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Highland Vacation Rentals

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Vacation Rentals in Highland

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

3.0 star property
Harvey
3.8 out of 10, (67)
"This place looked like a whole in the wall I didn’t even stay the place was so dirty and I could not receive a refund looks disgusting and not even worth a $50 stay at minimum. "
United States
Bria
$94 nightly
The price is $106
Nov 15 - Nov 16
Total with taxes and fees
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Cozy Studio in Hyde Park-Walk to Lake & University

Hyde Park
8.8 out of 10, Excellent, (10)
"Good communication and easy check-in"
United States
Chen
$147 nightly
The price is $163
Dec 2 - Dec 3
Total with taxes and fees
Cozy Studio in Hyde Park-Walk to Lake & University

LakeHouse

South Shore
9.4 out of 10, Exceptional, (23)
"Nice place, everything clean, the only downside is parking"
United States
quy u.
LakeHouse

Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Blue Island
7.6 out of 10, Good, (4)
"Very clean place . The host teddy was very nice and understanding and communicated with me about everything . Even when I had questions he answered each and everyone. Made sure I was as comfortable as possible. Great quiet neighborhood . 5 star rating "
United States
Amber M.
$324 nightly
The price is $346
Nov 15 - Nov 16
Total with taxes and fees
Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Modern 1BR in Historic HydePark

Hyde Park
7.8 out of 10, Good, (10)
"Comfortable space. All the necessary amenities. Extremely walkable to everything.Will stay again. "
United States
jasmine h.
$155 nightly
The price is $171
Dec 3 - Dec 4
Total with taxes and fees
Modern 1BR in Historic HydePark

Modern Studio Near UChicago

Hyde Park
9.4 out of 10, Exceptional, (9)
"Clean room and convenient location! "
United States
Gabriela
$147 nightly
The price is $163
Dec 2 - Dec 3
Total with taxes and fees
Modern Studio Near UChicago

15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

Gary
8.4 out of 10, Very Good, (16)
"Great place, nice location and the Hosts are extremely good to work with. Highly recommend this just out of the city stay!"
United States
Alyssa M.
$399 nightly
The price is $447
Nov 17 - Nov 18
Total with taxes and fees
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

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

Miller Beach
9.0 out of 10, Wonderful, (37)
"Lovely space to red a big group to gather,plus smaller living spaces fur sac mallet subgroups. "
United States
Lori W.
Beachfront Villa + Addition, Skyline views, Hot Tubs, Luxury Smart Home

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

1.0 star property
Portage
7.6 out of 10, Good, (7)
"We had a great stay at the Funky Turtle. The house was clean and just enough space for my family of 5. The house is close to campground bathrooms if the occasional extra bathroom is needed. We enjoyed the fire pit, use of the grill, and sitting on the porch. Our only complaint is about the noise but it was clear from the map that the campground was located near an interstate. While sitting outside you can hear the noise from the interstate and close by trains. However, inside was much...
United States
Sarah G.
On Lake Minnehaha, The Funky Turtle @ Lakeshore Camp Resort with all the Campground Amenities!

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.
$92 nightly
The price is $103
Nov 16 - Nov 17
Total with taxes and fees
Beautiful Rustic Cabin for Two!

Explore Hyde Park: 2BR Apt on Blackstone Ave

Hyde Park
9.4 out of 10, Exceptional, (3)
"All the necessities with no personal touches. Keys from lockbox to open second door were not needed as the second door is always open. Impeccable communication with host. Great location, close to restaurants and train to Millennium Station. Coffee service was excellent, just be sure to find extra pouches in cabinet. Bathtub faucet could not be turned far enough to prevent leaking. TV remote not great and I couldn’t get CNN or MSNBC. I’d stay here again. "
United States
lost whale press
$190 nightly
The price is $209
Dec 3 - Dec 4
Total with taxes and fees
Explore Hyde Park: 2BR Apt on Blackstone Ave

Spacious 3BR House With Firepit & Grill, Near Beach

2.0 star property
Miller Beach
5.0 out of 10, (2)
"While this is a nice property on the inside, there were still a few issues we ran into while staying there. The pillows smelled like cigarette smoke, there weren’t really any dishes to use, and there’s only three beds for what was a 10 person booking. The biggest issue of all was the WiFi. We were unable to connect the TV so there wasn’t entertainment, you can only connect up to 5 devices at a time (again, this is a 10 person booking) and even when connected the internet didn’t run on the...
United States
Mikeba
$336 nightly
The price is $353
Dec 15 - Dec 16
Total with taxes and fees
Spacious 3BR House With Firepit & Grill, Near Beach

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

Miller Beach
9.2 out of 10, Wonderful, (62)
"We had a great experience at the lake house. Everything was in great condition with all the amenities we could have asked for. Plenty of space and plenty of rooms for family of 12. The master bedroom was absolutely breathtaking. The host company was very responsive and help to make our stay comfortable. Would highly recommend! "
United States
Dmitri K.
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum

Bronzeville
9.6 out of 10, Exceptional, (73)
"Enough room for a quick get away"
United States
wendy C.
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum

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

South Chicago
10.0 out of 10, Exceptional, (1)
"Clean apartment and great communication with host. Fixed any small problems very quickly. "
United States
Catherine F.
South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly

The Chic Urban Oasis Near the Lake!

South Shore
8.0 out of 10, Very Good, (7)
"Great property in not the best part of town. "
United States
Scott S.
The Chic Urban Oasis Near the Lake!

Come experience The Lake Shore!

South Shore
10.0 out of 10, Exceptional, (4)
"The pictures does this place no justice! Very specious and clean it even smelt AMAZING walking in, He has everything you need for your stay. Great communication & fast replies 10/10 hands down the BEST place I’ve ever stayed money was WELL spent! I hope to go back for a solo trip just for the peacefulness & homely feel!!! Honestly 10000/10000"
United States
Drea W.
Come experience The Lake Shore!

Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails

Miller Beach
8.6 out of 10, Excellent, (45)
"Great location! Quiet, nice neighborhood and our pups loved the fenced in yard! The beach is a block away. All kinds of trails right there! Beautiful home! Will definitely be coming back!"
United States
Brandy W.
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails

Stay, Relax & Explore Chicago

Greater Grand Crossing
9.4 out of 10, Exceptional, (3)
"Our stay was a pleasant surprise. The house was newly renovated and even nicer than the online pictures. Our host Demarcus was quick to respond to our questions and needs. We will stay there again when we go back to visit my granddaughter, a student at UI C "
United States
Maria A.
Stay, Relax & Explore Chicago

Cozy Retreat w/Hot tub Indiana dunes Beaches Trails

Chesterton
10.0 out of 10, Exceptional, (11)
"This was one of the nicest, cleanest VRBO we have stated in. Don’t let the neighborhood detour you from staying. We felt safe and slept amazing in the VERY comfy king bed !! The master shower drain wasn’t working during our stay but the owner was very responsive and apologized for the inconvenience. "
United States
Dot Dot Smile Nichole W.
$247 nightly
The price is $277
Dec 9 - Dec 10
Total with taxes and fees
Cozy Retreat w/Hot tub Indiana dunes Beaches Trails
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 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 $103 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.

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?

LakeHouse: This vacation home rental near Highland is located on the beach and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 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.