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Highland Holiday Rentals

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Check prices for these dates

Tonight
25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Highland holiday rentals

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

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

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
9.0 out of 10, Wonderful, (12)
"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
esther Amber C.
The price is HK$455
HK$684 total
includes taxes & fees
29 Dec - 30 Dec
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Exterior
Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
9.4 out of 10, Exceptional, (18)
"Nice and cozy place to stay. We enjoyed our secluded area during our time here."
United States
Allison A.
The price is HK$521
HK$801 total
includes taxes & fees
30 Dec - 31 Dec
Beautiful Rustic Cabin for Two!
Private kitchen
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard

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

Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
2.0 star property
Merrilville
The price is HK$1,151
HK$2,926 total
includes taxes & fees
11 Jan - 12 Jan 2026
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Property grounds
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago

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

Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago
Chesterton
9.0 out of 10, Wonderful, (9)
"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
Nick R.
The price is HK$805
HK$2,513 total
includes taxes & fees
31 Dec - 1 Jan 2026
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago
Iron/ironing board, travel cot, WiFi, bed sheets
Modern Studio Near UChicago

Modern Studio Near UChicago

Modern Studio Near UChicago
Hyde Park
9.6 out of 10, Exceptional, (11)
"Clean room and convenient location! "
United States
Gabriela
The price is HK$443
HK$1,178 total
includes taxes & fees
5 Jan - 6 Jan 2026
Modern Studio Near UChicago
Fridge, microwave, oven, stovetop
Bright South Hyde Park Studio

Bright South Hyde Park Studio

Bright South Hyde Park Studio
Hyde Park
10.0 out of 10, Exceptional, (1)
"Comfortable space in a nice neighborhood. I highly recommend."
United States
BiggDas M.
The price is HK$443
HK$1,178 total
includes taxes & fees
6 Jan - 7 Jan 2026
Bright South Hyde Park Studio
Beach nearby
Dunes Escape - Minutes from Indiana Dunes National Park

Dunes Escape - Minutes from Indiana Dunes National Park

Dunes Escape - Minutes from Indiana Dunes National Park
Miller Beach
9.8 out of 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
Braden S.
The price is HK$692
HK$2,423 total
includes taxes & fees
5 Jan - 6 Jan 2026
Dunes Escape - Minutes from Indiana Dunes National Park
1 bedroom, iron/ironing board, WiFi, bed sheets
Charming 1BR/1BA Apt in Chicago

Charming 1BR/1BA Apt in Chicago

Charming 1BR/1BA Apt in Chicago
Hyde Park
10.0 out of 10, Exceptional, (1)
The price is HK$467
HK$1,283 total
includes taxes & fees
28 Dec - 29 Dec
Charming 1BR/1BA Apt in Chicago
Fridge, microwave, oven, stovetop
Explore Hyde Park: 2BR Apt on Blackstone Ave

Explore Hyde Park: 2BR Apt on Blackstone Ave

Explore Hyde Park: 2BR Apt on Blackstone Ave
Hyde Park
9.6 out of 10, Exceptional, (4)
"All the necessities with no personal touches. Keys from lockbox to open second door were not needed as the second door is always open. Impeccable communication with host. Great location, close to restaurants and train to Millennium Station. Coffee service was excellent, just be sure to find extra pouches in cabinet. Bathtub faucet could not be turned far enough to prevent leaking. TV remote not great and I couldn’t get CNN or MSNBC. I’d stay here again. "
United States
lost whale press
The price is HK$467
HK$1,399 total
includes taxes & fees
1 Jan - 2 Jan 2026
Explore Hyde Park: 2BR Apt on Blackstone Ave
Interior
Sleek & Functional 2-Bedroom Apt

Sleek & Functional 2-Bedroom Apt

Sleek & Functional 2-Bedroom Apt
Hyde Park
9.6 out of 10, Exceptional, (4)
"Nice place for a girls trip weekend. "
United States
Madonna A.
The price is HK$451
HK$1,381 total
includes taxes & fees
5 Jan - 6 Jan 2026
Sleek & Functional 2-Bedroom Apt
Iron/ironing board, travel cot, WiFi, bed sheets
Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago
Hyde Park
10.0 out of 10, Exceptional, (1)
The price is HK$443
HK$1,178 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Charm Studio Apt in Chicago
Beach nearby
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
Porter
8.8 out of 10, Excellent, (16)
"Great place to stay with kids."
United States
Jane H.
The price is HK$903
HK$1,186 total
includes taxes & fees
28 Dec - 29 Dec
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
Fridge, microwave, oven, stovetop
Bright 1BR Unit in a Prime Spot

Bright 1BR Unit in a Prime Spot

Bright 1BR Unit in a Prime Spot
Hyde Park
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.
The price is HK$490
HK$1,310 total
includes taxes & fees
4 Jan - 5 Jan 2026
Bright 1BR Unit in a Prime Spot
Fridge, microwave, oven, stovetop
Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago

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

Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago
Chesterton
9.4 out of 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
T J.
The price is HK$826
HK$3,007 total
includes taxes & fees
28 Dec - 29 Dec
Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago
Iron/ironing board, travel cot, WiFi, bed sheets
Studio Unit | Chic + Prime Location

Studio Unit | Chic + Prime Location

Studio Unit | Chic + Prime Location
Hyde Park
10.0 out of 10, Exceptional, (2)
"Location was just perfect!"
United States
Meg D.
The price is HK$443
HK$1,178 total
includes taxes & fees
5 Jan - 6 Jan 2026
Studio Unit | Chic + Prime Location
TV, offices
Bright & Cozy 1BR Near UChicago

Bright & Cozy 1BR Near UChicago

Bright & Cozy 1BR Near UChicago
Hyde Park
9.4 out of 10, Exceptional, (3)
"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.
The price is HK$467
HK$1,283 total
includes taxes & fees
29 Dec - 30 Dec
Bright & Cozy 1BR Near UChicago
Microwave, oven, stovetop
Your Home Away From Home in Sauk Village

Your Home Away From Home in Sauk Village

Your Home Away From Home in Sauk Village
2.0 star property
Sauk Village
10.0 out of 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
Aaron K.
The price is HK$716
HK$1,140 total
includes taxes & fees
30 Dec - 31 Dec
Your Home Away From Home in Sauk Village
Interior
Chic Retreat: Cozy 1BR Apartment

Chic Retreat: Cozy 1BR Apartment

Chic Retreat: Cozy 1BR Apartment
Hyde Park
9.0 out of 10, Wonderful, (7)
"Our stay was very nice, with simple checkin / check out, and excellent communication by our host. "
United States
Tom B.
The price is HK$467
HK$1,283 total
includes taxes & fees
28 Dec - 29 Dec
Chic Retreat: Cozy 1BR Apartment
1 bedroom, iron/ironing board, travel cot, WiFi
Bright & Modern 1BR in Hyde Park

Bright & Modern 1BR in Hyde Park

Bright & Modern 1BR in Hyde Park
Hyde Park
8.8 out of 10, Excellent, (3)
"Property was very clean. We enjoyed ourselves, Thank you!"
United States
Charles S.
The price is HK$467
HK$1,283 total
includes taxes & fees
28 Dec - 29 Dec
Bright & Modern 1BR in Hyde Park
Fridge, microwave, oven, stovetop
Studio Apt Comfy & Sunlit

Studio Apt Comfy & Sunlit

Studio Apt Comfy & Sunlit
Hyde Park
10.0 out of 10, Exceptional, (2)
"My stay was really good"
United States
Paramita B.
The price is HK$443
HK$1,255 total
includes taxes & fees
5 Jan - 6 Jan 2026
Studio Apt Comfy & Sunlit
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 Highland Hotel Reviews

Econo Lodge South Holland - Chicago Southland

Econo Lodge South Holland - Chicago Southland

10/10 Excellent
"Clean, Helpful service "
Destin 2-night trip
Posted 21 hours ago
Econo Lodge South Holland - Chicago Southland

Find out more about Highland

Search for holiday rentals in Highland on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland using one of the methods below:

  • View our selection of featured holiday rentals in Highland
  • Use the map to find apartments and other holiday homes in the Highland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Highland while they last

Look no further and take a look at our great range of rental properties in Highland!

Frequently asked questions

Are there holiday rentals in Highland?

Yes, there are holiday rentals close to the most popular sights in Highland, or you can select a more secluded option if you're looking for a relaxing stay. Highland is known for its churches and basketball games. Make sure you have time to check out the lake views while you're in the area.

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

Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago : This holiday home rental outside of Highland is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

What can I see and do in Highland?

Indiana Dunes National Park and Hoosier Prairie are a couple of lovely local spots to get outside and enjoy nature. Purdue University Northwest and Hard Rock Casino Northern Indiana are a couple of places you'll find in the wider area.

What are holiday rentals like in Highland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highland. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family getaway.