Photo by Joe Farmer

Holiday Homes in Highland

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Find holiday rentals that suit your style

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Apartments
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Cabins
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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Highland holiday homes

A living room with a brick fireplace, a television mounted above it, and a dining area with a table and chairs.

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

Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
Merrillville
9.8 out of 10, Exceptional, (9 reviews)
"The house was cozy and very clean. The hot tub was amazing! Check-in instructions were clear and easy to follow. The host was very helpful and responsive to messages. We would definitely stay again. Thank you!"
United States
Anonymous traveller
The price is NZ$809
includes taxes & fees
5 Dec - 6 Dec
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
An outdoor seating area with a sofa, chairs, and a table, surrounded by greenery and a house in the background.

2. Coastal Home | Patio & Firepit | Backyard Games

Coastal Home | Patio & Firepit | Backyard Games
Merrillville
The price is NZ$638
includes taxes & fees
6 Nov - 7 Nov
Coastal Home | Patio & Firepit | Backyard Games
A modern kitchen with wooden cabinets, stainless steel appliances, and a white countertop island.

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

Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Merrilville
8.6 out of 10, Excellent, (4 reviews)
"Great pet friendly home and yard. Host was responsive great communication. Excellent, easy to access location."
United States
Lynda L.
The price is NZ$753
includes taxes & fees
5 Nov - 6 Nov
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
A circular outdoor seating area with Adirondack chairs and a central fire pit.

4. The Grand Gathering Place -Making Forever Memories Near Chicago & Hard Rock

The Grand Gathering Place -Making Forever Memories Near Chicago & Hard Rock
Merrillville
10.0 out of 10, Exceptional, (2 reviews)
"Good location clean full amenities lots of space and convenience."
United States
david d.
The price is NZ$1,873
includes taxes & fees
1 Dec - 2 Dec
The Grand Gathering Place -Making Forever Memories Near Chicago & Hard Rock
A wooden deck with a railing, a staircase, and a window with a wreath.

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

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.8 out of 10, Exceptional, (37 reviews)
"I had a fun stay "
United States
Jusu K.
The price is NZ$349
includes taxes & fees
11 Nov - 12 Nov
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A large, two-story house with a covered patio and a well-maintained lawn.

6. Spacious 5-Bedroom Golf Course Home for Getaways

Spacious 5-Bedroom Golf Course Home for Getaways
Merrillville
10.0 out of 10, Exceptional, (8 reviews)
"It was a fantastic experience from arrival to departure. We've played the course every year and our group comes from all over Chicago. It was great to stay the night and enjoy the property versus driving back at the end of our round. The hospitality was great and the accommodations were first class."
United States
Jon R.
The price is NZ$2,800
includes taxes & fees
5 Nov - 6 Nov
Spacious 5-Bedroom Golf Course Home for Getaways
A hot tub with water, a wooden deck, and a chair.

7. Charming 1-bedroom apt in house by creek with AC, in delightful Portage

Charming 1-bedroom apt in house by creek with AC, in delightful Portage
Portage
9.8 out of 10, Exceptional, (11 reviews)
"Nice place close to the beach."
United States
Zdenek M.
The price is NZ$449
includes taxes & fees
30 Nov - 1 Dec
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
A bedroom with a bed, a nightstand, a wall-mounted lamp, and a plant.

8. Romantic Escape - Adult Playhouse with Exotic Dungeon

Romantic Escape - Adult Playhouse with Exotic Dungeon
South Holland
8.8 out of 10, Excellent, (15 reviews)
"enjoyed my stay cant wait to book again "
United States
Anonymous traveller
The price is NZ$773
includes taxes & fees
9 Nov - 10 Nov
Romantic Escape - Adult Playhouse with Exotic Dungeon
A two-story outdoor deck with a hot tub, fire pit, and seating area.

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

Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park
Miller Beach
9.2 out of 10, Wonderful, (69 reviews)
"This was a great spot for a quiet family vacation! It was great being so close to the lake!"
United States
Marcia M.
The price is NZ$2,481
includes taxes & fees
19 Nov - 20 Nov
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park
A modern kitchen with grey cabinets, a central island with stools, a microwave, and a dishwasher.

10. An Escape to a Dream of Green and relaxation.

An Escape to a Dream of Green and relaxation.
Miller Beach
9.6 out of 10, Exceptional, (28 reviews)
"Extremely clean. Kitchen needs more/newer cookware/bakeware to match how nice the house is. Hot tub was a wonderful addition along with the extra room on the back of the house. Overall we enjoyed our stay."
United States
Julie R.
The price is NZ$975
includes taxes & fees
9 Nov - 10 Nov
An Escape to a Dream of Green and relaxation.
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.

11. Tower Haus w/Private Hot Tub

Tower Haus w/Private Hot Tub
Chesterton
9.8 out of 10, Exceptional, (38 reviews)
"Great place to stay! It was really clean! Highly recommend!"
United States
Joshua N.
The price is NZ$481
includes taxes & fees
9 Nov - 10 Nov
Tower Haus w/Private Hot Tub
A modern living room with a sofa, armchair, and a coffee table. There is a bunk bed in the background, a large rug, and a ceiling fan.

12. Dunes & Beach Getaway - Sleeps 10 - Room for the Whole Crew

Dunes & Beach Getaway - Sleeps 10 - Room for the Whole Crew
Portage
The price is NZ$1,726
includes taxes & fees
6 Nov - 7 Nov
Dunes & Beach Getaway - Sleeps 10 - Room for the Whole Crew
A bedroom with a stone wall, a TV mounted on it, a bed with a white comforter, and a view of the outdoors through a window.

13. Beautifully furnished one bedroom loft located in Chicago's South side suburb

Beautifully furnished one bedroom loft located in Chicago's South side suburb
Hazel Green
10.0 out of 10, Exceptional, (1 review)
"Super great location, we had a concert at Tinley Park, then explored Chicago with a river cruise and Second City Everything was perfect and so eat to just chill, come and go as we pleased In a nice neighborhood and interior was furnished beautifully. Definitely worth the price !!"
United States
Nick L.
The price is NZ$576
includes taxes & fees
5 Nov - 6 Nov
Beautifully furnished one bedroom loft located in Chicago's South side suburb
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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Learn more about Highland

Stroll along the scenic Wicker Memorial Park's trails or cool off at its splash pad on hot summer days. Catch a show at the historic Towle Theatre, then sample local brews at 3 Floyds Brewing in nearby Munster.

See all hotels in Highland
A two-story brick building with a balcony, a front door, and steps leading up to the entrance.
Photo by Joe Farmer
Open Photo by Joe Farmer