Holiday houses in Glenwood

5 out of 5 average rating, 13 reviews

Suburban Haven: Cozy Escape with a Touch of Luxury

This newly updated home is the perfect place to enjoy some peace and quiet. You’ll find ample seating for your whole group, and sleeping accommodations for up to 16. Using this as a homebase, you can enjoy everything Chicagoland has to offer. This home is perfect for reunions, family getaways and vacations. You’ll find a light and airy home that is beautifully decorated and tastefully furnished, with everything you need in ready supply. Enjoy a restful stay in this beautiful suburban getaway!

4.79 out of 5 average rating, 126 reviews

Home in Lansing

Cozy at The Walter

Just 35 minutes from Downtown Chicago Center in a quiet residential area. Close proximity to I-94 & I-80 ! 52 mins from Ohare Airport & 40 mins from Midway Airport-In normal traffic drive. Smaller Home(854 sqft) - Perfect for a Business Traveler, Couple, or Single person seeking a Private Uninterrupted Accommodation. Indiana state line > 1 mile ( 4 casinos within 20 minutes-often shows & events),Local restaurants & breweries, Shopping, Trails, Golf courses( Ravisloe Golf Club & Centennial).

4.91 out of 5 average rating, 81 reviews

Apartment 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!

4.87 out of 5 average rating, 247 reviews

Cottage in Merrillville

The Hideaway

This Christian friendly cozy cottage, located 30 minutes from Chicago is located on a private 3 acre property. It’s a private detached cottage from main house that sleeps four. One king size bedroom (2 air mattresses) (sheets supplied), large full bathroom with deep tub w/ handle (towels supplied), full kitchen (dishes, pots and pans ect supplied) private covered parking and yard (directly in front of cottage) w/ its own fire pit for enjoyment. No plug for electric cars (station 2 m away).

4.86 out of 5 average rating, 21 reviews

Apartment in Thornton

Your quiet south suburban oasis

Relax and enjoy yourself in this south suburban duplex located in a safe and quiet location! We offer the entire unit so you don’t have to worry about sharing. 1 bedroom but the living room is spacious enough for an air mattress (must bring own). Large yard for you and your family to enjoy outdoor activities! Park less than 1 block away. 4 blocks from the famous rock quarry of Thornton. New casino less than 2 miles away. Bar right across the street! Animals allowed if trained.

4.84 out of 5 average rating, 70 reviews

Apartment 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!

4.84 out of 5 average rating, 149 reviews

Apartment in Hammond

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!

4.77 out of 5 average rating, 57 reviews

Home in Hammond

Cozy, King/Queen bed, 2 bedroom.

UPDATE: Central Air unit installed 5/2025!! You can forget your worries in this spacious and serene space. Located in Hammond Indiana, just 40-45 mins drive to downtown Chicago. Get where you need to go safely and worry-free. This home is located 5 mins from the nearest Interstate and 10 mins from the train station. Plenty of thoughtful detail was given to ensure that you enjoy your stay. My hope is that you enjoy this space as I have for many years.

4.94 out of 5 average rating, 105 reviews

Home in Munster

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.

4.97 out of 5 average rating, 109 reviews

Yurt in Homewood

Glamping Yurt&RV-Game Room-Pool-Sauna-Hotub Court

Glamping Experience to the NEXT LEVEL! Opened April - Nov. Contact during off season. Mini Resort Includes: RV w/bathroom - 2 beds & sofa sleeper 20' Safari Yurt - 4 beds w/sofa sleeper Game Room w/bathroom 1 bed & sofa sleeper Gazebo w/2 twin beds Outdoor wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Fresh Eggs seasonally Mini Golf lanes Basketball, Volleyball, Pickleball court Breakfast included is 1 dozen fresh eggs!

Guesthouse in Merrillville

4.92 out of 5 average rating, 110 reviews

Romantic Getaway Guesthouse/ Jacuzzi/Sauna/Pool

Romantic Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse/in-law suite offers ultimate relaxation with a private entrance, spa-like jacuzzi, sauna, pool access, and a fully equipped gym. Perfect for honeymoons, anniversaries, or weekend escapes, our space blends comfort, privacy, and elegance for an unforgettable stay.

5 out of 5 average rating, 6 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.

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Other great holiday rentals in Glenwood

4.72 out of 5 average rating, 71 reviews

A Dream Home in Chicagoland

DemetraRating, 5 stars3 weeks ago

I have been staying at this property for 5 months. My continued stays is a great indicator of pleasure with the location and the host. Farrah is very responsive. The home is always clean. This place is in a great location - close to restaurants, grocery stores, and the interstate. Other than the yard needing to have some maintenance, it was a great stay as always.

Apartment in Tinley Park

4.8 out of 5 average rating, 5 reviews

Retro- Organic- Apt/ 2 bedrooms

AjaRating, 5 stars1 week ago

The home was very nice and clean pictures matches the exact place very quiet neighborhood and also Adriana was very accommodating as I wanted to check in earlier than the check in time great and very communicative host ! The price was nice please book if you want a mini vacation time away from home or visiting !

4.77 out of 5 average rating, 26 reviews

Home in South Holland

Top-Rated Romantic Getaway | Couples' Escape

AlexisRating, 5 stars1 week ago

Nicole was very helpful and friendly. Her place was clean and looked like the pictures posted. I would definitely recommend this listing.

4.88 out of 5 average rating, 40 reviews

The executive suite

GustavoRating, 5 stars1 week ago

The place was very nice if I come back to Chicago I will definitely be staying here again!

4.92 out of 5 average rating, 104 reviews

Private room in Munster

Suburban, Family-Friendly House

AlexRating, 5 stars2 weeks ago

Mary was a wonderful host who welcomed us warmly even though we arrived late in the evening. She provided everything we needed to feel at home and comfortable. If I ever have the chance, I would gladly stay here again. Thank you, Mary, for your hospitality and kindness!

Home in Lynwood

4.51 out of 5 average rating, 70 reviews

CHEERFUL 3 BEDROOM HOME IN A QUIET AREA!

ChushanaRating, 5 stars3 weeks ago

Coming to my second home for a sad occasion the lost of my Grandfather this place was close to everything I needed to do. When I come with my whole family this place will be my go to from now on. Thank you for sharing your home with us.

Private room in Blue Island

4.9 out of 5 average rating, 231 reviews

Chicago commuter room

MargaretRating, 5 stars4 days ago

I throughly enjoyed my stay at Karen’s house. She knew Chicago very well and was helpful in guiding us to where we needed to go. Her home was very comfortable and we really felt at home.