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Highland Vacation Rentals

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Vacation Rentals in Highland

Our top choices for Highland vacation rentals

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

2.5 star property
3.8 out of 10, (54)
"Property is advertised as a Comfort Inn, but is actually undergoing the transformation of becoming a Comfort Inn. It is still very much so operating as a motel on the south side of Chicago. Be safe. "
The price is CA $117
CA $132 total
includes taxes & fees
Aug 28 - Aug 29
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Cozy Studio in Hyde Park-Walk to Lake & University

10.0 out of 10, Exceptional, (2)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
The price is CA $127
CA $266 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Studio in Hyde Park-Walk to Lake & University

Beautiful Rustic Cabin for Two!

9.6 out of 10, Exceptional, (15)
"This place was very cozy and amazing. Daniel was the greatest host and I would definitely stay here on future trips"
The price is CA $93
CA $143 total
includes taxes & fees
Sep 1 - Sep 2
Beautiful Rustic Cabin for Two!

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

8.8 out of 10, Excellent, (10)
"Great pool hostess was very helpful"
The price is CA $161
CA $211 total
includes taxes & fees
Sep 1 - Sep 2
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

LakeHouse

9.2 out of 10, Wonderful, (20)
"Everything was perfect with the property and the host even came to help right away when we had one issue with the lights."
LakeHouse

South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly

South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly

Perfect 1BR Spot near Attractions

7.2 out of 10, Good, (5)
"Freshly painted and clean. Hosts were responsive. Everything we needed for our stay. Walkable area. "
The price is CA $127
CA $280 total
includes taxes & fees
Sep 2 - Sep 3
Perfect 1BR Spot near Attractions

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

8.4 out of 10, Very good, (37)
"The yard is awesome, of course the hot tub at the top of the hill was the best, and we enjoyed the firepit as well. The house was a tidy little cottage at which we enjoyed our stay. It’s within a short walk to the National Park and downtown Miller Beach. The neighborhood is fine, pretty secluded, and still close to most attractions."
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

Comfortable Condo in the Heart of Bronzeville by RedAwning

6.6 out of 10, (4)
"There was confusion with VRBO regarding our arrival date, no fault of the property owner. They made arrangements to clean the unit and provide lunch for our group while we waited and offered a second night free for the inconvenience. Highly recommend. Property owner went above and beyond!"
The price is CA $201
CA $559 total
includes taxes & fees
Sep 2 - Sep 3
Comfortable Condo in the Heart of Bronzeville by RedAwning

Come experience The Lake Shore!

10.0 out of 10, Exceptional, (1)
"We had a great stay at the property. "
Come experience The Lake Shore!

Beachfront Villa + Addition, Skyline views, Hot Tubs, Luxury Smart Home

8.8 out of 10, Excellent, (33)
"Had a great time with our family for the weekend. "
Beachfront Villa + Addition, Skyline views, Hot Tubs, Luxury Smart Home

Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

9.2 out of 10, Wonderful, (61)
"With the exception of one bathroom being out of service and nearby location being a little sketchy everything else was a great place at this beautiful house."
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

A Home Away From Home!

9.6 out of 10, Exceptional, (7)
"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "
A Home Away From Home!

House with garage, outdoor dining and basement bar

7.4 out of 10, Good, (3)
"Property was very clean, warm and welcoming. Beds were comfortable. Property manager was great at checking in, and readily available. The place smells great! Everything is new! We will definitely book again!"
House with garage, outdoor dining and basement bar

Cozy Cabin w/ Loft, Grill and Fire Pit

The price is CA $261
CA $618 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Cabin w/ Loft, Grill and Fire Pit

Marvelous 3-bedroom apartment with WiFi, AC 18 minutes from downtown Chicago

8.6 out of 10, Excellent, (8)
"Very nice stay. Very clean, plenty of room, great location from Downtown Chicago. "
Marvelous 3-bedroom apartment with WiFi, AC 18 minutes from downtown Chicago

On Lake Minnehaha, The Funky Turtle @ Lakeshore Camp Resort with all the Campground Amenities!

1.0 star property
7.0 out of 10, Good, (4)
"It was great "
The price is CA $214
CA $471 total
includes taxes & fees
Sep 3 - Sep 4
On Lake Minnehaha, The Funky Turtle @ Lakeshore Camp Resort with all the Campground Amenities!

Spacious 4-bedroom Getaway in Portage, Perfect for family get togethers

8.8 out of 10, Excellent, (3)
"Spacious. Good outdoor area"
Spacious 4-bedroom Getaway in Portage, Perfect for family get togethers

Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community

9.0 out of 10, Wonderful, (23)
"Very comfortable, enjoyed my stay "
Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community

Miller Beach Blue Door By The Shore #2

6.8 out of 10, (11)
"Perfect!"
Miller Beach Blue Door By The Shore #2
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

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland vacation rentals we have selected for you start as low as CA $93 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 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?

Charming 1-bedroom apt in house by creek with AC, in delightful Portage: This vacation home rental near Highland offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a stovetop to make your meal-planning easier. Make the most of the selection of games in this rental home to help you unwind.

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.