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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 253 Vacation Homes in Highland with updated reviews, rates, and availability.

Cozy Home Sweet Homewood.
Fridge, microwave, oven, stovetop

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (20)
"Perfect for what we needed "
Cozy Home Sweet Homewood.
Miller Beach Blue Door By The Shore #2
Beach

Miller Beach Blue Door By The Shore #2

10.0 out of 10, Exceptional, (4)
"I had a very nice stay the property was very clean. I loved the location probably would’ve been better if I had rented in the summer because it was a little chilly in the home but otherwise everything was great. "
Miller Beach Blue Door By The Shore #2
Private Home Awaits
Fridge, microwave, oven, stovetop

Private Home Awaits

"The stay was excellent!! The house was so spacious clean and comfortable. I really enjoyed my stay here and would definitely book agsin"
The price is SAR 675
SAR 1,637 total
includes taxes & fees
8 Apr - 9 Apr
Private Home Awaits
House with garage, outdoor dining and basement bar
Fridge, microwave, oven, dishwasher

House with garage, outdoor dining and basement bar

House with garage, outdoor dining and basement bar
Private Wooded Acre, Soaring Windows in Nat’l Park, 2 blocks to the beach
Beach nearby, sun loungers

Private Wooded Acre, Soaring Windows in Nat’l Park, 2 blocks to the beach

10.0 out of 10, Exceptional, (33)
"Our stay was nothing short of amazing! The host was incredibly responsive and flexible, allowing us to make a last-minute change to our reservation. She went above & beyond to be accommodating, which made it possible for our family to still gather for a special Christmas and New Year celebration. The house itself was full of character, with unique artwork and quirky touches that made it feel like a fun, creative retreat. The serene location, surrounded by nature, provided the perfect backdrop...
Private Wooded Acre, Soaring Windows in Nat’l Park, 2 blocks to the beach
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Exterior

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

8.8 out of 10, Excellent, (5)
"The place was well maintained and very clean with no issues and the host was great and fast to respond."
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Casa Blanca in Miller Beach!
Exterior

Casa Blanca in Miller Beach!

9.8 out of 10, Exceptional, (69)
"8 of us stayed at the house, plenty of beds, plenty of places to sit and talk / watch TV, kitchen had everything we needed. Highly recommend"
Casa Blanca in Miller Beach!
Restored Cottage Across The Street From The Beach!
On the beach, sun loungers, beach towels

Restored Cottage Across The Street From The Beach!

9.8 out of 10, Exceptional, (95)
"Great house for large family. Very cozy, yet spacious. Fenced yard was great as was the close proximity to the beach"
Restored Cottage Across The Street From The Beach!
Charming 3-bedroom house in serene and lovely Evergreen Park. WiFi/ AC
Interior

Charming 3-bedroom house in serene and lovely Evergreen Park. WiFi/ AC

10.0 out of 10, Exceptional, (1)
"Lovely new (or well remodeled?) house in a nice neighborhood. Host was nice and communicative. Kitchen is well stocked. There’s only one shower but we had no problem sharing. "
Charming 3-bedroom house in serene and lovely Evergreen Park. WiFi/ AC
Chic & Stylish 3-bedroom house in Palos Heights
Private kitchen

Chic & Stylish 3-bedroom house in Palos Heights

Chic & Stylish 3-bedroom house in Palos Heights
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
Fridge, microwave, oven, stovetop

Gorgeous historic mansion on UChicago campus. Renovation with original detail.

10.0 out of 10, Exceptional, (4)
"Delightful home in charming neighborhood. The host was great to deal with, making sure we had what we needed for our toddler. All we had to bring was ourselves!"
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
Steps to Lake Michigan Beach: Gary Vacation Rental
Interior

Steps to Lake Michigan Beach: Gary Vacation Rental

9.2 out of 10, Wonderful, (34)
"Nice"
Steps to Lake Michigan Beach: Gary Vacation Rental
Spacious Family Glenwood Estates Home w/ Hot Tub!
Indoor spa tub

Spacious Family Glenwood Estates Home w/ Hot Tub!

9.4 out of 10, Exceptional, (14)
"Place was perfect! I grew up in the suburbs of Chicago and wanted to come back to honor my grandmother's 90th birthday. This place was perfect. It had a piano and the pastor was able to serinate her in playing church hymnals. Of course, her famiy, fch family, family and friends were all able to show"
Spacious Family Glenwood Estates Home w/ Hot Tub!
Pet-Friendly Lake Getaway: 1 Block to Beach!
Fridge, microwave, stovetop, dishwasher

Pet-Friendly Lake Getaway: 1 Block to Beach!

10.0 out of 10, Exceptional, (34)
"Property was very clean and photos accurate. Check in process was easy and we enjoyed a quick fall weekend get away to hike the Dunes. Good communication from owner. Thanks!"
Pet-Friendly Lake Getaway: 1 Block to Beach!
Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.
Fridge, microwave, oven, stovetop

Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.

10.0 out of 10, Exceptional, (20)
"Wonderful Experience, great location, easy access to close businesses, great communication with the home owner, overall a beautiful establishment "
Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.
Nestled just behind Marquette Park. 5 minute walk to beach.
Exterior

Nestled just behind Marquette Park. 5 minute walk to beach.

10.0 out of 10, Exceptional, (9)
"Could not be more thankful for her prompt replies and accommodations."
Nestled just behind Marquette Park. 5 minute walk to beach.
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
Terrace/patio

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

8.8 out of 10, Excellent, (33)
"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!"
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
Lux Home in Chicago 7mins Downtown
Fridge, microwave, oven, stovetop

Lux Home in Chicago 7mins Downtown

9.8 out of 10, Exceptional, (16)
"Beautiful stay and super nice host would recommend every time "
Lux Home in Chicago 7mins Downtown
Modern Historic Greystone - Near Lake - Free Prkg
Fridge, microwave, oven, stovetop

Modern Historic Greystone - Near Lake - Free Prkg

6.4 out of 10, (5)
"Great property in a quiet neighborhood. Not far from downtown and other tourist attractions. 10/10 would recommend. "
Modern Historic Greystone - Near Lake - Free Prkg
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago
Fridge, microwave, stovetop, dishwasher

Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

8.2 out of 10, Very Good, (20)
"We really love the home and the setup."
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago
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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Other property types in Highland

Comfort Inn Chicago Wind Creek Casino
Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi

Comfort Inn Chicago Wind Creek Casino

2.5 star property
4.0 out of 10, (14)
"The staff was polite and friendly! I didn't care that they were apparently under construction and I didn't are much for that "
The price is SAR 335
SAR 378 total
includes taxes & fees
10 Apr - 11 Apr
Comfort Inn Chicago Wind Creek Casino
Cozy Home Sweet Homewood.
Fridge, microwave, oven, stovetop

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (20)
"Perfect for what we needed "
Cozy Home Sweet Homewood.
Modern Condo-Obama & University of Chicago Area
Fridge, microwave, oven, stovetop

Modern Condo-Obama & University of Chicago Area

9.2 out of 10, Wonderful, (5)
"Property was very well kept and accommodated us well. We didn’t spend much time there as we were out most of the day but it was nice to come back to a place like this."
Modern Condo-Obama & University of Chicago Area
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.