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Compare 174 Vacation Homes in Glenwood with updated reviews, rates, and availability.

Cozy Midway Home
2.0 star property
10.0 out of 10, Exceptional, (12)
"This was a perfect little house to stay for our weekend trip! "
Cozy Midway Home
Casa Blanca in Miller Beach!
9.8 out of 10, Exceptional, (65)
"The whole family enjoyed our stay and loved the location to the beach. We had a wonderful time."
Casa Blanca in Miller Beach!
Cozy Home Sweet Homewood.
10.0 out of 10, Exceptional, (14)
"My mom and I live in Huntsville Alabama and came to visit family and friends in the area and the Homewood house was the perfect location to stay. I miss home so much. It was very comfortable and cute. I will definitely make reservations for next year. Forget staying in a hotel. 😉😅"
Cozy Home Sweet Homewood.
Nestled just behind Marquette Park. 5 minute walk to beach.
10.0 out of 10, Exceptional, (9)
"Could not be more thankful for her prompt replies and accommodations."
Nestled just behind Marquette Park. 5 minute walk to beach.
5 minutes from Midway Int'l Airport Single Family Home.
9.2 out of 10, Wonderful, (5)
"Good area super easy process "
5 minutes from Midway Int'l Airport Single Family Home.
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
8.8 out of 10, Excellent, (33)
"We enjoyed our stay at Sandhill Flat. The check in process was easy and communication was clear. The place is spacious, clean and stocked well. I was impressed they provided some coffee and sugar packets. We enjoyed the spacious backyard, grill and hot tub in the evenings. We were close to the park and beach . We would return."
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.
10.0 out of 10, Exceptional, (14)
"We absolutely LOVED staying here with our two dogs! It felt very clean and cozy and most importantly we felt very safe. The host did such a great job having so much available if you were to forget something everything was very well stocked. There was plenty of space and a fully fenced in back yard for our dogs too! Would stay again if in the area and would recommend to anyone looking to book!!"
Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.
Dreamsville Gateway to Indiana Dunes National Park
6.0 out of 10, (1)
"Listed as private home , once you get there and read the house rules it states shared refrigerator with owner. Owner comes in while you are gone and turns off all lights and the Ac, even goes into your locked room to turn off ac."
Dreamsville Gateway to Indiana Dunes National Park
LakeHouse
10.0 out of 10, Exceptional, (13)
"Overall great experience! Great home, I love the decor of the entire home. And I will definitely recommend to others and will book again "
LakeHouse
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
Welcome to Boss Barbie’s Dreamhouse! Everything is pink.
9.8 out of 10, Exceptional, (7)
"It was everything we imagined it to be!!!"
Welcome to Boss Barbie’s Dreamhouse! Everything is pink.
Lux Home in Chicago 7mins Downtown
9.8 out of 10, Exceptional, (14)
"Lovely house. Host was responsive to questions during our stay. "
Lux Home in Chicago 7mins Downtown
Beautiful Modern Historic Greystone - Near Lake Michigan- Free Parking
5.4 out of 10, (3)
"the unit had plenty of room; the internet was fast and we watched a long movie on Netflix. Everything was clean and comfortable and there was plenty of soaps and towels. Close to Washington Park so we walked there every day. Quiet neighborhood, safe location, we didn't want to leave."
Beautiful Modern Historic Greystone - Near Lake Michigan- Free Parking
Beautiful Bronzeville Duplex!
10.0 out of 10, Exceptional, (3)
"This rental property is in a very quiet neighborhood with ample street parking. The unit was spacious, comfortable and had all the amenities needed for our stay. The host answered all questions and made himself available as needed."
Beautiful Bronzeville Duplex!
Panoramic views, Hot Tub, Sauna, Firepit, Sand Vball, Foosball, Dunes Nat'l Park
9.2 out of 10, Wonderful, (63)
"The home was just as it was listed. The host staff was fantastic with working with us. The house was very nice and had all the needs you need"
Panoramic views, Hot Tub, Sauna, Firepit, Sand Vball, Foosball, Dunes Nat'l Park
HardRock Hideaway - 5br, Cozy, Steps from Casino!
9.0 out of 10, Wonderful, (2)
"Great stay"
HardRock Hideaway - 5br, Cozy, Steps from Casino!
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
10.0 out of 10, Exceptional, (1)
"We loved our stay. The house was beautiful. We hope to come back. "
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
Charming 4-Bedroom Home Backyard 8 gusts with AC and WiFi in Chicago Ridge
2.0 star property
The price is AED 1,065
AED 1,981 total
includes taxes & fees
17 Nov - 18 Nov
Charming 4-Bedroom Home Backyard 8 gusts with AC and WiFi in Chicago Ridge
Mokena Manor: Luxury Living - Your Elite Escape!
2.0 star property
10.0 out of 10, Exceptional, (2)
"Lovely suburb outside Chicago, with all the amenities you'd need for a relaxing getaway. The area was peaceful with plenty of local restaurants and shops. I’d definitely recommend it for a cozy and convenient stay near Chicago. I had a great time!"
Mokena Manor: Luxury Living - Your Elite Escape!
Relax in style: Chic 2 bedroom haven in brickell.
4.0 out of 10, (1)
"This home was not ready for a hospitable stay as depicted in the picture when we booked it. It looked like someone had been living there for quite a while, with hair everywhere—in the bathtub, beds, and sink. The bed was made, and it seemed like someone just walked out the door. There were many issues. One of the bedsheets was damp, and the other looked like it had been slept in for a week or two without being washed. The heat did not work, and the toilet paper was only 1-ply. Additionally,...
Relax in style: Chic 2 bedroom haven in brickell.
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 property types in Glenwood

Spacious Family Glenwood Estates Home w/ Hot Tub!
9.4 out of 10, Exceptional, (13)
"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!
Cozy 2- bedroom w/ patio mins from Midway Airport
10.0 out of 10, Exceptional, (8)
"This place was perfect for three of us in town for family reunion. Has well stocked kitchen, nice bath, decent beds. Best feature is back yard/patio with lights & privacy. Street parking was not a problem while we were there."
Cozy 2- bedroom w/ patio mins from Midway Airport
The Comfy King Ranch /King Bed/Fast WiFi & Free Parking
9.6 out of 10, Exceptional, (43)
"House was great, clean, and the owners were wonderful to work with. Welcome emails and they even checked in via email during our stay to make sure we were comfortable. If I ever travel back I will stay here again!!! Highly recommend "
The price is AED 806
AED 1,471 total
includes taxes & fees
18 Nov - 19 Nov
The Comfy King Ranch /King Bed/Fast WiFi & Free Parking
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.