Highland Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Highland vacation rentals

Property grounds

Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago

Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago
Chesterton
9.0 out of 10, Wonderful, (10 reviews)
"Thank you for a great stay for both the humans and fur babies! Very responsive hosts and easy check-in."
United States
Kara K.
The price is ￥16,419
￥50,728 total
includes taxes & fees
Apr 19 - Apr 20
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago
Beach nearby

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
9.0 out of 10, Wonderful, (12 reviews)
"Great Stay!"
United States
Erin
The price is ￥13,564
￥18,747 total
includes taxes & fees
Apr 19 - Apr 20
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Interior

Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
9.0 out of 10, Wonderful, (22 reviews)
"The cabin was cute and cozy and the host was very welcoming. "
United States
Deric D.
The price is ￥13,643
￥18,834 total
includes taxes & fees
May 5 - May 6
Beautiful Rustic Cabin for Two!
Fridge, microwave, oven, stovetop

Cozy Modern Townhome in Unbeatable Chesterton Location

Cozy Modern Townhome in Unbeatable Chesterton Location
Chesterton
Cozy Modern Townhome in Unbeatable Chesterton Location
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, (20 reviews)
"Very clean and well stocked! The kids loved the game area when they visited. Thanks for letting us stay. "
United States
julie b.
The price is ￥48,980
￥98,921 total
includes taxes & fees
Apr 21 - Apr 22
Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake
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
9.6 out of 10, Exceptional, (24 reviews)
"I had a fun stay "
United States
Jusu K.
The price is ￥19,846
￥28,447 total
includes taxes & fees
Apr 20 - Apr 21
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Exterior

Comfort & Space for the Whole family! Sleeps 8+

Comfort & Space for the Whole family! Sleeps 8+
Crown Point
7.6 out of 10, Good, (4 reviews)
"Very nice, clean property. Loved the patio area. "
United States
Austin P.
The price is ￥47,751
￥60,410 total
includes taxes & fees
Apr 19 - Apr 20
Comfort & Space for the Whole family! Sleeps 8+
Interior

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is ￥19,037
￥91,662 total
includes taxes & fees
Apr 27 - Apr 28
Near Lake and Museum • Modern • Game Area
Iron/ironing board, travel crib, WiFi, bed sheets

Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago
Hyde Park
10.0 out of 10, Exceptional, (7 reviews)
"Room was clean, check in was easy, and the owner was very communicative."
United States
David
The price is ￥13,960
￥29,786 total
includes taxes & fees
Apr 19 - Apr 20
Cozy Charm Studio Apt in Chicago
WiFi, bed sheets

Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park
The price is ￥12,533
￥28,115 total
includes taxes & fees
Apr 21 - Apr 22
Hyde Park Trendy Studio Apartment in Good Spot
1 bedroom, iron/ironing board, travel crib, WiFi

Hyde Park 1BR Apt | Easy & Fully Equipped Stay

Hyde Park 1BR Apt | Easy & Fully Equipped Stay
Hyde Park
The price is ￥11,422
￥28,400 total
includes taxes & fees
Apr 22 - Apr 23
Hyde Park 1BR Apt | Easy & Fully Equipped Stay
Interior

Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Blue Island
7.6 out of 10, Good, (4 reviews)
"Only issue was the water pressure in the bathroom was very very low. "
United States
Derrick M.
The price is ￥23,415
￥53,731 total
includes taxes & fees
Apr 19 - Apr 20
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Iron/ironing board, travel crib, WiFi, bed sheets

Cozy Well-Equipped Studio Apartment

Cozy Well-Equipped Studio Apartment
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Wow, this is a wonderful Place to stay. The host Is very responsive and friendly The apartment is immaculate I recommend this place highly . "
United States
pnina
The price is ￥13,960
￥29,786 total
includes taxes & fees
Apr 19 - Apr 20
Cozy Well-Equipped Studio Apartment
TV

Explore Hyde Park: 2BR Apartment on Blackstone Ave

Explore Hyde Park: 2BR Apartment on Blackstone Ave
Hyde Park
7.0 out of 10, Good, (7 reviews)
"Host was responsive to my questions. Apartment is located in a great area of Hyde Park. "
United States
Lind A.
The price is ￥16,340
￥37,128 total
includes taxes & fees
Apr 23 - Apr 24
Explore Hyde Park: 2BR Apartment on Blackstone Ave
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 ￥29,348
￥71,070 total
includes taxes & fees
Apr 19 - Apr 20
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
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, (22 reviews)
"The location was perfect! The house very spacious, with more than enough room for my boys!"
United States
Carmen
The price is ￥28,270
￥67,579 total
includes taxes & fees
Apr 22 - Apr 23
Spacious 3br home near Chicago, fenced yard for pets
3 bedrooms, iron/ironing board, WiFi, bed sheets

Furnished 3BR Apt w/ Laundry

Furnished 3BR Apt w/ Laundry
Hyde Park
9.6 out of 10, Exceptional, (8 reviews)
"We loved our stay! The apartment was clean and nicely furnished. The beds were comfy and we loved being right next to the best pizza in Chicago & a wonderful coffee shop right around the corner. The host was super helpful & answered any questions we had very quickly."
United States
Rissa B.
The price is ￥14,278
￥37,094 total
includes taxes & fees
Apr 20 - Apr 21
Furnished 3BR Apt w/ Laundry
Beach nearby

The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
Porter
9.0 out of 10, Wonderful, (17 reviews)
"Great place to stay with kids."
United States
Jane H.
The price is ￥32,125
￥39,890 total
includes taxes & fees
Apr 20 - Apr 21
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
1 bedroom, desk, iron/ironing board, travel crib

Bright & Cozy 1BR Near UChicago

Bright & Cozy 1BR Near UChicago
Hyde Park
9.6 out of 10, Exceptional, (4 reviews)
"This apartment is a very basic rental unit – – had what we needed for our three nights stay, and we were very pleased. Great value for the money."
United States
Alan F.
The price is ￥11,422
￥28,400 total
includes taxes & fees
Apr 21 - Apr 22
Bright & Cozy 1BR Near UChicago
Iron/ironing board, travel crib, WiFi, bed sheets

Modern Studio Unit Near UChicago

Modern Studio Unit Near UChicago
Hyde Park
9.0 out of 10, Wonderful, (18 reviews)
"Clean room and convenient location! "
United States
Gabriela
The price is ￥14,912
￥31,293 total
includes taxes & fees
Apr 28 - Apr 29
Modern Studio Unit Near UChicago
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

Days Inn and Suites by Wyndham Hammond, IN

Days Inn and Suites by Wyndham Hammond, IN

10/10 Excellent
"Everything was great"
Tameika 1-night trip
Posted 2 hours ago
Days Inn and Suites by Wyndham Hammond, IN

Find out more about Highland

Search for holiday rentals in Highland on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland using one of the methods below:

  • View our selection of featured holiday rentals in Highland
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  • Enter your travel dates to view the best deals on holiday rentals in Highland while they last

Look no further and take a look at our great range of rental properties in Highland!

Frequently asked questions

Are there vacation rentals in Highland?

Yes, you can find vacation rentals close to top points of interest in Highland, or you can select a more secluded option if you're looking for relaxation. Highland is known for its churches and basketball games. Make sure you have time to check out the lake views while you're in the area.

What are some of the best vacation rentals in Highland?

A Home Away From Home!: This vacation home rental near Highland offers a fireplace, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

How many vacation rentals are there in Highland?

Expedia has 3 vacation rentals for your stay in Highland.

What can I see and do in Highland?

Indiana Dunes National Park and Hoosier Prairie are a couple of lovely local spots to get outside and enjoy nature. Purdue University Northwest and Hard Rock Casino Northern Indiana are a couple of places you'll find in the larger area.

What are vacation rentals like in Highland?

Vacation rentals are privately owned properties you can stay in for several days or more in Highland. Vacation rentals provide amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family trip.