Vacation rentals in Chesterton

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. 😁

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! 🌞🏖️🌳

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. ✌️

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.

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!

The Little House at Tryon Farm

The little house is located within a 170-acre modern farm community filled with open meadows, woods and dunes. Minutes to beach, 1 hour to Chicago. Relax and enjoy the property or head out to explore the lakeshore, wineries, and great area restaurants! Two bedrooms, 1.5 baths, a fully appointed kitchen, living area w/fireplace, and a large screened in porch. Large windows flood the house with natural light and will make you feel like you're living in the treetops. A perfect getaway!

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.

Bro’s Place 6 mile drive to Indiana Dune’s

Welcome if you like country life Bro’s place is the place to be...watching the sheep, chickens and wildlife on you back deck making dinner on the grill with a full kitchen. Pick your own veggies outside the back door when in season. You will find a welcome basket with snacks, wine and homemade soap in bathroom fresh eggs from our chickens when available if your planning to visit our Beautiful Indiana Dunes you’ll find everything you need..chairs, towels, cooler Queen size sofa sleeper

Chesterton Charmer: Lower Unit

Just a 15-minute drive from the Indiana Dunes/Lake Michigan, & a two-minute walk to downtown Chesterton! Guests will love this lower 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 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!

The House Near The Lakes

Relax with the beautiful nature surroundings at this peaceful place to stay. Enjoy your visit to NWI at this beautiful cottage with vaulted ceilings. It is the perfect space to relax and unwind. When requested for an additional fee, children items are available (hatch sound machine, pack and play, , bed bumpers, baby bath support and or high chair. This location is close the to Indiana National Lakeshore(17 minutes), downtown Valparaiso(7 minutes), and right next to Long Lake.

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.

Cozy Guest House with Pool near National Park

Tucked into the wood's edge on 2 beautiful acres, you will find this charming get-away. You have a private keyless entry, parking enough for two cars and the entire guest house to yourself. Whether you are visiting family and friends, or just enjoying all that "Duneland" has to offer, we are conveniently located near everything. Please note: Our property is not suitable for children or toddlers. However, infants under 12 mos old are always welcome.