Pet-friendly holiday rentals in Chesterton

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Top-rated pet-friendly home rentals in Chesterton

Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

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Luxe
An open entryway reveals a modern kitchen with a large island and four high stools. Natural light flows through multiple windows, highlighting the sleek countertops and rich cabinetry. A tasteful artwork adorns the wall beside the entrance, adding character to the space.
Home in Lakeside
4.93 out of 5 average rating, 113 reviews

Landmark Home 1 Blk from Lk MI w/Game Rm + EV Chgr

Sumptuous 4 BR/2.5 BA vacation home, just 1 block from Lake Michigan. Fully refurbished with reclaimed flooring, antique beams, custom doors, and fixtures. High-end kitchen, dining, and living areas with French windows. Living room features a stone fireplace, stylish couches, and a wide-screen TV. Three ground-floor bedrooms and baths with a second-floor bunk bed loft. Detached garage is a posh game room with high-end tables and a big TV. Covered patio, 4-seat dining, and bluestone courtyard. This property has been selected for inclusion in The 100 Collection, a global designation awarded to only the top professionally managed vacation rentals based on consistent quality and service. Classy, awe-inspiring, and sumptuous, this 1928 4 BR/2.5 BA vacation home, located just a block from Lake Michigan in “Harbor Country,” was once a local retail gathering place. Recently refurbished into a stunning residential home, it includes gorgeous reclaimed flooring from antique beams, custom doors, light fixtures, and hardware, as well as top-of-the-line plumbing fixtures. The kitchen-dining room-living room area—a massive, superbly well-lit space—features entire walls of French windows, original glass-block, and a wide array of seating options for meals: 4 chic stools at the white marble island, 4 leather seats around a circular marble coffee table, and a 10-seat reclaimed wood dining table. The beautifully lit living room has a classic stone fireplace at its center, stylish (yet ultra-comfortable) couches and chairs, and a wide-screen TV. In addition to the three bedrooms and bathrooms on the ground floor, there’s a second-floor sleeping loft, perfect for kids with cute bunk beds and a real (mini) teepee. All bedrooms feature top-quality bedding and linens, ensuring a sound sleep and sweet dreams for you and your guests. Black Door Bungalow can sleep up to 10. MAIN FLOOR Primary Bedroom: 1 King bed Bedroom 2: 1 Queen bed Bedroom 3: 1 Queen bed UPSTAIRS FLOOR Bedroom 4: Full-over-full bunk bed that sleeps 4 Another “extra” is the detached garage, which has been turned into a posh game room, with high-end shuffleboard and foosball tables, a big-screen TV, and a sound system. The exterior—featuring a spacious covered patio with cozy rattan couch, chairs, and a 4-seat dining table, leading to a bluestone courtyard—has been extensively landscaped with lush plantings, trees, and professional lighting. The home also includes a high-end kitchen, EV charger, and laundry appliances. In addition to being an easy walk from a majestic, crystal-sand Lake Michigan beach—and a super-short drive to popular beaches like Pier Street Beach and Cherry Beach—you and your guests can also enjoy the many activities afforded by being near Warren Woods State Park, which offers all sorts of woodland hiking and biking trails. The region’s largest recreational harbor provides countless water-related excursions and rentals, from fishing trips to boat, kayak, jet-ski, and paddleboard rentals, as well as day and evening cruises. There’s also the Acorn Theater, a local treasure for live performances by nationally recognized music artists, and a number of nearby breweries, wineries, brew pubs, and even an award-winning distillery for you to check out. Of course, you and your guests can also enjoy sampling to your heart's content the many popular restaurants, cafes, art galleries, boutiques, and antique shops just a hop, skip, and a jump away in Union Pier and downtown New Buffalo.

Top Guest favourite
A spacious living area showcases a light-colored sectional sofa adorned with plush pillows. Large windows allow natural light to fill the room, revealing wooden flooring and eye-catching artwork on the walls. A dining table is visible in the background, complemented by a minimalist plant.
Home in Michigan City
4.98 out of 5 average rating, 314 reviews

House of Zen: Peaceful Modern Cabin on Tryon Farm

The House of Zen is an architect designed home situated in the woods, part of a sustainable farm community on 170 acres. Only an hour drive from Chicago, and close to Indiana Dunes National Park, it is the ultimate escape. The perfect getaway for couples, creatives and nature lovers who want some peace, quiet and space. Explore the farm trails & enjoy the wildlife and soothing sounds. Note: We have a 3 night minimum stay during summer, but open up 2 night stays 1-2 weeks before if possible.

Top Guest favourite
A multi-level house is set on a grassy area, featuring a stairway leading to a deck adorned with flower pots. Vibrant red canopies provide shade, and bicycles are stationed nearby, creating an inviting environment. The exterior showcases a mix of wooden and painted surfaces.
Home in Chesterton
4.83 out of 5 average rating, 354 reviews

South Shore Studio Apartment {National Park}

I have to warn you definitely not a hook up spot or party house!!! typically rise with rooster on this 5 acre country setting with a small fishing pond. 420 friendly .. Quiet hours are 11 -8 generally some music playing, musicians are welcome !! if you happen to book on a Sunday i host an Open Mic in my Barn every Sunday ..... pretty relaxed. Upon arriving, turn into the driveway, and then right into the yard. Apartment is upstairs, the door is open with the keys inside. ✌️

Guest favourite
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.
Home in Michigan City
4.93 out of 5 average rating, 371 reviews

Lake Michigan Farm Retreat w/ Yoga Shed & Hot Tub

Luxury farm retreat on 7 wooded acres with hot tub, yoga shed, fire pit, fully fenced yard & pond! This home is a five minute drive to the beach, blueberry picking, Burn 'Em Brewing, Shady Creek Winery, next to Tryon Farm or 10 minute drive to downtown, the casino, and the outlet mall, but our guess is that you won't want to leave the property! This designer home has super comfy beds, 800 thread count sheets, a gourmet coffee bar, screened in porch, and even a tiny library in the laundry room

Guest favourite
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
4.9 out of 5 average rating, 136 reviews

Downtown Chesterton "Grant-Cottage"

Charming downtown house with a front porch, back deck & covered patio. Beautifully decorated with a small fenced in 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.

Top Guest favourite
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.
Home in Michigan City
4.95 out of 5 average rating, 300 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.

Guest favourite
A hot tub is positioned in a grassy area, surrounded by a white fence. It features a raised, circular design with a protective cover partially open. A set of steps leads up to the tub, positioned adjacent to a bright blue Adirondack chair.
Home in Michigan City
4.93 out of 5 average rating, 108 reviews

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

You've found it – the perfect fun spot for your family beach vacation! Just a road trip away and less than half a mile from the beautiful beaches. Guests rave about the supplied beach accessories! You'll love the quiet, peaceful neighborhood close to the Michigan City's Washington Park beach, downtown, zoo, restaurants, outlet-mall shopping, and more. Grill outside; gather the family around the firepit , roast marshmallows, Smores Board provided. Play games like cornhole and board games.

Top Guest favourite
A screened three-season porch features a comfortable hammock and two chairs with cushions. A small table sits between the chairs, and natural light filters through the surrounding windows, allowing views of the greenery outside.
Place to stay in Michigan City
4.98 out of 5 average rating, 132 reviews

Tryon Farm "Bees Place" 100 acres of nature/trails

Charming 2 bed 2 bath, unique modern barn house. Relaxing screened three-season porch. In warm weather hammock is up and ready for you! Private courtyard with Swing. Chilly weather come warm up next to the wood stove. Large overhead windows offer natural light & night sky views. Great views throughout. Leashed pet welcome. Tryon Farm community offers over 100 acres of wooded walking trails, a fishing pond & tree swing. One mile to Shady Creek Winery, close to beaches, and brewery’s.

Guest favourite
The front exterior of a single-story home is presented, featuring a light grey facade with white shutters. A welcoming porch is visible, adorned with vibrant plants. The property is surrounded by lush greenery, with trees providing natural shade in the background.
Home in Michigan City
4.91 out of 5 average rating, 235 reviews

Casinos, Shopping, Pets, and Parking a Plenty!

1 mile from BLUE CHIP CASINO - with its new SPORTS BOOK and is where the away team stays for NOTRE DAME FOOTBALL, 2 miles from the outlet mall, 7 blocks to the beach, and plenty of parking! 3 bedrooms (4 beds) and 1 bathroom. This is a great place regardless of the season and though in the city; it backs up to woods with lovely walking trails. The home also has hi speed internet/WiFi and HD cable television. Simple, practical home in a safe neighborhood - and it’s a bargain!

Guest favourite
A bright living room is showcased, featuring a comfortable seating arrangement with a sofa and armchair. Natural light enters through large windows, illuminating the wood-tone flooring. A ceiling fan and framed wall art add to the welcoming ambiance.
Home in Porter
4.92 out of 5 average rating, 102 reviews

The Dune Den! Huge Yard/Firepit/Near Town+Dunes

Right in-between The Dunes National Park and downtown Chesterton, you will be close to everything when you stay at this centrally-located home. Things to look forward to: Less than 10 minutes to the Dunes and beaches or head 3 minutes the other way to downtown for food, drinks and plenty of small town fun. This charismatic home greets you with all new furniture, front porch, HUGE fenced yard, and local decor. You will fall in love with this family town so bring the kids!

Top Guest favourite
A cozy bedroom features a spacious bed adorned with layered textiles and decorative pillows. Large windows provide views of the outdoors, while natural light is enhanced by wooden ceiling beams. A small dining area with chairs and a table is positioned nearby.
Guesthouse in New Buffalo
4.97 out of 5 average rating, 644 reviews

Rainbows End 🌈 Plensa

Escape to a tranquil countryside cottage on a 20-acre farm. Enjoy breathtaking sunrises from the picture window, relax in lounge chairs, and gather around the fire pit and grill or take a trail walk down to the south branch of the Galien River. Just 10 minutes from Lake Michigan, and within 5 miles of a casino and a golf course, it's the perfect retreat for nature lovers and entertainment seekers. Book now and experience rural bliss with nearby attractions!

Top Guest favourite
A welcoming living space features soft lighting from a table lamp beside a wooden accent table. The walls are adorned with decorative panels and wall art, while a circular wreath adds a natural touch. A ceiling fan provides airflow, enhancing comfort in the room.
Home in Chesterton
4.98 out of 5 average rating, 175 reviews

Hotel Whiskey

Fully remodeled and tastefully decorated two bedroom home for short or long term stays. Office space for work travelers. Pet friendly with secure fenced in back yard. Walking distance from downtown with quaint shops, wine bar, craft beer bar, restaurants and bike trails. Whether you're in town for work, visiting family or just looking for a weekend getaway, this house and location are perfect for short or long term stays.

Popular amenities for Chesterton pet-friendly home rentals

When is the best time to visit Chesterton?

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Quick stats about holiday rentals that are pet-friendly in Chesterton

  • Total holiday rentals

    Explore 20 holiday rentals in Chesterton

  • Nightly prices starting at

    Chesterton holiday rentals start at $165 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,460 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Chesterton holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Chesterton rentals

  • 4.9 Average rating

    Chesterton stays are highly rated by guests—averaging 4.9 out of 5!