Vacation rentals in Westchester

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. 😁

Value · Location · Comfort

Cozy Log Cabin Near Indiana Dunes & Lake Michigan!

Less than 10 minutes from Indiana Dunes National Park and Lake Michigan, our beautiful log cabin sits on 2 acres while still being in the heart of Portage! Our large front deck overlooks state land giving a beautiful, private view out of our large windows. Our cozy cabin has 3 bedrooms and 3.5 bathrooms with fun, thoughtful touches for your family including video game consoles, movies, books, a LOT of games, a pool/ping pong table, 2 fire pits, and more! Age limit: 25+ years old Sorry no pets

Value · Family · Hot tub

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. ✌️

Value · Family · Air conditioning

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.

Value · Location · Indoor spaces

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

Family · Location · Amenities

Chesterton Charmer: Upper Unit

Just a 15-minute drive from the Indiana Dunes/Lake Michigan, & a two-minute walk to downtown Chesterton! Guests will love this upper unit in a historic home. The prime location and fully stocked kitchen allow you to walk downtown for a meal or dine in. Watch a movie in the spacious living room, enjoy a cup of coffee on the cozy back porch, or venture out to explore nearby attractions. Whether you want to lay low & relax, or explore all the area has to offer, this rental has you covered!

Family · Location · Nearby

Charming Old Town Retreat in the Heart of Duneland

Welcome to your perfect Duneland getaway! This beautiful Craftsman-style home blends historic charm with modern comfort— just minutes from the sandy shores of Lake Michigan and the Indiana Dunes. Relax with coffee in hand, explore the European market across the street, spend the day exploring the beaches, and then come home to relax. With its classic architecture, warm finishes, and peaceful neighborhood setting, this home is ideal for families and couples looking to unwind and explore.

Location · Family · Amenities

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.

Location · Value · Comfort

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.

Family · Location · Kitchen

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.

Location · Family · Quiet

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.

Family · Location · Accuracy

Lakeside Dome Retreat w Hot Tub Near Indiana Dunes

Cozy up under the twinkling lights of your own geodesic dome, then soak away the day in the hot tub just steps away. This lakeside retreat is made for couples craving a slow, quiet escape: private dome, hot tub, fire pit, kayaks, and a 20 minute drive to Indiana Dunes National Park. Your private backyard opens onto Long Lake, with public access for kayaking and swimming a short walk away (the dock next door belongs to our neighbors).

Family · Value · Sleep quality