Photo by Joe Farmer

Highland Holiday Rentals

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Holiday Rentals in Highland

Fridge, microwave, oven, stovetop
LakeHouse
10.0 out of 10, Exceptional, (6)
"I loved this house. It was clean, spacious, the piano made it that much better. I will definitely be back again."
LakeHouse
Private kitchen
Amazing 4 Bedrm Twnhm-30 Miles to Dwntwn Chicago Private Off Street Parking
10.0 out of 10, Exceptional, (2)
"My family really enjoyed this townhouse. It was very nice clean, location was perfect. Would definitely stay here again. The host Sherice was very very nice, kind, friendly and patient with my family."
Amazing 4 Bedrm Twnhm-30 Miles to Dwntwn Chicago Private Off Street Parking
Fridge, microwave, oven, stovetop
Cozy Home Sweet Homewood.
10.0 out of 10, Exceptional, (4)
"Neighborhood was quiet! Rental was exactly as shown online. Was able to easily find the rental with no problem. Overall great stay."
Cozy Home Sweet Homewood.
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Property grounds
"My Quaint Little Escape"
10.0 out of 10, Exceptional, (3)
"Loved our stay,not extremely far from the city! Comfortable furniture and clean! I loved how the old time family picture was hanging up! The back yard was awesome but we couldn't enjoy it due to rain,but thats okay! At first,i was a little put back that there was not a tv in the living room but we ended up chillin,talking and laughing which is what we needed! Thanks for the short but sweet stay!"
"My Quaint Little Escape"
Property grounds
Only 4 minutes to Hard Rock Casino and 25 minutes to Chicago!
10.0 out of 10, Exceptional, (1)
"Great property. Clean, modern and stocked with all the essentials. Owner is available and extremely helpful, would definitely stay again if in the area!"
The price is AU$229
per night
23 May - 24 May
Only 4 minutes to Hard Rock Casino and 25 minutes to Chicago!
Beach nearby
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
10.0 out of 10, Exceptional, (6)
"Great Stay!"
The price is AU$347
per night
21 May - 22 May
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Beach nearby, sun-loungers
Private Wooded Acre, Soaring Windows in Nat’l Park, 2 blocks to the beach
10.0 out of 10, Exceptional, (24)
"Spent three nights for a visit to the Dunes, drive down to see eclipse and great walks on the beach. The house was perfect for our group of six and puppy. Plusses: Short walk to gorgeous beach! The yard was a perfect place for pup to play and get some energy out. Didn’t use the fire pit or grill but nice to have. Kitchen was well stocked and we made several meals. Beds were comfortable and extra blankets were available. Opps: One of the rooms the blinds were not blackout so kids woke up...
Private Wooded Acre, Soaring Windows in Nat’l Park, 2 blocks to the beach
Smart TV, video games, stereo
Stay near family or close to downtown, this loft in Beverly has it all!
10.0 out of 10, Exceptional, (1)
"I went with 4 other friends, and this place was super clean, came with everything we needed, and even includes a cute small gaming room! Definitely would stay again!"
Stay near family or close to downtown, this loft in Beverly has it all!
Beach nearby
Dunes Escape - Minutes from Indiana Dunes National Park
9.8 out of 10, Exceptional, (28)
"We had a great stay! Everything was just as listed! Every area was very clean, kitchen well stocked, plenty of towels provided for our 2 night stay. If i could change anything it would have been to add a nightlight of some sort in the twin room. Unfamiliar place/noises and it was completely dark for my daughter. No lamp or nightlight in that room. Also a few of the cabinet doors need tightened down."
The price is AU$507
per night
4 June - 5 June
Dunes Escape - Minutes from Indiana Dunes National Park
Exterior
Cozy, King bed with heated bathroom!
9.8 out of 10, Exceptional, (8)
"Great"
Cozy, King bed with heated bathroom!
Fridge, microwave, stovetop, dishwasher
Pet-Friendly Lake Getaway: 1 Block to Beach!
9.8 out of 10, Exceptional, (25)
"Weather was awful…. Wish they could have done something that!😂 kids like seeing Chicago across the lake! Good location for the National Park. Comfortable!"
Pet-Friendly Lake Getaway: 1 Block to Beach!
Exterior
Casa Blanca in Miller Beach!
9.8 out of 10, Exceptional, (59)
"Nice property"
Casa Blanca in Miller Beach!
TV
Newly Renovated with Finished Basement
9.8 out of 10, Exceptional, (57)
"Everything was perfect! We needed a home base for graduation at Valpo and this home more than supplied it. A lovely home."
The price is AU$486
per night
21 May - 22 May
Newly Renovated with Finished Basement
Interior
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
9.8 out of 10, Exceptional, (60)
"The location is perfect for plans to the museums and easy access to Lake Shore Drive. It also has plenty of street parking."
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
Exterior
Rare Private Heated Pool w/in 1.5 Blocks to the Beach!
9.8 out of 10, Exceptional, (72)
"Six female relatives spent two nights here planning a bigger reunion. The house was clean and well supplied as stated in the listing. We had a great week-end."
Rare Private Heated Pool w/in 1.5 Blocks to the Beach!
Property grounds
Charming Crete Home with Hot Tub, Deck & Fire Pit
9.8 out of 10, Exceptional, (13)
"The stay was the way to go for our family. All being under one roof relaxing and enjoying what the house had to offer.Thanks to the owner for accommodating our early check in to attend our brother’s service. The house is beautiful!!"
Charming Crete Home with Hot Tub, Deck & Fire Pit
On the beach
Cozy Gary Vacation Rental: Steps to Beach!
9.6 out of 10, Exceptional, (20)
"We enjoyed our stay at this house! There was plenty of beds and the weather was perfect for us to have a bonfire! The wood provided was a little green but burnt well after we got the coals nice and hot. The beach was a quick walk away and a great place to relax and catch some sun. There was plenty of great beach stuff at the house but the umbrella was older and looked broken so we didn't take it. I would rent this house again! If your looking for a place that has a lot of places to eat or things...
Cozy Gary Vacation Rental: Steps to Beach!
Spa
Welcome to Boss Barbie’s Dreamhouse! Everything is pink.
9.6 out of 10, Exceptional, (4)
"Was cute, had a good time"
Welcome to Boss Barbie’s Dreamhouse! Everything is pink.
Beach nearby, sun-loungers
Miller Beach Getaway!
9.6 out of 10, Exceptional, (57)
"From the minute we walked inside we felt right at home! It was very clean and the layout of the house is very welcoming and open. The kitchen had all the necessities to make dinner and enjoy each other with plenty of seating. The hot tub was perfect with the waterfall and lights. It was a short walk to the beach where we enjoyed the day in the sun! We will definitely rent this location again if our travels bring us back up to northern Indiana! This was a mother / daughter weekend to remember."
Miller Beach Getaway!
Balcony
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park
9.2 out of 10, Wonderful, (45)
"The properties were extremely clean and well-stocked. We appreciated the responsiveness of Miller Beach Vacation Rentals team. We appreciated that the properties accepted dogs. Everyone loved the beaches and dunes, and lots of delicious meals were enjoyed. Check in and check out were super easy."
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park
Don't see what you're looking for?
See all available properties in Highland
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.

Highland Holiday Home Travel Info

Number of holiday homes
5
Popular accommodation
Highland private holiday homes
Known landmarks
Mascot Hall Of Fame, Theatre at the Centre and Hard Rock Casino Northern Indiana
International airports
Chicago, IL (ORD-O'Hare Intl.), Chicago, IL (MDW-Midway Intl.) and Belo Horizonte (PLU)

Other types of properties in Highland you may be interested in

View from property
Hyatt Place Chicago-South/University Medical Center
3.0 star property
8.8 out of 10, Excellent, (1003)
"It was a wonderful stay for my birthday. The staff was helpful and friendly. The hotel was clean. I would definitely stay again. "
The price is AU$282
per night
27 May - 28 May
Hyatt Place Chicago-South/University Medical Center
In-room safe, desk, laptop workspace, iron/ironing board
Hilton Chicago/Oak Lawn
3.5 star property
7.8 out of 10, Good, (1004)
"Hotel was clean and quiet. Room very spacious."
The price is AU$205
per night
28 May - 29 May
Hilton Chicago/Oak Lawn
Exterior
Holiday Inn Chicago Matteson Conf Center, an IHG Hotel
3.0 star property
7.2 out of 10, Good, (1006)
"The hotel was very clean. The people were very friendly and I would recommend this hotel to friends and family."
The price is AU$149
per night
27 May - 28 May
Holiday Inn Chicago Matteson Conf Center, an IHG Hotel
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.

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 favourite 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 depend 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 AU$229 per night. Entering your travel dates in the search wizard might find you 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 balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Highland?

Expedia has 3 holiday 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 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.

Recent reviews of Highland properties
Expedia verified reviews

Wingate by Wyndham Tinley Park

Wingate by Wyndham Tinley Park

5/5 Excellent
"Our visit was very enjoyable. The staff was amazing !"
A verified traveller stayed at Wingate by Wyndham Tinley Park
Posted 8 hours ago
Wingate by Wyndham Tinley Park