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Top Holiday Rentals in Glenwood

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

2.5 star property
3.6 out of 10, (51)
"Property is advertised as a Comfort Inn, but is actually undergoing the transformation of becoming a Comfort Inn. It is still very much so operating as a motel on the south side of Chicago. Be safe. "
The price is £71
includes taxes & fees
11 Aug - 12 Aug
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Come experience The Lake Shore!

10.0 out of 10, Exceptional, (1)
"We had a great stay at the property. "
Come experience The Lake Shore!

LakeHouse

9.2 out of 10, Wonderful, (20)
"Host was perfect an house was perfect!!! It's my second time renting an I will be back again!!"
LakeHouse

Beautiful Rustic Cabin for Two!

9.8 out of 10, Exceptional, (13)
"This place was very cozy and amazing. Daniel was the greatest host and I would definitely stay here on future trips"
The price is £80
includes taxes & fees
8 Sept - 9 Sept
Beautiful Rustic Cabin for Two!

Charming 2-bedroom apartment in marvelous Blue Island with WiFi

2.0 out of 10, (1)
The price is £257
includes taxes & fees
11 Aug - 12 Aug
Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Charming 2-bedroom house with WiFi in peaceful Hazel Crest

7.0 out of 10, Good, (7)
The price is £288
includes taxes & fees
18 Aug - 19 Aug
Charming 2-bedroom house with WiFi in peaceful Hazel Crest

3BR Prime Hyde Park Location Near University of Chicago and Dining

2.0 star property
10.0 out of 10, Exceptional, (5)
"Excellent stay in a good location. The place is comfortable and big, the host was very kind and attentive. I hope to comeback soon. ☺️"
3BR Prime Hyde Park Location Near University of Chicago and Dining

Perfect 1BR Spot near Attractions

7.4 out of 10, Good, (3)
"Freshly painted and clean. Hosts were responsive. Everything we needed for our stay. Walkable area. "
The price is £156
includes taxes & fees
10 Aug - 11 Aug
Perfect 1BR Spot near Attractions

Cozy Studio in Hyde Park-Walk to Lake & University

10.0 out of 10, Exceptional, (2)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
The price is £149
includes taxes & fees
11 Aug - 12 Aug
Cozy Studio in Hyde Park-Walk to Lake & University

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

8.4 out of 10, Very good, (37)
"The yard is awesome, of course the hot tub at the top of the hill was the best, and we enjoyed the firepit as well. The house was a tidy little cottage at which we enjoyed our stay. It’s within a short walk to the National Park and downtown Miller Beach. The neighborhood is fine, pretty secluded, and still close to most attractions."
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

Cozy Home Sweet Homewood.

9.6 out of 10, Exceptional, (32)
"Nice location outside of Chicago, cozy and clean, good communication, would definitely recommend! "
Cozy Home Sweet Homewood.

Luxury Camper in Dunes | Grill + Fire Pit

Luxury Camper in Dunes | Grill + Fire Pit

Spacious home overlooking Indiana National Dunes. Five minute drive to beach.

9.2 out of 10, Wonderful, (5)
Spacious home overlooking Indiana National Dunes. Five minute drive to beach.

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

8.8 out of 10, Excellent, (39)
"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"
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails

Dunland Cottage W/hot tub, paddle boards, fire pit

8.2 out of 10, Very good, (20)
"Great house near the beach (host will give you ideas on how to park closer) perfect for hosting a group of friends or family! Host was also super responsive and helpful in accommodating us all for a wonderful birthday weekend!"
Dunland Cottage W/hot tub, paddle boards, fire pit

15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

8.6 out of 10, Excellent, (13)
"Great place, nice location and the Hosts are extremely good to work with. Highly recommend this just out of the city stay!"
The price is £402
includes taxes & fees
20 Aug - 21 Aug
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

Cozy Cabin w/ Loft, Grill and Fire Pit

The price is £300
includes taxes & fees
10 Aug - 11 Aug
Cozy Cabin w/ Loft, Grill and Fire Pit

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

9.2 out of 10, Wonderful, (60)
"With the exception of one bathroom being out of service and nearby location being a little sketchy everything else was a great place at this beautiful house."
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/

2.0 star property
7.4 out of 10, Good, (3)
"The property was beautiful and very modern. There was plenty of space. It had all the amenities to make you feel right at home. It was close to restaurants and casino in Gary. I would definitely stay again!!!!"
The price is £502
includes taxes & fees
18 Aug - 19 Aug
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/

Cozy Cabin w/ Loft, Grill & Fire Pit

2.0 star property
The price is £308
includes taxes & fees
10 Aug - 11 Aug
Cozy Cabin w/ Loft, Grill & Fire Pit
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

Frequently asked questions

Are there holiday rentals in Glenwood?

Yes, there are holiday rentals close to the most popular sights in Glenwood, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Glenwood has to offer?

LakeHouse: This holiday home rental outside of Glenwood is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals will I find in Glenwood?

Choose from 3 Expedia holiday rentals in Glenwood for a memorable holiday.

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 wider area.

What are holiday rentals like in Glenwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Glenwood. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a family getaway.