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Holiday Homes in Highland

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Our top choices for Highland holiday homes

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 AU$627
includes taxes & fees
5 Nov - 6 Nov
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool

2. Coastal Home | Patio & Firepit | Backyard Games

Coastal Home | Patio & Firepit | Backyard Games
Merrillville
The price is AU$504
includes taxes & fees
6 Nov - 7 Nov
Coastal Home | Patio & Firepit | Backyard Games

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 AU$606
includes taxes & fees
5 Nov - 6 Nov
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard

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 AU$1,486
includes taxes & fees
1 Dec - 2 Dec
The Grand Gathering Place -Making Forever Memories Near Chicago & Hard Rock

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 AU$285
includes taxes & fees
11 Nov - 12 Nov
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

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 AU$2,265
includes taxes & fees
7 Nov - 8 Nov
Spacious 5-Bedroom Golf Course Home for Getaways

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 AU$369
includes taxes & fees
30 Nov - 1 Dec
Charming 1-bedroom apt in house by creek with AC, in delightful Portage

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 AU$638
includes taxes & fees
16 Nov - 17 Nov
Romantic Escape - Adult Playhouse with Exotic Dungeon

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 AU$1,962
includes taxes & fees
19 Nov - 20 Nov
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

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 AU$801
includes taxes & fees
12 Nov - 13 Nov
An Escape to a Dream of Green and relaxation.

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 AU$388
includes taxes & fees
9 Nov - 10 Nov
Tower Haus w/Private Hot Tub

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 AU$1,387
includes taxes & fees
16 Nov - 17 Nov
Dunes & Beach Getaway - Sleeps 10 - Room for the Whole Crew

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 AU$464
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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Top Highland Hotel Reviews

Find out more about Highland

Highland Holiday Homes information

Number of reviews
153
Accommodation
219 Holiday Homes
Lowest Price
AU$285
Highest Price
AU$2,265