Glenwood Vacation Rentals

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Vacation Rentals in Glenwood

Charming 1BR/1BA Apt in Chicago
10.0 out of 10, Exceptional, (1)
$172 nightly
The price is $191
Nov 2 - Nov 3
Total with taxes and fees
Charming 1BR/1BA Apt in Chicago
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
Bright & Modern 1BR in Hyde Park
10.0 out of 10, Exceptional, (1)
"Great place to stay. It was easy to settle in and relax after a long day of traveling. The bed was comfortable and great to sleep on. Will definitely try for this property again if I need to come to the area."
United States
Michael S.
$174 nightly
The price is $193
Nov 4 - Nov 5
Total with taxes and fees
Bright & Modern 1BR in Hyde 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!
Beautiful Rustic Cabin for Two!
9.8 out of 10, Exceptional, (16)
"We had a very nice stay. The cabin was quite cozy and comfortable."
United States
Jeremy & Rebecca F.
$92 nightly
The price is $103
Nov 20 - Nov 21
Total with taxes and fees
Beautiful Rustic Cabin for Two!
Chic Retreat: Cozy 1BR Apartment
10.0 out of 10, Exceptional, (3)
"Our stay was very nice, with simple checkin / check out, and excellent communication by our host. "
United States
Tom B.
$174 nightly
The price is $193
Nov 4 - Nov 5
Total with taxes and fees
Chic Retreat: Cozy 1BR Apartment
Contemporary 2BR Apartment in Vibrant Hyde Park
10.0 out of 10, Exceptional, (1)
"We stayed in this comfortable, quiet apartment for four weeks when my husband was undergoing radiation treatments for cancer at the University of Chicago Medical Center. It was just what we needed. The location—a block from Lake Michigan with its endless miles of parks and green spaces—was spectacular, and we spent long hours walking our dogs and biking along the lake on the beautifully landscaped walking and biking trails. The apartment itself is well appointed, clean, and blessedly quiet...
United States
Heidi H.
$204 nightly
The price is $226
Oct 26 - Oct 27
Total with taxes and fees
Contemporary 2BR Apartment in Vibrant Hyde Park
Explore Hyde Park: 2BR Apt on Blackstone Ave
10.0 out of 10, Exceptional, (1)
"Host was responsive to my questions. Apartment is located in a great area of Hyde Park. "
United States
Lind A.
$201 nightly
The price is $222
Oct 27 - Oct 28
Total with taxes and fees
Explore Hyde Park: 2BR Apt on Blackstone Ave
Cozy Charm Studio Apt in Chicago
10.0 out of 10, Exceptional, (1)
$163 nightly
The price is $182
Nov 3 - Nov 4
Total with taxes and fees
Cozy Charm Studio Apt in Chicago
Plant MOOD2! FREE STREET PARKING & Wi-Fi!
10.0 out of 10, Exceptional, (2)
"It was a great experience!!! Very clean and decorated very beautiful. The host is very friendly and responds fast."
United States
Alexis L.
$187 nightly
The price is $209
Nov 20 - Nov 21
Total with taxes and fees
Plant MOOD2! FREE STREET PARKING & Wi-Fi!
Sleek & Functional 2-Bedroom Apt
9.6 out of 10, Exceptional, (4)
"Nice place for a girls trip weekend. "
United States
Madonna A.
$206 nightly
The price is $228
Nov 6 - Nov 7
Total with taxes and fees
Sleek & Functional 2-Bedroom Apt
Studio Apt Comfy & Sunlit
10.0 out of 10, Exceptional, (1)
"My stay was really good"
United States
Paramita B.
$174 nightly
The price is $193
Nov 4 - Nov 5
Total with taxes and fees
Studio Apt Comfy & Sunlit
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
Bright 1BR Unit in a Prime Spot
10.0 out of 10, Exceptional, (1)
"We had a great stay. Location is in nice neighborhood with walking access to restaurants and university of Chicago. Apartment was clean and as pictured. Would stay again!!"
United States
christine m.
Bright 1BR Unit in a Prime Spot
Furnished 3BR Apt w/ Laundry
9.6 out of 10, Exceptional, (4)
"Apartment and neighborhood were beautiful. We really enjoyed our stay and would book the same place again!"
United States
Kristin W.
$214 nightly
The price is $235
Oct 26 - Oct 27
Total with taxes and fees
Furnished 3BR Apt w/ Laundry
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
Pleasant 3-bedroom house in Sauk Village
2.0 star property
$125 nightly
The price is $134
Oct 27 - Oct 28
Total with taxes and fees
Pleasant 3-bedroom house in Sauk Village
Spacious 3BR Home Firepit & Grill
2.0 star property
$389 nightly
The price is $407
Oct 26 - Oct 27
Total with taxes and fees
Spacious 3BR Home Firepit & Grill
20mins from beach, 10guests/WIFI/1.2 baths/ping pong/pool table/treadmill
10.0 out of 10, Exceptional, (4)
"Very nice property. Kids loved staying here! "
United States
Sydney D.
$363 nightly
The price is $407
Nov 10 - Nov 11
Total with taxes and fees
20mins from beach, 10guests/WIFI/1.2 baths/ping pong/pool table/treadmill
Modern Studio Retreat– Near Museum & Parks
$164 nightly
The price is $183
Oct 26 - Oct 27
Total with taxes and fees
Modern Studio Retreat– Near Museum & Parks
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.