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Glenwood Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Glenwood holiday rentals

Interior

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

Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Merrilville
6.0 out of 10, (1 review)
"This is not a place to stay with small children; glad mine are grown for this stay. Also, the host really needs to have people they know stay there a bit to see what guests are really looking for. This property really felt like someone is just trying to make money and they don't really care about the people using the property. One of our beds was broken, there were limited furnishings and the tv in the living room was not user friendly at all. I would not recommend this property for any long...
United States
Paula H.
The price is HK$1,623
HK$3,757 total
includes taxes & fees
28 Sept - 29 Sept
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Private kitchen

2. Charming & Cozy Getaway - A Heroic Stay Awaits!

Charming & Cozy Getaway - A Heroic Stay Awaits!
Homewood
10.0 out of 10, Exceptional, (20 reviews)
"We had such a lovely stay. It was cute, quaint, and the perfect place to spend Mother’s Day with my mother. The space was cozy, clean, and had such a peaceful charm to it. We truly enjoyed our time here and would absolutely stay again!"
United States
Nikki B.
The price is HK$1,496
HK$3,394 total
includes taxes & fees
15 Sept - 16 Sept
Charming & Cozy Getaway - A Heroic Stay Awaits!
Interior

3. 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 HK$3,088
HK$3,951 total
includes taxes & fees
6 Sept - 7 Sept
King Bed Suite | Indoor Pool. Free Breakfast.
Interior

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

King Studio. Free Breakfast. Indoor Pool. Gym.
Schererville
The price is HK$1,521
HK$1,949 total
includes taxes & fees
6 Sept - 7 Sept
King Studio. Free Breakfast. Indoor Pool. Gym.
Property grounds

5. 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, (34 reviews)
"I had a fun stay "
United States
Jusu K.
The price is HK$1,122
HK$1,634 total
includes taxes & fees
30 Aug - 31 Aug
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Living area

6. 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, (7 reviews)
The price is HK$2,352
HK$3,766 total
includes taxes & fees
1 Sept - 2 Sept
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
Interior

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

Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Blue Island
7.0 out of 10, Good, (9 reviews)
"Town was quite walkable which was fun. Teddy is very nice. "
United States
India L.
The price is HK$1,157
HK$2,714 total
includes taxes & fees
29 Aug - 30 Aug
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Dining

8. 3-bedroom house in lovely Matteson with cool AC breeze

3-bedroom house in lovely Matteson with cool AC breeze
Matteson
10.0 out of 10, Exceptional, (1 review)
"clean, comfortable, hosts very responsive to communications, neighborhood felt safe, perfect location for our stay to attend sectionals NTRP tennis tournament at HF Racquet and Fitness Club"
United States
Susan H.
The price is HK$2,642
HK$5,124 total
includes taxes & fees
28 Sept - 29 Sept
3-bedroom house in lovely Matteson with cool AC breeze
Living area

9. Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Calumet Park
9.2 out of 10, Wonderful, (11 reviews)
"Cozy home, perfect for our stay. Highly recommend."
United States
Alisa G.
The price is HK$847
HK$1,996 total
includes taxes & fees
15 Sept - 16 Sept
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Living area

10. Spacious 3br home near Chicago, fenced yard for pets

Spacious 3br home near Chicago, fenced yard for pets
Richton Park
9.0 out of 10, Wonderful, (27 reviews)
"Very spacious accommodations in a very nice neighborhood. Convenient to food and shopping. Great value for the cost. "
United States
Greg S.
The price is HK$1,580
HK$3,594 total
includes taxes & fees
7 Sept - 8 Sept
Spacious 3br home near Chicago, fenced yard for pets
Interior

11. Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake

Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake
Cedar Lake
10.0 out of 10, Exceptional, (25 reviews)
"Host was great/ home was great! "
United States
Darcey W.
The price is HK$2,941
HK$5,621 total
includes taxes & fees
7 Sept - 8 Sept
Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake
Exterior

12. Spacious 5-Bedroom Golf Course Home for Getaways

Spacious 5-Bedroom Golf Course Home for Getaways
Merrillville
10.0 out of 10, Exceptional, (7 reviews)
"Huge property with many sleeping options and multiple bathrooms. Outside patio area is great for hosting and late night fires. Great spot for 4 or 8 guys to stay and play at Innsbrook CC."
United States
Jon R.
The price is HK$8,466
HK$10,833 total
includes taxes & fees
30 Aug - 31 Aug
Spacious 5-Bedroom Golf Course Home for Getaways
Private kitchen

13. *The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.4 out of 10, Exceptional, (63 reviews)
"Checking in was easy, the place is as advertised, communication was easy as well, had no problems, will be staying there again. "
United States
Joe M.
The price is HK$1,524
HK$3,341 total
includes taxes & fees
30 Aug - 31 Aug
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Interior

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

2 Bedroom | Free Daily Breakfast. Indoor Pool.
Schererville
The price is HK$3,167
HK$4,021 total
includes taxes & fees
27 Sept - 28 Sept
2 Bedroom | Free Daily Breakfast. Indoor Pool.
Private kitchen

15. The Grand Gathering Place -Making Forever Memories Near Chicago & Hard Rock

The Grand Gathering Place -Making Forever Memories Near Chicago & Hard Rock
Merrillville
The price is HK$3,238
HK$7,103 total
includes taxes & fees
30 Aug - 31 Aug
The Grand Gathering Place -Making Forever Memories Near Chicago & Hard Rock
Interior

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

Free Breakfast. Indoor Pool. Gym. Business Center.
Schererville
The price is HK$1,834
HK$2,353 total
includes taxes & fees
6 Sept - 7 Sept
Free Breakfast. Indoor Pool. Gym. Business Center.
Interior

17. Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.6 out of 10, Excellent, (32 reviews)
"Easy to find little cabin in Griffith"
United States
Allison R.
The price is HK$651
HK$904 total
includes taxes & fees
1 Sept - 2 Sept
Beautiful Rustic Cabin for Two!
Living area

18. Cedar Lake 4br Home For 8 W/ Lake Views 4 Bedroom Home

Cedar Lake 4br Home For 8 W/ Lake Views 4 Bedroom Home
3.0 star property
Cedar Lake
The price is HK$1,892
HK$4,916 total
includes taxes & fees
10 Sept - 11 Sept
Cedar Lake 4br Home For 8 W/ Lake Views 4 Bedroom Home
Room

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
The price is HK$1,920
HK$2,734 total
includes taxes & fees
14 Sept - 15 Sept
Beautifully furnished one bedroom loft located in Chicago's South side suburb
Interior

20. La Petite • Piano • Serene Organic • Long Stays

La Petite • Piano • Serene Organic • Long Stays
Merrillville
The price is HK$2,487
HK$3,189 total
includes taxes & fees
1 Sept - 2 Sept
La Petite • Piano • Serene Organic • Long Stays
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

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent
"We arrived super late and the front desk was exceptional! Amazing stay! 10/10 will return to this hotel on our next visit"
Joyce 2-night trip
Posted 5 hours ago
Holiday Inn Chicago – Midway Airport S by IHG

Find out more about Glenwood

Search for holiday rentals in Glenwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Glenwood using one of the methods below:

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Look no further and take a look at our great range of rental properties in Glenwood!

Frequently asked questions

Are there holiday rentals in Glenwood?

Yes, there are holiday rentals close to the most popular sights in Glenwood, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Glenwood has to offer?

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!: This holiday home rental outside of Glenwood is on a lake, and equipped with air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 wider area.

What are holiday rentals like in Glenwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Glenwood. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a family getaway.