just a short drive away. Quiet, comfortable stay in a convenient location.

The Den: 2BR-1BT w/ 2 Living Rooms

Welcome to your cozy home away from home. This charming 2-bedroom, 1-bath retreat offers relaxed den vibes with two separate living spaces—perfect for unwinding, movie nights, or spreading out comfortably. Whether you’re here for a weekend escape or an extended stay, you’ll enjoy a warm, inviting atmosphere designed for rest and ease.