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Compare 247 Vacation Homes in Glenwood with updated reviews, rates, and availability.

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (22)
"Liked very much"
Cozy Home Sweet Homewood.

Private Home Awaits

10.0 out of 10, Exceptional, (2)
"Very convenient to all my activities for my 55th Birthday "
Private Home Awaits

House with garage, outdoor dining and basement bar

House with garage, outdoor dining and basement bar

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

7.8 out of 10, Good, (7)
"I would stay again and the communication was on point. Thank you for having us."
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

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

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!

Charming 3-bedroom house in serene and lovely Evergreen Park. WiFi/ AC

10.0 out of 10, Exceptional, (1)
"Lovely new (or well remodeled?) house in a nice neighborhood. Host was nice and communicative. Kitchen is well stocked. There’s only one shower but we had no problem sharing. "
Charming 3-bedroom house in serene and lovely Evergreen Park. WiFi/ AC

Chic & Stylish 3-bedroom house in Palos Heights

8.0 out of 10, Very Good, (1)
"We enjoyed our stay at this vrbo property - it was very conveniently located as we were visiting family in the Palos Heights area and there are grocery stores and other shopping and restaurants within a few minutes drive. The property was clean and had most basic conveniences like shampoo, conditioner, dish soap, and detergent. The only surprise was that there was another group staying in the basement (with a separate entrance) which wasn't mentioned at all in the property description. "
Chic & Stylish 3-bedroom house in Palos Heights

Gorgeous historic mansion on UChicago campus. Renovation with original detail.

10.0 out of 10, Exceptional, (7)
"Two grandmas, a mom and a daughter came to experience open house for The University of Chicago. This home was so nice as it was a close and safe walk to campus. We all had an extremely comfortable bedroom as well as our own bathroom. The neighborhood felt safe and had beautiful buildings to admire while we walked. We never felt like we lacked for anything. "
Gorgeous historic mansion on UChicago campus. Renovation with original detail.

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 AED 690
AED 1,413 total
includes taxes & fees
15 Apr - 16 Apr
The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

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!

Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.

10.0 out of 10, Exceptional, (21)
"Nice sice fenced in yard. Dog park within a short walk. Nice smaller home with 3 good size bedrooms. Kitchen was convenient for cooking meals."
Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.

Charming 3-bedroom house with AC and WiFi in serene Bridgeview

Charming 3-bedroom house with AC and WiFi in serene Bridgeview

Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails

8.8 out of 10, Excellent, (34)
"We had a great stay! The property was perfect- hot tub, plenty of beds, comfortable beds, walking distance to Lake Michigan! Home was comfortable and clean and the managers were easy to reach with questions-just a text away. Would definitely stay here again"
The price is AED 630
AED 2,304 total
includes taxes & fees
17 Apr - 18 Apr
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails

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

Modern Historic Greystone - Near Lake - Free Prkg

6.4 out of 10, (5)
"Great property in a quiet neighborhood. Not far from downtown and other tourist attractions. 10/10 would recommend. "
Modern Historic Greystone - Near Lake - Free Prkg

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

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, (16)
"Host was perfect an house was perfect!!! It's my second time renting an I will be back again!!"
LakeHouse

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

9.6 out of 10, Exceptional, (11)
"The home is nice."
Luxury Chicago TH is a 10-minute drive to DWTN, perfect for city access 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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Other property types 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
3.6 out of 10, (17)
"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 AED 328
AED 371 total
includes taxes & fees
15 Apr - 16 Apr
Comfort Inn Chicago Wind Creek Casino

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (22)
"Liked very much"
Cozy Home Sweet Homewood.
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.