Glenwood Holiday Rentals

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Holiday Rentals in Glenwood

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

3.0 star property
3.8 out of 10, (62)
"Good "
The price is NZ$166
includes taxes & fees
1 Oct - 2 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, (6)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
The price is NZ$307
includes taxes & fees
6 Oct - 7 Oct
Cozy Studio in Hyde Park-Walk to Lake & University

Modern Studio Near UChicago

10.0 out of 10, Exceptional, (3)
"Great location. Clean, nicely decorated room. "
The price is NZ$333
includes taxes & fees
29 Sept - 30 Sept
Modern Studio Near UChicago

A Home Away From Home!

9.6 out of 10, Exceptional, (11)
"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "
A Home Away From Home!

Charming 2-bedroom apartment in marvelous Blue Island with WiFi

6.8 out of 10, (3)
"Only issue was the water pressure in the bathroom was very very low. "
The price is NZ$600
includes taxes & fees
4 Oct - 5 Oct
Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Modern 1BR in Historic HydePark

10.0 out of 10, Exceptional, (2)
"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 NZ$324
includes taxes & fees
1 Oct - 2 Oct
Modern 1BR in Historic HydePark

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
9.0 out of 10, Wonderful, (12)
"Nice property easy check in. Experience was amazing. Thank you again "
The price is NZ$787
includes taxes & fees
6 Oct - 7 Oct
Spacious 3br home near Chicago, fenced yard for pets

Wildwood Camper: Grill, Firepit & Pets OK

2.0 star property
Wildwood Camper: Grill, Firepit & Pets OK

LakeHouse

9.4 out of 10, Exceptional, (21)
"Everything was perfect with the property and the host even came to help right away when we had one issue with the lights."
LakeHouse

Cheerful 4 bedroom smart home w/ indoor fireplace

8.0 out of 10, Very good, (16)
"The property is shown accurately in the photos. It was pretty clean. Its centrally located to eateries and shopping. Need more pillows, had no window coverings and had to contact tbe host for the correct code to the door.Would stay again."
Cheerful 4 bedroom smart home w/ indoor fireplace

Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

9.2 out of 10, Wonderful, (62)
"With the exception of one bathroom being out of service and nearby location being a little sketchy everything else was a great place at this beautiful house."
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, (25)
"Could not have picked a better place to stay. Location was grea,fenced in area fir the dogs was perfecy. "
The price is NZ$362
includes taxes & fees
29 Sept - 30 Sept
Less is more! Pet friendly Tiny Home near Chicago!

Explore Hyde Park: 2BR Apt on Blackstone Ave

The price is NZ$373
includes taxes & fees
1 Oct - 2 Oct
Explore Hyde Park: 2BR Apt on Blackstone Ave

House with garage, outdoor dining and basement bar

7.4 out of 10, Good, (3)
"Property was very clean, warm and welcoming. Beds were comfortable. Property manager was great at checking in, and readily available. The place smells great! Everything is new! We will definitely book again!"
House with garage, outdoor dining and basement bar

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 NZ$551
includes taxes & fees
1 Oct - 2 Oct
Spacious 3BR House With Firepit & Grill, Near Beach

Comfortable Condo in the Heart of Bronzeville by RedAwning

7.2 out of 10, Good, (5)
"There was confusion with VRBO regarding our arrival date, no fault of the property owner. They made arrangements to clean the unit and provide lunch for our group while we waited and offered a second night free for the inconvenience. Highly recommend. Property owner went above and beyond!"
Comfortable Condo in the Heart of Bronzeville by RedAwning

Beautiful Rustic Cabin for Two!

9.8 out of 10, Exceptional, (16)
"We had a very nice stay. The cabin was quite cozy and comfortable."
Beautiful Rustic Cabin for Two!

South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly

10.0 out of 10, Exceptional, (1)
"Clean apartment and great communication with host. Fixed any small problems very quickly. "
South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly

Pet Friendly Brick House

The price is NZ$621
includes taxes & fees
28 Sept - 29 Sept
Pet Friendly Brick House

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

8.4 out of 10, Very good, (38)
"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
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

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 favorite 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 depends 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 NZ$166 per night. Entering your travel dates in the search wizard you might find 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.