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Glenwood Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Glenwood vacation 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 ￥29,104
￥70,655 total
includes taxes & fees
Aug 17 - Aug 18
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Exterior

2. 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, (3 reviews)
"Kind hosts will help out with any needs. Quiet area, nice parking space."
United States
Garth T.
The price is ￥10,194
￥31,313 total
includes taxes & fees
Aug 6 - Aug 7
Quaint Studio Unit in fantastic Beecher with refreshing AC
Room

3. Designer 3BR Near Beach & Obama Center

Designer 3BR Near Beach & Obama Center
Woodlawn
The price is ￥81,555
￥160,970 total
includes taxes & fees
Aug 10 - Aug 11
Designer 3BR Near Beach & Obama Center
Interior

4. Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.6 out of 10, Excellent, (31 reviews)
"Easy to find little cabin in Griffith"
United States
Allison R.
The price is ￥13,058
￥18,149 total
includes taxes & fees
Aug 5 - Aug 6
Beautiful Rustic Cabin for Two!
Interior

5. 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 ￥61,512
￥78,761 total
includes taxes & fees
Aug 19 - Aug 20
King Bed Suite | Indoor Pool. Free Breakfast.
Dining

6. A Dream Home in Chicagoland

A Dream Home in Chicagoland
Homewood
6.0 out of 10, (6 reviews)
"Beautiful neighborhood. Property was just as described. Host was very accommodating to our needs. Quickly responded to me. Would highly recommend. Thank you again "
United States
Jennifer C.
The price is ￥31,602
￥74,705 total
includes taxes & fees
Aug 25 - Aug 26
A Dream Home in Chicagoland
Exterior

7. Spacious 5-bedroom house in charming Orland Park with AC

Spacious 5-bedroom house in charming Orland Park with AC
Orland Park
The price is ￥169,906
￥228,398 total
includes taxes & fees
Aug 17 - Aug 18
Spacious 5-bedroom house in charming Orland Park with AC
Smart TV

8. 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 ￥35,397
￥75,904 total
includes taxes & fees
Aug 17 - Aug 18
Spacious 3br home near Chicago, fenced yard for pets
Interior

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

La Petite • Piano • Serene Organic • Long Stays
Merrillville
The price is ￥61,622
￥77,360 total
includes taxes & fees
Aug 25 - Aug 26
La Petite • Piano • Serene Organic • Long Stays
Interior

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

King Studio. Free Breakfast. Indoor Pool. Gym.
Schererville
The price is ￥26,853
￥34,127 total
includes taxes & fees
Sep 3 - Sep 4
King Studio. Free Breakfast. Indoor Pool. Gym.
Coffee/tea maker, fridge, microwave, oven

11. *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 ￥31,464
￥65,168 total
includes taxes & fees
Aug 9 - Aug 10
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
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)
"Great House, and everything is brand new! Loved the sheets and the towels, and the beds were all super comfy. The outdoor fire pit was a nice touch and made our night a great experience. "
United States
Jim A.
The price is ￥212,382
￥271,698 total
includes taxes & fees
Aug 9 - Aug 10
Spacious 5-Bedroom Golf Course Home for Getaways
Smart TV, fireplace

13. 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 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 ￥47,196
￥74,532 total
includes taxes & fees
Aug 9 - Aug 10
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
Dining

14. 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 ￥54,747
￥104,684 total
includes taxes & fees
Sep 1 - Sep 2
3-bedroom house in lovely Matteson with cool AC breeze
Interior

15. 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)
"Appreciate the hospitality and the space !"
United States
Kaydon D.
The price is ￥23,220
￥54,294 total
includes taxes & fees
Aug 10 - Aug 11
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Property grounds

16. 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, (28 reviews)
"I had a fun stay "
United States
Jusu K.
The price is ￥25,014
￥34,887 total
includes taxes & fees
Aug 20 - Aug 21
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
House, 4 Bedrooms | Dining

17. 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 ￥39,054
￥99,877 total
includes taxes & fees
Aug 5 - Aug 6
Cedar Lake 4br Home For 8 W/ Lake Views 4 Bedroom Home
Living area

18. Designer Home | Steps to the Obama Center & Beach

Designer Home | Steps to the Obama Center & Beach
Woodlawn
The price is ￥84,953
￥197,243 total
includes taxes & fees
Aug 9 - Aug 10
Designer Home | Steps to the Obama Center & Beach
Smart TV, fireplace, video games, DVD player

19. 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 ￥16,991
￥39,551 total
includes taxes & fees
Aug 17 - Aug 18
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Game room

20. W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
Brighton Park
9.2 out of 10, Wonderful, (10 reviews)
"It was great it had the basic amenities for a family to enjoy the stay"
United States
Damary T.
The price is ￥12,601
￥43,272 total
includes taxes & fees
Aug 10 - Aug 11
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
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

Carlton Inn Midway

Carlton Inn Midway

8/10 Good
"Room clean and air worked. Lots of plugs. Shuttle to airport nice, clean and on time. Didn’t eat breakfast there so no comment on that. Staff very friendly. Bathroom small but appears recently updated and nice. Overall room very dated but fit price for the area. Cons: no phone to contact front desk/ one set of sheets stained / pillows very hard/ WiFi only worked for one person/ holes in walls in several places/ no hot water in shower/ cheap towels / only 3 hangers. "
Christine 1-night trip
Posted 14 hours ago
Carlton Inn Midway

Find out more about Glenwood

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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?

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!: Visitors like this Glenwood vacation home rental. It 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 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 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.