A two-story brick building with a balcony, a front door, and steps leading up to the entrance.

Highland Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Highland vacation homes

A wooden deck with a railing, a staircase, and a window with a wreath.

1. 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, (34 reviews)
"I had a fun stay "
United States
Jusu K.
The price is CA $198
CA $287 total
includes taxes & fees
Sep 14 - Sep 15
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A hot tub with water, a wooden deck, and a chair.

2. 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 CA $156
CA $348 total
includes taxes & fees
Sep 17 - Sep 18
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
A living room with a brick fireplace, a television mounted above it, and a dining area with a table and chairs.

3. 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, (7 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 CA $415
CA $662 total
includes taxes & fees
Sep 14 - Sep 15
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
A two-story house with a front porch and a small attached garage.

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

Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Merrilville
6.0 out of 10, (1 review)
"This is not a place to stay with small children; glad mine are grown for this stay. Also, the host really needs to have people they know stay there a bit to see what guests are really looking for. This property really felt like someone is just trying to make money and they don't really care about the people using the property. One of our beds was broken, there were limited furnishings and the tv in the living room was not user friendly at all. I would not recommend this property for any long...
United States
Paula H.
The price is CA $275
CA $651 total
includes taxes & fees
Oct 5 - Oct 6
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
A modern building with a white exterior, a black door, and a large window.

5. Dune Haus + Indiana National Dunes Park

Dune Haus + Indiana National Dunes Park
Portage
10.0 out of 10, Exceptional, (1 review)
"Very great stay all around"
United States
Devan G.
The price is CA $249
CA $496 total
includes taxes & fees
Sep 13 - Sep 14
Dune Haus + Indiana National Dunes Park
A laundry room with a washer and dryer, a folding table, and a chair.

6. La Petite • Piano • Serene Organic • Long Stays

La Petite • Piano • Serene Organic • Long Stays
Merrillville
8.0 out of 10, Very good, (1 review)
"Stairs in this bilevel were very narrow and NO railings.A/c was very loud.Some plants or bushes in front of house would have given it some curb appeal, instead just beds of dirt."
United States
Joe M.
The price is CA $527
CA $673 total
includes taxes & fees
Oct 7 - Oct 8
La Petite • Piano • Serene Organic • Long Stays
A room with a sofa, ottoman, foosball table, and wall decorations including sports posters.

7. 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, (1 review)
"Good location clean full amenities lots of space and convenience."
United States
david d.
The price is CA $831
CA $1,586 total
includes taxes & fees
Sep 16 - Sep 17
The Grand Gathering Place -Making Forever Memories Near Chicago & Hard Rock
A beach with a sunset, waves, and sparse vegetation.

8. Tower Haus w/Private Hot Tub

Tower Haus w/Private Hot Tub
Chesterton
9.8 out of 10, Exceptional, (34 reviews)
"Great place to stay! It was really clean! Highly recommend!"
United States
Joshua N.
The price is CA $311
CA $576 total
includes taxes & fees
Sep 13 - Sep 14
Tower Haus w/Private Hot Tub
A large, two-story house with a covered patio and a well-maintained lawn.

9. Spacious 5-Bedroom Golf Course Home for Getaways

Spacious 5-Bedroom Golf Course Home for Getaways
Merrillville
10.0 out of 10, Exceptional, (7 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 CA $1,384
CA $1,759 total
includes taxes & fees
Oct 1 - Oct 2
Spacious 5-Bedroom Golf Course Home for Getaways
A spacious living room with a wooden staircase, a grey sofa, and a large window with blinds.

10. 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, (27 reviews)
"We had a good stay, the owner communicated well. There was alot of steps but the gate was so helpful with a toddler. The only things we wished was changed to make it 5 star was the lawn in the back yard mowed and the bathtub jets cleaned."
United States
Cassy R.
The price is CA $411
CA $851 total
includes taxes & fees
Sep 13 - Sep 14
Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake
A living room with a brown sofa, a coffee table, and a patterned rug. There is a staircase leading to another room.

11. 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, (28 reviews)
"Very spacious accommodations in a very nice neighborhood. Convenient to food and shopping. Great value for the cost. "
United States
Greg S.
The price is CA $279
CA $633 total
includes taxes & fees
Sep 21 - Sep 22
Spacious 3br home near Chicago, fenced yard for pets
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.

12. 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
The price is CA $339
CA $483 total
includes taxes & fees
Sep 15 - Sep 16
Beautifully furnished one bedroom loft located in Chicago's South side suburb
A dining area with a black table set for four, surrounded by chairs. A vase with dried flowers and a candle holder are on the table.

13. 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 CA $461
CA $882 total
includes taxes & fees
Sep 28 - Sep 29
3-bedroom house in lovely Matteson with cool AC breeze
A residential area with two houses, one with a turret and another with a gabled roof.

14. Private Yard Near Beach & Obama Center

Private Yard Near Beach & Obama Center
Woodlawn
The price is CA $523
CA $1,226 total
includes taxes & fees
Sep 29 - Sep 30
Private Yard Near Beach & Obama Center
A living room with a sofa, two armchairs, a coffee table, a flat-screen TV, and a painting on the wall.

15. Designer 3BR Near Beach & Obama Center

Designer 3BR Near Beach & Obama Center
Woodlawn
The price is CA $486
CA $1,131 total
includes taxes & fees
Sep 29 - Sep 30
Designer 3BR Near Beach & Obama Center
A room with a bunk bed, a door, a flat-screen TV, and a window with curtains.

16. Designer Home | Steps to the Obama Center & Beach

Designer Home | Steps to the Obama Center & Beach
Woodlawn
The price is CA $607
CA $1,523 total
includes taxes & fees
Sep 29 - Sep 30
Designer Home | Steps to the Obama Center & Beach
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

Comfort Inn Hammond I-94

Comfort Inn Hammond I-94

10/10 Excellent
"It was very clean food was g8"
Tolice 2-night trip
Posted 3 hours ago
Comfort Inn Hammond I-94

Find out more about Highland

Highland Vacation Homes information

Number of reviews
92
Accommodation
226 Vacation Homes
Lowest Price
CA $287
Highest Price
CA $1,759

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