Holiday houses in Glenwood

Spacious home 28 miles from Downtown Chicago

This lovely 4B/2B home features an open concept floor plan. Property features a living/dining room and kitchen with a Keurig for your morning coffee. This home is located close to I80-94 making it convenient for guests to explore the area! Our guests have access to the entire home. This property is located less than 30 minutes from downtown Chicago and Schererville, IN and less than an hour from Orland Park and Oak Brook Mall where there are plenty of restaurants and stores for shopping.

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

Luxury Townhome in Tinley Park Near Shops & Train

Welcome to your luxury retreat in Tinley Park! This 3-level townhome features 3 spacious bedrooms, including a primary suite with en-suite, 2.5 bathrooms, a fully stocked kitchen, a large dining area, and an in-unit washer/dryer. Perfectly located near shops, restaurants, the Credit Union 1 Amphitheater, and just a short Metra train ride to downtown Chicago. Ideal for relaxation, business, or adventure—this space offers the perfect blend of comfort and convenience. Book your stay today!

Beverly Hills of Chicago Luxury Guest Favorite

Escape to luxury in this beautifully designed 5 bedroom, 3.5-bath home in Chicago's prestigious Beverly Hills neighborhood. Spacious living and high-end finishes, full finished basement have fun with air hockey, pool table, and video gaming, this entertainment space is for guests of all ages. Unwind on the private deck or enclosed front porch. explore retail shops and upscale dining. Metra train station provides a quick 15 minute downtown Chicago area. Close to downtown Chicago!

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.

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.

5-BR Home: 1.5-Acre Yard & Fire Pit

Welcome to your private oasis! - Spacious open concept with 5 bedrooms and 2 bathrooms. - Cozy downstairs living room with a wood-burning fireplace and lounge area. - Expansive backyard featuring BBQ grill, fire pit, and direct access to Butterfield Creek. - Large two-car garage and abundant parking space for guests. - Relax in nature on 1.5 acres while being minutes away from shopping and dining.

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.