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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

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, (24)
"It felt like home. Didnt want to leave."
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)
"Perfect!"
Miller Beach Blue Door By The Shore #2
Private Home Awaits
Fridge, microwave, oven, stovetop

Private Home Awaits

10.0 out of 10, Exceptional, (2)
"Very convenient to all my activities for my 55th Birthday "
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, (34)
"Clean, quiet and comfortable! The host was pleasant!"
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!

7.8 out of 10, Good, (7)
"Overall it was a great experience and I’ll be coming back sooner"
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

9.0 out of 10, Wonderful, (2)
"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
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, (8)
"We loved our stay. The house was beautiful. We hope to come back. "
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)
"This was a lovely place to stay and enjoy a short walk to a lovely beach."
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)
"Can’t wait to book again for the summer"
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, (36)
"Great location. Home is very clean. Enjoyed our stay."
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, (21)
"Property was nice"
Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.
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, (34)
"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, (17)
"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
Dreamsville Gateway to Indiana Dunes National Park
Exterior

Dreamsville Gateway to Indiana Dunes National Park

6.0 out of 10, (1)
"Listed as private home , once you get there and read the house rules it states shared refrigerator with owner. Owner comes in while you are gone and turns off all lights and the Ac, even goes into your locked room to turn off ac."
Dreamsville Gateway to Indiana Dunes National Park
LakeHouse
Fridge, microwave, oven, stovetop

LakeHouse

10.0 out of 10, Exceptional, (16)
"Great"
LakeHouse
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 Southland I-80 & I-294 Near Casino
Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi

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

2.5 star property
4.0 out of 10, (24)
"Nice inside room but it’s not safe outside area"
The price is AED 328
AED 371 total
includes taxes & fees
9 May - 10 May
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Terrace/patio

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

8.2 out of 10, Very Good, (34)
"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
LakeHouse
Fridge, microwave, oven, stovetop

LakeHouse

10.0 out of 10, Exceptional, (16)
"Great"
LakeHouse
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.