Glenwood Vacation Rentals

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Vacation Rentals in Glenwood

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

3.0 star property
3.8 out of 10, (60)
"Good "
$94 nightly
The price is $106
Sep 10 - Sep 11
Total with taxes and fees
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Cozy Studio in Hyde Park-Walk to Lake & University

8.0 out of 10, Very Good, (3)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
$172 nightly
The price is $192
Sep 10 - Sep 11
Total with taxes and fees
Cozy Studio in Hyde Park-Walk to Lake & University

Charming 2-bedroom apartment in marvelous Blue Island with WiFi

6.0 out of 10, (2)
"Only issue was the water pressure in the bathroom was very very low. "
$324 nightly
The price is $346
Sep 10 - Sep 11
Total with taxes and fees
Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Beautiful Rustic Cabin for Two!

9.8 out of 10, Exceptional, (16)
"This place was very cozy and amazing. Daniel was the greatest host and I would definitely stay here on future trips"
$102 nightly
The price is $114
Sep 26 - Sep 27
Total with taxes and fees
Beautiful Rustic Cabin for Two!

LakeHouse

9.2 out of 10, Wonderful, (20)
"Everything was perfect with the property and the host even came to help right away when we had one issue with the lights."
LakeHouse

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

9.2 out of 10, Wonderful, (61)
"Management responded quickly to all questions. It was a nice spot that worked well for a group of couples with kids. Nice to have a beach area in back to Play volleyball. A nice walk through the dunes to a nice big beach on Lake Michigan."
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

A Home Away From Home!

9.4 out of 10, Exceptional, (10)
"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "
A Home Away From Home!

Less is more! Pet friendly Tiny Home near Chicago!

9.8 out of 10, Exceptional, (24)
"Could not have picked a better place to stay. Location was grea,fenced in area fir the dogs was perfecy. "
$177 nightly
The price is $189
Sep 13 - Sep 14
Total with taxes and fees
Less is more! Pet friendly Tiny Home near Chicago!

Sleek & Functional 2-Bedroom Apt

10.0 out of 10, Exceptional, (2)
"I really enjoyed my stay at this property! Everything was exactly as described and the property was exceptionally clean and centrally located. The check-in process was smooth and the hosts were very communicative from booking to check-out. "
$199 nightly
The price is $220
Sep 15 - Sep 16
Total with taxes and fees
Sleek & Functional 2-Bedroom Apt

Comfortable Condo in the Heart of Bronzeville by RedAwning

7.2 out of 10, Good, (5)
"There was confusion with VRBO regarding our arrival date, no fault of the property owner. They made arrangements to clean the unit and provide lunch for our group while we waited and offered a second night free for the inconvenience. Highly recommend. Property owner went above and beyond!"
Comfortable Condo in the Heart of Bronzeville by RedAwning

Cozy Cabin w/ Loft, Grill and Fire Pit

$440 nightly
The price is $447
Sep 14 - Sep 15
Total with taxes and fees
Cozy Cabin w/ Loft, Grill and Fire Pit

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!"
House with garage, outdoor dining and basement bar

Cozy Cabin w/ Loft, Grill & Fire Pit

2.0 star property
4.0 out of 10, (1)
"No curtains at all. Small window air conditioning that doesn't cool the whole cabin down. Sketchy ladder screwed into the wall to got to the loft. Any mobility issues beware. Wifi has no internet. Was there less than 30 minutes no reund offered. It is new and clean. "
$353 nightly
The price is $378
Sep 10 - Sep 11
Total with taxes and fees
Cozy Cabin w/ Loft, Grill & Fire Pit

Cheerful 4 bedroom smart home w/ indoor fireplace

8.0 out of 10, Very Good, (16)
"Loved the place and host was super helpful when needed! "
Cheerful 4 bedroom smart home w/ indoor fireplace

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

8.4 out of 10, Very Good, (38)
"This place offers very clean private secure property that makes you feel like your up in Michigan with the ease and access of the local shopping and food options and Lake Michigan beaches walking distance from the home.. oh and throw in a hot tub for relaxation .. this place offers everything you need if your staying in the area."
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

Cozy Full Home + Free Parking + Fast Wi-fi & Central Area

Cozy Full Home + Free Parking + Fast Wi-fi & Central Area

Perfect 1BR Spot near Attractions

7.2 out of 10, Good, (5)
"Freshly painted and clean. Hosts were responsive. Everything we needed for our stay. Walkable area. "
$182 nightly
The price is $202
Sep 10 - Sep 11
Total with taxes and fees
Perfect 1BR Spot near Attractions

Charming 2-bedroom house with WiFi in peaceful Hazel Crest

7.4 out of 10, Good, (10)
"The property was very spacious and clean and customer service is very responsive and quick. "
$307 nightly
The price is $328
Sep 10 - Sep 11
Total with taxes and fees
Charming 2-bedroom house with WiFi in peaceful Hazel Crest

Dalia Flat - Sleeps 10 - 10 minutes to Downtown

9.4 out of 10, Exceptional, (14)
"Nice amenities, and centrally located, grocery store near, nice full kitchen, nothing we didn’t like about."
Dalia Flat - Sleeps 10 - 10 minutes to Downtown

Stay near family or close to downtown, this loft in Beverly has it all!

9.8 out of 10, Exceptional, (8)
"I went with 4 other friends, and this place was super clean, came with everything we needed, and even includes a cute small gaming room! Definitely would stay again!"
Stay near family or close to downtown, this loft in Beverly has it all!
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

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?

A Home Away From Home!: Visitors like this Glenwood vacation home rental. It offers a fireplace, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

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.