Highland Vacation Rentals
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Vacation Rentals in Highland
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago
Chesterton IN
$286 nightly
The price is $320 total per night
$320 total
May 9 - May 10
Total with taxes and fees
With a stay at this vacation home, you'll be centrally located in Chesterton, within a 10-minute drive of Indiana Dunes National Park and Indiana Dunes State Park.
Hot Tub
Kitchen
A Home Away From Home!
Chicago IL
With a stay at this vacation home in Chicago (Calumet Heights), you'll be within a 10-minute drive of Lake Michigan and University of Chicago.
Washer
Dryer
Dunes Escape - Minutes from Indiana Dunes National Park
Gary IN
With a stay at this vacation home in Gary (Miller Beach), you'll be a 1-minute drive from Indiana Dunes National Park and 6 minutes from Lake Michigan.
Kitchen
Washer
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Whiting IN
$178 nightly
The price is $199 total per night
$199 total
May 4 - May 5
Total with taxes and fees
With a stay at this vacation home in Whiting (Robertsdale), you'll be within a 15-minute walk of Lake Michigan and Whihala Boat Launch Beach.
Kitchen
Washer
Pool, Gym & Basketball Court: Olympia Fields Home
Olympia Fields IL
Located in Olympia Fields, this vacation home is within a 10-minute drive of Coyote Run Golf Course and Franciscan St. James Health - Chicago Heights.
Pool
Kitchen
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Miller Beach IN
With a stay at this vacation home in Gary (Miller Beach), you'll be within a 5-minute drive of Indiana Dunes National Park and Lake Michigan.
Hot Tub
Kitchen
A Stone’s Throw Winter + Summer 2026!
Gary IN
With a stay at this vacation home in Gary (Miller Beach), you'll be steps from Lake Michigan and 11 minutes by foot from Indiana Dunes National Park.
Kitchen
Washer
Private Home Awaits
Homewood IL
With a stay at this vacation home in Homewood, you'll be within a 5-minute drive of Coyote Run Golf Course and Advocate South Suburban Hospital.
Hot Tub
Kitchen
Lovely three bedroom Loft, University Of Chicago, Obama Library
Chicago IL
With a stay at this vacation home in Chicago (Woodlawn), you'll be within a 5-minute drive of Lake Michigan and University of Chicago.
Kitchen
Washer
Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago
Chesterton IN
With a stay at this vacation home in Chesterton, you'll be within a 10-minute drive of Indiana Dunes National Park and Indiana Dunes State Park.
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.
Highland Vacation Rentals essential information
Accommodation | 231 Vacation Rentals |
|---|---|
Lowest Price | $199 |
Highest Price | $320 |
Popular accommodation | Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago , A Home Away From Home!, Dunes Escape - Minutes from Indiana Dunes National Park, Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront., Pool, Gym & Basketball Court: Olympia Fields Home, Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park, A Stone’s Throw Winter + Summer 2026!, Private Home Awaits, Lovely three bedroom Loft, University Of Chicago, Obama Library , Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago , Delightful 5-bedroom house with AC in vibrant Chicago, Superb townhome with Near Lake in vibrant Chicago |