Glenwood Holiday Rentals

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Holiday Rentals in Glenwood

Spacious Family Glenwood Estates Home w/ Hot Tub!
9.4 out of 10, Exceptional, (19)
"The house was really great. Very clean and very nice. Spacious and well stocked. The backyard was great especially the pool because it was so hot outside. I give this rental property a 10/10 and would definitely recommend to others because it was so cozy"
Spacious Family Glenwood Estates Home w/ Hot Tub!
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
3.0 star property
3.8 out of 10, (63)
"Good "
The price is AU$147
includes taxes & fees
20 Oct - 21 Oct
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Cozy Studio in Hyde Park-Walk to Lake & University
9.0 out of 10, Wonderful, (7)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
The price is AU$275
includes taxes & fees
15 Oct - 16 Oct
Cozy Studio in Hyde Park-Walk to Lake & University
Modern Studio Near UChicago
10.0 out of 10, Exceptional, (6)
The price is AU$275
includes taxes & fees
15 Oct - 16 Oct
Modern Studio Near UChicago
Modern 1BR in Historic HydePark
7.6 out of 10, Good, (4)
"The location couldn't be beat. The beds were super comfortable and the room was perfect for my husband and I. We'll definitely stay here again!"
The price is AU$292
includes taxes & fees
26 Oct - 27 Oct
Modern 1BR in Historic HydePark
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
7.6 out of 10, Good, (4)
"Only issue was the water pressure in the bathroom was very very low. "
The price is AU$537
includes taxes & fees
17 Oct - 18 Oct
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
A Home Away From Home!
9.6 out of 10, Exceptional, (12)
"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "
A Home Away From Home!
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park
9.2 out of 10, Wonderful, (62)
"We had a great experience at the lake house. Everything was in great condition with all the amenities we could have asked for. Plenty of space and plenty of rooms for family of 12. The master bedroom was absolutely breathtaking. The host company was very responsive and help to make our stay comfortable. Would highly recommend! "
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park
Less is more! Pet friendly Tiny Home near Chicago!
9.8 out of 10, Exceptional, (27)
"It was a cute and quiet and private area really nice and relaxing experience"
The price is AU$228
includes taxes & fees
20 Oct - 21 Oct
Less is more! Pet friendly Tiny Home near Chicago!
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
8.4 out of 10, Very good, (40)
"This place offers very clean private secure property that makes you feel like your up in Michigan with the ease and access of the local shopping and food options and Lake Michigan beaches walking distance from the home.. oh and throw in a hot tub for relaxation .. this place offers everything you need if your staying in the area."
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Bright & Cozy 1BR Near UChicago
10.0 out of 10, Exceptional, (1)
"This stay was very pleasant. The place was clean and the area safe. They provided two towel sets, dishware set, pans, utensils, cups, mugs, and coffee. Also a travel crib. I will definitely be back to show my littles the city. The apartment is located on the third floor. However the elevator is out of service. So if you’re handicapped I would not recommend this place. We however didn’t mind the haul upstairs three flights. It was very short and very few steps. We had packed light as we only...
The price is AU$297
includes taxes & fees
20 Oct - 21 Oct
Bright & Cozy 1BR Near UChicago
Charming Full Modern Home+Free Parking+Fast Wi-Fi & Centrally located
4.0 out of 10, (1)
"The house was normal. No major issues. We were told there would be a washer and dryer, but it did not have one accessible. It appeared to be in the garage, but the garage was locked and no one would respond.Our check in was 3:00 pm on Friday, at noon on Friday the company managing the property tetzy? told me that I needed to provide everyones first and last name and their cell phone. Seemed strange. 1. Why wait until the last minute and 2. Why do you need everyone's contact? I saw this request,...
Charming Full Modern Home+Free Parking+Fast Wi-Fi & Centrally located
LakeHouse
9.4 out of 10, Exceptional, (22)
"Everything was perfect with the property and the host even came to help right away when we had one issue with the lights."
LakeHouse
Spacious 3BR House With Firepit & Grill, Near Beach
2.0 star property
5.0 out of 10, (2)
"It is a beautiful residence. This is a relatively new residence, evidenced by all the brand new with tags furniture, lamps, appliances etc. No internet or cable, which was sort of a downer. Did not get the code until 15 minutes after check in time. No coffee or silverware. We only found one spoon. "
The price is AU$588
includes taxes & fees
12 Nov - 13 Nov
Spacious 3BR House With Firepit & Grill, Near Beach
The Chic Urban Oasis Near the Lake!
8.0 out of 10, Very good, (7)
"Everything about the host and stay was amazing this will be my go to spot for my family and me"
The Chic Urban Oasis Near the Lake!
Cozy Charm Studio Apt in Chicago
10.0 out of 10, Exceptional, (1)
The price is AU$275
includes taxes & fees
15 Oct - 16 Oct
Cozy Charm Studio Apt in Chicago
Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake
2.0 star property
10.0 out of 10, Exceptional, (15)
"Fantastic!!!! Was a great getaway for my guys while they worked on a project up around there! "
The price is AU$829
includes taxes & fees
15 Oct - 16 Oct
Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake
Stay, Relax & Explore Chicago
9.0 out of 10, Wonderful, (2)
"Very nice property!"
Stay, Relax & Explore Chicago
Come experience The Lake Shore!
10.0 out of 10, Exceptional, (3)
"Very spacious, quiet and comfortable. Great place to stay!"
Come experience The Lake Shore!
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
8.0 out of 10, Very good, (10)
"Came for a concert, enjoyed sight seeing. Apartment was a nice place to stay."
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
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

Find out more about Glenwood

Everything you need to know about Glenwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Glenwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Glenwood holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Glenwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Glenwood holiday rentals we have selected for you start as low as AU$147 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Glenwood rentals

At Expedia, we put the best Glenwood holiday 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 holiday.

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 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?

A Home Away From Home!: This holiday home rental outside of Glenwood offers a fireplace, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, 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 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.