Pet-friendly holiday rentals in Gary

The kitchen features contemporary blue cabinetry paired with light wood accents. A large stainless steel refrigerator stands beside a gas stove. A white farmhouse sink is centered beneath a window, while a modern light fixture illuminates the space.

4.88 out of 5 average rating, 129 reviews

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

Outdoor spacesWalkabilityBeach

The open living area showcases a cozy seating arrangement with a brown sofa and modern chairs. A ceiling fan hangs above, and the space is illuminated by warm light from the nearby kitchen. A large TV is mounted on the wall opposite the seating area.

4.96 out of 5 average rating, 130 reviews

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. 😁

PetsWalkabilityKitchen

4.96 out of 5 average rating, 108 reviews

New sauna, steps from beach and 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.

Outdoor spacesPetsLaundry

4.96 out of 5 average rating, 254 reviews

The cabin's exterior is framed by colorful autumn foliage, with vibrant red leaves and dappled sunlight filtering through the surrounding trees. Stone steps lead to the entrance, enhancing the rustic charm of the well-maintained landscape.

Cabin in Michiana

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

Luxury meets nature: forest cabin steps from the beach, 1 hour from Chicago. Book your escape to our designer log cabin on Lake Michigan just steps from the beach and nestled in a peaceful forest, it’s the perfect retreat. Built in 1932, our charming cabin sleeps 8 in 4 bedrooms. Enjoy 2 living areas, a stone fireplace, fire pit, games, puzzles & books. Featured in Country Living and the NYT, it’s perfect for families, friends, or retreats. Book now and create lasting memories in Michiana.

WalkabilityPetsCleanliness

A single-story cottage with light gray siding is accompanied by a neatly landscaped front yard. A welcoming front porch is framed by white railings. A paved driveway leads to a garage on the right, while surrounding trees provide ample shade.

4.92 out of 5 average rating, 114 reviews

Lake Trail Cottage

Located just 1 mile from Lake Michigan. Lake Trail Cottage is the closest home in Pines and just minutes from Beverly Shores beaches! The cottage has two bedrooms one bath. With basement Rec room. Home sleeps 7. The primary bedroom features a Queen bed, 42in Smart TV. The second room has a full size bed. Pullout couch/ living room. Calumet Trail and South Shore Train (Chicago)is located directly behind home. South Shore train to Chicago is 1 mile from house. Bikes & beach supplies included.

WalkabilityPetsFamily

The modern tree-house structure is illuminated by warm lighting, showcasing large windows that reflect the surrounding trees. A screened porch with seating is visible, extending from the main building, creating a connection with nature.

4.95 out of 5 average rating, 333 reviews

TRYON FARM MID-MODERN SPA IN THE WOODS

Come, enjoy our Tryon Farm modern spa. A Sustainable luxurious open concept tree-house in the woods. Minutes from the beach with an outdoor sauna, Hottub, shower, and Mr. Steam. Perfect for two or a family/group adventure. A true destination with Yoga studio, Mirror by LuLu lemon and wellness elements. The house is a perfect balance of art and nature and luxury and spiritual. Treat yourself to a farm to table, hand made, locally sourced chef services for an extra special experience.

Outdoor spacesWalkabilityPool

5.0 out of 5 average rating, 153 reviews

A bright living area features a comfortable gray sofa adorned with decorative pillows, paired with a light brown armchair. Large windows provide views of lush greenery, while a striped rug anchors the space. A coffee table with a bowl sits at the center, enhancing the cozy atmosphere.

Home in Sawyer

The treehouse at Warren Dunes

Looking for the perfect Harbor Country getaway? We've got you covered! Just 90 miles from Chicago and adjacent to Warren Dunes State Park, this beautifully remodeled home hidden in the trees is the perfect escape. With accommodations up to 6 on four levels of living space, you'll enjoy an indoor/outdoor living experience like no other. Conveniently just 200 yards from the beach with walking path access at the end of the street and easy access to all the activities this area has to offer.

PetsWalkabilityAmenities

4.82 out of 5 average rating, 212 reviews

The exterior of Miller Cottage features a striking red facade with modern midcentury architecture. A stone chimney adds character to the entrance, partially shaded by lush greenery. A manicured lawn and a paved driveway enhance the inviting atmosphere of the home.

Cottage in Miller

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.

WalkabilityPetsParks

4.9 out of 5 average rating, 152 reviews

The front of a charming house is presented, featuring a welcoming porch with decorative railings. Lush greenery surrounds the entrance, and a bright yellow door enhances the facade. The roof is sloped, and large windows allow for ample natural light.

Home in Chesterton

Downtown Chesterton "Grant-Cottage"

Charming downtown house with a front porch, back deck & covered patio. Beautifully decorated with a small backyard. Minutes from the Indiana Dunes National Park and beaches. Near the South Shore Commuter train if you wish to visit Chicago without the drive and expense of parking. We are across from an active train track so if you like trains you can watch them from the front porch. Walk to restaurants, wineries and beer pubs. European market on Saturdays from May to end of October.

Outdoor spacesWalkabilityHospitality

4.8 out of 5 average rating, 105 reviews

A spacious living area features a large flat-screen TV mounted on the wall. Comfortable gray sofas with vibrant red accent pillows are arranged around a marble coffee table. Natural light brightens the space, which includes a glimpse of the dining area and staircase in the background.

Home in Chesterton

Roomy Retreat–Family&Friends|2 King Beds|Game Room

🏡Welcome to Your No-Train-Noise, Pet-Friendly Stay in Chesterton! Property Highlights: 🛏️4 Bedrooms | 🛁 3 Bathrooms | 🛋️ 3 Living Areas with Smart TVs 🍸Bar in the Basement 🍽️Outdoor Dining 🚶‍♂️Minutes from historic Chesterton Downtown 🌲 4 miles to Indiana Dunes National Park & the beach 🍳 Fully Stocked Kitchen 👶 High Chair & Crib included Get ready for endless adventures along the sandy shores and tree-lined trails of Indiana Dunes. Enjoy every moment of your stay

PetsOutdoor spacesTV

4.95 out of 5 average rating, 201 reviews

Home in Whiting

MiniGolfHouse-Chicago Close Beach & Indoor Fun!

*REQUIRED* ✅ Will you bring a pet? ✅ Have you read and agree to all rules? 🌆 30min drive to downtown Chicago ⭐️ Near Horseshoe Casino, Lake Michigan, Whihala Beach, Whoa Zone ⛳️ Heated basement with mini golf, arcade games and big TV ⭐️ Close To: Wolf Lake, Indiana Dunes, HardRock 🏠 cots, air mattress, futon sofa 🍼 pack & play, high chair avail ❤️ Guests love: -short drive into Chicago -comfortable beds -indoor mini golf -nearby shops & food -heated bidet toilets

WalkabilityPetsQuiet

4.96 out of 5 average rating, 459 reviews

An open studio space features a black leather sofa alongside a wooden coffee table on a textured rug. Colorful wall art adds vibrancy, with a light fixture illuminating the area. A chair with a unique design offers additional seating, enhancing the contemporary aesthetic.

Guest suite in Miller

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!

WalkabilityPetsAmenities

Popular amenities for Gary pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.84 out of 5 average rating, 121 reviews

The exterior of the house is shown with a deck that features white railings and steps leading down to a grassy area. Lush greenery surrounds the home, providing a secluded atmosphere. A large window on the right allows natural light into the interior.

Home in Chesterton

Dune National Park - Nature Lover's Retreat

Outdoor spacesPetsBeach

A modern kitchen space is presented, featuring a large dining table accompanied by black chairs. White cabinetry and light countertops provide a bright appearance, while decorative elements like a shelving unit and fixtures enhance the welcoming aesthetic. Natural light is allowed in through a nearby window.

4.86 out of 5 average rating, 149 reviews

New Dunes Escape

Outdoor spacesPetsHospitality

A dining area showcases a long, dark wooden table paired with a bench and a stylish chair. An industrial-style light fixture hangs above, illuminating the space. A decorative plant and artwork add warmth to the setting, accented by textured wall coverings and natural light.

4.93 out of 5 average rating, 419 reviews

Lake Michigan Farm Retreat w/ Yoga Shed & Hot Tub

PetsOutdoor spacesCheckout

A large hot tub is positioned in a well-maintained backyard, surrounded by lush trees. Nearby, a sandy firepit area is complemented by seated benches, while a swing set is visible towards the rear, all enclosed by a tall wooden fence.

4.89 out of 5 average rating, 140 reviews

Singing Sands Trl | Hot Tub Retreat | Dogs OK

Outdoor spacesPetsNearby

A sandy pathway winds through tall grasses, leading to Lake Michigan. The tranquil water reflects the soft hues of the sky, with clouds adding texture to the serene scene. The beach's inviting atmosphere creates a perfect setting for relaxation and exploration.

4.89 out of 5 average rating, 137 reviews

Blue Birdhouse - Indiana Dunes

PetsOutdoor spacesHiking

4.91 out of 5 average rating, 136 reviews

A spacious living room features large windows allowing natural light. A modular sectional sofa is arranged invitingly in front of a sleek fireplace. A modern coffee table sits atop an area rug with geometric patterns, and an expansive wall-mounted TV awaits entertainment.

Home in Chicago

Gorgeous 5 BR Gem Sleeps 18 with Tons of Games!

HospitalityWi-FiBathroom

4.9 out of 5 average rating, 156 reviews

Home in Valparaiso

2 bedroom 2 bathroom home away from the noise.

PetsOutdoor spacesParking

4.94 out of 5 average rating, 122 reviews

A ranch-style home is showcased with a welcoming facade of brick and siding. Large windows provide ample natural light, while a well-maintained garden features a variety of colorful flowers. A manicured lawn and sidewalk lead to the entryway, enhancing the inviting exterior.

Home in Worth

Worth It! 3 bedroom ranch home

WalkabilityPetsParks

Pet-friendly home rentals with a pool

4.96 out of 5 average rating, 104 reviews

An inviting pool area is surrounded by a wooden deck, featuring comfortable seating arrangements and a large red umbrella providing shade. Lush greenery stands tall in the background, complementing the serene atmosphere of the private fenced space.

Home in Lakeside

Lakeside with heated pool & pvt beach access!

PetsWalkabilityCondition

4.91 out of 5 average rating, 134 reviews

A blue cottage is surrounded by tall trees, featuring large windows that provide ample natural light. A spacious deck extends around the front, with steps leading to the entrance. A chimney is visible on the side, adding to the cottage's charm.

Cottage in Sawyer

The Cranny at Michaels Nook

PetsOutdoor spacesBathroom

4.84 out of 5 average rating, 104 reviews

A private pool is surrounded by a spacious patio, featuring lounge chairs for relaxation. The area is enclosed by a wooden fence, offering privacy, and a storage shed is visible in the background, complemented by a lush green landscape.

Home in New Buffalo

Secluded Pool Playhouse: Hot Tub, Game Room, Fire

Outdoor spacesPetsHospitality

4.96 out of 5 average rating, 113 reviews

Home in New Buffalo

NB Getaway with HotTub, Pool & Priv Screening Room

Outdoor spacesWalkabilityNearby

4.97 out of 5 average rating, 250 reviews

A bright living room features high ceilings with a chandelier above a central wooden coffee table. Comfortable dark gray sofas are positioned around the table, complemented by decorative cushions. Large windows allow natural light to fill the space, and a stone fireplace adds a cozy focal point.

Cottage in Union Pier

Designer Cottage Relax Pool Beach & Spa—Windjammer

Outdoor spacesPetsHospitality

4.85 out of 5 average rating, 112 reviews

A spacious outdoor area features a hot tub beside a well-maintained pool. Lounge chairs are positioned around the pool, with a covered seating area in the back. A wooden pergola provides shade, while string lights add a touch of ambiance.

Home in Three Oaks

Play @ The Hideaway - hot tub, sauna, gymnasium

Outdoor spacesLayoutHospitality

4.98 out of 5 average rating, 146 reviews

A natural pathway leads to a charming safari yurt, adorned with greenery and decorative elements. A wooden archway introduces the entrance, while a nearby barrel sauna complements the serene outdoor setting, surrounded by trees and mulch landscaping.

Yurt in Flossmoor

Glamping Yurts, RV RecRoom, Pool&Hotub 16 guest

WalkabilityOutdoor spacesLong stay

4.76 out of 5 average rating, 233 reviews

A modern living area features a dark gray sofa, complemented by decorative pillows and a coffee table. Large windows provide ample natural light and city views, while plants add a touch of greenery. The space is designed with clean lines and a neutral palette.

Apartment in The Loop

Beautiful Corner 2 Bedroom in the Loop | Roof Deck

PetsOutdoor spacesView

Private, pet-friendly home rentals

Apartment in Downtown Chicago

Luxury Loft Collection 01 - Terrace - River North

WalkabilityOutdoor spacesHeating

4.9 out of 5 average rating, 126 reviews

Guesthouse in New Buffalo

A cozy living area features a mix of modern and rustic decor, highlighted by large glass doors that open to scenic views. Warm wooden paneling surrounds comfortable leather seating and a coffee table, while large windows invite natural light into the space.

Rainbows End 🌈 Bourgeois

PetsOutdoor spacesView

4.99 out of 5 average rating, 444 reviews

A serene patio area is surrounded by mature trees, with sunlight filtering through the leaves. Four black wooden chairs are arranged around a central fire pit. A small table sits on the concrete surface, with glasses and a bottle placed on it, creating a peaceful outdoor retreat.

4.97 out of 5 average rating, 37 reviews

DuneHouse Miller Beach - 1.5 blocks to beach

WalkabilityPetsComfort

A single-story home is surrounded by a white picket fence, with a well-maintained lawn and a variety of greenery. Bright blue siding contrasts with the natural surroundings, while a shaded porch provides a welcoming entry. A street lined with trees enhances the peaceful atmosphere.

4.98 out of 5 average rating, 48 reviews

Mid-Century Beach Oasis

Outdoor spacesWalkabilityCheckout

A serene beach scene is presented, featuring gentle waves lapping at a sandy shore under a clear blue sky. The unobstructed horizon highlights the tranquil water, inviting relaxation and enjoyment of the natural surroundings.

4.88 out of 5 average rating, 42 reviews

Dunes Haven

Outdoor spacesWalkabilityBiking

5.0 out of 5 average rating, 46 reviews

The Porter Nook | Walk to Trails + Dining

Outdoor spacesWalkabilityCondition

A modern living area showcases large windows that flood the space with natural light, surrounded by lush greenery. A sleek couch is positioned near a mantel with a mounted television above, while a coffee table offers a welcoming touch.

4.88 out of 5 average rating, 85 reviews

Private Wooded Acre, Soaring Windows in Nat’l Park

WalkabilityPetsNearby