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

Crestwood Gem! Family and pets friendly 3-bedroom house with WiFi, AC
Living area

Crestwood Gem! Family and pets friendly 3-bedroom house with WiFi, AC

2.0 star property
10.0 out of 10, Exceptional, (2)
"So cute and lots of space. Would definitely stay here again!"
Crestwood Gem! Family and pets friendly 3-bedroom house with WiFi, AC
Cozy Home Sweet Homewood.
Living area

Cozy Home Sweet Homewood.

10.0 out of 10, Exceptional, (15)
"We were in Homewood for a wedding and this was a perfect location. Besides its proximity to the wedding venue, we walked to the train station for a day in the city. The house is exactly as listed. It was very clean, organized and comfortable. Everything we needed was supplied. My husband especially liked the TVs. 😊 Since we were there on Halloween, we had the added bonus of seeing a truly family-oriented neighborhood in action. Lots of happy trick-or-treaters showed up accompanied by lots of...
Cozy Home Sweet Homewood.
Luxury Chicago TH is a 10-minute drive to DWTN, perfect for city access RSV Now
Living area

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

9.6 out of 10, Exceptional, (9)
"Stayed at the property for a conference at McCormick. Very convenient and nice."
Luxury Chicago TH is a 10-minute drive to DWTN, perfect for city access RSV Now
Nestled just behind Marquette Park. 5 minute walk to beach.
Interior

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.
Luxury 3-bedroom house in Northern Indiana with new EVERYTHING!
Interior

Luxury 3-bedroom house in Northern Indiana with new EVERYTHING!

10.0 out of 10, Exceptional, (4)
" The home was very clean. The host was very helpful and easy to communicate with. My family enjoyed our stay."
The price is SAR 736
SAR 1,060 total
includes taxes & fees
1 Dec - 2 Dec
Luxury 3-bedroom house in Northern Indiana with new EVERYTHING!
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Exterior

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!
Full Luxurious Modern House Near Chicago
Living area

Full Luxurious Modern House Near Chicago

2.8 out of 10, (5)
"Cob webs nothing to clean with tv in room don’t work no remote no cleaning supplies like broom mop no wash clothes wouldn’t stay here again "
Full Luxurious Modern House Near Chicago
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago
Matteson Vacation Rental | 4BR | 2.5BA | 1,800 Sq Ft | Stairs Required

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
Private kitchen

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

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

9.2 out of 10, Wonderful, (56)
"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
Lux Home in Chicago 7mins Downtown
1st Floor Living Room

Lux Home in Chicago 7mins Downtown

9.8 out of 10, Exceptional, (14)
"Headed to Chicago for weekend getaway and stayed again at Larry's property. Our friends were impressed with the entire house and had such a great time. Kitchen and living room was perfect space for dinners and watching the games. The property again was immaculate, spotless and made us feel at home. Anytime we come to Chicago, will always look to stay here as it is our home away from home now!! ;-)"
Lux Home in Chicago 7mins Downtown
Mi Casa Dune Casa - North Star Properties
Game room

Mi Casa Dune Casa - North Star Properties

10.0 out of 10, Exceptional, (5)
"The location is great. The beach is within a long walk (not ideal for those with mobility issues). The backyard was a dream and perfect for hanging out. We had a group of ten (adults and teens) and there was plenty of room for everyone to spread out and lounge around. Plenty of towels and blankets to go around. The hot tub was a hit and everyone is looking forward to returning. "
Mi Casa Dune Casa - North Star Properties
Cedar Sunrise-1 BR Lake House
Property grounds

Cedar Sunrise-1 BR Lake House

10.0 out of 10, Exceptional, (13)
"Good, comfortable, quiet."
Cedar Sunrise-1 BR Lake House
Accessible ranch home on an acre of land with finished basement, games & comfort

Accessible ranch home on an acre of land with finished basement, games & comfort

9.8 out of 10, Exceptional, (12)
"Home was very clean great location lots if amenities "
Accessible ranch home on an acre of land with finished basement, games & comfort
Cedar Sunset On the Lake
Miscellaneous

Cedar Sunset On the Lake

10.0 out of 10, Exceptional, (11)
"We thoroughly enjoyed our stay at Cedar Sunset on the Lake! The home was extremely clean and provided every necessity that you could ever need! The bed and furnishings were extremely comfortable and by far the best I’ve experienced in a rental property. The lake was right out the back door and we spent a lot of time on the dock while the kids were always in the lake and provided paddle board. The home was also in close proximity to Crown Point, but the town of Cedar Lake offered everything...
Cedar Sunset On the Lake
Luxurious House - 25 min Downtown - 10min Midway Airport
Living area

Luxurious House - 25 min Downtown - 10min Midway Airport

10.0 out of 10, Exceptional, (3)
"Super clean, excellent host"
Luxurious House - 25 min Downtown - 10min Midway Airport
HardRock Hideaway - 5br, Cozy, Steps from Casino!
Exterior

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.
Exterior

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

10.0 out of 10, Exceptional, (2)
"Our family of eight had a great time in Caryl's beautiful house in the heart of Hyde Park. The house was spacious and within easy walking distance of eateries and shopping opportunities but well situation in a quiet residential area with plenty of available parking. We really enjoyed the time and would stay again. "
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
Spacious 3 Level Home with 4 BDR/3 BA & full Kitchen
Private kitchen

Spacious 3 Level Home with 4 BDR/3 BA & full Kitchen

Spacious 3 Level Home with 4 BDR/3 BA & full Kitchen
Cozy Midway Home
Exterior detail

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
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!
Glenwood Vacation Rental | 4BR | 2.5BA | 2,442 Sq Ft | Step-Free Entry

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!
Cozy 2- bedroom w/ patio mins from Midway Airport
Living room

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
Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community
Room

Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community

9.4 out of 10, Exceptional, (12)
"Thank you for the great stay. I really appreciate the little touches like the bath bomb. Much needed. Communication was great. Good location to stay. "
Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community
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.