
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.

Cabin on Swede Hill
Welcome to "Cabin on Swede Hill". Our family has farmed this land since 1871. My great grandparents, Swan and Johanna Johnson immigrated to America in the 1860's, found this land which was similar to Sweden. They raised their family here. Approximately 65 Swedish families settled in this community, became to be know as the "Swede Hills". We just received the Hoosier Homestead Award from Indiana celebrating the Sesquicentennial Award. We invite you to come...... and experience country life.

Dunes Homestead - Near Dunes + Lake + Dog Friendly
Welcome to "The Dunes Homestead". Where all pets are welcome! Right in-between The Dunes National Park and downtown Chesterton, you will be close to everything when you stay at this centrally located home. Artfully crafted, this charismatic, dog themed home greets you with all new furniture, a front porch, big yard, and focuses the design around your "man's best friend"! Less than 10 minutes to the Dunes and beaches or head 5 minutes to downtown for food, drinks and plenty of small-town fun. 😁

Lakeside Dome Retreat w Hot Tub Near Indiana Dunes
Welcome to Valparaiso Lakeside Retreat a private getaway on Long Lake featuring a one-of-a-kind outdoor geodesic dome (11 feet), hot tub, fire pit, & kayaks. 20 minutes from Indiana Dunes National Park. Perfect for couples, remote workers & nature lovers seeking a tranquil escape. Enjoy stunning Long Lake views from your private backyard & dome. Long Lake public beach access is just around the corner. Perfect for kayaking, swimming, or a morning walk to the water. Book this unique stay today!

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 and fenced yard. 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

Newly Renovated with Finished Basement
This beautiful house is located near Lake Michigan in Northwest Indiana, less than 10 minutes from the expressway and toll road. There is a stainless steel kitchen, spa bathroom, finished basement and bar with sleeping capacity to accommodate two families. This is a smart home with Ring db, lights and thermostat controlled by your voice. We are less than an hour drive from downtown Chicago, and there are many great beaches nearby. Shopping and great dining options are also within a close drive.

Steps from the beach and a mile from National Park
Perfect for family or friends to relax and enjoy Indiana’s Dunes National Park! The Holliday House is a 2022 custom built home with lake views and a beach path just STEPS from the front door! This 2000 sq ft open concept design features 3 bedrooms and 3 bathrooms, 16’ ceilings, open great room with beautiful indoor/outdoor kitchen, custom dining seating for 8, and loft hammock. Hosts live next door and are easily available if needed! Everything is on the 1st floor except for the 3rd bedroom.

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.

Quiet Farmhouse Retreat
Looking for a tranquil farmhouse destination? Get away at Wadsworth Acres- a Scottish Highland hobby farm! This modern farmhouse is the perfect space to relax. Complete with a very spacious primary suite, large eat-in kitchen, exercise room, and space to play outside- you’ll never have to leave! Enjoy your morning coffee with breathtaking farm sunrises on the patio and evenings in the hammocks.Peaceful escape just 5 minutes from the highway, 10 from historical downtown, 35 from the Dunes!

Enchanted Garden Treehouse (Amenity*)
Summer's here, the treehouse air conditioned and cozy, and the hot tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

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.

Miller Mermaid Suite-100 yds from the beach!
100 yds from the beach, the cozy MERMAID BASEMENT SUITE is best for a young family or 2-3 adult friends. This 400 sq ft 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!
Popular amenities for Gary family-friendly rentals
Family-friendly home rentals with a hot tub

Couples Getaway, Jacuzzi, Sauna, Pool is Open

Private Cottage in Gated Nudist Community

The Studio at the Dunes

UncleLarrysLakePlace HotTubKayaksPingPong

Pool, Hot tub, Kayaks, Waterfront, SW Michigan

Singing Sands Trl | Hot Tub Retreat | Dogs OK

The Lake Escape -Cozy Lakefront Cottage Valparaiso

Pool Opens May 25! | Hot Tub • Walk to Lake
Family- and pet-friendly home rentals

Rainbows End 🌈 Plensa

South Shore Studio Apartment {National Park}

MiniGolfHouse-Chicago Close Beach & Indoor Fun!

Luxury Cabin Getaway •2 min to Beach• 1hr Chicago

2 bedroom 2 bathroom home away from the noise.

Pet friendly, lakefront home directly on Pine Lake

Downtown Chesterton "Grant-Cottage"

cozy new buffalo cabin, hot tub, 14m walk to beach
Family-friendly home rentals with a pool

Comfy 3BR 2BA, Liv+Fam Rm, Prime, 3-Car Parking

"Serenity of Evanston" 2 BDR/2Bath Modern Suite

Pool & Beach Haven-private pool, steps to beach!

Cabin with POOL in family resort!

Beautiful home in Beachwalk/Notre Dame weekends

5 Bedroom Luxury Home In Heart of Beachwalk Resort

50 Private Acres w/ Trails & Pool: Cozy Cabin

Cheerful 4 bedroom 2 king size beds, 2 queen size
When is the best time to visit Gary?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $249 SGD | $217 SGD | $226 SGD | $227 SGD | $272 SGD | $327 SGD | $336 SGD | $317 SGD | $263 SGD | $256 SGD | $256 SGD | $242 SGD |
| 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 130 holiday rentals in Gary

Nightly prices starting at
Gary holiday rentals start at $77 SGD per night before taxes and fees

Verified guest reviews
Over 5,440 verified reviews to help you choose

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
80 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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- Family-friendly rentals Lake County
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- Family-friendly rentals United States
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Soldier Field
- 875 North Michigan Avenue
- Warren Dunes State Park
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Union Park
- Lincoln Park Zoo
- Chicago River Walk
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Washington Park Zoo
- Indiana Dunes State Park
- Oak Street Beach
- Museum of Science and Industry
- Willis Tower
- Riviera Theatre





