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Highland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Highland

Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

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
The price is ￥13,075
￥14,772 total
includes taxes & fees
Nov 16 - Nov 17
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Microwave, oven, stovetop, coffee/tea maker
Cozy Studio in Hyde Park-Walk to Lake & University

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
The price is ￥10,046
￥24,855 total
includes taxes & fees
Dec 3 - Dec 4
Cozy Studio in Hyde Park-Walk to Lake & University
Fridge, microwave, oven, stovetop
LakeHouse

LakeHouse

South Shore
9.4 out of 10, Exceptional, (23)
"Nice place, everything clean, the only downside is parking"
United States
quy u.
LakeHouse
2 bedrooms, WiFi, wheelchair access
Charming 2-bedroom apartment in marvelous Blue Island with WiFi

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.
The price is ￥22,812
￥53,504 total
includes taxes & fees
Nov 18 - Nov 19
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
1 bedroom, iron/ironing board, travel crib, WiFi
Modern 1BR in Historic HydePark

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.
The price is ￥10,051
￥26,414 total
includes taxes & fees
Dec 10 - Dec 11
Modern 1BR in Historic HydePark
Iron/ironing board, travel crib, WiFi, bed sheets
Modern Studio Near UChicago

Modern Studio Near UChicago

Hyde Park
9.4 out of 10, Exceptional, (9)
"Clean room and convenient location! "
United States
Gabriela
The price is ￥9,273
￥23,949 total
includes taxes & fees
Dec 3 - Dec 4
Modern Studio Near UChicago
Fridge, microwave, oven, stovetop
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

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.
The price is ￥24,911
￥69,120 total
includes taxes & fees
Nov 17 - Nov 18
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
10 bedrooms, desk, blackout drapes, iron/ironing board
Beachfront Villa + Addition, Skyline views, Hot Tubs, Luxury Smart Home

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

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!
Exterior
Beautiful Rustic Cabin for Two!

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 ￥10,355
￥15,925 total
includes taxes & fees
Dec 14 - Dec 15
Beautiful Rustic Cabin for Two!
Fridge, microwave, oven, stovetop
Explore Hyde Park: 2BR Apt on Blackstone Ave

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
The price is ￥12,982
￥32,540 total
includes taxes & fees
Dec 3 - Dec 4
Explore Hyde Park: 2BR Apt on Blackstone Ave
Front of property
Spacious 3BR House With Firepit & Grill, Near Beach

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
The price is ￥20,708
￥53,501 total
includes taxes & fees
Dec 16 - Dec 17
Spacious 3BR House With Firepit & Grill, Near Beach
Spa
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

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

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
Dining
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

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
Beach
The Chic Urban Oasis Near the Lake!

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!
Fridge, microwave, oven, stovetop
Come experience The Lake Shore!

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

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
Microwave, oven, stovetop, dishwasher
Stay, Relax & Explore Chicago

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
Beach
Cozy Retreat w/Hot tub Indiana dunes Beaches Trails

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.
The price is ￥20,092
￥45,005 total
includes taxes & fees
Dec 8 - Dec 9
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

Wingate by Wyndham Tinley Park

Wingate by Wyndham Tinley Park

10/10 Excellent
"Clean room clean bathroom clean towels "
Tatiana 1-night trip
Posted 21 hours ago
Wingate by Wyndham Tinley Park

Find out more about Highland

Search for holiday rentals in Highland on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland using one of the methods below:

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Look no further and take a look at our great range of rental properties in Highland!

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.