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Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

Compare 260 Vacation Homes in Highland with updated reviews, rates, and availability.

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
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.
Private Home Awaits
Fridge, microwave, oven, stovetop

Private Home Awaits

The price is SAR 675
SAR 1,625 total
includes taxes & fees
23 Mar - 24 Mar
Private Home Awaits
Spacious 3br home near Chicago, fenced yard for pets
Fridge, microwave, oven, stovetop

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
9.2 out of 10, Wonderful, (5)
"As advertised. We enjoyed our stay. Thank you!"
The price is SAR 510
SAR 1,216 total
includes taxes & fees
24 Mar - 25 Mar
Spacious 3br home near Chicago, fenced yard for pets
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.
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!
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
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
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.
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!
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
Charming and spacious 3-bedroom townhome with WiFi and amenities in Gary
Beach

Charming and spacious 3-bedroom townhome with WiFi and amenities in Gary

7.0 out of 10, Good, (2)
"The property itself was ver clean just an older house. Very clean! The neighborhood was a little questionable for families who have never travelex to that area from a rural area. The stay was good and worked for what we needed!"
The price is SAR 469
SAR 1,201 total
includes taxes & fees
25 Mar - 26 Mar
Charming and spacious 3-bedroom townhome with WiFi and amenities in Gary
Woodlawn Oasis...10 Minutes to Dining & Downtown
Smart TV

Woodlawn Oasis...10 Minutes to Dining & Downtown

9.6 out of 10, Exceptional, (10)
"The property has lots of space and a game room, ideal for a fun getaway with a large group. Close to bus stops and Metra station (different from metro station, we learned this the hard way). Walking distance from the U of Chicago."
Woodlawn Oasis...10 Minutes to Dining & Downtown
A Stone`s Throw, 4 bedroom 2 bath home a block from Lake Michigan
Fridge, microwave, oven, stovetop

A Stone`s Throw, 4 bedroom 2 bath home a block from Lake Michigan

9.6 out of 10, Exceptional, (9)
"Good stay. Very nice property. Recommended "
A Stone`s Throw, 4 bedroom 2 bath home a block from Lake Michigan
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
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!
HARD ROCK HAVEN!!
Fridge, microwave, oven, stovetop

HARD ROCK HAVEN!!

10.0 out of 10, Exceptional, (6)
"One of the best experiences any time I’m in Indiana I wouldn’t look any place else I will be coming back"
HARD ROCK HAVEN!!
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
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.
Cozy house in Schererville, IN
Exterior detail

Cozy house in Schererville, IN

9.8 out of 10, Exceptional, (9)
"Perfect for the perfect couples getaway"
The price is SAR 563
SAR 1,265 total
includes taxes & fees
21 Apr - 22 Apr
Cozy house in Schererville, IN
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
3.6 out of 10, (12)
"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
28 Mar - 29 Mar
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.