Glenwood Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Glenwood vacation rentals

A hotel lobby with a stone fireplace, wooden flooring, and a seating area with chairs and a sofa.

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

King Bed Suite | Indoor Pool. Free Breakfast.
Schererville
8.0 out of 10, Very good, (1 review)
$406 nightly
The price is $454
Nov 18 - Nov 19
Total with taxes and fees
King Bed Suite | Indoor Pool. Free Breakfast.
A bedroom with a bed, a nightstand, a wall-mounted lamp, and a plant.

2. Romantic Escape - Adult Playhouse with Red Room & Exotic Dungeon

Romantic Escape - Adult Playhouse with Red Room & Exotic Dungeon
South Holland
8.8 out of 10, Excellent, (15 reviews)
"enjoyed my stay cant wait to book again "
United States
Anonymous traveler
$421 nightly
The price is $450
Nov 16 - Nov 17
Total with taxes and fees
Romantic Escape - Adult Playhouse with Red Room & Exotic Dungeon
A bunk bed with a ladder, a small table, a potted plant, and a window with blinds.

3. Vintage meets Modern 20 min from Chicago.

Vintage meets Modern 20 min from Chicago.
Calumet City
$320 nightly
The price is $342
Nov 15 - Nov 16
Total with taxes and fees
Vintage meets Modern 20 min from Chicago.
A hotel lobby with a reception desk, a staircase, and a small seating area.

4. 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 traveler
$66 nightly
The price is $74
Nov 15 - Nov 16
Total with taxes and fees
1 Queen Bed | Smoking
A modern kitchen with wooden cabinets, stainless steel appliances, and a white countertop island.

5. 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.
$391 nightly
The price is $438
Nov 12 - Nov 13
Total with taxes and fees
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
A hotel lobby with a stone fireplace, wooden flooring, and a seating area with chairs and a sofa.

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

King Studio. Free Breakfast. Indoor Pool. Gym.
Schererville
$215 nightly
The price is $241
Nov 15 - Nov 16
Total with taxes and fees
King Studio. Free Breakfast. Indoor Pool. Gym.
A single-story building with a porch, a brick facade, and a number '531' on the front.

7. 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.
$180 nightly
The price is $191
Nov 13 - Nov 14
Total with taxes and fees
Quaint Studio Unit in fantastic Beecher with refreshing AC
A wooden deck with a railing, a staircase, and a window with a wreath.

8. 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)
"Quiet neighborhood, comfy beds, attentive hosts. Would stay again."
United States
Scott n Holly K.
$176 nightly
The price is $197
Nov 13 - Nov 14
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A compact kitchen with a sink, a microwave, a refrigerator, a small table with stools, and a ceiling fan.

9. Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.6 out of 10, Excellent, (36 reviews)
"It was a very nice property and was near many great places like Toast and Jam"
United States
jaco C.
$95 nightly
The price is $106
Dec 6 - Dec 7
Total with taxes and fees
Beautiful Rustic Cabin for Two!
A modern living room with a leather sofa, a desk with a computer, a bookshelf, and a large abstract painting.

10. 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.
$450 nightly
The price is $457
Nov 12 - Nov 13
Total with taxes and fees
Spacious 3BR Near Hyde Park | Garage + Pets
A neatly arranged bedroom with a bed, bedside tables, and abstract wall art.

11. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"Location could not be beat of looking to be near University of Chicago. Within walking distance to several restaurants, coffee, shops, and stores. Perfect for our trip!"
United States
rebecca
$144 nightly
The price is $159
Nov 16 - Nov 17
Total with taxes and fees
Hyde Park Trendy Studio Apartment in Good Spot
A modern hotel room with a wooden floor, a large bed with patterned bedding, a bedside table with a lamp, a desk with a chair, and a window with curtains.

12. 1 King Bed | Micfridge

1 King Bed | Micfridge
MERRILLVILLE
8.4 out of 10, Very good, (5 reviews)
$79 nightly
The price is $89
Nov 12 - Nov 13
Total with taxes and fees
1 King Bed | Micfridge
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.
$305 nightly
The price is $326
Nov 12 - Nov 13
Total with taxes and fees
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
A hotel lobby with a stone fireplace, wooden flooring, and a seating area with chairs and a sofa.

14. 2 Bedroom | Free Daily Breakfast. Indoor Pool.

2 Bedroom | Free Daily Breakfast. Indoor Pool.
Schererville
$406 nightly
The price is $454
Nov 18 - Nov 19
Total with taxes and fees
2 Bedroom | Free Daily Breakfast. Indoor Pool.
A living room with a brick fireplace, a television mounted above it, and a dining area with a table and chairs.

15. 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 traveler
$404 nightly
The price is $452
Nov 12 - Nov 13
Total with taxes and fees
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
A hotel lobby with a stone fireplace, wooden flooring, and a seating area with chairs and a sofa.

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

Free Breakfast. Indoor Pool. Gym. Business Center.
Schererville
$253 nightly
The price is $283
Nov 15 - Nov 16
Total with taxes and fees
Free Breakfast. Indoor Pool. Gym. Business Center.
A modern living room with a sofa, coffee table, and TV. There are windows with blinds, a radiator, and a plant.

17. Sleek & Functional 2-Bedroom Apt

Sleek & Functional 2-Bedroom Apt
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Great place, great location!"
United States
Lisa T.
$193 nightly
The price is $212
Nov 12 - Nov 13
Total with taxes and fees
Sleek & Functional 2-Bedroom Apt
A modern living room with a grey sofa, a glass coffee table, and a potted plant.

18. Conveniently Situated 1BR Apartment

Conveniently Situated 1BR Apartment
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Cute, cozy place in walking distance to UChicago. Would stay here again."
United States
Jane L.
$206 nightly
The price is $222
Nov 12 - Nov 13
Total with taxes and fees
Conveniently Situated 1BR Apartment
A bedroom with a bed, desk, chair, and two bedside lamps.

19. Group-Friendly 4BR Hyde Park Retreat Near UChicago

Group-Friendly 4BR Hyde Park Retreat Near UChicago
Hyde Park
7.0 out of 10, Good, (7 reviews)
"Pretty standard for a VRBO property. No frills but excellent location and great that it had 4 bedrooms for our group. "
United States
Cuoghi E.
$302 nightly
The price is $321
Nov 12 - Nov 13
Total with taxes and fees
Group-Friendly 4BR Hyde Park Retreat Near UChicago
A modern living room with a gray sofa, a round coffee table, and a dining area with a white table and black chairs.

20. Hyde Park Getaway | 1BR with WiFi & Workspace

Hyde Park Getaway | 1BR with WiFi & Workspace
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.
$202 nightly
The price is $217
Nov 12 - Nov 13
Total with taxes and fees
Hyde Park Getaway | 1BR with WiFi & Workspace
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
cabin image
Cabins
Cabins

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

Great experience much needed thank you
United States
Thomas
Reviewed April 30, 2025
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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Glenwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $74 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.