Photo by Joe Farmer

Highland Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

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, (52)
"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 $118
CA $133 total
includes taxes & fees
Aug 23 - Aug 24
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 $128
CA $269 total
includes taxes & fees
Sep 3 - Sep 4
Cozy Studio in Hyde Park-Walk to Lake & University

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
Aug 28 - Aug 29
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

LakeHouse

9.2 out of 10, Wonderful, (20)
"Host was perfect an house was perfect!!! It's my second time renting an I will be back again!!"
LakeHouse

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
Aug 25 - Aug 26
Beautiful Rustic Cabin for Two!

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

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 $128
CA $282 total
includes taxes & fees
Sep 2 - Sep 3
Perfect 1BR Spot near Attractions

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 $200
CA $561 total
includes taxes & fees
Aug 25 - Aug 26
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

Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit.

2.5 star property
10.0 out of 10, Exceptional, (2)
"The house was absolutely beautiful ! Very spacious and nice! Comfy beds and clean. "
Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit.

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 $262
CA $546 total
includes taxes & fees
Aug 28 - Aug 29
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, (7)
"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 $215
CA $469 total
includes taxes & fees
Aug 26 - Aug 27
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

Miller Beach Blue Door By The Shore #2

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

Charming 3BR Chicago Apt in Prime Location

9.0 out of 10, Wonderful, (14)
"We truly enjoyed our stayed and will be back next month. The host/owner responds quickly to questions and is a great resource. The neighborhood is safe and many shops and restaurants are easily walkable. The only option is street parking but we did not have trouble finding a spot when needed. "
Charming 3BR Chicago Apt in Prime Location
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Highland Hotel Reviews

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.