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. 😁

Lakeside Dome Retreat w Hot Tub Near Indiana Dunes

Welcome to Valparaiso Lakeside Retreat a private getaway on Long Lake featuring a one-of-a-kind outdoor geodesic dome (11 feet), hot tub, fire pit, & kayaks. 20 minutes from Indiana Dunes National Park. Perfect for couples, remote workers & nature lovers seeking a tranquil escape. Enjoy stunning Long Lake views from your private backyard & dome. Long Lake public beach access is just around the corner. Perfect for kayaking, swimming, or a morning walk to the water. Book this unique stay today!

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! 🌞🏖️🌳

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.

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.

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!

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

South Shore RV National Park.

Warning this is not a hook up or a party spot ! ..This is older but,very clean & well kept camper, located on five acres. 420 Friendly...It's a quarter mile from the National Park and under 2 mi to the Lake Michigan Waterfront of Kimel Beach. On a beautifully stocked pond with catfish,bluegill,bass, & croppie. Plenty of wildlife. If you book on a Sunday? I host Open Mic in my barn. 2 PM. Open to the public and musicians welcome. Normally, there is music playing around the property.

"myhathouse" detached studio downtown Chesterton

Vaulted skylights allow natural light. Ksize bed. Couch opens into a full size bed. (DEEP cleaned to AirBnb COVID-19 disinfectant standards) Fully stocked kitchen, sm. bathroom w/ shower. Parking ft. of house, 1.5 M from Lake Michigan Shoreline, 2 blocks to 15th St. entry to Prairie-Dune Trail. European Market (May -Oct) each Saturday downtown. Fall season drives along U.S. HW 12 & 20 for foliage Winter day hikes, x-county skis trail, shopping trips to the Michigan City Outlet mall.

Jefferson

Nestled in the desirable Chesterton area, just a short distance from downtown, this charming 4-bedroom, 2-bathroom home offers the perfect combination of convenience and comfort. The main floor features 2 cozy bedrooms, an office space, and a full bathroom, making it ideal for a variety of living arrangements. The property also includes a spacious 2-car garage.Enjoy the convenience of being close to downtown Chesterton, with easy access to shops, restaurants, and parks.

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.