Holiday Homes in Highland

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

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 NZ$780
includes taxes & fees
9 June - 10 June
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 NZ$344
includes taxes & fees
9 June - 10 June
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
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, (22 reviews)
"Host was great/ home was great! "
United States
Darcey W.
The price is NZ$1,197
includes taxes & fees
9 June - 10 June
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 NZ$774
includes taxes & fees
8 June - 9 June
Spacious 3br home near Chicago, fenced yard for pets
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 NZ$643
includes taxes & fees
7 June - 8 June
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 NZ$1,278
includes taxes & fees
17 June - 18 June
Modern Beach Bungalow, Hot tub, Firepit, Foosball, IN Dunes Nat`l Park
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 NZ$801
includes taxes & fees
7 June - 8 June
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
Beach nearby

Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails

Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
Miller Beach
8.8 out of 10, Excellent, (48 reviews)
"Great place and great location "
United States
Travis B.
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
Interior

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is NZ$949
includes taxes & fees
6 July - 7 July
Near Lake and Museum • Modern • Game Area
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 NZ$1,097
includes taxes & fees
8 June - 9 June
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 NZ$822
includes taxes & fees
9 June - 10 June
Modern Stylish Comfort Near Casino and Hwy
Interior

The brief escape with saltwater pool and working fireplaces.

The brief escape with saltwater pool and working fireplaces.
Lynwood
10.0 out of 10, Exceptional, (1 review)
"Nice place "
United States
Michael M.
The price is NZ$1,931
includes taxes & fees
8 June - 9 June
The brief escape with saltwater pool and working fireplaces.
Living area

The Hamilton Hideaway at Lake Street Beach

The Hamilton Hideaway at Lake Street Beach
Miller Beach
The price is NZ$1,118
includes taxes & fees
30 June - 1 July
The Hamilton Hideaway at Lake Street Beach
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 NZ$2,870
includes taxes & fees
17 June - 18 June
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park
Fridge, microwave, oven, stovetop

Spacious Group Getaway Near Hard Rock Casino & Chicago

Spacious Group Getaway Near Hard Rock Casino & Chicago
Merrillville
The price is NZ$1,818
includes taxes & fees
7 June - 8 June
Spacious Group Getaway Near Hard Rock Casino & Chicago
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 NZ$3,801
includes taxes & fees
8 June - 9 June
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

DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

10/10 Excellent
"Overall not a bad experience. Just rooms need to be cleaned much better. More attention to detail"
LaWanda 2-night trip
Posted 6 hours ago
DoubleTree by Hilton Chicago - Alsip

Find out more about Highland

Highland Holiday Homes information

Number of reviews
237
Accommodation
249 Holiday Homes
Lowest Price
NZ$344
Highest Price
NZ$3,801