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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.

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Top guest favorite

Cottage in New Buffalo

4.96 out of 5 average rating, 183 reviews

Voted #1 Family Getaway In SW MI for 2019-2024

NicoleRating, 5 stars8 months ago

Great property for two families with small kids! The listing has everything you need, including pack and plays & a highchair. Dana was super responsive and laid out easy instructions + local recommendations. S’mores on our last night was a big hit!

Top guest favorite

A cabin-style home is nestled among tall pine trees, featuring a large facade with distinctive tall windows that allow natural light to flood the interior. Colorful chairs are positioned on the screened porch, surrounded by well-maintained greenery and flower beds.

Cottage in Union Pier

4.98 out of 5 average rating, 220 reviews

"The Pines" in Union Pier: Year-round getaway

VictoriaRating, 5 stars3 weeks ago

I have been renting Airbnb for years and hands down John’s house was the best house I have ever stayed at. The beds were incredible ( please tell me where you got your pillows and bedding). There was lovely screened porch and great room. Every amenity was available. It was a very special weekend and we had a front row view of many deer in the area. Thank you for being such a great host. We will be back !

A spa hot tub sits on a grassy area, designed for relaxation. Surrounding the tub is lush greenery, offering a sense of privacy. The hot tub features a smooth blue surface with built-in jets, inviting for a peaceful soak after outdoor activities.

Home in Three Oaks

4.82 out of 5 average rating, 96 reviews

Three Oaks Creek House Perfect

BenRating, 5 stars5 months ago

I will call it "Mary Poppins", practically perfect in every way. If you are looking for a quite scenic vacation spot, this is it. Their are obviously things that could have been better, but we got exactly what we wanted, no notes, no issues, no problems.

A cozy living room is presented, featuring a light-colored sectional sofa adorned with a green and floral throw. A natural wood coffee table sits centrally, complemented by a round pouf. Bright curtains with floral patterns frame a large window, allowing ample natural light.

Home in Stevensville

5 out of 5 average rating, 13 reviews

Cozy Bluebird Cott. w/ Hot Tub!

AliceRating, 5 stars3 weeks ago

We had a relaxing time at the cottage. Host was very helpful and responsive. Space has a simple elegance to it. Home is in a quiet area, close to a view of Lake Michigan and close to hiking at Grand Mere State Park. We love the area! Really enjoyed the hot tub!

A sunset over Lake Michigan is captured through silhouetted trees. The sun's reflection glimmers on the water, creating a serene atmosphere. The peaceful scene is framed by a wooden railing, emphasizing the natural beauty of the lakeside setting.

Apartment in Michigan City

4.94 out of 5 average rating, 136 reviews

Charming apartment in Arts District

MariaRating, 5 stars8 months ago

We've stayed here before. It's always really clean and nice. The towels are super soft, and the pillows and linens are awesome. You're right across from the outlet mall, and a farmers market type store across the other way. There's a cute little ice cream shop on the corner. You're close to the beach and the zoo. It's just a nice place to rest and reset. I highly recommend it.

Top guest favorite

The exterior of the cabin is framed by lush greenery, showcasing rustic wooden siding with bright red window shutters. A cozy seating area with white Adirondack chairs is positioned near the entrance, complemented by a decorative trellis and vibrant flower beds along a curved path.

Cabin in Benton Harbor

4.99 out of 5 average rating, 267 reviews

Charming Cabin-Private Beach & Golf

EmilyRating, 5 stars6 months ago

I brought my four kids age 2-16 for some special time at the lake, dunes, and St Joseph. We really enjoyed the home, it was very comfortable, clean and tastefully decorated… comfy beds, well stocked but not cluttered kitchen, and my little ones absolutely loved the children’s bedroom. The private beach is an easy walk and it’s beautiful. Kristi had great recommendations and is the most gracious and hospitable host.

A circle of Adirondack chairs surrounds a central fire pit, positioned on gravel. Potted plants and flowers add greenery, while a backdrop of trees and a storage shed enhance the natural setting of the outdoor space.

Cottage in Three Oaks

4.91 out of 5 average rating, 112 reviews

Private, Sun-filled Union Pier Cottage

WhitneyRating, 5 stars6 months ago

Highly recommend staying at Ken’s place! He was a great host, always responsive and more than happy to provide us with local recommendations. The place was clean and looked exactly as described. It was the perfect place for a mom’s weekend getaway!

A spacious screened-in porch is presented, featuring a wooden floor and exposed beams overhead. Large windows on three sides allow natural light to flow in, offering views of the surrounding neighborhood. Two wicker chairs and a small table are arranged for relaxation.

Townhouse in New Buffalo

4.92 out of 5 average rating, 104 reviews

Downtown NB! Walk Everywhere! Huge screened porch

DevanRating, 5 stars2 weeks ago

Joe allowed us to check-in early without us having to ask, which was awesome! The place was extremely clean and matched the description perfectly. We were able to walk a short distance everywhere we wanted to go, which is a game changer! Joe was extremely friendly and gave us great recommendations. I highly recommend staying here!

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations and amenities

Popular amenities for Gary vacation rentals

Laptop-friendly workspace

Stay near Gary's top sights

Flamingo Pizza of Miller49 locals recommend

18th Street Brewery Tap Room and Craft Cocktails45 locals recommend

Miller Pizza Co38 locals recommend

Vibrations Health, Wellness And Juice Bar28 locals recommend

Beach Cafe26 locals recommend

Tequila and Tacos26 locals recommend

Other great vacation rentals in Gary

A bright and functional kitchen features teal cabinets and modern stainless-steel appliances. A white countertop provides ample workspace, while dishes and utensils rest on open shelves. Dining seating for four is available at a small wooden table, enhancing the kitchen’s welcoming atmosphere.

Home in Michigan City

4.86 out of 5 average rating, 28 reviews

"Sip, Sun & Fun: The Perfect Girls Beach Getaway!"

JennaRating, 5 stars8 months ago

My friends and I had a wonderful stay! The house is super cute and is close to the beach, shops, restaurants , the grocery store, and more! We were out of a few things but they responded immediately and dropped it off asap! We would definitely come back! Thank you!

A welcoming outdoor area features string lights overhead, illuminating a paved path. A set of patio chairs surrounds a table, while additional seating is provided by adirondack chairs. The well-lit space invites relaxation and social gatherings in the evening.

Home in Saint Joseph

5 out of 5 average rating, 3 reviews

Rhain Rentals 3 Bed in St. Joe

AshleyRating, 5 stars19 months ago

We very much enjoyed our stay at this rental! It the perfect size and location to all of the shops downtown and very accessible to the beach. The host was very responsive and so helpful with our stay. Highly recommend for a lovely weekend getaway!

A modern dining area is highlighted by a wooden table surrounded by four chairs. The open-concept layout connects to a stylish kitchen featuring dark cabinetry and stainless steel appliances. Natural light fills the space, reflecting off the hard surface flooring and a cozy living room in the background.

Apartment in Jefferson Park

4.63 out of 5 average rating, 24 reviews

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars1 month ago

Peaceful, felt like home, very spacious and comfortable

An inground swimming pool features clear, blue water surrounded by a spacious deck area. Several lounge chairs are arranged alongside the pool, and pool floats are visible in the water. A secure fence encloses the area, providing safety and privacy.

Home in Michigan City

4.92 out of 5 average rating, 64 reviews

Home near the lake with an inground pool

FreddieRating, 5 stars2 months ago

Clean house and will definitely book again for our needs. Very comfortable with everything.

Top guest favorite

The exterior of the estate is showcased, featuring a dark-colored building nestled among greenery. Tall trees frame the house, with clear skies visible above. Lush foliage complements the natural surroundings, providing a serene outdoor setting.

Vacation home in Baroda

4.94 out of 5 average rating, 17 reviews

Location location

GabrielRating, 5 stars1 month ago

I don’t think the pictures do this house any justice. House is tremendously big. Lots of space for large families. The views? Amazing. With the vineyard next door and the woods surrounding it, it was a great view. Very ample parking. Easy to find and close to the highway. There’s plenty of wineries near the house. Also grocery stores for any quick essentials. Back to the house. Very clean and big kitchen. Has everything you need from plates to cups. The living room is big. Tv is huge to keep the kids entertained. It was a little chilly so we stayed inside. But the deck looks really new and big with a girl. The backyard was huge. Rooms were big with nice beds and clean as well. All bathrooms were super clean and big. Basement had an entire other living area with rooms as well. Pool table kept everyone entertained. Dining room had a nice table for the large family dinners. In conclusion, I will definitely love to book this for the summer. You won’t regret it.

Top guest favorite

A modern kitchen area features a white bar counter with four dark wooden stools. Minimalistic tableware is arranged on woven placemats. Large windows allow natural light to fill the space, showcasing a glimpse of the outdoors through the decorative glass door.

Home in Lombard

5 out of 5 average rating, 25 reviews

Spacious Home in Chicago Suburbs

JenniferRating, 5 stars2 weeks ago

It was great! The house was lovely and looked newly renovated. It was much roomier than I expected. The beds were very comfortable.

4.85 out of 5 average rating, 68 reviews

A Comfortable Stay While You are Away in Oak Park

KarenRating, 5 stars2 weeks ago

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.

Top guest favorite

Cottage in Union Pier

4.96 out of 5 average rating, 201 reviews

Designer Cottage Relax Beach Pool & Spa—Windjammer

HilaryRating, 5 stars2 weeks ago

Beautiful house, very well thought out for guests. Host and Co-Host were absolutely wonderful through the whole process. Lots to do in the area. Would highly recommend!

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 120 vacation rentals in Miller Beach, over 10 vacation rentals in Tolleston, and over 10 vacation rentals in Glen Park.
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 cottage rentals in Gary?
Experience the best of Gary with our cottage rentals, starting at about $50 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.
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 apartment rentals in Gary have wireless internet?
Absolutely! We offer over 10 apartment rentals with wireless internet in Gary. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Gary?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with wireless internet, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
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!

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