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Holiday Homes in Highland

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Highland holiday homes

Interior

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

Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Merrilville
The price is €408
includes taxes & fees
16 Jun - 17 Jun
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Property grounds

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, (27 reviews)
"I had a fun stay "
United States
Jusu K.
The price is €176
includes taxes & fees
16 Jun - 17 Jun
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Beach

Tower Haus w/Private Hot Tub

Tower Haus w/Private Hot Tub
Chesterton
9.8 out of 10, Exceptional, (27 reviews)
"We had a nice evening for a girls weekend. The place was very clean and comfortable. We highly recommend. "
United States
Mary L.
The price is €470
includes taxes & fees
15 Jun - 16 Jun
Tower Haus w/Private Hot Tub
Interior

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is €486
includes taxes & fees
6 Jul - 7 Jul
Near Lake and Museum • Modern • Game Area
Exterior

Comfort & Space for the Whole family! Sleeps 8+

Comfort & Space for the Whole family! Sleeps 8+
Crown Point
8.0 out of 10, Very good, (5 reviews)
"Very nice, clean property. Loved the patio area. "
United States
Austin P.
The price is €329
includes taxes & fees
16 Jun - 17 Jun
Comfort & Space for the Whole family! Sleeps 8+
Fridge, microwave, oven, stovetop

Modern Beach Bungalow, Hot tub, Firepit, Foosball, IN Dunes Nat`l Park

Modern Beach Bungalow, Hot tub, Firepit, Foosball, IN Dunes Nat`l Park
Miller Beach
8.6 out of 10, Excellent, (29 reviews)
"A plus thanks"
United States
Anonymous traveller
The price is €630
includes taxes & fees
17 Jun - 18 Jun
Modern Beach Bungalow, Hot tub, Firepit, Foosball, IN Dunes Nat`l Park
Interior

Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake

Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake
Cedar Lake
10.0 out of 10, Exceptional, (21 reviews)
"Host was great/ home was great! "
United States
Darcey W.
The price is €561
includes taxes & fees
15 Jun - 16 Jun
Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake
Smart TV

Spacious 3br home near Chicago, fenced yard for pets

Spacious 3br home near Chicago, fenced yard for pets
Richton Park
9.0 out of 10, Wonderful, (25 reviews)
"The host was great and communication for her to respond was great. The amenities were good as well"
United States
Shantel U.
The price is €393
includes taxes & fees
22 Jun - 23 Jun
Spacious 3br home near Chicago, fenced yard for pets
Smart TV, fireplace

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, (6 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
Janina
The price is €414
includes taxes & fees
18 Jun - 19 Jun
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
Fridge, microwave, oven, stovetop

Smart Home, direct Beach Dunes Nat’l Park access, luxury amenities

Smart Home, direct Beach Dunes Nat’l Park access, luxury amenities
Miller Beach
8.0 out of 10, Very good, (22 reviews)
"Short drive to National Park and State Park hikes! Short walk to very nice beach area! Wonderful place to stay, fully stocked and plenty of room for 2 adults and 2 teens… and a dog!"
United States
Erica R.
The price is €660
includes taxes & fees
12 Jul - 13 Jul
Smart Home, direct Beach Dunes Nat’l Park access, luxury amenities
Dining

3-bedroom house in lovely Matteson with cool AC breeze

3-bedroom house in lovely Matteson with cool AC breeze
Matteson
10.0 out of 10, Exceptional, (1 review)
"clean, comfortable, hosts very responsive to communications, neighborhood felt safe, perfect location for our stay to attend sectionals NTRP tennis tournament at HF Racquet and Fitness Club"
United States
Susan H.
The price is €566
includes taxes & fees
15 Jun - 16 Jun
3-bedroom house in lovely Matteson with cool AC breeze
Fridge, microwave, oven, stovetop

Modern Stylish Comfort Near Casino and Hwy

Modern Stylish Comfort Near Casino and Hwy
Homewood
10.0 out of 10, Exceptional, (1 review)
"Very clean..out side garbage needs to be picked up. Toilet seats were loose and under kitchen sink was wet. Could use a toaster and some basic condiments. "
United States
margaret
The price is €446
includes taxes & fees
15 Jul - 16 Jul
Modern Stylish Comfort Near Casino and Hwy
Living area

The Hamilton Hideaway at Lake Street Beach

The Hamilton Hideaway at Lake Street Beach
Miller Beach
The price is €572
includes taxes & fees
7 Jul - 8 Jul
The Hamilton Hideaway at Lake Street Beach
Fridge, microwave, oven, stovetop

Spacious Group Getaway Near Hard Rock Casino & Chicago

Spacious Group Getaway Near Hard Rock Casino & Chicago
Merrillville
The price is €951
includes taxes & fees
15 Jun - 16 Jun
Spacious Group Getaway Near Hard Rock Casino & Chicago
Outdoor dining

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, (66 reviews)
"The host was great to work with and answered questions quickly! The house is beautiful and accommodates A LOT of people. It was perfect for 3 siblings and families to gather together. We will definitely be scheduling more stays here. "
United States
Shelly S.
The price is €1,324
includes taxes & fees
17 Jun - 18 Jun
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park
Exterior

Spacious 5-Bedroom Golf Course Home for Getaways

Spacious 5-Bedroom Golf Course Home for Getaways
Merrillville
10.0 out of 10, Exceptional, (6 reviews)
"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
Jim A.
The price is €1,989
includes taxes & fees
15 Jun - 16 Jun
Spacious 5-Bedroom Golf Course Home for Getaways
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

Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

2/10 Terrible
"The hotel was clean and the staff were amazing and very helpful. However, I did not feel safe during my stay, and in my opinion, it is not the right hotel for families."
Rania 2-night trip
Posted 3 hours ago
Wind Creek Southland Casino and Hotel

Find out more about Highland

Highland Holiday Homes information

Number of reviews
236
Accommodation
227 Holiday Homes
Lowest Price
€176
Highest Price
€1,989