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Highland Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Highland vacation rentals

Exterior

Quaint Studio Unit in fantastic Beecher with refreshing AC

Quaint Studio Unit in fantastic Beecher with refreshing AC
Beecher
10.0 out of 10, Exceptional, (2 reviews)
"Kind hosts will help out with any needs. Quiet area, nice parking space."
United States
Garth T.
$186 nightly
The price is $197
Jun 22 - Jun 23
Total with taxes and fees
Quaint Studio Unit in fantastic Beecher with refreshing AC
Interior

Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.6 out of 10, Excellent, (29 reviews)
"The cabin was cute and cozy and the host was very welcoming. "
United States
Deric D.
$103 nightly
The price is $115
Jun 22 - Jun 23
Total with taxes and fees
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, (13 reviews)
"Great Stay!"
United States
Erin
$172 nightly
The price is $193
Jun 29 - Jun 30
Total with taxes and fees
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Private kitchen

Soothing 1 bedroom apartment with AC in charming Oak Lawn,

Soothing 1 bedroom apartment with AC in charming Oak Lawn,
Oak Lawn
10.0 out of 10, Exceptional, (1 review)
"The host was very friendly and helpful. There was a massive storm before and the host accommodated us with everything we needed"
United States
Bailey H.
$165 nightly
The price is $176
Jun 24 - Jun 25
Total with taxes and fees
Soothing 1 bedroom apartment with AC in charming Oak Lawn,
Interior

King Studio. Free Breakfast. Indoor Pool. Gym.

King Studio. Free Breakfast. Indoor Pool. Gym.
Schererville
$193 nightly
The price is $216
Jul 5 - Jul 6
Total with taxes and fees
King Studio. Free Breakfast. Indoor Pool. Gym.
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.
$197 nightly
The price is $221
Jun 28 - Jun 29
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
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
9.2 out of 10, Wonderful, (7 reviews)
"Lakeia was very accommodating throughout our stay."
United States
Timothy K.
$251 nightly
The price is $269
Jul 7 - Jul 8
Total with taxes and fees
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Interior

Dog-Friendly Apt w/ Yard: 10 Mi to Downtown

Dog-Friendly Apt w/ Yard: 10 Mi to Downtown
Woodlawn
10.0 out of 10, Exceptional, (2 reviews)
"Great host very accommodating."
United States
Kali P.
$267 nightly
The price is $324
Jun 22 - Jun 23
Total with taxes and fees
Dog-Friendly Apt w/ Yard: 10 Mi to Downtown
Interior

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
$517 nightly
The price is $579
Jul 6 - Jul 7
Total with taxes and fees
Near Lake and Museum • Modern • Game Area
Interior

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

Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Merrilville
$423 nightly
The price is $474
Jun 22 - Jun 23
Total with taxes and fees
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
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.
$340 nightly
The price is $381
Jun 23 - Jun 24
Total with taxes and fees
Comfort & Space for the Whole family! Sleeps 8+
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, (7 reviews)
"Clean room, within walking distance to U of Chicago, comfortable bed"
United States
Corbin P.
$190 nightly
The price is $212
Jun 30 - Jul 1
Total with taxes and fees
Bright & Cozy 1BR Near UChicago
Iron/ironing board, travel crib, WiFi, bed sheets

Homey Hyde Park Studio Near UChicago

Homey Hyde Park Studio Near UChicago
Hyde Park
9.4 out of 10, Exceptional, (6 reviews)
"Location was just perfect!"
United States
Meg D.
$151 nightly
The price is $168
Jun 22 - Jun 23
Total with taxes and fees
Homey Hyde Park Studio Near UChicago
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, (2 reviews)
"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
$200 nightly
The price is $225
Jun 30 - Jul 1
Total with taxes and fees
Cozy Well-Equipped Studio Apartment
Exterior

Panoramic views, Hot Tub, Sauna, Firepit, Sand Vball, Foosball, Dunes Nat`l Park

Panoramic views, Hot Tub, Sauna, Firepit, Sand Vball, Foosball, Dunes Nat`l Park
Miller Beach
9.0 out of 10, Wonderful, (70 reviews)
"Our host was very quick to respond to our inquiries. We had a few challenges with the master suite, the shower doors would not slide. Hopefully this will be remedied soon as it felt dangerous.Otherwise, the space was clean, comfortable, spectacular views, wonderful amenities!"
United States
Lora F.
$1,121 nightly
The price is $1,243
Jun 25 - Jun 26
Total with taxes and fees
Panoramic views, Hot Tub, Sauna, Firepit, Sand Vball, Foosball, 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
$422 nightly
The price is $473
Jun 29 - Jun 30
Total with taxes and fees
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
Fridge, microwave, oven, stovetop

3BR | Complete & Well-Located Apt in Hyde Park

3BR | Complete & Well-Located Apt in Hyde Park
Hyde Park
7.6 out of 10, Good, (5 reviews)
"Enjoyed our stay. Thank you"
United States
Nicolle C.
$233 nightly
The price is $258
Jul 1 - Jul 2
Total with taxes and fees
3BR | Complete & Well-Located Apt in Hyde Park
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.
$431 nightly
The price is $462
Jun 22 - Jun 23
Total with taxes and fees
Spacious 3br home near Chicago, fenced yard for pets
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
$193 nightly
The price is $215
Jun 30 - Jul 1
Total with taxes and fees
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
8.0 out of 10, Very Good, (6 reviews)
"Only issue was the water pressure in the bathroom was very very low. "
United States
Derrick M.
$317 nightly
The price is $339
Jun 22 - Jun 23
Total with taxes and fees
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
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

8/10 Good
"The revolving front door and two of the elevators weren’t operable. The ice machine on our floor was not working either. This made coming and going more challenging than necessary. The room was excellent. It was clean, spacious and very comfortable. The morning breakfast was inconsistent. The first morning, part of the buffet was difficult to access because the foldable walls were extended early. There was also a scramble when they started to shut down the breakfast a few minutes early. The food itself was good and plentiful. The manager’s reception was nice. The bartenders were friendly and efficient. The snacks were limited but didn’t run out. The overall experience was good. These few access points and amenities being addressed would have made it great. A last point, I wish the hotel would have been more forthcoming about the parking charge. I don’t mind paying for parking but was surprised to be chador a self parking surface lot."
Charles 3-night trip
Posted 9 hours ago
Days Inn and Suites by Wyndham Hammond, IN

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 $193 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.

Explore a world of travel with Expedia

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?

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!: This vacation home near Highland is on a lake and equipped with air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.