Highland Vacation Rentals

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Our top choices for Highland vacation rentals

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)
"Every aspect of my booking & stay was convenient & seamless; from the reasonable price, online reservation process, host communication, beautiful grounds, to the abundant amenities offered there was nothing I or my family wanted for. Don & Kim are accommodating, professional & experienced hosts and it showed. Thank you for the wonderful experience I recommend their multiple spaces to anyone & would stay with them again without hesitation! "
United States
esther Amber C.
$79 nightly
The price is $88
Feb 9 - Feb 10
Total with taxes and fees
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

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

Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Merrilville
$341 nightly
The price is $382
Feb 4 - Feb 5
Total with taxes and fees
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard

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)
"Excellent spot for several people to stay and enjoy the Dunes. Clean, quiet, centrally located to lots of Dunes hotspots. Thanks for the great stay!"
United States
Nick R.
$287 nightly
The price is $321
Feb 4 - Feb 5
Total with taxes and fees
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago

Dunes Retreat w/Private Hot Tub

Dunes Retreat w/Private Hot Tub
Chesterton
10.0 out of 10, Exceptional, (15 reviews)
"Great host, everything was clean, many little extras for comfort and convenience!"
United States
Kara K.
$230 nightly
The price is $257
Feb 4 - Feb 5
Total with taxes and fees
Dunes Retreat w/Private Hot Tub

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.
$345 nightly
The price is $387
Feb 4 - Feb 5
Total with taxes and fees
Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago

Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.8 out of 10, Excellent, (20 reviews)
"Nice and cozy place to stay. We enjoyed our secluded area during our time here."
United States
Allison A.
$92 nightly
The price is $103
Feb 8 - Feb 9
Total with taxes and fees
Beautiful Rustic Cabin for Two!

Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago
Hyde Park
10.0 out of 10, Exceptional, (3 reviews)
"Everying was great."
United States
Ryan D.
$138 nightly
The price is $153
Feb 4 - Feb 5
Total with taxes and fees
Cozy Charm Studio Apt in Chicago

Studio Unit | Chic + Prime Location

Studio Unit | Chic + Prime Location
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"Location was just perfect!"
United States
Meg D.
$138 nightly
The price is $153
Feb 4 - Feb 5
Total with taxes and fees
Studio Unit | Chic + Prime Location

Sleek & Functional 2-Bedroom Apt

Sleek & Functional 2-Bedroom Apt
Hyde Park
9.6 out of 10, Exceptional, (4 reviews)
"Nice place for a girls trip weekend. "
United States
Madonna A.
$178 nightly
The price is $195
Feb 4 - Feb 5
Total with taxes and fees
Sleek & Functional 2-Bedroom Apt

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, (20 reviews)
"Wonderful property and nice owners. I definitely recommend and will stay again if I'm ever in the area."
United States
Karen D.
$142 nightly
The price is $159
Feb 4 - Feb 5
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Modern & Spacious Stay by Northwestern Hospital Bronzeville

Modern & Spacious Stay by Northwestern Hospital Bronzeville
Bronzeville
10.0 out of 10, Exceptional, (3 reviews)
"What a great place to stay! Interior of the unit was very nice and modern. Amenities were great. We felt safe and secure the entire time. Our host was in constant communication to make sure our needs were met. We would definitely recommend this stay!"
United States
Matt D.
$303 nightly
The price is $335
Feb 4 - Feb 5
Total with taxes and fees
Modern & Spacious Stay by Northwestern Hospital Bronzeville

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.
$159 nightly
The price is $176
Feb 4 - Feb 5
Total with taxes and fees
Bright 1BR Unit in a Prime Spot

Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool

Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
Merrillville
9.6 out of 10, Exceptional, (5 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
$206 nightly
The price is $231
Feb 4 - Feb 5
Total with taxes and fees
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool

Modern Studio Unit Near UChicago

Modern Studio Unit Near UChicago
Hyde Park
9.4 out of 10, Exceptional, (12 reviews)
"Clean room and convenient location! "
United States
Gabriela
$138 nightly
The price is $153
Feb 4 - Feb 5
Total with taxes and fees
Modern Studio Unit Near UChicago

Bright South Hyde Park Studio

Bright South Hyde Park Studio
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Comfortable space in a nice neighborhood. I highly recommend."
United States
BiggDas M.
$138 nightly
The price is $153
Feb 8 - Feb 9
Total with taxes and fees
Bright South Hyde Park Studio

Stylish 4BR South Loop Home

Stylish 4BR South Loop Home
Greater Grand Crossing
10.0 out of 10, Exceptional, (2 reviews)
"Very happy with stay. Good communication from property host. "
United States
Nicole E.
$332 nightly
The price is $357
Feb 4 - Feb 5
Total with taxes and fees
Stylish 4BR South Loop Home

Furnished 3BR Apt w/ Laundry

Furnished 3BR Apt w/ Laundry
Hyde Park
9.6 out of 10, Exceptional, (5 reviews)
"Apartment and neighborhood were beautiful. We really enjoyed our stay and would book the same place again!"
United States
Kristin W.
$194 nightly
The price is $211
Feb 4 - Feb 5
Total with taxes and fees
Furnished 3BR Apt w/ Laundry

Compact Studio for a Relaxed Stay

Compact Studio for a Relaxed Stay
Hyde Park
8.0 out of 10, Very Good, (1 review)
$138 nightly
The price is $153
Feb 4 - Feb 5
Total with taxes and fees
Compact Studio for a Relaxed Stay

Serenity on the Shores - with easy transport to Chicago/SouthShore across the St

Serenity on the Shores - with easy transport to Chicago/SouthShore across the St
Portage
9.6 out of 10, Exceptional, (12 reviews)
"Very nice place "
United States
LeAnna M.
$203 nightly
The price is $227
Feb 4 - Feb 5
Total with taxes and fees
Serenity on the Shores - with easy transport to Chicago/SouthShore across the St

Bright & Cozy 1BR Near UChicago

Bright & Cozy 1BR Near UChicago
Hyde Park
9.4 out of 10, Exceptional, (3 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.
$159 nightly
The price is $176
Feb 4 - Feb 5
Total with taxes and fees
Bright & Cozy 1BR 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

Find out more about Highland

Everything you need to know about Highland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Highland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Highland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $88 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Highland rentals

At Expedia, we put the best Highland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Highland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.