Glenwood Vacation Rentals

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Check prices for these dates

Tonight
Dec 10 - Dec 11
Tomorrow
Dec 11 - Dec 12
This weekend
Dec 12 - Dec 14
Next weekend
Dec 19 - Dec 21

Our top choices for Glenwood vacation rentals

Indoor spa tub
Spacious Family Glenwood Estates Home w/ Hot Tub!

Vacation Home in 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 Double Room | Desk, laptop workspace, blackout drapes, free WiFi
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Aparthotel in Harvey

3.0 star property
3.8 out of 10, (67)
"Good "
United States
Abel
The price is ￥13,180
￥14,890 total
includes taxes & fees
Dec 22 - Dec 23
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Fridge, microwave, oven, stovetop
LakeHouse

Vacation Home in South Shore

9.4 out of 10, Exceptional, (25)
"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
2 bedrooms, WiFi, wheelchair access
Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Apartment in 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 ￥22,995
￥53,933 total
includes taxes & fees
Dec 11 - Dec 12
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Interior
A Home Away From Home!

Vacation Home in 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!
Smart TV
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair

Condo in Bronzeville

10.0 out of 10, Exceptional, (26)
"Perfect for what we needed"
United States
Richard G.
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
Iron/ironing board, travel crib, WiFi, bed sheets
Modern Studio Near UChicago

Apartment in Hyde Park

9.4 out of 10, Exceptional, (10)
"Clean room and convenient location! "
United States
Gabriela
The price is ￥9,347
￥24,141 total
includes taxes & fees
Dec 11 - Dec 12
Modern Studio Near UChicago
1 bedroom, iron/ironing board, travel crib, WiFi
Modern 1BR in Historic HydePark

Apartment in Hyde Park

8.4 out of 10, Very Good, (13)
"Comfortable space. All the necessary amenities. Extremely walkable to everything.Will stay again. "
United States
jasmine h.
The price is ￥9,347
￥25,699 total
includes taxes & fees
Dec 16 - Dec 17
Modern 1BR in Historic HydePark
Interior
Less is more! Pet friendly Tiny Home near Chicago!

Mobile Home in 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 ￥16,231
￥33,302 total
includes taxes & fees
Dec 21 - Dec 22
Less is more! Pet friendly Tiny Home near Chicago!
Front of property
Spacious 3BR House With Firepit & Grill, Near Beach

Cottage in Miller 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. "
United States
Kaitlyn
Spacious 3BR House With Firepit & Grill, Near Beach
Exterior
Beautiful Rustic Cabin for Two!

Cabin in Griffith

9.6 out of 10, Exceptional, (17)
"Nice and cozy place to stay. We enjoyed our secluded area during our time here."
United States
Allison A.
The price is ￥10,507
￥16,159 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Beautiful Rustic Cabin for Two!
Fridge, microwave, oven, stovetop
Explore Hyde Park: 2BR Apt on Blackstone Ave

Apartment in Hyde Park

9.4 out of 10, Exceptional, (3)
"All the necessities with no personal touches. Keys from lockbox to open second door were not needed as the second door is always open. Impeccable communication with host. Great location, close to restaurants and train to Millennium Station. Coffee service was excellent, just be sure to find extra pouches in cabinet. Bathtub faucet could not be turned far enough to prevent leaking. TV remote not great and I couldn’t get CNN or MSNBC. I’d stay here again. "
United States
lost whale press
The price is ￥9,815
￥28,585 total
includes taxes & fees
Dec 11 - Dec 12
Explore Hyde Park: 2BR Apt on Blackstone Ave
Exterior detail
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

Vacation Home in Robertsdale

2.0 star property
9.8 out of 10, Exceptional, (15)
"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 ￥22,294
￥31,077 total
includes taxes & fees
Dec 11 - Dec 12
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Exterior
Casa Blanca in Miller Beach!

Vacation Home in 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!
Fridge, microwave, oven, stovetop
1-bedroom condo next to Chicago Midway International Airport

Condo in 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
5 bedrooms, iron/ironing board, free WiFi, bed sheets
Spacious 5-Bedroom Golf Course Home Perfect for Getaways & Special Occasions

Vacation Home in Merrillville

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 ￥311,580
￥386,309 total
includes taxes & fees
Dec 11 - Dec 12
Spacious 5-Bedroom Golf Course Home Perfect for Getaways & Special Occasions
Dining
South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly

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

Vacation Home in Greater Grand Crossing

8.4 out of 10, Very Good, (12)
"The place was well maintained and very clean with no issues and the host was great and fast to respond."
United States
Tenika P.
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Outdoor dining
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

Vacation Home in 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
Interior
Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!

Apartment in Bronzeville

8.8 out of 10, Excellent, (15)
"Clean, nice"
United States
Autumn R.
Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
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

Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

10/10 Excellent
"The staff made it so easy to check in and check out, the room was clean and the breakfast was good. "
donqunay 1-night trip
Posted 1 day ago
Hilton Chicago/Oak Lawn

Find out more about Glenwood

Search for holiday rentals in Glenwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Glenwood using one of the methods below:

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Look no further and take a look at our great range of rental properties in Glenwood!

Frequently asked questions

Are there vacation rentals in Glenwood?

Yes, you can find vacation rentals close to the most popular attractions in Glenwood, or you can choose a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental that Glenwood has to offer?

LakeHouse: Visitors like this Glenwood vacation home rental. It is located on the beach and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 larger area.

What are vacation rentals like in Glenwood?

Vacation rentals are privately owned accommodations you can book for a few days or a quick weekend in Glenwood. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy front desks while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family trip or a small group gathering.