
Family-friendly holiday rentals in Gary
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Top-rated family-friendly rentals in Gary
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Home near Indiana Dunes, Lake Michigan, Chicago!
Enjoy home away from home in this beautiful two bedroom, THREE beds, one bath home with plenty of living room and kitchen sunlight . Relax in a comfortable living room with recliner chairs while you enjoy a warm cup of coffee or your beverage of choice.Home has plenty of parking including a driveway for two cars and free street parking. If you enjoy the outdoors, you'll love our extra large back yard! Enjoy a short walk down the block to a beautiful trail and enjoy winter sledding and disc golf.

Unique Dome escape by Indiana Dunes with Lake View
Escape to our Valparaiso Lakeside Retreat with king bed, lake views, unique dome experience, fire pit, grill & hot tub, all near Indiana Dunes National Park, Valparaiso University & 4 local parks! Experience a nature getaway at our newly renovated lake guest house on the ground level of our home with keyless entry & unique outdoor amenities, ideal for friend groups, small families, business travelers & couples. 10 min - downtown Valparaiso. Book now to experience this unique tranquil retreat.

Beachfront- Lake Michigan-Hot Tub-Heated Pool
Lake Michigan - Beachfront w/Heated In-Ground Pool- Hot Tub - Indiana Dunes National Park - Private Basement Guest Suite - 2 Bedroom/2 Bathrooms - Beautifully Decorated This guest suite has everything you need for a comfy and relaxing stay. Enjoy the 3-person hot tub, perfect for unwinding after a day of adventure. In the summer months, enjoy the heated, in-ground pool. Hiking, beaches and so much more await—and less than an hour’s drive to Chicago. Heated Pool Open from Mid-May to Mid-Oct.

1930’s Cozy Cottage in the Woods.Walk to the beach
Come fall in love with Michiana Shores, we promise you'll love the peace and quiet. Our charming cottage sits back tucked away, nestled among pine trees and twinkle lights. Roast marshmallows while sitting around the fire with 6 modern adirondack chairs, take a stroll to the beach, ride bikes, BBQ, watch the sunset along lakeshore drive. Play tennis or pickle at the local park. 10 minute walk to the beach. Far away enough to relax yet close enough to new Buffalo, Union Pier or Long Beach

The Little House at Tryon Farm
The little house is located within a 170-acre modern farm community filled with open meadows, woods and dunes. Minutes to beach, 1 hour to Chicago. Relax and enjoy the property or head out to explore the lakeshore, wineries, and great area restaurants! Two bedrooms, 1.5 baths, a fully appointed kitchen, living area w/fireplace, and a large screened in porch. Large windows flood the house with natural light and will make you feel like you're living in the treetops. A perfect getaway!

Neon Dunes Vista Beachfront Cottage
Neon Dunes Cottage is a one bedroom romantic getaway. A newly renovated cottage with new kitchen, modern appliances and new bathroom all in a bright airy home. It is located in Indiana Dunes National Park/Miller Beach. Only 1.5 blocks to the beach, you can hike trails nearby and come back to relax in a unique, comfortable setting with ambiance and charm. It's perfect for summer/holidays. Wifi, onsite parking and self check in, allow you to enjoy our wonderful home in privacy and peace.

Midcentury Cottage 3bd IN Dunes Natl Park, Lake MI
If you're looking for a laid-back [aka not fancy] getaway, this is it. The Midcentury Miller Cottage features 3bd, 1ba, and has the perfect blend of updates and original midcentury modern details that will make you swoon. Home feels private and faces a wooded dune. Beach and restaurants are a 9-min walk away. More restaurants, beaches and hiking are a short car drive away. Take time at Miller Cottage to unwind, reconnect and explore. Located in the 61st National Park, Indiana Dunes.

Updated House Close to Beach + National Park
Walk to the Beach & National Park This newly renovated home is just 2.5 blocks from the beach and a two-minute drive to the National Park at West Beach. The home’s main level features a large living room and dining area,full bathroom, 2 bedrooms, modern eat-in kitchen, large patio for outdoor entertaining, gas grill and propane fire pit. The fully finished basement has two bedrooms, a full bathroom, laundry room and rec room with a full-sized ping pong table and smart TV

'Pool Barn Camper' w/Hot Tub near Indiana Dunes
Hot tub open all year! Pool will reopen May 1. Fully equipped RV sleeps 5, has bathroom w/shower, stove, microwave, TV, heat & A/C, & running water all year. Located on the bike trail & only minutes from the sand beaches of Indiana Dunes on Lake Michigan. Hike in the Indiana Dunes National Park along the Little Calumet River & the historic Bailley homestead, only 1 block from the RV. Enjoy our large pool, hot tub, grill, campfire, & playground too. Schedule your visit today!

Miller Mermaid Suite-100 yds from the beach!
100 yds from the beach, the cozy MERMAID SUITE is best for a young family or 2-3 adult friends. This artsy basement/studio includes: private entrance, kitchenette, unique art, cozy reading/sleeping nook. There is one small window with no lake view but you can see the lake from the upstairs deck. BBQ on the grill. Visit local restaurants, shops & galleries. Hike wooded trails & swim by sandy, dune-grass beaches. . House-trained dogs welcome! Sorry no cats (allergies)

Cute Skylar: Valparaiso University ShortTerm
Welcome to Skylar's Relaxing Spot! This cozy one-bedroom on the second level features a queen-size bed, its own entrance, deck space, and building laundry facilities. Perfect for accessing downtown and Valpo University. Enjoy strong WiFi for remote work and relaxing movie nights on the TV. Located near Route 30 and I-49, it’s an hour from Chicago and 15 minutes from Indiana Dunes, close to malls, ice cream parlors, and great restaurants! ☺️

IT'S THE WRIGHT PLACE
Private guest house newly remodeled. One bedroom queen bed, bath w/shower, full kitchen stocked, including microwave and Keurig coffee maker pods included, family room TV, and WIFI. No matter if you are in town for work, sport competition, family or just vacationing we offer all the comforts of home. Air Mattress available upon request. Please treat as your own home, follow all house rules. No party or gatherings. This is a no smoking home.
Popular amenities for Gary family-friendly rentals
Family-friendly home rentals with a hot tub

Romantic Spa Getaway -Private Jacuzzi, Sauna, Pool

Relax - SW Mi Getaway/Hot Tub-Beaches & Wine Tours

Duplex | Firepit | Game Room | Hot Tub-all year

Top Floor Views + Central Comfort

The Cottage of Harbor Country - Close to it all!

Couples alert! PVT beach access, hot tub, firepit!

Secluded Modern Retreat Near Beach - "Sandlot"

J’s Beach House: Hot Tub & short walk to beach!
Family- and pet-friendly home rentals

South Shore Studio Apartment {National Park}

Charming Garden Apartment

Cozy Luxe Downtown Valparaiso Stay

Retro Modern Bungalow | free parking | fire pit

Casa Gitana - Boutique Style Stay in Three Oaks

Rainbows End 🌈 Puryear

Newly Renovated, Spacious 2BR in Andersonville

Avondale Cozy 1 Bedroom Attic Apartment 4th FL
Family-friendly home rentals with a pool

Lake House Retreat on the water

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

5 Bedroom Luxury Home In Heart of Beachwalk Resort

Winter & Holiday Couples getaway Pvt Hot tub

The Metropolitan Retreat (2BD / 2BA)

Designer Cottage Relax Pool Beach & Spa—Windjammer

Whole Flat in Private Club. Walk to L, Dining & Shows

Farm Themed Guesthouse!
When is the best time to visit Gary?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £131 | £138 | £138 | £133 | £159 | £191 | £196 | £185 | £154 | £143 | £134 | £133 |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about holiday rentals that are family-friendly in Gary

Total holiday rentals
Explore 120 holiday rentals in Gary

Nightly prices starting at
Gary holiday rentals start at £45 per night before taxes and fees

Verified guest reviews
Over 5,250 verified reviews to help you choose

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wifi availability
120 of Gary holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Gary rentals

4.8 Average rating
Gary stays are highly rated by guests – averaging 4.8 out of 5!
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Warren Dunes State Park
- Wicker Park
- Oak Street Beach
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Willis Tower
- Washington Park Zoo
- Grant Park
- The 606
- Chicago Cultural Center
- Chicago History Museum




