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Highland Holiday Rentals

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Holiday Rentals in Highland

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

Porter
9.0 out of 10, Wonderful, (12)
"Great pool hostess was very helpful"
United States
regina
The price is NZ$157
includes taxes & fees
23 Nov - 24 Nov
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

Beautiful Rustic Cabin for Two!

Griffith
9.8 out of 10, Exceptional, (16)
"We had a very nice stay. The cabin was quite cozy and comfortable."
United States
Jeremy & Rebecca F.
The price is NZ$184
includes taxes & fees
19 Dec - 20 Dec
Beautiful Rustic Cabin for Two!

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

Chesterton
8.6 out of 10, Excellent, (7)
"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.
The price is NZ$530
includes taxes & fees
24 Nov - 25 Nov
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago

Bright & Cozy 1BR Near UChicago

Hyde Park
10.0 out of 10, Exceptional, (2)
"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 NZ$284
includes taxes & fees
30 Nov - 1 Dec
Bright & Cozy 1BR Near UChicago

Pleasant 3-bedroom house in Sauk Village

2.0 star property
Sauk Village
10.0 out of 10, Exceptional, (1)
"My Experience Was (NOTHING) Short Of Perfect! The Place Is Nice & The Host Was Even Better! I’ll Forsure Be Booking Again! "
United States
Aaron K.
The price is NZ$238
includes taxes & fees
23 Nov - 24 Nov
Pleasant 3-bedroom house in Sauk Village

Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

2.0 star property
Robertsdale
10.0 out of 10, Exceptional, (12)
"Very clean in a safe neighborhood. I would stay here again"
United States
Charles W.
The price is NZ$255
includes taxes & fees
24 Nov - 25 Nov
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

Plant MOOD2! FREE STREET PARKING & Wi-Fi!

Hammond
10.0 out of 10, Exceptional, (2)
"It was a great experience!!! Very clean and decorated very beautiful. The host is very friendly and responds fast."
United States
Alexis L.
The price is NZ$357
includes taxes & fees
23 Nov - 24 Nov
Plant MOOD2! FREE STREET PARKING & Wi-Fi!

Studio Unit | Chic + Prime Location

Hyde Park
10.0 out of 10, Exceptional, (2)
"Location was just perfect!"
United States
Meg D.
The price is NZ$276
includes taxes & fees
1 Dec - 2 Dec
Studio Unit | Chic + Prime Location

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

Porter
8.8 out of 10, Excellent, (16)
"Great place to stay with kids."
United States
Jane H.
The price is NZ$272
includes taxes & fees
24 Nov - 25 Nov
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

Sleek & Functional 2-Bedroom Apt

Hyde Park
9.6 out of 10, Exceptional, (4)
"Nice place for a girls trip weekend. "
United States
Madonna A.
The price is NZ$326
includes taxes & fees
30 Nov - 1 Dec
Sleek & Functional 2-Bedroom Apt

Studio Apt Comfy & Sunlit

Hyde Park
10.0 out of 10, Exceptional, (2)
"My stay was really good"
United States
Paramita B.
The price is NZ$304
includes taxes & fees
17 Dec - 18 Dec
Studio Apt Comfy & Sunlit

Bright & Spacious 2BR– Prime Hyde Park Location

Hyde Park
7.0 out of 10, Good, (2)
"Great stay! The owners were easy to communicate with and were accompanying! The property was clean and close to stores, restaurants, and shops! Would stay again in the future! "
United States
Jeremy M.
Bright & Spacious 2BR– Prime Hyde Park Location

Dunes Escape - Minutes from Indiana Dunes National Park

Miller Beach
9.8 out of 10, Exceptional, (36)
"We loved our stay and had a relaxing time in the area. Buying groceries to cook was great with a full kitchen to cook with. Rooms were super nice and also had every accommodation we could need. Definitely will be looking to stay again!"
United States
Braden S.
The price is NZ$550
includes taxes & fees
1 Dec - 2 Dec
Dunes Escape - Minutes from Indiana Dunes National Park

Cozy Charm Studio Apt in Chicago

Hyde Park
10.0 out of 10, Exceptional, (1)
The price is NZ$276
includes taxes & fees
1 Dec - 2 Dec
Cozy Charm Studio Apt in Chicago

Modern Studio Near UChicago

Hyde Park
9.4 out of 10, Exceptional, (9)
"Clean room and convenient location! "
United States
Gabriela
The price is NZ$276
includes taxes & fees
9 Dec - 10 Dec
Modern Studio Near UChicago

Bright & Modern 1BR in Hyde Park

Hyde Park
10.0 out of 10, Exceptional, (1)
"Great place to stay. It was easy to settle in and relax after a long day of traveling. The bed was comfortable and great to sleep on. Will definitely try for this property again if I need to come to the area."
United States
Michael S.
The price is NZ$369
includes taxes & fees
23 Dec - 24 Dec
Bright & Modern 1BR in Hyde Park

Spacious 3BR Home Firepit & Grill

2.0 star property
Miller Beach
The price is NZ$732
includes taxes & fees
30 Nov - 1 Dec
Spacious 3BR Home Firepit & Grill
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Highland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Highland holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Highland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland holiday rentals we have selected for you start as low as NZ$146 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Highland rentals

At Expedia, we put the best Highland holiday 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 holiday.

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 holiday rentals in Highland?

Yes, there are holiday rentals close to the most popular sights in Highland, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Highland has to offer?

LakeHouse: This holiday home rental outside of Highland is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 wider area.

What are holiday rentals like in Highland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highland. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family getaway.