Glenwood Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Glenwood vacation rentals

A hotel lobby with a reception desk, a staircase, and a small seating area.

1. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Harvey
10.0 out of 10, Exceptional, (2 reviews)
"Exceeded expectations considering proximity to key sites like Museum of Science and Industry, rooms featured clean bathrooms with choice between tub or shower facilities uncommon in similar motels we have tried before."
United States
Anonymous traveller
The price is CA $93
CA $105 total
includes taxes & fees
Nov 8 - Nov 9
1 Queen Bed | Smoking
A ceiling with exposed wooden beams and a central fan.

2. Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.4 out of 10, Very good, (35 reviews)
"It was a very nice property and was near many great places like Toast and Jam"
United States
jaco C.
The price is CA $116
CA $149 total
includes taxes & fees
Dec 5 - Dec 6
Beautiful Rustic Cabin for Two!
A hotel lobby with a stone fireplace, wooden flooring, and a seating area with chairs and a sofa.

3. King Studio. Free Breakfast. Indoor Pool. Gym.

King Studio. Free Breakfast. Indoor Pool. Gym.
Schererville
The price is CA $293
CA $347 total
includes taxes & fees
Nov 11 - Nov 12
King Studio. Free Breakfast. Indoor Pool. Gym.
A single-story building with a porch, a brick facade, and a number '531' on the front.

4. Quaint Studio Unit in fantastic Beecher with refreshing AC

Quaint Studio Unit in fantastic Beecher with refreshing AC
Beecher
10.0 out of 10, Exceptional, (4 reviews)
"Clean, comfortable, quiet, excellent place to stay"
United States
Aaron S.
The price is CA $91
CA $265 total
includes taxes & fees
Nov 12 - Nov 13
Quaint Studio Unit in fantastic Beecher with refreshing AC
A bedroom with a bed, a nightstand, a wall-mounted lamp, and a plant.

5. Romantic Escape - Adult Playhouse with Exotic Dungeon

Romantic Escape - Adult Playhouse with Exotic Dungeon
South Holland
8.8 out of 10, Excellent, (15 reviews)
"enjoyed my stay cant wait to book again "
United States
Anonymous traveller
The price is CA $545
CA $634 total
includes taxes & fees
Nov 16 - Nov 17
Romantic Escape - Adult Playhouse with Exotic Dungeon
A hotel lobby with a stone fireplace, wooden flooring, and a seating area with chairs and a sofa.

6. King Bed Suite | Indoor Pool. Free Breakfast.

King Bed Suite | Indoor Pool. Free Breakfast.
Schererville
8.0 out of 10, Very good, (1 review)
The price is CA $538
CA $625 total
includes taxes & fees
Nov 9 - Nov 10
King Bed Suite | Indoor Pool. Free Breakfast.
A reception desk with a staff member, a guest, and a child.

7. 1 King Bed | Micfridge

1 King Bed | Micfridge
MERRILLVILLE
10.0 out of 10, Exceptional, (4 reviews)
"Loved how quick check-in was!"
United States
Anonymous traveller
The price is CA $111
CA $125 total
includes taxes & fees
Nov 8 - Nov 9
1 King Bed | Micfridge
A modern kitchen with wooden cabinets, stainless steel appliances, and a white countertop island.

8. Modern 3BR w/Deck · Minutes from I-65. Fenced Yard

Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Merrilville
8.6 out of 10, Excellent, (4 reviews)
"Great pet friendly home and yard. Host was responsive great communication. Excellent, easy to access location."
United States
Lynda L.
The price is CA $259
CA $588 total
includes taxes & fees
Nov 9 - Nov 10
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
A neatly arranged bedroom with a bed, bedside tables, and abstract wall art.

9. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Such a cozy stay! Definitely recommend!"
United States
Angelina
The price is CA $91
CA $211 total
includes taxes & fees
Nov 12 - Nov 13
Hyde Park Trendy Studio Apartment in Good Spot
A wooden deck with a railing, a staircase, and a window with a wreath.

10. Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.8 out of 10, Exceptional, (37 reviews)
"I had a fun stay "
United States
Jusu K.
The price is CA $200
CA $265 total
includes taxes & fees
Nov 9 - Nov 10
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A hotel lobby with a stone fireplace, wooden flooring, and a seating area with chairs and a sofa.

11. Free Breakfast. Indoor Pool. Gym. Business Center.

Free Breakfast. Indoor Pool. Gym. Business Center.
Schererville
The price is CA $342
CA $397 total
includes taxes & fees
Nov 9 - Nov 10
Free Breakfast. Indoor Pool. Gym. Business Center.
A living room with a brick fireplace, a television mounted above it, and a dining area with a table and chairs.

12. Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool

Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
Merrillville
9.8 out of 10, Exceptional, (9 reviews)
"The house was cozy and very clean. The hot tub was amazing! Check-in instructions were clear and easy to follow. The host was very helpful and responsive to messages. We would definitely stay again. Thank you!"
United States
Anonymous traveller
The price is CA $419
CA $637 total
includes taxes & fees
Nov 12 - Nov 13
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
A dining area with a wooden table and chairs, a ceiling fan, and a couch.

13. Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Blue Island
6.4 out of 10, (11 reviews)
"Town was quite walkable which was fun. Teddy is very nice. "
United States
India L.
The price is CA $206
CA $457 total
includes taxes & fees
Nov 6 - Nov 7
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
A compact RV interior with a kitchenette, seating area, and a small dining table.

14. Beautiful 32' RV located in Chicago's South suburb - A unique experience!

Beautiful 32' RV located in Chicago's South suburb - A unique experience!
Hazel Green
The price is CA $203
CA $304 total
includes taxes & fees
Nov 10 - Nov 11
Beautiful 32' RV located in Chicago's South suburb - A unique experience!
A modern living room with a grey sofa, a dining table with chairs, and a kitchen area with a kettle.

15. Perfect 1BR Spot near Attractions

Perfect 1BR Spot near Attractions
Hyde Park
6.0 out of 10, (1 review)
"I would characterize this property as “fine”. I only needed to stay one night for a business trip and it got the job done. Getting in/out was a little cumbersome with a lockbox to retrieve a set of keys. Hot water took quite a long time to heat up and deliver for a shower. Shower bathtub and amenities were lacking. Again, it got the job done for a night of sleep."
United States
Andrew M.
The price is CA $103
CA $316 total
includes taxes & fees
Nov 11 - Nov 12
Perfect 1BR Spot near Attractions
A hotel lobby with a stone fireplace, wooden flooring, and a seating area with chairs and a sofa.

16. 2 Bedroom | Free Daily Breakfast. Indoor Pool.

2 Bedroom | Free Daily Breakfast. Indoor Pool.
Schererville
The price is CA $538
CA $625 total
includes taxes & fees
Nov 9 - Nov 10
2 Bedroom | Free Daily Breakfast. Indoor Pool.
A neatly made bed with pillows, a bedside lamp, and a small table with a lamp. There are two abstract paintings on the wall above the bed.

17. Trendy Studio Apartment in Chicago

Trendy Studio Apartment in Chicago
Hyde Park
The price is CA $101
CA $294 total
includes taxes & fees
Nov 10 - Nov 11
Trendy Studio Apartment in Chicago
A modern living room with a leather sofa, a desk with a computer, a bookshelf, and a large abstract painting.

18. Spacious 3BR Near Hyde Park | Garage + Pets

Spacious 3BR Near Hyde Park | Garage + Pets
Bronzeville
6.0 out of 10, (1 review)
"Cove didn’t work for first dayBad mattress and bed in master suite No toilet paper when we arrived"
United States
Allen S.
The price is CA $241
CA $646 total
includes taxes & fees
Nov 10 - Nov 11
Spacious 3BR Near Hyde Park | Garage + Pets
A bedroom with a stone wall, a TV mounted on it, a bed with a white comforter, and a view of the outdoors through a window.

19. Beautifully furnished one bedroom loft located in Chicago's South side suburb

Beautifully furnished one bedroom loft located in Chicago's South side suburb
Hazel Green
10.0 out of 10, Exceptional, (1 review)
"Super great location, we had a concert at Tinley Park, then explored Chicago with a river cruise and Second City Everything was perfect and so eat to just chill, come and go as we pleased In a nice neighborhood and interior was furnished beautifully. Definitely worth the price !!"
United States
Nick L.
The price is CA $342
CA $450 total
includes taxes & fees
Nov 9 - Nov 10
Beautifully furnished one bedroom loft located in Chicago's South side suburb
A modern kitchen with a double sink, stainless steel appliances, and white cabinetry.

20. 1BR Chic Apt in Downtown Chicago

1BR Chic Apt in Downtown Chicago
Hyde Park
The price is CA $99
CA $297 total
includes taxes & fees
Nov 9 - Nov 10
1BR Chic Apt in Downtown Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Find vacation rentals that suit your style

Apartment image
Apartments
Apartments
Condo image
Condos
Condos

Top Glenwood Hotel Reviews

A modern spa with a circular hot tub, a sofa, and a view of the city.
Wind Creek Chicago Southland Casino and Hotel

Wind Creek Chicago Southland Casino and Hotel

Wind Creek Chicago Southland Casino and Hotel
East Hazel Crest

10/10 Excellent

Gorgeous hotel and casino. Super staff. I would definitely recommend this place for all
Canada
RITA
Reviewed October 13, 2026
Wind Creek Chicago Southland Casino and Hotel

Find out more about Glenwood

Everything you need to know about Glenwood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Glenwood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Glenwood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Glenwood vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Glenwood. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Glenwood vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Glenwood vacation rentals we have selected for you start as low as CA $85 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Glenwood rentals

At Expedia, we put the best Glenwood vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Glenwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Glenwood vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Glenwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there vacation rentals in Glenwood?

Yes, you can find vacation rentals close to the most popular attractions in Glenwood, or you can choose a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental that Glenwood has to offer?

Your Home Away From Home in Sauk Village: Visitors like this Glenwood vacation home rental. It comes with WiFi so you can feel at home during your trip. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave.

What can I see and do in Glenwood?

Explore the area and family-friendly sights such as Odyssey Fun World, or get out into nature at a spot like Centennial Park. Ravisloe Country Club and River Oaks Center are a couple of places you'll find in the larger area.

What are vacation rentals like in Glenwood?

Vacation rentals are privately owned accommodations you can book for a few days or a quick weekend in Glenwood. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy front desks while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family trip or a small group gathering.