Holiday Rentals in Glenwood

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Holiday Rentals in Glenwood

Spacious Family Glenwood Estates Home w/ Hot Tub!

9.4 out of 10, Exceptional, (14)
"Place was perfect! I grew up in the suburbs of Chicago and wanted to come back to honor my grandmother's 90th birthday. This place was perfect. It had a piano and the pastor was able to serinate her in playing church hymnals. Of course, her famiy, fch family, family and friends were all able to show"
Spacious Family Glenwood Estates Home w/ Hot Tub!

Comfort Inn Chicago Wind Creek Casino

2.5 star property
4.0 out of 10, (7)
"The staff was polite and friendly! I didn't care that they were apparently under construction and I didn't are much for that "
The price is €97
includes taxes & fees
16 Mar - 17 Mar
Comfort Inn Chicago Wind Creek Casino

The Vibe Headquarters

2.0 star property
9.0 out of 10, Wonderful, (2)
"Very clean and cozy! Home away from home!"
The Vibe Headquarters

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (19)
"This was perfect for our needs. Great location, comfortable and clean. I'm sure we'll be back."
Cozy Home Sweet Homewood.

Modern Condo-Obama & University of Chicago Area

9.2 out of 10, Wonderful, (5)
"Property was very well kept and accommodated us well. We didn’t spend much time there as we were out most of the day but it was nice to come back to a place like this."
Modern Condo-Obama & University of Chicago Area

Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum

9.6 out of 10, Exceptional, (69)
"Nice place, not alot of parking "
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum

The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

9.6 out of 10, Exceptional, (47)
"Nice property with 3 bedrooms & a fenced in back yard. Great communication with owner. "
The price is €330
includes taxes & fees
31 Mar - 1 Apr
The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

Luxury Chicago TH is a 10-minute drive to DWTN, perfect for city access RSV Now

9.4 out of 10, Exceptional, (10)
"The home is nice."
Luxury Chicago TH is a 10-minute drive to DWTN, perfect for city access RSV Now

Private Home Awaits

The price is €411
includes taxes & fees
16 Mar - 17 Mar
Private Home Awaits

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

9.0 out of 10, Wonderful, (7)
"To say we enjoyed our stay, is an understatement. My sister was able you bring in her 21st birthday properly along with her close friends. It was so spacious, everyone had their own area to hang out. The master bedroom is gorgeous, a real selling point. My only regret is that it is winter && we were unable to enjoy the backyard. Our host was amazing and very helpful during the whole process, any question was promptly answered. If you’re looking for a nice place in a quiet area, don’t hesitate to...
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

Less is more! Pet friendly Tiny Home near Chicago!

10.0 out of 10, Exceptional, (10)
"Could not have picked a better place to stay. Location was grea,fenced in area fir the dogs was perfecy. "
The price is €180
includes taxes & fees
16 Mar - 17 Mar
Less is more! Pet friendly Tiny Home near Chicago!

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

8.2 out of 10, Very good, (34)
"The yard is awesome, of course the hot tub at the top of the hill was the best, and we enjoyed the firepit as well. The house was a tidy little cottage at which we enjoyed our stay. It’s within a short walk to the National Park and downtown Miller Beach. The neighborhood is fine, pretty secluded, and still close to most attractions."
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

Beautiful Rustic Cabin for Two!

10.0 out of 10, Exceptional, (2)
"This place was very cozy and amazing. Daniel was the greatest host and I would definitely stay here on future trips"
The price is €88
includes taxes & fees
21 Mar - 22 Mar
Beautiful Rustic Cabin for Two!

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
9.2 out of 10, Wonderful, (5)
"As advertised. We enjoyed our stay. Thank you!"
The price is €302
includes taxes & fees
24 Mar - 25 Mar
Spacious 3br home near Chicago, fenced yard for pets

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

8.8 out of 10, Excellent, (5)
"The place was well maintained and very clean with no issues and the host was great and fast to respond."
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

Tranquil 2-bedroom condo in charming Chicago with WiFi, AC

Tranquil 2-bedroom condo in charming Chicago with WiFi, AC

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

9.2 out of 10, Wonderful, (57)
"We recently rented this home for our church's women's fall spiritual retreat. This stay for our group of 21 ladies was more than we expected. We chose this home for its size, proximity to the shore, and great accommodations. Upon our arrival we were pleasantly surprised to find the house had been recently updated. It was absolutely beautiful...bright, serene, and peaceful! The cleanliness of the home was great! The attention to detail was appreciated. I love a well stocked kitchen and this...
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

Charming and spacious 3-bedroom townhome with WiFi and amenities in Gary

7.0 out of 10, Good, (2)
"The property itself was ver clean just an older house. Very clean! The neighborhood was a little questionable for families who have never travelex to that area from a rural area. The stay was good and worked for what we needed!"
The price is €263
includes taxes & fees
4 Apr - 5 Apr
Charming and spacious 3-bedroom townhome with WiFi and amenities in Gary

Cozy 1-bedroom apartment with WiFi, AC in gorgeous Chicago

2.0 star property
9.6 out of 10, Exceptional, (5)
"I stayed at this rental during my birthday trip to Chicago, and overall, it was a great experience. Communication with the host was absolutely on point—responsive, accommodating, and very helpful. My plane landed late, and I arrived at the rental around 1 a.m. They made everything seamless, which I appreciated. This was my first visit to Chicago, so arriving late and staying in a basement apartment initially felt a little sketchy, but once I got settled, I felt completely safe. The place had...
Cozy 1-bedroom apartment with WiFi, AC in gorgeous Chicago

Cozy 2- bedroom w/ patio mins from Midway Airport

9.8 out of 10, Exceptional, (10)
"We very much enjoyed our long weekend here. The kitchen items were somewhat limited, but we managed to cook a lovely breakfast while there and enjoyed several meals at the house. It was a warm and welcoming environment, and we’d gladly stay again. Street parking was somewhat of a challenge when we arrived late at night, but it all worked out."
Cozy 2- bedroom w/ patio mins from Midway Airport
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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Other types of properties in Glenwood you may be interested in

Hilton Chicago/Oak Lawn

3.5 star property
8.0 out of 10, Very good, (1009)
"."
The price is €117
includes taxes & fees
26 Mar - 27 Mar
Hilton Chicago/Oak Lawn

Motel 6 Bridgeview, IL

2.0 star property
7.0 out of 10, Good, (1130)
"Jacuzzi tub was nice."
The price is €46
includes taxes & fees
25 Mar - 26 Mar
Motel 6 Bridgeview, IL

EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG

3.5 star property
8.8 out of 10, Excellent, (1003)
"Enjoyed"
The price is €108
includes taxes & fees
21 Mar - 22 Mar
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
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.

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?

Spacious Family Glenwood Estates Home w/ Hot Tub!: This highly rated holiday home rental in Glenwood is located in the suburbs, and has a fireplace, a patio and air conditioning to put you at ease 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. It offers a private garden, 1 hot tub and a selection of books so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Glenwood?

Choose from 3 Expedia holiday rentals in Glenwood for a memorable holiday.

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.