Title: Highland Vacation Rentals from CA $120: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=177657&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two 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)

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=177657&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=177657&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Highland vacation rentals

![Beach nearby](https://images.trvl-media.com/lodging/70000000/69390000/69386000/69385955/3c1f7b34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/70000000/69390000/69386000/69385955/d174f20d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/70000000/69390000/69386000/69385955/w894h683x65y0-0fccdb4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/70000000/69390000/69386000/69385955/47cadd90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

[](https://www.expedia.ca/Chesterton-Hotels-The-Pool-Barn-Camper-WHot-Tub-Near-Indiana-Dunes.h69385955.Hotel-Information)

Porter

9.0/10

Wonderful

(12 reviews)

"Every aspect of my booking & stay was convenient & seamless; from the reasonable price, online reservation process, host communication, beautiful grounds, to the abundant amenities offered there was nothing I or my family wanted for. Don & Kim are accommodating, professional & experienced hosts and it showed. Thank you for the wonderful experience I recommend their multiple spaces to anyone & would stay with them again without hesitation! "

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

esther Amber C.

CA $80

CA $120 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Chesterton-Hotels-The-Pool-Barn-Camper-WHot-Tub-Near-Indiana-Dunes.h69385955.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/123000000/122930000/122921300/122921247/w1290h854x0y11-6bdc879f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/123000000/122930000/122921300/122921247/w1290h857x0y6-f6fedf26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122930000/122921300/122921247/764afeff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122930000/122921300/122921247/w1290h850x0y25-29256ad9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern 3BR w/Deck · Minutes from I-65\. Fenced Yard

[](https://www.expedia.ca/Merrillville-Hotels-Modern-3BR-WDeck-Minutes-From-I-65-Fenced-Yard.h122921247.Hotel-Information)

Merrilville

CA $202

CA $519 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Merrillville-Hotels-Modern-3BR-WDeck-Minutes-From-I-65-Fenced-Yard.h122921247.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95050000/95044300/95044250/a5e3e3f2.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)

![Smart TV, offices](https://images.trvl-media.com/lodging/96000000/95050000/95044300/95044250/927385a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95050000/95044300/95044250/37fd4a15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago 

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

Chesterton

9.0/10

Wonderful

(10 reviews)

"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 $142

CA $442 total

includes taxes & fees

Feb 9 - Feb 10

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

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/26959619.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/bda4219b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/deae7b79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dunes Retreat w/Private Hot Tub

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

Chesterton

10/10

Exceptional

(15 reviews)

"Great host, everything was clean, many little extras for comfort and convenience!"

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

Kara K.

CA $142

CA $356 total

includes taxes & fees

Feb 10 - Feb 11

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

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

![Smart TV, offices](https://images.trvl-media.com/lodging/96000000/95040000/95038900/95038818/c15b3e2b.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)

![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95040000/95038900/95038818/a2b68ac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago 

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

Chesterton

9.4/10

Exceptional

(3 reviews)

"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 $145

CA $533 total

includes taxes & fees

Feb 10 - Feb 11

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

![Interior](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821529/01933d46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821529/39ec5645.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821529/ded3c13e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821529/ee53c125.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Rustic Cabin for Two!

[](https://www.expedia.ca/Griffith-Hotels-Beautiful-Rustic-Cabin-For-Two.h111821529.Hotel-Information)

Griffith

8.8/10

Excellent

(20 reviews)

"Nice and cozy place to stay. We enjoyed our secluded area during our time here."

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

Allison A.

CA $92

CA $141 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Griffith-Hotels-Beautiful-Rustic-Cabin-For-Two.h111821529.Hotel-Information)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124263/88a6a75b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124263/8074f855.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124263/fc07c1c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124263/431d74e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Charm Studio Apt in Chicago

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Charm-Studio-Apt-In-Chicago.h117124263.Hotel-Information)

Hyde Park

10/10

Exceptional

(3 reviews)

"Everying was great."

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

Ryan D.

CA $79

CA $209 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Charm-Studio-Apt-In-Chicago.h117124263.Hotel-Information)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/f869465d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/66917406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/7e60538d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/dc03e46f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Studio Unit | Chic + Prime Location

[](https://www.expedia.ca/Chicago-Hotels-Studio-Unit-Chic-Prime-Location.h116792582.Hotel-Information)

Hyde Park

10/10

Exceptional

(2 reviews)

"Location was just perfect!"

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

Meg D.

CA $79

CA $209 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Studio-Unit-Chic-Prime-Location.h116792582.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/cf195af6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/fe86e080.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/f6353a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/dd9a1f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleek & Functional 2-Bedroom Apt

[](https://www.expedia.ca/Chicago-Hotels-Sleek-Functional-2-Bedroom-Apt.h116792489.Hotel-Information)

Hyde Park

9.6/10

Exceptional

(4 reviews)

"Nice place for a girls trip weekend. "

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

Madonna A.

CA $100

CA $269 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Sleek-Functional-2-Bedroom-Apt.h116792489.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/e3fd1233.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![Smart TV, books](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/f698e846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

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

Robertsdale

9.8/10

Exceptional

(20 reviews)

"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 $146

CA $218 total

includes taxes & fees

Feb 9 - Feb 10

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

![Exterior](https://images.trvl-media.com/lodging/113000000/112540000/112534100/112534056/w1024h674x0y4-c8d01466.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/113000000/112540000/112534100/112534056/59cc12db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/113000000/112540000/112534100/112534056/7a89868d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/113000000/112540000/112534100/112534056/7608b471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern & Spacious Stay by Northwestern Hospital Bronzeville

[](https://www.expedia.ca/Chicago-Hotels-Modern-Spacious-Stay-By-Northwestern-Hospital-Bronzeville.h112534056.Hotel-Information)

Bronzeville

10/10

Exceptional

(3 reviews)

"What a great place to stay! Interior of the unit was very nice and modern. Amenities were great. We felt safe and secure the entire time. Our host was in constant communication to make sure our needs were met. We would definitely recommend this stay!"

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

Matt D.

CA $111

CA $459 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Modern-Spacious-Stay-By-Northwestern-Hospital-Bronzeville.h112534056.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792457/75d1dc95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792457/c4d843cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792457/0d5faef2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792457/5f21f45c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bright 1BR Unit in a Prime Spot

[](https://www.expedia.ca/Chicago-Hotels-Modern-1BR-Gem-In-Chicago-Kenwood-501.h116792457.Hotel-Information)

Hyde Park

10/10

Exceptional

(1 review)

"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](https://a.travel-assets.com/egds/marks/flags/us.svg)

christine m.

CA $94

CA $240 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Modern-1BR-Gem-In-Chicago-Kenwood-501.h116792457.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110940000/110931500/110931495/47709229.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)

![Interior](https://images.trvl-media.com/lodging/111000000/110940000/110931500/110931495/80da7c13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110940000/110931500/110931495/6e5164c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool

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

Merrillville

9.6/10

Exceptional

(5 reviews)

"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 $156

CA $329 total

includes taxes & fees

Feb 9 - Feb 10

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

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/ba9db8cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/a44fb78b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/6c56b652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/19ac687a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Studio Unit Near UChicago

[](https://www.expedia.ca/Chicago-Hotels-Modern-Studio-Near-UChicago.h116793083.Hotel-Information)

Hyde Park

9.4/10

Exceptional

(12 reviews)

"Clean room and convenient location! "

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

Gabriela

CA $79

CA $209 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Modern-Studio-Near-UChicago.h116793083.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792528/dd9e0f78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792528/3ed7ce53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792528/1ee73694.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792528/e8067ee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bright South Hyde Park Studio

[](https://www.expedia.ca/Chicago-Hotels-Bright-South-Hyde-Park-Studio.h116792528.Hotel-Information)

Hyde Park

10/10

Exceptional

(1 review)

"Comfortable space in a nice neighborhood. I highly recommend."

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

BiggDas M.

CA $79

CA $209 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Bright-South-Hyde-Park-Studio.h116792528.Hotel-Information)

![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792423/327989d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792423/235673cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792423/fb5bad1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792423/269d384b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish 4BR South Loop Home

[](https://www.expedia.ca/Chicago-Hotels-Stylish-4BR-South-Loop-Home.h116792423.Hotel-Information)

Greater Grand Crossing

10/10

Exceptional

(2 reviews)

"Very happy with stay. Good communication from property host. "

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

Nicole E.

CA $134

CA $496 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Stylish-4BR-South-Loop-Home.h116792423.Hotel-Information)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792497/49b10dc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792497/83ec6dc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792497/0327bf8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792497/270caa93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Furnished 3BR Apt w/ Laundry

[](https://www.expedia.ca/Chicago-Hotels-Furnished-3BR-Apt-W-Laundry.h116792497.Hotel-Information)

Hyde Park

9.8/10

Exceptional

(6 reviews)

"Apartment and neighborhood were beautiful. We really enjoyed our stay and would book the same place again!"

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

Kristin W.

CA $101

CA $297 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Chicago-Hotels-Furnished-3BR-Apt-W-Laundry.h116792497.Hotel-Information)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792541/900036cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792541/2140a32e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792541/ab2a4e99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792541/279f144b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Compact Studio for a Relaxed Stay

[](https://www.expedia.ca/Chicago-Hotels-Compact-Studio-For-A-Relaxed-Stay.h116792541.Hotel-Information)

Hyde Park

8.0/10

Very good

(1 review)

CA $79

CA $209 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Compact-Studio-For-A-Relaxed-Stay.h116792541.Hotel-Information)

![Beach nearby, beach towels](https://images.trvl-media.com/lodging/100000000/99550000/99542100/99542070/0226147a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/100000000/99550000/99542100/99542070/183e6efa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99550000/99542100/99542070/92dc4cf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99550000/99542100/99542070/4463d78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Serenity on the Shores - with easy transport to Chicago/SouthShore across the St

[](https://www.expedia.ca/Portage-Hotels-Serenity-On-The-Shores-With-Easy-Transport-To-ChicagoSouthShore-Across-The-St.h99542070.Hotel-Information)

Portage

9.6/10

Exceptional

(12 reviews)

"Very nice place "

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

LeAnna M.

CA $244

CA $310 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Portage-Hotels-Serenity-On-The-Shores-With-Easy-Transport-To-ChicagoSouthShore-Across-The-St.h99542070.Hotel-Information)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793062/w1536h1012x0y0-b81df5b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793062/ba76d560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793062/56a939d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793062/4472d85b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bright & Cozy 1BR Near UChicago

[](https://www.expedia.ca/Chicago-Hotels-Bright-Cozy-1BR-Near-UChicago.h116793062.Hotel-Information)

Hyde Park

9.4/10

Exceptional

(3 reviews)

"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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alan F.

CA $94

CA $240 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Bright-Cozy-1BR-Near-UChicago.h116793062.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=2026-02-21&endDate=2026-02-22&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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=VACATION_HOME)

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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=COTTAGE)

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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CABIN)

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## Top Highland Hotel Reviews

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

### Hilton Chicago/Oak Lawn

10/10 Excellent

"Clean room "

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

![Wingate by Wyndham Tinley Park](https://images.trvl-media.com/lodging/1000000/210000/203200/203191/4446a44e_y.jpg)

### Wingate by Wyndham Tinley Park

10/10 Excellent

"Clean room, great mattress and great staff!"

[](https://expedia.ca/Tinley-Park-Hotels-Wingate-By-Wyndham-Tinley-Park.h203191.Hotel-Information)

![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

"Joy was awesome explaining everything to me. "

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

"Front desk staff was very helpful . I can’t rennet her name but, she had beautiful long and red hair .She was exceptionally and also the gentleman with the glasses on the night shift.. House keeper need to service room or least amenities"

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

"Always a great time for New Year’s Eve "

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

![Econo Lodge South Holland - Chicago Southland](https://images.trvl-media.com/lodging/1000000/10000/4000/3986/72bd041c_y.jpg)

### Econo Lodge South Holland - Chicago Southland

10/10 Excellent

"Was cold but overall cool "

[](https://expedia.ca/Chicago-Hotels-Econo-Lodge.h3986.Hotel-Information)

![Days Inn and Suites by Wyndham Hammond, IN](https://images.trvl-media.com/lodging/2000000/1360000/1357200/1357103/a642082c_y.jpg)

### Days Inn and Suites by Wyndham Hammond, IN

10/10 Excellent

"I enjoy my stay "

[](https://expedia.ca/Hammond-Hotels-Days-Inn-And-Suites-By-Wyndham-Hammond.h1357103.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

"Staff was amazing! Chuck at breakfast was the absolute best. Can’t say enough about how great of a job he did to make us feel welcomed."

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

![Comfort Suites near I-80 and I-94](https://images.trvl-media.com/lodging/1000000/130000/120700/120653/09e7293e_y.jpg)

### Comfort Suites near I-80 and I-94

10/10 Excellent

"Clean room. Jacuzzi tub was nice. Decent breakfast. Lot of bang for little bucks"

[](https://expedia.ca/Chicago-Hotels-Comfort-Suites-Lansing.h120653.Hotel-Information)

## Find out more about Highland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Highland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Vacation Homes in Highland ](https://expedia.ca/Highland-Private-Vacation-Homes.d177657-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Highland ](https://expedia.ca/Highland-Apartments.d177657-aaApartments.Travel-Guide-Accommodation)
- [Condo Rentals in Highland ](https://expedia.ca/Highland-Condos.d177657-aaCondos.Travel-Guide-Accommodation)
- [Motels in Highland ](https://expedia.ca/Highland-Motels.d177657-aaMotels.Travel-Guide-Accommodation)
- [Cottages in Highland ](https://expedia.ca/Highland-Cottages.d177657-aaCottages.Travel-Guide-Accommodation)
- [Cabin Rentals in Highland ](https://expedia.ca/Highland-Cabins.d177657-aaCabins.Travel-Guide-Accommodation)
- [RV Parks in Highland ](https://expedia.ca/Highland-RV-Parks.d177657-aaRVParks.Travel-Guide-Accommodation)
- [Guest Houses in Highland ](https://expedia.ca/Highland-Guest-Houses.d177657-aaGuestHouses.Travel-Guide-Accommodation)
- [Villas in Highland ](https://expedia.ca/Highland-Villas.d177657-aaVillas.Travel-Guide-Accommodation)
- [Farmstay in Highland ](https://expedia.ca/Highland-Agritourism.d177657-aaAgritourism.Travel-Guide-Accommodation)
- [Aparthotels in Highland ](https://expedia.ca/Highland-Apart-Hotels.d177657-aaApartHotels.Travel-Guide-Accommodation)
- [Resorts in Highland ](https://expedia.ca/Highland-Resort-Hotels.d177657-aaResortHotels.Travel-Guide-Accommodation)
- [B&B in Highland ](https://expedia.ca/Highland-Bed-And-Breakfast.d177657-aaBedAndBreakfast.Travel-Guide-Accommodation)

## Frequently asked questions

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