Highland Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Highland vacation rentals

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 ￥13,160
￥18,291 total
includes taxes & fees
Apr 26 - Apr 27
Beautiful Rustic Cabin for Two!
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 ￥13,602
￥18,799 total
includes taxes & fees
Apr 12 - Apr 13
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
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 ￥16,411
￥50,170 total
includes taxes & fees
Apr 21 - Apr 22
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago
Terrace/patio

MTM Premier Funky Jungle sleeps 4 in a charming log cabin with serene lakefront views. Rustic yet comfortable, ideal for small families or groups, with access to campground amenities and seasonal activities.

MTM Premier Funky Jungle sleeps 4 in a charming log cabin with serene lakefront views. Rustic yet comfortable, ideal for small families or groups, with access to campground amenities and seasonal activities.
Portage
10.0 out of 10, Exceptional, (2 reviews)
"We liked the location and all of the amenities. "
United States
Cindy
The price is ￥21,272
￥48,138 total
includes taxes & fees
May 3 - May 4
MTM Premier Funky Jungle sleeps 4 in a charming log cabin with serene lakefront views. Rustic yet comfortable, ideal for small families or groups, with access to campground amenities and seasonal activities.
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 ￥19,836
￥28,433 total
includes taxes & fees
Apr 13 - Apr 14
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, (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 ￥48,363
￥98,355 total
includes taxes & fees
Apr 14 - Apr 15
Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake
Property grounds

Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago

Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago
Chesterton
9.4 out of 10, Exceptional, (3 reviews)
"I enjoyed my short stay and visit to The Indiana National Dunes. The Host was friendly and she put special effort into setting the place up for my stay. I 100% would rent again from this host and would recommend "
United States
T J.
The price is ￥19,820
￥65,707 total
includes taxes & fees
May 1 - May 2
Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago
Beach

Dunes Retreat w/Private Hot Tub

Dunes Retreat w/Private Hot Tub
Chesterton
9.8 out of 10, Exceptional, (20 reviews)
"We love staying here, by far our favorite hosts! Incredibly clean and all the little extras to make the stay feel like home. Great communication and easy check-in.Thanks again!"
United States
Kara K.
Dunes Retreat w/Private Hot Tub
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 ￥47,727
￥60,380 total
includes taxes & fees
Apr 12 - Apr 13
Comfort & Space for the Whole family! Sleeps 8+
Living area

Quaint Studio Unit in fantastic Beecher with refreshing AC

Quaint Studio Unit in fantastic Beecher with refreshing AC
Beecher
The price is ￥10,275
￥31,056 total
includes taxes & fees
Apr 25 - Apr 26
Quaint Studio Unit in fantastic Beecher with refreshing AC
1 bedroom, iron/ironing board, WiFi, bed sheets

Private cozy Apartment 1Bed+1Bath “Entire place only for you” WiFi-Parking

Private cozy Apartment 1Bed+1Bath “Entire place only for you” WiFi-Parking
Tinley Park
The price is ￥11,099
￥22,052 total
includes taxes & fees
Apr 12 - Apr 13
Private cozy Apartment 1Bed+1Bath “Entire place only for you” WiFi-Parking
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 ￥27,399
￥66,630 total
includes taxes & fees
Apr 13 - Apr 14
Spacious 3br home near Chicago, fenced yard for pets
Interior

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is ￥19,027
￥92,202 total
includes taxes & fees
Apr 14 - Apr 15
Near Lake and Museum • Modern • Game Area
Property grounds

MTM Premier Funky Turtle sleeps 8 in a classic park model with beautiful lakefront views. Features lofted bedrooms, cozy living spaces, and access to campground activities for a fun and peaceful lakeside stay.

MTM Premier Funky Turtle sleeps 8 in a classic park model with beautiful lakefront views. Features lofted bedrooms, cozy living spaces, and access to campground activities for a fun and peaceful lakeside stay.
Portage
7.6 out of 10, Good, (7 reviews)
"It was great "
United States
Stephen D.
The price is ￥24,570
￥53,076 total
includes taxes & fees
May 1 - May 2
MTM Premier Funky Turtle sleeps 8 in a classic park model with beautiful lakefront views. Features lofted bedrooms, cozy living spaces, and access to campground activities for a fun and peaceful lakeside stay.
Interior

King Studio. Free Breakfast. Indoor Pool. Gym.

King Studio. Free Breakfast. Indoor Pool. Gym.
Schererville
The price is ￥25,030
￥31,585 total
includes taxes & fees
Apr 12 - Apr 13
King Studio. Free Breakfast. Indoor Pool. Gym.
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 ￥10,941
￥27,829 total
includes taxes & fees
Apr 14 - Apr 15
Bright & Cozy 1BR Near UChicago
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 ￥32,108
￥40,580 total
includes taxes & fees
Apr 12 - Apr 13
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
TV, offices

Private 1BR Haven in a Prime Area

Private 1BR Haven in a Prime Area
Hyde Park
9.0 out of 10, Wonderful, (7 reviews)
"It was a cozy place and clean. Sleeping was comfy minus outside noise at night can be a bit much. "
United States
Brandie O.
The price is ￥10,941
￥27,829 total
includes taxes & fees
Apr 22 - Apr 23
Private 1BR Haven in a Prime Area
TV, offices

Bright 1BR Unit in a Prime Spot

Bright 1BR Unit in a Prime Spot
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"We had a great stay. Location is in nice neighborhood with walking access to restaurants and university of Chicago. Apartment was clean and as pictured. Would stay again!!"
United States
christine m.
The price is ￥10,941
￥27,829 total
includes taxes & fees
Apr 14 - Apr 15
Bright 1BR Unit in a Prime Spot
Smart TV, fireplace, video games, DVD player

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Calumet Park
10.0 out of 10, Exceptional, (5 reviews)
"Lakeia was very accommodating throughout our stay."
United States
Timothy K.
The price is ￥17,124
￥39,862 total
includes taxes & fees
Apr 22 - Apr 23
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
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

2/10 Terrible
"I had a terrible experience! I had bed bugs crawling all over me!!!! With bites on my leg the next morning my hot tub was broken NASTY WORK!!!!! And the manager of the property will not call me at all for some reason! And all I asked for was a refund!!!!! But it’s cool you can talk to me now or we will definitely talk later!!!!!"
James 2-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
  • Use the map to find apartments and other holiday homes in the Highland neighbourhood you prefer
  • 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.