Glenwood Holiday Rentals

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Our top choices for Glenwood holiday rentals

2.0 star property
The price is NZ$635
includes taxes & fees
3 Jan - 4 Jan 2026
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
9.4 out of 10, Exceptional, (18)
"Nice and cozy place to stay. We enjoyed our secluded area during our time here."
United States
Allison A.
The price is NZ$177
includes taxes & fees
31 Dec - 1 Jan 2026
Beautiful Rustic Cabin for Two!
The price is NZ$723
includes taxes & fees
2 Jan - 3 Jan 2026
Honeycomb Hideout w/ 2 bedrooms
8.6 out of 10, Excellent, (17)
"i had a good time here. the house was great. thank you"
United States
Alvaro C.
The price is NZ$772
includes taxes & fees
31 Dec - 1 Jan 2026
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
9.8 out of 10, Exceptional, (17)
"Wonderful property and nice owners. I definitely recommend and will stay again if I'm ever in the area."
United States
Karen D.
The price is NZ$307
includes taxes & fees
5 Jan - 6 Jan 2026
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Holiday Home in Sauk Village

Your Home Away From Home in Sauk Village
2.0 star property
10.0 out of 10, Exceptional, (1)
"My Experience Was (NOTHING) Short Of Perfect! The Place Is Nice & The Host Was Even Better! I’ll Forsure Be Booking Again! "
United States
Aaron K.
The price is NZ$251
includes taxes & fees
31 Dec - 1 Jan 2026
Your Home Away From Home in Sauk Village
8.8 out of 10, Excellent, (6)
"Enjoyed staying at this place. Definitely will stay again"
United States
Devonta J.
The price is NZ$1,132
includes taxes & fees
1 Jan - 2 Jan 2026
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/
10.0 out of 10, Exceptional, (2)
"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 NZ$4,191
includes taxes & fees
31 Dec - 1 Jan 2026
Spacious 5-Bedroom Golf Course Home Perfect for Getaways & Special Occasions

Apartment in Hyde Park

Modern Studio Near UChicago
9.6 out of 10, Exceptional, (11)
"Clean room and convenient location! "
United States
Gabriela
The price is NZ$260
includes taxes & fees
4 Jan - 5 Jan 2026
Modern Studio Near UChicago
7.6 out of 10, Good, (4)
"Very nice, clean property. Loved the patio area. "
United States
Austin P.
The price is NZ$660
includes taxes & fees
4 Jan - 5 Jan 2026
Comfort & Space for the Whole family! Sleeps 8+

Apartment in Hyde Park

Sleek & Functional 2-Bedroom Apt
9.6 out of 10, Exceptional, (4)
"Nice place for a girls trip weekend. "
United States
Madonna A.
The price is NZ$322
includes taxes & fees
11 Jan - 12 Jan 2026
Sleek & Functional 2-Bedroom Apt

Apartment in Hyde Park

Bright South Hyde Park Studio
10.0 out of 10, Exceptional, (1)
"Comfortable space in a nice neighborhood. I highly recommend."
United States
BiggDas M.
The price is NZ$260
includes taxes & fees
7 Jan - 8 Jan 2026
Bright South Hyde Park Studio
10.0 out of 10, Exceptional, (4)
"Very nice property. Kids loved staying here! "
United States
Sydney D.
The price is NZ$779
includes taxes & fees
5 Jan - 6 Jan 2026
20mins from beach, 10guests/WIFI/1.2 baths/ping pong/pool table/treadmill

Apartment in Hyde Park

Cozy Charm Studio Apt in Chicago
10.0 out of 10, Exceptional, (1)
The price is NZ$260
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Charm Studio Apt in Chicago
2.0 star property
The price is NZ$257
includes taxes & fees
31 Dec - 1 Jan 2026
Soothing studio with AC/Heat in charming Hammond

Apartment in Hyde Park

Bright 1BR Unit in a Prime Spot
10.0 out of 10, Exceptional, (1)
"We had a great stay. Location is in nice neighborhood with walking access to restaurants and university of Chicago. Apartment was clean and as pictured. Would stay again!!"
United States
christine m.
The price is NZ$289
includes taxes & fees
4 Jan - 5 Jan 2026
Bright 1BR Unit in a Prime Spot
10.0 out of 10, Exceptional, (1)
"We stayed in this comfortable, quiet apartment for four weeks when my husband was undergoing radiation treatments for cancer at the University of Chicago Medical Center. It was just what we needed. The location—a block from Lake Michigan with its endless miles of parks and green spaces—was spectacular, and we spent long hours walking our dogs and biking along the lake on the beautifully landscaped walking and biking trails. The apartment itself is well appointed, clean, and blessedly quiet...
United States
Heidi H.
The price is NZ$304
includes taxes & fees
4 Jan - 5 Jan 2026
Contemporary 2BR Apartment in Vibrant Hyde Park
10.0 out of 10, Exceptional, (2)
"Location was just perfect!"
United States
Meg D.
The price is NZ$260
includes taxes & fees
4 Jan - 5 Jan 2026
Studio Unit | Chic + Prime Location
8.4 out of 10, Very good, (5)
"Host was responsive to my questions. Apartment is located in a great area of Hyde Park. "
United States
Lind A.
The price is NZ$304
includes taxes & fees
4 Jan - 5 Jan 2026
Explore Hyde Park: 2BR Apt on Blackstone Ave

Apartment in Hyde Park

Compact Studio for a Relaxed Stay
The price is NZ$260
includes taxes & fees
1 Jan - 2 Jan 2026
Compact Studio for a Relaxed Stay
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 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$147 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?

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!: This holiday home rental outside of Glenwood 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 that 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 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.