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, (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!

Cheerful 4 bedroom smart home w/ indoor fireplace

7.8 out of 10, Good, (12)
"Loved the place and host was super helpful when needed! "
Cheerful 4 bedroom smart home w/ indoor fireplace

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, (45)
"We had a short stay in this property and we wished it could have been longer. The house was very nice, clean and the communication was great!! It is a short drive to the airport and to downtown. We would definitely stay here again"
The price is AU$574
includes taxes & fees
23 Feb - 24 Feb
The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

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

Full Luxurious Modern House Near Chicago

3.4 out of 10, (6)
"I stayed in this home for two nights. It was cold as ever. The heat did not work at all, no matter how high I turned it up and I couldn’t even heat up my food in the microwave because that didn’t work either. My food was not getting warm no matter how long I put it on in the microwave me and my company was cold For both nights."
Full Luxurious Modern House Near Chicago

Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

8.2 out of 10, Very good, (20)
"We really love the home and the setup."
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

Lux Home in Chicago 7mins Downtown

9.8 out of 10, Exceptional, (16)
"Beautiful stay and super nice host would recommend every time "
Lux Home in Chicago 7mins Downtown

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (17)
"For the most part this was a great place to stay. If you want to be in the south suburbs this is ideal for getting to other places in other burbs or to the city. Our only caveat would be it should be emphasized that this is a much better property for two rather than four people. We had our adult children with us. Only one bathroom is just inconvenient- not a deal breaker. But having literally no place for four people to share a meal was very annoying unless you eat out every meal. "
Cozy Home Sweet Homewood.

Dunland Cottage W/hot tub, paddle boards, fire pit

8.2 out of 10, Very good, (20)
"Stayed in Naomi’s home for a weekend with some friends visiting from out of town! We had a great time and was pleased with the home + it was very comfortable and easy to drive to the beach. The paddleboards and beach chairs that came included for our use were awesome! There were some small issues - one of the bedrooms had a duvet that unfortunately smelled and we had to remove it, and while we were staying we experienced issues with the hot tub that were not resolved by the time our stay ended,...
Dunland Cottage W/hot tub, paddle boards, fire pit

Great suburban location! Perfect for solo or couple travelers

8.4 out of 10, Very good, (16)
"Perfect.for a short stay"
The price is AU$274
includes taxes & fees
5 Feb - 6 Feb
Great suburban location! Perfect for solo or couple travelers

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

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

Cedar Sunrise-1 BR Lake House

10.0 out of 10, Exceptional, (14)
"…for me. Clean, cozy, close to everything, quiet and well appointed. This was my second stay and I will continue to return for my family holiday visits. Comfy bed with great pillow’s! "
Cedar Sunrise-1 BR Lake House

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

8.6 out of 10, Excellent, (4)
"Overall it was a great experience and I’ll be coming back sooner"
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

Modern Beach Bungalow, Hot tub, Firepit, Foosball, IN Dunes Nat'l Park

8.4 out of 10, Very good, (23)
"Came into town for a family event with our kids and grandkids. This was a nice spot to stay to enjoy yhe heach tor a couple days. Fenced "
Modern Beach Bungalow, Hot tub, Firepit, Foosball, IN Dunes Nat'l Park

Stay near family or close to downtown, this loft in Beverly has it all!

9.8 out of 10, Exceptional, (6)
"The place was very clean and the pac man was super fun for my husband and I. Check in was easy. I like a soft bed and these were not but not everyone likes a soft bed. Post is accurate."
Stay near family or close to downtown, this loft in Beverly has it all!

Cozy, king and queen bed Indiana home!

9.0 out of 10, Wonderful, (12)
"We all enjoyed our stay."
Cozy, king and queen bed Indiana home!

Casa Blanca in Miller Beach!

9.8 out of 10, Exceptional, (69)
"8 of us stayed at the house, plenty of beds, plenty of places to sit and talk / watch TV, kitchen had everything we needed. Highly recommend"
Casa Blanca in Miller Beach!

LONG STAY,4BED,UC 2MI,FREE PRKG,DWTN 15MIN

9.4 out of 10, Exceptional, (6)
"Was concerned about the neighborhood. Was pleasantly surprised that I was concerned for no reason at all. Nice four-bedroom apartment. Would recommend."
LONG STAY,4BED,UC 2MI,FREE PRKG,DWTN 15MIN
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

Motel 6 Bridgeview, IL

2.0 star property
7.0 out of 10, Good, (1096)
"So so "
The price is AU$80
includes taxes & fees
30 Jan - 31 Jan
Motel 6 Bridgeview, IL

Sleep Inn Midway Airport Bedford Park

2.5 star property
7.6 out of 10, Good, (1328)
"Basic and fine for quick night before an airport ride. No frills. Comfy bed "
The price is AU$142
includes taxes & fees
5 Feb - 6 Feb
Sleep Inn Midway Airport Bedford Park

Hyatt Place Chicago Midway Airport

3.0 star property
9.0 out of 10, Wonderful, (1053)
"Check in easy snd effortless. Front desk customer was excellent. I was able to get a microwave sent to the room. It was a wonderful visit"
The price is AU$238
includes taxes & fees
2 Feb - 3 Feb
Hyatt Place Chicago 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.

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.