Glenwood Vacation Rentals

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Check prices for these dates

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

Our top choices for Glenwood vacation rentals

Let the on-site guest services team help you plan your stay.

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)
The price is AEDĀ 1,372
AEDĀ 1,669 total
includes taxes & fees
18 Nov - 19 Nov
King Bed Suite | Indoor Pool. Free Breakfast.
A modern living room with a sectional sofa, a pool table, and a view of the outdoors.

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
The price is AEDĀ 1,432
AEDĀ 1,650 total
includes taxes & fees
15 Nov - 16 Nov
Romantic Escape - Adult Playhouse with Red Room & Exotic Dungeon
A bedroom with a bed, a ceiling fan, a nightstand, a lamp, and two abstract wall art pieces.

3. Vintage meets Modern 20 min from Chicago.

Vintage meets Modern 20 min from Chicago.
Calumet City
The price is AEDĀ 674
AEDĀ 1,425 total
includes taxes & fees
16 Nov - 17 Nov
Vintage meets Modern 20 min from Chicago.
A motel with a single-story building, a parking lot, and a row of parked cars.

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
The price is AEDĀ 239
AEDĀ 271 total
includes taxes & fees
19 Nov - 20 Nov
1 Queen Bed | Smoking
A modern kitchen with wooden cabinets, stainless steel appliances, and a white countertop island.

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

Modern 3BR w/Deck Ā· 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 AEDĀ 680
AEDĀ 1,608 total
includes taxes & fees
15 Nov - 16 Nov
Modern 3BR w/Deck Ā· Minutes from I-65. Fenced Yard
Let the on-site guest services team help you plan your stay.

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

King Studio. Free Breakfast. Indoor Pool. Gym.
Schererville
The price is AEDĀ 727
AEDĀ 884 total
includes taxes & fees
19 Nov - 20 Nov
King Studio. Free Breakfast. Indoor Pool. Gym.
A kitchen with wooden cabinets, a stainless steel sink, a microwave, and a built-in oven.

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.
The price is AEDĀ 238
AEDĀ 700 total
includes taxes & fees
15 Nov - 16 Nov
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.
The price is AEDĀ 526
AEDĀ 724 total
includes taxes & fees
15 Nov - 16 Nov
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.
The price is AEDĀ 305
AEDĀ 391 total
includes taxes & fees
6 Dec - 7 Dec
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 didnā€™t work for first dayBad mattress and bed in master suite No toilet paper when we arrived"
United States
Allen S.
The price is AEDĀ 635
AEDĀ 1,684 total
includes taxes & fees
1 Dec - 2 Dec
Spacious 3BR Near Hyde Park | Garage + Pets
A modern kitchen with a stainless steel stove, double sink, and white cabinetry.

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
The price is AEDĀ 257
AEDĀ 576 total
includes taxes & fees
15 Nov - 16 Nov
Hyde Park Trendy Studio Apartment in Good Spot
A reception desk with a staff member, a guest, and a child.

12. 1 King Bed | Micfridge

1 King Bed | Micfridge
MERRILLVILLE
8.4 out of 10, Very good, (5 reviews)
The price is AEDĀ 288
AEDĀ 323 total
includes taxes & fees
15 Nov - 16 Nov
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.
The price is AEDĀ 542
AEDĀ 1,197 total
includes taxes & fees
15 Nov - 16 Nov
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Let the on-site guest services team help you plan your stay.

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

2 Bedroom | Free Daily Breakfast. Indoor Pool.
Schererville
The price is AEDĀ 1,372
AEDĀ 1,669 total
includes taxes & fees
18 Nov - 19 Nov
2 Bedroom | Free Daily Breakfast. Indoor Pool.
A hot tub under a covered patio with a wooden deck and outdoor furniture.

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
The price is AEDĀ 1,102
AEDĀ 1,670 total
includes taxes & fees
16 Nov - 17 Nov
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
Let the on-site guest services team help you plan your stay.

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

Free Breakfast. Indoor Pool. Gym. Business Center.
Schererville
The price is AEDĀ 856
AEDĀ 1,041 total
includes taxes & fees
16 Nov - 17 Nov
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.
The price is AEDĀ 334
AEDĀ 767 total
includes taxes & fees
15 Nov - 16 Nov
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.
The price is AEDĀ 279
AEDĀ 840 total
includes taxes & fees
24 Nov - 25 Nov
Conveniently Situated 1BR Apartment
A bedroom with a bed, two wall-mounted abstract art pieces, a window with blinds, 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.
The price is AEDĀ 338
AEDĀ 1,239 total
includes taxes & fees
16 Nov - 17 Nov
Group-Friendly 4BR Hyde Park Retreat Near UChicago
A modern living room with a sofa, a coffee table, and a TV. There is a dining area with a table and chairs. The kitchen has wooden cabinets and a microwave.

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 ā€œfineā€. 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 AEDĀ 360
AEDĀ 899 total
includes taxes & fees
22 Nov - 23 Nov
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.
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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

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.