Glenwood Vacation Rentals

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Vacation Rentals in Glenwood

Spacious Family Glenwood Estates Home w/ Hot Tub!
9.4 out of 10, Exceptional, (19)
"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 Inn Chicago Southland I-80 & I-294 Near Casino
3.0 star property
3.8 out of 10, (64)
"Good "
United States
Abel
$94 nightly
The price is $106
Oct 26 - Oct 27
Total with taxes and fees
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Cozy Studio in Hyde Park-Walk to Lake & University
9.0 out of 10, Wonderful, (8)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
United States
Nancy
$163 nightly
The price is $182
Nov 2 - Nov 3
Total with taxes and fees
Cozy Studio in Hyde Park-Walk to Lake & University
Modern Studio Near UChicago
10.0 out of 10, Exceptional, (6)
"The studio apartment was just what we needed in a great location in Hyde Park. Super clean and quiet. "
United States
Heather B.
$163 nightly
The price is $182
Nov 4 - Nov 5
Total with taxes and fees
Modern Studio Near UChicago
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
7.6 out of 10, Good, (4)
"Only issue was the water pressure in the bathroom was very very low. "
United States
Derrick M.
$324 nightly
The price is $346
Oct 25 - Oct 26
Total with taxes and fees
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Modern 1BR in Historic HydePark
8.0 out of 10, Very Good, (5)
"The location couldn't be beat. The beds were super comfortable and the room was perfect for my husband and I. We'll definitely stay here again!"
United States
Lisa O.
$174 nightly
The price is $193
Nov 3 - Nov 4
Total with taxes and fees
Modern 1BR in Historic HydePark
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
8.4 out of 10, Very Good, (41)
"Awesome place!"
United States
Justin M.
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Less is more! Pet friendly Tiny Home near Chicago!
9.8 out of 10, Exceptional, (29)
"It was a cute and quiet and private area really nice and relaxing experience"
United States
Darien G.
$135 nightly
The price is $145
Oct 26 - Oct 27
Total with taxes and fees
Less is more! Pet friendly Tiny Home near Chicago!
South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly
10.0 out of 10, Exceptional, (1)
"Clean apartment and great communication with host. Fixed any small problems very quickly. "
United States
Catherine F.
South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly
LakeHouse
9.4 out of 10, Exceptional, (22)
"Everything was perfect with the property and the host even came to help right away when we had one issue with the lights."
United States
Isaiah P.
LakeHouse
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
8.6 out of 10, Excellent, (14)
"i had a good time here. the house was great. thank you"
United States
Alvaro C.
$399 nightly
The price is $447
Oct 27 - Oct 28
Total with taxes and fees
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
8.0 out of 10, Very Good, (10)
"Came for a concert, enjoyed sight seeing. Apartment was a nice place to stay."
United States
APRIL T.
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
A Home Away From Home!
9.6 out of 10, Exceptional, (12)
"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!
Come experience The Lake Shore!
10.0 out of 10, Exceptional, (4)
"Very spacious, quiet and comfortable. Great place to stay!"
United States
Kylie M.
Come experience The Lake Shore!
Spacious 3BR House With Firepit & Grill, Near 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
$355 nightly
The price is $375
Nov 6 - Nov 7
Total with taxes and fees
Spacious 3BR House With Firepit & Grill, Near Beach
Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit.
2.5 star property
7.4 out of 10, Good, (3)
"The house was absolutely beautiful ! Very spacious and nice! Comfy beds and clean. "
United States
Brandy W.
Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit.
Bright & Cozy 1BR Near UChicago
10.0 out of 10, Exceptional, (2)
"This apartment is a very basic rental unit – – had what we needed for our three nights stay, and we were very pleased. Great value for the money."
United States
Alan F.
$173 nightly
The price is $192
Oct 26 - Oct 27
Total with taxes and fees
Bright & Cozy 1BR Near UChicago
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
9.6 out of 10, Exceptional, (72)
"Enough room for a quick get away"
United States
wendy C.
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park
9.2 out of 10, Wonderful, (62)
"The property was wonderful. So many amenities that our team loved! The sauna, proximity to the beach and the two kitchens were highlights. It was clean and well-maintained."
United States
Audrey H.
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park
House with garage, outdoor dining and basement bar
7.4 out of 10, Good, (3)
"Property was very clean, warm and welcoming. Beds were comfortable. Property manager was great at checking in, and readily available. The place smells great! Everything is new! We will definitely book again!"
United States
Jessica M.
House with garage, outdoor dining and basement bar
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

Find out more about Glenwood

Everything you need to know about Glenwood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Glenwood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Glenwood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Glenwood vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Glenwood. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Glenwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $106 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Glenwood rentals

At Expedia, we put the best Glenwood vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Glenwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Glenwood vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Glenwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park: Visitors like this Glenwood vacation home rental. It is located on a lake and has a balcony, a private yard, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a selection of games and a hot tub.

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 Oak Hill 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.