Holiday rentals in Chesterton

Dunes Home – Walk to Town, Fenced Yard, Near Dunes

Welcome to our historically pet-friendly home, featuring chic and updated interior furnishings. 3 bedrooms | 2 bathrooms | 2 living rooms with Smart TVs and a porch Prime Location: Just a few minutes' walk to historic Chesterton downtown Proximity: 4 miles to Indiana Dunes National Park and the beach Fully Equipped Kitchen Family-Friendly: High chair and crib available Get ready for endless adventures at the sandy shores and tree-lined trails of Indiana Dunes National Park! Other things to note

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. 😁

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.

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!

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.

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.

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.

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.

Flint Lake Cottage.

This is a rustic cottage with old world charm. There are 2 fireplaces,. The home sits on a hill overlooking the channel that leads to Flint Lake. - Pet free -May not be appropriate for people with mobility issues. - Earth friendly cleaning products - Private beach & park access - Easy access to city center & university - One hour from downtown Chicago - National Lakeshore and Dunes State Park nearby - Wood fireplaces (winter only!)

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).

Country Retreat

Relax at this peaceful home with a lot of local activities and sights to see and do! You will enjoy all of the creature comforts of home away from home. Close to Indiana Dunes National Park and Lake Michigan. Dunes Bird Festival coming May 15-18th, 2025! Book now. Full kitchen, shampoo, conditioner, body soap, basic washing supplies, Keurig, coffee, tea, hot chocolate, spices and lots of other things available for your convenience.