Title: Highland Vacation Home Rentals from CA $203: Search Top Private Vacation Homes for Rent | Expedia.ca

[Hotels in Highland](https://expedia.ca/Highland-Hotels.d177657.Travel-Guide-Hotels)[Vacation Rentals in Highland](https://expedia.ca/Highland-Vacation-Rentals.d177657.Travel-Guide-VacationRentals)[Things to do in Highland](https://expedia.ca/Things-To-Do-In-Highland.d177657.Travel-Guide-Activities)[Highland Car Rentals](https://expedia.ca/Car-Rentals-In-Highland.d177657.Car-Rental-Guide)[Highland Vacation Packages](https://expedia.ca/Highland.d177657.Destination-Travel-Guides)

![Al Capone's old Prairie avenue home before and today, 7244 South Prairie Avenue.
Built by it's original owners in 1914 at a cost of $5,000. With their roots still in New York , Al Capone and family began to move into the place on August 8, 1923. The ownership was under Mae and Theresa Capone. Frank Capone's funeral was held here. Theresa Capone passed away in this house in 1952.
On November 26,1947, the ownership was transferred to Mafalda Maritote. (Al's sister).  After Theresa's death, she sold the house on January 15,1953, to a William B. Petty. It has changed hands since then and is currently for sale. ](https://images.trvl-media.com/place/177657/87fb36ed-26eb-46b0-a77d-72c76798465e.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Joe Farmer

# Highland Vacation Rentals

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## Check prices for these dates

In two weeks

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=177657&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=177657&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=177657&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=177657&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Highland Vacation Homes

![Property grounds](https://images.trvl-media.com/lodging/96000000/95050000/95044300/95044250/a5e3e3f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95050000/95044300/95044250/845afee6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/96000000/95050000/95044300/95044250/bceb9ab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/96000000/95050000/95044300/95044250/ecb842fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Chesterton

8.6/10

Excellent

(7)

"Excellent spot for several people to stay and enjoy the Dunes. Clean, quiet, centrally located to lots of Dunes hotspots. Thanks for the great stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nick R.

CA $69

CA $345 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Chesterton-Hotels-BalconyPatio-Separate-Fenced-Yard-Beach.h95044250.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/119000000/118260000/118254100/118254007/84ad0fdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/119000000/118260000/118254100/118254007/485e4f87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/119000000/118260000/118254100/118254007/2e3f2077.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118260000/118254100/118254007/0a83dc4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Miller Beach

10/10

Exceptional

(1)

"Lovely, relaxing and clean. Host is very responsive. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer L.

CA $145

CA $477 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Gary-Hotels-Spacious-3BR-House-With-Firepit-And-Grill.h118254007.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/d8580e49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/6a00edbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Toilet paper](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/0d8c5080.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/48a5d932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sauk Village

10/10

Exceptional

(1)

"My Experience Was (NOTHING) Short Of Perfect! The Place Is Nice & The Host Was Even Better! I’ll Forsure Be Booking Again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Aaron K.

CA $127

CA $203 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Sauk-Village-Hotels-Pleasant-3-Bedroom-House-In-Sauk-Village.h121815186.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95040000/95038900/95038818/046bf033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95040000/95038900/95038818/4a9c4df8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/96000000/95040000/95038900/95038818/cacec885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95040000/95038900/95038818/8f20fe7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Chesterton

9.4/10

Exceptional

(3)

"I enjoyed my short stay and visit to The Indiana National Dunes. The Host was friendly and she put special effort into setting the place up for my stay. I 100% would rent again from this host and would recommend "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

T J.

CA $155

CA $553 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Chesterton-Hotels-BalconyPatio-Fenced-Yard-Attached-Garagenear-Beach.h95038818.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/bf2ce6c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, printers](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/87b39ac8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/57fac6ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/10848660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Chesterton

10/10

Exceptional

(12)

"This rental was amazing!!! So very clean, amazingly comfortable bed, and every amenity thought off. You will not be sorry that you stayed here. We hope to stay again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Leiann N.

CA $162

CA $379 total

includes taxes & fees

Dec 11 - Dec 12

[](https://www.expedia.ca/Chesterton-Hotels-Moody-Modern-Dunes-Hot-Tub-Beaches-Trails.h119048616.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88180000/88178900/88178891/w506h639x259y44-83e61931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88180000/88178900/88178891/w508h683x259y0-938c1ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/89000000/88180000/88178900/88178891/w505h683x260y0-7687ead9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/89000000/88180000/88178900/88178891/w505h683x260y0-df8876b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Gary

CA $180

CA $581 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Gary-Hotels-Honeycomb-Hideout-W-2-Bedrooms.h88178891.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/e79449bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/da25d2c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/5ccfbbbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/dfa31946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Robertsdale

9.8/10

Exceptional

(15)

"Wonderful property and nice owners. I definitely recommend and will stay again if I'm ever in the area."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Karen D.

CA $198

CA $276 total

includes taxes & fees

Dec 11 - Dec 12

[](https://www.expedia.ca/Whiting-Hotels-Charming-3-BR-Home-On-A-Cobblestone-Street-Near-The-Lake-Michigan-Lakefront.h108219403.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/9d278ba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/5b7a273e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/138bf941.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/3c3ca737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Richton Park

9.0/10

Wonderful

(14)

"The house was average needs some cosmetic repairs to improve the appeal to the eye. Utilities not available for more than four, we were a party of 4 so it did not matter. The master bedroom bed was rather uncomfortable."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lynette H.

CA $149

CA $430 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Richton-Park-Hotels-Spacious-3br-Home-Near-Chicago.h108885786.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/84000000/83030000/83025900/83025813/7374e6e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83030000/83025900/83025813/b86200c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/84000000/83030000/83025900/83025813/327a76af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83030000/83025900/83025813/e0894c26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Miller Beach

9.8/10

Exceptional

(36)

"We loved our stay and had a relaxing time in the area. Buying groceries to cook was great with a full kitchen to cook with. Rooms were super nice and also had every accommodation we could need. Definitely will be looking to stay again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Braden S.

CA $112

CA $416 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Gary-Hotels-Dunes-Escape-Minutes-From-Indiana-Dunes-National-Park.h83025813.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/010eed58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/b52cb489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/7448b12a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/56333a9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Gary

8.6/10

Excellent

(17)

"i had a good time here. the house was great. thank you"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alvaro C.

CA $223

CA $618 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Gary-Hotels-Theater-RMKG-BdFam-Friendly-Home-NR-DunesBeach.h102515612.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111670000/111668700/111668679/a03596e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111670000/111668700/111668679/a531c8c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111670000/111668700/111668679/cd881412.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/112000000/111670000/111668700/111668679/dd9a3475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Gary

10/10

Exceptional

(4)

"Very nice property. Kids loved staying here! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sydney D.

CA $284

CA $629 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Gary-Hotels-COMFORTABLE-ALLUSION.h111668679.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/118000000/117470000/117462700/117462645/ff3980a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/118000000/117470000/117462700/117462645/f670e4e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117470000/117462700/117462645/b3ebc668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117470000/117462700/117462645/139732fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Miller Beach

CA $180

CA $447 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Gary-Hotels-Cozy-Family-Getaway-4-Blocks-Or-A-9-Minute-Walk-To-The-Beach.h117462645.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122660000/122655500/122655441/443df914.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/123000000/122660000/122655500/122655441/6d5ce3ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122660000/122655500/122655441/230d1f90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/123000000/122660000/122655500/122655441/074afb4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Homewood

CA $206

CA $568 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Chicago-Hotels-Modern-Stylish-Comfort-Near-Casino-And-Hwy.h122655441.Hotel-Information)

![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117070000/117062900/117062826/f0e5bad1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117070000/117062900/117062826/4a89d3fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/118000000/117070000/117062900/117062826/dbeceb4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117070000/117062900/117062826/w2840h1891x0y1-112c3149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Merrillville

10/10

Exceptional

(2)

"Great House, and everything is brand new! Loved the sheets and the towels, and the beds were all super comfy. The outdoor fire pit was a nice touch and made our night a great experience. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jim A.

CA $2,763

CA $3,426 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Merrillville-Hotels-Spacious-5-Bedroom-Golf-Course-Home-Perfect-For-Getaways-Special-Occasions.h117062826.Hotel-Information)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/108000000/107760000/107751500/107751486/de764151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107760000/107751500/107751486/3337bff4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/108000000/107760000/107751500/107751486/9b8fe2e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107760000/107751500/107751486/b7079b93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Gary

8.4/10

Very good

(5)

"Enjoyed staying at this place. Definitely will stay again"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Devonta J.

CA $402

CA $912 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Gary-Hotels-Tarquatic-Dreamsicle.h107751486.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110940000/110931500/110931495/27939c1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/111000000/110940000/110931500/110931495/21819c4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110940000/110931500/110931495/f74c2539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110940000/110931500/110931495/ec2039a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Merrillville

9.6/10

Exceptional

(5)

"Me and my partner had so much fun! The host was very kind, we had our privacy and everything we could've needed during our stay. We truly had a great time! I'd love to come back someday!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Janina

CA $290

CA $501 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Merrillville-Hotels-Couples-Getaway-Guesthouse-In-Law-Suite-With-JacuzziSaunaPool.h110931495.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/35000000/34490000/34487700/34487682/270-c0315ba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bathroom](https://images.trvl-media.com/lodging/35000000/34490000/34487700/34487682/270-c4627a25_edited_48a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bathroom](https://images.trvl-media.com/lodging/35000000/34490000/34487700/34487682/270-dfddec09_edited_79fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/35000000/34490000/34487700/34487682/270-2de150a9_edited_d938.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Dolton

CA $995

CA $2,061 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Chicago-Hotels-Nice-Cozy-Home-To-Experience-On-Your-Vacation.h34487682.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/122000000/121030000/121027600/121027504/061c60c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121030000/121027600/121027504/db8e3318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/122000000/121030000/121027600/121027504/9ac4e822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121030000/121027600/121027504/db303c07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Valparaiso

CA $1,244

CA $2,069 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Valparaiso-Hotels-Welcome-To-The-Chateau-At-Pepper-Creek-Luxury-Estate-Retreat.h121027504.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90140000/90130600/90130507/da929090.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books, offices](https://images.trvl-media.com/lodging/91000000/90140000/90130600/90130507/def133b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/91000000/90140000/90130600/90130507/f93a4c0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90140000/90130600/90130507/e0dfbd43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Matteson

9.4/10

Exceptional

(10)

"House was nicer than i expected. Great hosts"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Darian C.

CA $457

CA $1,279 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Matteson-Hotels-Private-Oasis-With-Spacious-Backyard.h90130507.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-23&endDate=2025-12-24&regionId=177657&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Highland%2C+Indiana%2C+United+States+of+America&regionId=177657&latLong=41.553647%2C-87.451984&adults=2&startDate=2026-03-08&d1=2026-03-08&endDate=2026-03-11&d2=2026-03-11&lodging=APART_HOTEL)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Highland%2C+Indiana%2C+United+States+of+America&regionId=177657&latLong=41.553647%2C-87.451984&adults=2&startDate=2026-03-08&d1=2026-03-08&endDate=2026-03-11&d2=2026-03-11&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Highland%2C+Indiana%2C+United+States+of+America&regionId=177657&latLong=41.553647%2C-87.451984&adults=2&startDate=2026-03-08&d1=2026-03-08&endDate=2026-03-11&d2=2026-03-11&lodging=APARTMENT)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Highland%2C+Indiana%2C+United+States+of+America&regionId=177657&latLong=41.553647%2C-87.451984&adults=2&startDate=2026-03-08&d1=2026-03-08&endDate=2026-03-11&d2=2026-03-11&lodging=CONDO)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Highland%2C+Indiana%2C+United+States+of+America&regionId=177657&latLong=41.553647%2C-87.451984&adults=2&startDate=2026-03-08&d1=2026-03-08&endDate=2026-03-11&d2=2026-03-11&lodging=CABIN)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Highland%2C+Indiana%2C+United+States+of+America&regionId=177657&latLong=41.553647%2C-87.451984&adults=2&startDate=2026-03-08&d1=2026-03-08&endDate=2026-03-11&d2=2026-03-11&lodging=COTTAGE)

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## Top Highland Hotel Reviews

![Wind Creek Southland Casino and Hotel](https://images.trvl-media.com/lodging/113000000/112060000/112051600/112051593/1fba48a9_y.jpg)

### Wind Creek Southland Casino and Hotel

10/10 Excellent

"Beautiful hotel! It was spotless, had a neutral smell when entering, staff was nice too! "

[](https://expedia.ca/Chicago-Hotels-Wind-Creek-Southland-Casino-And-Hotel.h112051593.Hotel-Information)

![Baymont by Wyndham Chicago/Alsip](https://images.trvl-media.com/lodging/1000000/60000/50900/50833/fae988da_y.jpg)

### Baymont by Wyndham Chicago/Alsip

10/10 Excellent

"Nice size room with a good view, very clean."

[](https://expedia.ca/Chicago-Hotels-Baymont-By-Wyndham-ChicagoAlsip.h50833.Hotel-Information)

![Ameristar Casino Hotel East Chicago](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/429a2c05_y.jpg)

### Ameristar Casino Hotel East Chicago

10/10 Excellent

"nothing to say about it. was very lovely "

[](https://expedia.ca/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.Hotel-Information)

![Luxe Inn and Suites](https://images.trvl-media.com/lodging/22000000/21640000/21633700/21633629/51b4b686_y.jpg)

### Luxe Inn and Suites

10/10 Excellent

"Nice and clean everybody was friendly that's all I got"

[](https://expedia.ca/Chicago-Hotels-Prestige-Inn-Suites-Extended-Stay.h21633629.Hotel-Information)

![Hilton Chicago/Oak Lawn](https://images.trvl-media.com/lodging/1000000/20000/17700/17618/6279b55c_y.jpg)

### Hilton Chicago/Oak Lawn

10/10 Excellent

"The room was very clean. The bed was comfortable and staff were all friendly. There wasn't any free coffee station in the lobby bc they only have a coffee shop where you have to pay for it, that's the only downside. Everything else was fantastic."

[](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoOak-Lawn.h17618.Hotel-Information)

![EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG](https://images.trvl-media.com/lodging/1000000/590000/582600/582513/8dba8d05_y.jpg)

### EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG

10/10 Excellent

"The staff at checkin was awesome"

[](https://expedia.ca/Tinley-Park-Hotels-Even-Hotel-Tinley-Park-Hotel-Convention-Center.h582513.Hotel-Information)

![DoubleTree by Hilton Chicago - Alsip](https://images.trvl-media.com/lodging/1000000/30000/25600/25507/fcb66f28_y.jpg)

### DoubleTree by Hilton Chicago - Alsip

10/10 Excellent

"Got stranded due to a storm and last minute reserved a room and enjoyed the hospitality and the service. They were very accommodating and even offered a free shuttle that started an hour earlier at 3 AM for me to bring me back to the airport when my flight was ready."

[](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Alsip.h25507.Hotel-Information)

![Hyatt Place Chicago-South/University Medical Center](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a_y.jpg)

### Hyatt Place Chicago-South/University Medical Center

10/10 Excellent

"Everything is great. Ill be staying here again in my next visit."

[](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information)

![Quality Inn & Suites Matteson near I-57](https://images.trvl-media.com/lodging/1000000/10000/4600/4530/42578f4f_y.jpg)

### Quality Inn & Suites Matteson near I-57

10/10 Excellent

"Clean place and great service."

[](https://expedia.ca/Matteson-Hotels-Quality-Inn-Suites.h4530.Hotel-Information)

## Find out more about Highland

## Highland Vacation Homes information

| Number of reviews | 83                 |
| ----------------- | ------------------ |
| Accommodation     | 240 Vacation Homes |
| Lowest Price      | CA $203            |
| Highest Price     | CA $3,426          |

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