Photo by Lawrence Tellez
Gary holiday homes
We found 615 holiday rentals — enter your dates for availability
Select the perfect holiday home within close proximity to Gary, IN (GYY-Gary - Chicago Intl.). Holiday rentals provide the best amenities for you and your friends, family or even pets, such as a hot tub and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Gary, IN (GYY-Gary - Chicago Intl.)
Showing deals for:22 Aug - 29 Aug
Image gallery for Large historic home minutes from downtown Chicago and the lakefront.
1010 out of 10 rating
Exceptional
(8 reviews)
Large historic home minutes from downtown Chicago and the lakefront.
Chicago, IL
8% off
Price is NZ$9,476
NZ$9,476
NZ$1,354 per night
includes taxes & fees
Image gallery for Lakefront property , minutes from McCormick Place and Downtown Chicago.
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Lakefront property , minutes from McCormick Place and Downtown Chicago.
Chicago, IL
12% off
Price is NZ$6,845
NZ$6,845
NZ$978 per night
includes taxes & fees
Image gallery for Charming Lake House, Lake View, Private Pier, Bugaboo Bar and Water Sports!
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Charming Lake House, Lake View, Private Pier, Bugaboo Bar and Water Sports!
Cedar Lake, IN
8% off
Price is NZ$4,844
NZ$4,844
NZ$692 per night
includes taxes & fees
Image gallery for ⭐️ Fast WiFi/Comfy beds/Free parking/Getaway/3bdr House
9.29.2 out of 10 rating
Wonderful
(7 reviews)
⭐️ Fast WiFi/Comfy beds/Free parking/Getaway/3bdr House
Glenwood, IL
8% off
Price is NZ$2,776
NZ$2,776
NZ$397 per night
includes taxes & fees
Image gallery for Cheerful, Lake Home with amazing backyard!
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Cheerful, Lake Home with amazing backyard!
Cedar Lake, IN
8% off
Price is NZ$5,754
NZ$5,754
NZ$822 per night
includes taxes & fees
Image gallery for LakeHouse
1010 out of 10 rating
Exceptional
(16 reviews)
LakeHouse
Chicago, IL
22% off
Price is NZ$3,703
NZ$3,703
NZ$529 per night
includes taxes & fees
Image gallery for Private Oasis with Spacious Backyard
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Private Oasis with Spacious Backyard
Matteson, IL
33% off
Price is NZ$6,672
NZ$6,672
NZ$953 per night
includes taxes & fees
Image gallery for Cheerful, charming, super comfy 2BR 2Bath Condo
1010 out of 10 rating
Exceptional
(15 reviews)
Cheerful, charming, super comfy 2BR 2Bath Condo
Valparaiso, IN
8% off
Price is NZ$2,847
NZ$2,847
NZ$407 per night
includes taxes & fees
Image gallery for Home Away From Home
1010 out of 10 rating
Exceptional
(7 reviews)
Home Away From Home
Chicago, IL
11% off
Price is NZ$4,361
NZ$4,361
NZ$623 per night
includes taxes & fees
Image gallery for 6 Bed 3 BA Spacious A-Frame Near Crown Point
9.89.8 out of 10 rating
Exceptional
(12 reviews)
6 Bed 3 BA Spacious A-Frame Near Crown Point
Cedar Lake, IN
8% off
Price is NZ$5,735
NZ$5,735
NZ$819 per night
includes taxes & fees
Image gallery for Spacious 4 Bedroom (5 queen beds) 2 Bath in the kenwood neighborhood
9.49.4 out of 10 rating
Exceptional
(41 reviews)
Spacious 4 Bedroom (5 queen beds) 2 Bath in the kenwood neighborhood
Chicago, IL
7% off
Price is NZ$4,576
NZ$4,576
NZ$654 per night
includes taxes & fees
Image gallery for Suburban Haven: Cozy Escape with a Touch of Luxury
1010 out of 10 rating
Exceptional
(5 reviews)
Suburban Haven: Cozy Escape with a Touch of Luxury
Homewood, IL
6% off
Price is NZ$8,750
NZ$8,750
NZ$1,250 per night
includes taxes & fees
Image gallery for Charming 3BR Chicago Apt in Prime Location
9.49.4 out of 10 rating
Exceptional
(11 reviews)
Charming 3BR Chicago Apt in Prime Location
Chicago, IL
5% off
Price is NZ$7,145
NZ$7,145
NZ$1,021 per night
includes taxes & fees
Image gallery for Cozy 3-bedroom condo near University of Chicago
9.89.8 out of 10 rating
Exceptional
(48 reviews)
Cozy 3-bedroom condo near University of Chicago
Chicago, IL
11% off
Price is NZ$3,546
NZ$3,546
NZ$507 per night
includes taxes & fees
Image gallery for An Escape to a Dream of Green and relaxation.
1010 out of 10 rating
Exceptional
(12 reviews)
An Escape to a Dream of Green and relaxation.
Gary, IN
8% off
Price is NZ$4,319
NZ$4,319
NZ$617 per night
includes taxes & fees
Image gallery for Modern Oasis • 2 blocks to Beach • Rooftop Terrace
1010 out of 10 rating
Exceptional
(10 reviews)
Modern Oasis • 2 blocks to Beach • Rooftop Terrace
Gary, IN
8% off
Price is NZ$4,385
NZ$4,385
NZ$626 per night
includes taxes & fees
Image gallery for Cozy brick home in a quiet neighborhood
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Cozy brick home in a quiet neighborhood
Gary, IN
8% off
Price is NZ$2,608
NZ$2,608
NZ$373 per night
includes taxes & fees
Image gallery for Urban Home near 80/94
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Urban Home near 80/94
Hammond, IN
7% off
Price is NZ$2,366
NZ$2,366
NZ$338 per night
includes taxes & fees
Image gallery for Entire 3bd home Comfortable Private
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Entire 3bd home Comfortable Private
Markham, IL
6% off
Price is NZ$2,559
NZ$2,559
NZ$366 per night
includes taxes & fees
Image gallery for Beautiful home with Arcade and Movie Theater for you and your family to enjoy.
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Beautiful home with Arcade and Movie Theater for you and your family to enjoy.
Chicago, IL
9% off
Price is NZ$5,013
NZ$5,013
NZ$716 per night
includes taxes & fees
Image gallery for Laurna Dune
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Laurna Dune
Gary, IN
7% off
Price is NZ$2,107
NZ$2,107
NZ$301 per night
includes taxes & fees
Image gallery for Toca Bella ~ 7mins to Downtown
1010 out of 10 rating
Exceptional
(11 reviews)
Toca Bella ~ 7mins to Downtown
Chicago, IL
7% off
Price is NZ$3,412
NZ$3,412
NZ$487 per night
includes taxes & fees
Image gallery for The Cozy Nest: King Bed in Quiet and Safe Condo by McCormick Place and Midway!
9.09.0 out of 10 rating
Wonderful
(6 reviews)
The Cozy Nest: King Bed in Quiet and Safe Condo by McCormick Place and Midway!
Chicago, IL
16% off
Price is NZ$2,851
NZ$2,851
NZ$407 per night
includes taxes & fees
Image gallery for Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
9.09.0 out of 10 rating
Wonderful
(8 reviews)
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
Chicago, IL
7% off
Price is NZ$7,754
NZ$7,754
NZ$1,108 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Gary
Charming 4-bedroom house with WiFi and AC in Park Forest
Sleeps 8 · 4 bedrooms · 1 bathroom
A Chic 8th Floor Studio Inside Vintage Style Building With Spectacular Lake View
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
Sleeps 12 · 5 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
9 reviews(9 reviews)
Astonishing 4 bdrm home 30 min to Dwntwn!
Sleeps 8 · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
7 reviews(7 reviews)
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Sleeps 6 · 2 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
9 reviews(9 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value