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 rentals

Interior

1. Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.6 out of 10, Excellent, (34 reviews)
"Great stay. Clean place. Happy to come back."
United States
David F.
$103 nightly
The price is $115
Sep 13 - Sep 14
Total with taxes and fees
Beautiful Rustic Cabin for Two!
Property grounds

2. 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.
$184 nightly
The price is $206
Sep 14 - Sep 15
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Interior

3. King Studio. Free Breakfast. Indoor Pool. Gym.

King Studio. Free Breakfast. Indoor Pool. Gym.
Schererville
$211 nightly
The price is $236
Oct 11 - Oct 12
Total with taxes and fees
King Studio. Free Breakfast. Indoor Pool. Gym.
Interior

4. Free Breakfast. Indoor Pool. Gym. Business Center.

Free Breakfast. Indoor Pool. Gym. Business Center.
Schererville
$245 nightly
The price is $274
Oct 11 - Oct 12
Total with taxes and fees
Free Breakfast. Indoor Pool. Gym. Business Center.
Terrace/patio

5. 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.
$225 nightly
The price is $251
Sep 17 - Sep 18
Total with taxes and fees
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
WiFi (free)

6. 2 Full Beds | Micfridge

2 Full Beds | Micfridge
MERRILLVILLE
$70 nightly
The price is $78
Sep 13 - Sep 14
Total with taxes and fees
2 Full Beds | Micfridge
Smart TV, fireplace

7. 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 traveler
$426 nightly
The price is $477
Sep 11 - Sep 12
Total with taxes and fees
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
Interior

8. 2 Full Bed | Non-Smoking

2 Full Bed | Non-Smoking
Portage
10.0 out of 10, Exceptional, (62 reviews)
"Room was spacious with a nice layout, perfect for our group. Enjoyed the tea and coffee maker too. Free parking made it easy to explore the area without hassle."
United States
Anonymous traveler
$95 nightly
The price is $105
Sep 12 - Sep 13
Total with taxes and fees
2 Full Bed | Non-Smoking
Exterior

9. 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, (4 reviews)
"Clean, comfortable, quiet, excellent place to stay"
United States
Aaron S.
$188 nightly
The price is $199
Sep 20 - Sep 21
Total with taxes and fees
Quaint Studio Unit in fantastic Beecher with refreshing AC
Exterior

10. 1 Queen Bed|Mobility|Tub|Nsmk

1 Queen Bed|Mobility|Tub|Nsmk
Harvey
$65 nightly
The price is $74
Oct 1 - Oct 2
Total with taxes and fees
1 Queen Bed|Mobility|Tub|Nsmk
Interior

11. Premium King Bed|Portage

Premium King Bed|Portage
Portage
10.0 out of 10, Exceptional, (63 reviews)
"A solid choice if you're in town. Felt welcomed by friendly staff at the 24-hour front desk who assisted us promptly when we arrived late at night."
United States
Anonymous traveler
$103 nightly
The price is $113
Sep 12 - Sep 13
Total with taxes and fees
Premium King Bed|Portage
Smart TV, fireplace, video games, DVD player

12. Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Calumet Park
8.8 out of 10, Excellent, (12 reviews)
"Cozy home, perfect for our stay. Highly recommend."
United States
Alisa G.
$241 nightly
The price is $258
Sep 29 - Sep 30
Total with taxes and fees
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Exterior

13. 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.
$414 nightly
The price is $464
Oct 5 - Oct 6
Total with taxes and fees
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Game room

14. The Grand Gathering Place -Making Forever Memories Near Chicago & Hard Rock

The Grand Gathering Place -Making Forever Memories Near Chicago & Hard Rock
Merrillville
$1,018 nightly
The price is $1,140
Sep 29 - Sep 30
Total with taxes and fees
The Grand Gathering Place -Making Forever Memories Near Chicago & Hard Rock
Interior

15. 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.
$440 nightly
The price is $492
Oct 6 - Oct 7
Total with taxes and fees
La Petite • Piano • Serene Organic • Long Stays
Beach nearby

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

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
8.4 out of 10, Very Good, (22 reviews)
"Communication were great. The hosts we close so anything that we needed it got taken care of right away. Close to great food and lake"
United States
Jerrell G.
$149 nightly
The price is $167
Sep 13 - Sep 14
Total with taxes and fees
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Interior

17. 2 Bedroom | Free Daily Breakfast. Indoor Pool.

2 Bedroom | Free Daily Breakfast. Indoor Pool.
Schererville
$382 nightly
The price is $428
Oct 11 - Oct 12
Total with taxes and fees
2 Bedroom | Free Daily Breakfast. Indoor Pool.
Pet-friendly

18. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
MERRILLVILLE
$70 nightly
The price is $78
Sep 13 - Sep 14
Total with taxes and fees
1 King Bed | Non-Smoking
Exterior

19. 1 King Bed | Mobil Access Tub Nsmk

1 King Bed | Mobil Access Tub Nsmk
MERRILLVILLE
$70 nightly
The price is $78
Sep 13 - Sep 14
Total with taxes and fees
1 King Bed | Mobil Access Tub Nsmk
WiFi (free)

20. 1 King Bed | Micfridge

1 King Bed | Micfridge
MERRILLVILLE
$70 nightly
The price is $78
Sep 13 - Sep 14
Total with taxes and fees
1 King Bed | Micfridge
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

Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

10/10 Excellent
"clean room and friendly staff"
John 2-night trip
Posted 1 hour ago
Chicago Lake Shore Hotel

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 $105 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 rental 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.