Glenwood Holiday Rentals

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Holiday Rentals in Glenwood

Spacious Family Glenwood Estates Home w/ Hot Tub!

Glenwood
9.4 out of 10, Exceptional, (20)
"IT IS A BEAUTIFUL HOME AND WE ENJOY IT WAS A STAYCATION FOR THE SUMMER WITH FAMILY AND FRIENDS WE ENJOYED OURSELVES WE BARBECUE AND WE HAD A WONDERFUL TIME SWIMMING THE OWNER IS NICE..."
United States
Selelar
Spacious Family Glenwood Estates Home w/ Hot Tub!

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

3.0 star property
Harvey
3.8 out of 10, (67)
"Good "
United States
Abel
The price is AU$144
includes taxes & fees
20 Dec - 21 Dec
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Cozy Studio in Hyde Park-Walk to Lake & University

Hyde Park
8.8 out of 10, Excellent, (15)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
United States
Nancy
The price is AU$238
includes taxes & fees
7 Dec - 8 Dec
Cozy Studio in Hyde Park-Walk to Lake & University

LakeHouse

South Shore
9.4 out of 10, Exceptional, (24)
"This was a cute place with a lot of space. Nice backyard with areas to chill. The grand piano is beautiful and in tune!"
United States
Kenna C.
LakeHouse

Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Blue Island
7.6 out of 10, Good, (4)
"Only issue was the water pressure in the bathroom was very very low. "
United States
Derrick M.
The price is AU$528
includes taxes & fees
19 Dec - 20 Dec
Charming 2-bedroom apartment in marvelous Blue Island with WiFi

A Home Away From Home!

Calumet Heights
9.6 out of 10, Exceptional, (14)
"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "
United States
Marchand J.
A Home Away From Home!

Less is more! Pet friendly Tiny Home near Chicago!

Burr Ridge
9.8 out of 10, Exceptional, (34)
"Nice stay. Dog friendly. Great location. Helpful and communicative owners. Well laid out tiny home. "
United States
Laura P.
The price is AU$323
includes taxes & fees
19 Dec - 20 Dec
Less is more! Pet friendly Tiny Home near Chicago!

1-bedroom condo next to Chicago Midway International Airport

Garfield Ridge
10.0 out of 10, Exceptional, (12)
"We were in town for a concert at Soldier Field, and overall tourism activities in Chicago. The bnb was very clean, and as advertised. "
United States
Griffin H.
1-bedroom condo next to Chicago Midway International Airport

House with garage, outdoor dining and basement bar

Auburn Gresham
8.8 out of 10, Excellent, (6)
"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!"
United States
Jessica M.
House with garage, outdoor dining and basement bar

Spacious 3BR House With Firepit & Grill, Near Beach

2.0 star property
Miller Beach
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. "
United States
Kaitlyn
The price is AU$471
includes taxes & fees
7 Dec - 8 Dec
Spacious 3BR House With Firepit & Grill, Near Beach

Penthouse Condo in Chicago featuring Zero Gravity Massage Chair

Bronzeville
10.0 out of 10, Exceptional, (25)
"Perfect for what we needed"
United States
Richard G.
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair

Modern Studio Near UChicago

Hyde Park
9.4 out of 10, Exceptional, (10)
"Clean room and convenient location! "
United States
Gabriela
The price is AU$238
includes taxes & fees
7 Dec - 8 Dec
Modern Studio Near UChicago

Modern 1BR in Historic HydePark

Hyde Park
8.2 out of 10, Very good, (12)
"Comfortable space. All the necessary amenities. Extremely walkable to everything.Will stay again. "
United States
jasmine h.
The price is AU$251
includes taxes & fees
9 Dec - 10 Dec
Modern 1BR in Historic HydePark

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

Miller Beach
9.2 out of 10, Wonderful, (63)
"Very beautiful house. Just enough space for everyone to spread out. The walk to the beach was a little hike, but the beach felt private and was well worth it. "
United States
Sherri E.
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

Casa Blanca in Miller Beach!

Miller Beach
9.8 out of 10, Exceptional, (75)
"Fantastic house and great location, easily walkable to the beach and park. Everyone had a great time. "
United States
Joseph K.
Casa Blanca in Miller Beach!

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

South Chicago
10.0 out of 10, Exceptional, (4)
"Great place to stay host was very communicative which made the stay a lot easier highly recommend "
United States
Alcario B.
South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly

Toca Bella ~ 7mins to Downtown

Bronzeville
9.8 out of 10, Exceptional, (19)
"We had a good time here!"
United States
Shane C.
Toca Bella ~ 7mins to Downtown

Lux Home in Chicago 7mins Downtown

Bronzeville
9.8 out of 10, Exceptional, (28)
"Larry was super responsive, the property was spotless, the location perfect. Our group of friends loved it. We will be back! "
United States
Kyle B.
Lux Home in Chicago 7mins Downtown

Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions

Bronzeville
8.4 out of 10, Very good, (11)
"We found the place to be extremly clean and comfortable . Its really close to down town and great resturants. Definetly would book again ."
United States
sean r.
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions

Relax & Unwind in This Comfortable 3BR Unit

Calumet Park
10.0 out of 10, Exceptional, (5)
"Lakeia was very accommodating throughout our stay."
United States
Timothy K.
The price is AU$503
includes taxes & fees
18 Dec - 19 Dec
Relax & Unwind in This Comfortable 3BR Unit
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$144 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?

LakeHouse: This holiday home rental outside of Glenwood is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.