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Glenwood Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Glenwood vacation rentals

A building with a covered entrance, a parking lot, and a tree.

1. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Harvey
10.0 out of 10, Exceptional, (2 reviews)
"Wifi worked well enough for me to get some work done without interruptions."
United States
Anonymous traveler
$67 nightly
The price is $75
Oct 1 - Oct 2
Total with taxes and fees
1 Queen Bed | Smoking
A single-story building with a porch, a brick facade, and a number '531' on the front.

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, (4 reviews)
"Clean, comfortable, quiet, excellent place to stay"
United States
Aaron S.
$185 nightly
The price is $196
Sep 28 - Sep 29
Total with taxes and fees
Quaint Studio Unit in fantastic Beecher with refreshing AC
A compact kitchen with a sink, a microwave, a refrigerator, a small table with stools, and a ceiling fan.

3. Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.4 out of 10, Very good, (35 reviews)
"Great stay. Clean place. Happy to come back."
United States
David F.
$103 nightly
The price is $115
Oct 4 - Oct 5
Total with taxes and fees
Beautiful Rustic Cabin for Two!
A hotel lobby with a stone fireplace, wooden flooring, and a seating area with chairs and a sofa.

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

King Studio. Free Breakfast. Indoor Pool. Gym.
Schererville
$209 nightly
The price is $234
Oct 22 - Oct 23
Total with taxes and fees
King Studio. Free Breakfast. Indoor Pool. Gym.
A living room with a brown sofa, a coffee table, and a patterned rug. There is a staircase leading to another room.

5. 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, (28 reviews)
"Very spacious accommodations in a very nice neighborhood. Convenient to food and shopping. Great value for the cost. "
United States
Greg S.
$404 nightly
The price is $433
Sep 28 - Sep 29
Total with taxes and fees
Spacious 3br home near Chicago, fenced yard for pets
A hotel lobby with a stone fireplace, wooden flooring, and a seating area with chairs and a sofa.

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

Free Breakfast. Indoor Pool. Gym. Business Center.
Schererville
$239 nightly
The price is $268
Oct 22 - Oct 23
Total with taxes and fees
Free Breakfast. Indoor Pool. Gym. Business Center.
A dining area with a wooden table and chairs, a ceiling fan, and a couch.

7. 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, (10 reviews)
"Town was quite walkable which was fun. Teddy is very nice. "
United States
India L.
$303 nightly
The price is $324
Sep 28 - Sep 29
Total with taxes and fees
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
A living room with a blue sectional sofa, a glass coffee table, and yellow curtains.

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

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Calumet Park
8.8 out of 10, Excellent, (12 reviews)
"Cozy home, perfect for our stay. Highly recommend."
United States
Alisa G.
$240 nightly
The price is $256
Oct 27 - Oct 28
Total with taxes and fees
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
A bedroom with a bed, a nightstand, a wall-mounted lamp, and a plant.

9. Romantic Escape - Adult Playhouse with Exotic Dungeon

Romantic Escape - Adult Playhouse with Exotic Dungeon
South Holland
8.8 out of 10, Excellent, (13 reviews)
"enjoyed my stay cant wait to book again "
United States
Anonymous traveler
$427 nightly
The price is $457
Sep 28 - Sep 29
Total with taxes and fees
Romantic Escape - Adult Playhouse with Exotic Dungeon
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, (35 reviews)
"I had a fun stay "
United States
Jusu K.
$183 nightly
The price is $205
Oct 4 - Oct 5
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A bathroom with a toilet, sink, and radiator.

11. Perfect 1BR Spot near Attractions

Perfect 1BR Spot near Attractions
Hyde Park
$220 nightly
The price is $238
Sep 28 - Sep 29
Total with taxes and fees
Perfect 1BR Spot near Attractions
A compact RV interior with a kitchenette, seating area, and a small dining table.

12. 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
$210 nightly
The price is $225
Oct 1 - Oct 2
Total with taxes and fees
Beautiful 32' RV located in Chicago's South suburb - A unique experience!
A living room with a brick fireplace, a television mounted above it, and a dining area with a table and chairs.

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
$346 nightly
The price is $388
Sep 28 - Sep 29
Total with taxes and fees
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
A dining area with a black table set for four, surrounded by chairs. A vase with dried flowers and a candle holder are on the table.

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.
$568 nightly
The price is $608
Sep 28 - Sep 29
Total with taxes and fees
3-bedroom house in lovely Matteson with cool AC breeze
A modern kitchen with a stainless steel refrigerator, a wooden floor, and a beige chair with a cushion.

15. 2MI to Obama Center - Pet-Friendly near UOC!

2MI to Obama Center - Pet-Friendly near UOC!
Woodlawn
9.6 out of 10, Exceptional, (4 reviews)
"Great host very accommodating."
United States
Kali P.
$269 nightly
The price is $332
Oct 1 - Oct 2
Total with taxes and fees
2MI to Obama Center - Pet-Friendly near UOC!
A modern kitchen with a stainless steel refrigerator, a stove, and white cabinets.

16. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park
$147 nightly
The price is $163
Sep 29 - Sep 30
Total with taxes and fees
Hyde Park Trendy Studio Apartment in Good Spot

17. Hyde Park 1BR Apt | Easy & Fully Equipped Stay

Hyde Park 1BR Apt | Easy & Fully Equipped Stay
Hyde Park
$239 nightly
The price is $261
Sep 30 - Oct 1
Total with taxes and fees
Hyde Park 1BR Apt | Easy & Fully Equipped Stay
A hotel room with a bed, a TV mounted on the wall, a desk with a chair, and a door.

18. Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.

Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
Hickory Hills
9.6 out of 10, Exceptional, (8 reviews)
"Easy to locate shopping mall close by friendly neighborhood and safe. when you're looking at stay away from home that's where you want to be."
United States
Ralph
$183 nightly
The price is $196
Oct 5 - Oct 6
Total with taxes and fees
Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
A modern living room with a grey sofa, a coffee table, and a view of the outside through large windows.

19. Conveniently Situated 1BR Apartment

Conveniently Situated 1BR Apartment
Hyde Park
$215 nightly
The price is $233
Sep 29 - Sep 30
Total with taxes and fees
Conveniently Situated 1BR Apartment

20. Trendy Studio Apartment in Chicago

Trendy Studio Apartment in Chicago
Hyde Park
$196 nightly
The price is $212
Sep 28 - Sep 29
Total with taxes and fees
Trendy Studio Apartment in 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.
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Top Glenwood Hotel Reviews

Fairfield Inn and Suites by Marriott Chicago Midway Airport

Fairfield Inn and Suites by Marriott Chicago Midway Airport

10/10 Excellent
"Will be going back"
Carrie 1-night trip
Posted 2 hours ago
Fairfield Inn and Suites by Marriott Chicago Midway Airport

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 $115 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.