Vacation rentals in Westchester

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, 122 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. 😁

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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, 131 reviews

Blue Birdhouse - Indiana Dunes

Welcome to The Birdhouse - Your Perfect Getaway! 🐦🌿 Nestled near the Indiana Dunes National Lakeshore, our cozy 2-bedroom, 1-bathroom home is perfect for families, couples, and nature lovers. Enjoy a pet-friendly, fully fenced yard, free parking for 2 vehicles, a fully equipped kitchen, laundry, and a BBQ grill with patio for outdoor dining. Minutes from Lake Michigan beaches, hiking trails, and local dining, it’s the ideal spot for beachgoers and adventurers. Book your stay today! 🌞🏖️🌳

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Guest favorite

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.

4.83 out of 5 average rating, 417 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. ✌️

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Guest favorite

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.

4.91 out of 5 average rating, 148 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.

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4.98 out of 5 average rating, 118 reviews

The exterior of a charming guesthouse is depicted, featuring a light blue facade with gabled roof and a door leading to a small outdoor seating area. The space includes a garage door and two lantern-style lights flanking the door.

Bungalow in Chesterton

Charming Country Cottage

Take it easy at this unique and tranquil getaway. "Barn" turned into a guesthouse on 4 acres of owners residential property where you will enjoy peace and quiet, take a walk on trails through 2 acres of woods, take a short drive to Lake Michigan or the Indiana Dunes National Park or just sit inside at an electric fireplace. We are located 5.9 miles (approximately 12 minutes) from the Dunes National Park. Second STR available on same property that also sleeps 5 people if you have a group!

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5.0 out of 5 average rating, 16 reviews

Camper/RV in Porter

The Dunes Escape/ Dunes National Lakeshore

🌟 Family-Friendly Glamping Camper | Outdoor Tub, Shower, Fire Pit + Play Area | 3.9 Miles from Lake Michigan Dunes ( 9 minutes) Unplug and unwind at our cozy, private RV camper — a one-of-a-kind glamping experience Sleeps 2–3 comfortably – ideal for couples, solo travelers, or small families Outdoor shower + clawfoot tub 🔥 Fire pit + grill area Children’s play area 🌳 Quiet, wooded setting – to relax in the hammock 📍 Close to hiking, beaches, and charming local dining spots,market

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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.

4.87 out of 5 average rating, 139 reviews

New Dunes Escape

Your family will be close to everything when you stay at this centrally-located place. Located just 3 minutes from the entrance of the Indiana Dunes National Park, 45 minutes from Chicago, 45 minutes from New Buffalo, MI , and 3 minutes from the Dunes Park South Shore Station, this completely remodeled home is the perfect place for a get-away. With free wifi, firepit with firewood, and a 4-seasons room, this house is the perfect place to relax after a great day swimming or hiking.

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4.79 out of 5 average rating, 19 reviews

Porter Beach home minutes to Dune State park

Forget your worries in this spacious and serene space. Modern and cozy 3 bedroom , 2 bath home in the town of Porter surrounded by Indiana Dunes National Lakeshore. Minutes from from Lake Michigan Beaches, bike and hiking trails, breweries, casinos, wineries, Lighthouse mall and Southshore train line to Chicago or Southbend. Close to downtown Chesterton which offers a European Market from May to October. Many antique stores and unique shops and restaurants.

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A spacious dining area features a large wooden table surrounded by vibrant blue chairs. Large windows showcase views of the lush wooded surroundings, allowing natural light to illuminate the room. A unique light fixture adds a modern touch to the retro decor.

4.98 out of 5 average rating, 95 reviews

Retro 1950s Estate w Hot Tub Near Indiana Dunes

Welcome to the Retro Bird Retreat a 1950s architect-designed estate, sleeping 12 guests on 3 private wooded acres, just 10 minutes from Indiana Dunes National Park. NO cleaning fees. Hot tub greenhouse, speakeasy basement bar, games garage, 5 themed rooms, 2 fire pits, and more entertainment than you can handle in a weekend. Built for large Multi-generational families, group, work retreats & anyone who wants to disappear into a retro world. Book Today!

LocationFamilyBeach

5.0 out of 5 average rating, 33 reviews

The Porter Nook | Walk to Trails + Dining

Unwind after the dunes with a glass of wine on the patio under string lights. This thoughtfully designed 2-bedroom retreat is perfect for couples and small groups looking to relax, recharge, and enjoy a slower pace. Comfortably sleeping up to four guests, the home features a fully equipped kitchen, inviting living space, and a prime location just minutes from beaches, restaurants, and local shops ideal for a weekend escape or an easy getaway from Chicago.

LocationFamilyOutdoor spaces

A single-story home with a sloped roof is set on a well-maintained lawn. The front porch features steps leading to a central door, flanked by windows. Lush green grass surrounds the house, with trees and open space visible in the background.

4.8 out of 5 average rating, 20 reviews

Close to the Dunes State Park!

Indiana Dunes State Park with its beautiful beach is only an 8 mile drive. Other beaches close by are Porter beach, Kemil and Portage Riverwalk. Jump on the train and head to Chicago for the day, or its only an hour drive. There are miles of trails near by for walking or biking. Downtown Chesterton has its weekly European Market on Saturday morning, a great place to but fresh veggies and pastries. There are numerous great restaurants in the area.

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