
Vacation rentals in Gary
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Top-rated vacation rentals in Gary
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Gary vacation rentals
Other great vacation rentals in Gary

Across Street From Lake MI, Blocks To Beach Golf T
Great location in adorable Grand Beach! A true old school Beach house perfect for our extended family. Just steps to the beach and a short drive to New Buffalo. We loved it and will be back. Chris was super responsive when we had questions and an issue with the door lock.

Great Living Too
I cannot say enough about how clean the house was. Wonderful space for everyone. Kitchen table was large enough for my group to play games at and the basement space was large enough for everyone too! If we are back in the area we would stay here again!

City Gem: Stylish 3BR for Urban Explorers
Peaceful, felt like home, very spacious and comfortable

Home near the lake with an inground pool
Clean house and will definitely book again for our needs. Very comfortable with everything.

Awesome Family Escape with pool and private beach
Patty's place was GREAT! My 3 sisters and I had a very relaxing and enjoyable vacation. The Condo was exactly as pictured. It was very clean, had everything we needed in the living room, bathrooms and in the kitchen to cook meals. All 3 beds were very comfortable with plenty of blankets and pillows. We were able to drive North, South & East less than 30 minutes to visit wineries, shops, antique malls and fine restaurants. There are lots of things to do close to Coloma for 4 retired ladies. We loved walking down to the beach every evening to watch the sunset and waves as they rolled in.

A Comfortable Stay While You are Away in Oak Park
The house looked just like the beautiful photos & Jay was incredibly responsive throughout the visit. This home is located close to 290 to go downtown or further out to the 'burbs quickly. We needed a home to stay last minute, and Jay was accommodating to that as well - we were happy to find this spot with all the space we needed inside and out. As a bonus, we met neighbors who were very friendly.

Livingston's fabulous Beachhouse
The house was everything you could ask for. Very comfortable and made you feel at home. Nice little walk to the lake and country surroundings. The host was nice and friendly.

Designer Cottage Relax Beach Pool & Spa—Windjammer
Rented the house for a girls weekend and it was perfect - comfortable to rest and relax in, spacious, quiet and private while still walkable to the beach and markets! Loved the decor and kitchen! We felt right at home!
Quick stats about vacation rentals in Gary
Total rentals
170 properties
Total number of reviews
6.2K reviews
Family-friendly rentals
130 properties are a good fit for families
Pet-friendly rentals
80 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
100 properties have a dedicated workspace
Frequently Asked Questions
Where should I stay in Gary?
Make yourself at home in Gary by choosing from our most frequently booked neighborhoods. We have over 10 vacation rentals in Glen Park, over 10 vacation rentals in Tolleston, and over 120 vacation rentals in Miller Beach.
Are there vacation rentals with a dedicated workspace in Gary?
Yes! Work meets play with ease at over 100 vacation rentals in Gary featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in apartment rentals in Gary?
Experience the best of Gary with our apartment rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Gary?
Four-legged friends are welcome in Gary. Choose from more than 80 vacation rentals for guests traveling with pets.
Are there Gary vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Gary, available on Airbnb. Make a splash and soak up the sun in style!
Do cottage rentals in Gary have a bbq area?
Absolutely! We offer over 10 cottage rentals with a bbq area in Gary. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Gary have air conditioning?
Absolutely! We offer over 110 house rentals with air conditioning in Gary. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Gary have a gym?
Absolutely! We offer over 10 house rentals with a gym in Gary. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Gary have wireless internet?
Absolutely! We offer over 110 house rentals with wireless internet in Gary. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Cottage Rentals in Gary?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wireless internet, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Warren Dunes State Park
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park Zoo
- Flossmoor Golf Club
- Willis Tower
- Museum of Science and Industry
- Wicker Park
- Lincoln Park
- Chicago History Museum
- Skokie Country Club
- Brookfield Zoo
- Promontory Point
- Washington Park Zoo
- Garfield Park Conservatory
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