Places to stay in Chesterton

4.92 out of 5 average rating, 12 reviews

Apartment in Chesterton

Large Town Home close to the Dunes short-term

❤️Our cozy 1100 sq ft 2-bedroom townhome in Chesterton is ideal for extended stays. You won’t hear any train here! 🏡The home is in a family-friendly neighborhood with modern amenities, stylish decor, a dishwasher, & laundry facilities. It’s also prepared for work! With a full kitchen, living room with recliners, 82” TV, laundry, & 2 large bedrooms, it's perfect for families or friends. 🛋️ 10-minute drive to 🏖️Indiana Dunes Park & minutes from Dogwood Park. Beautiful place for you to enjoy‼️

4.99 out of 5 average rating, 494 reviews

A rustic kitchen area showcases wooden cabinetry and a spacious countertop. Stools made of logs are positioned at the bar, while an open loft area above features wooden railing and a quilt draped over the banister. Natural light filters through large windows.

Farm stay in La Porte

Cabin on Swede Hill

Welcome to "Cabin on Swede Hill". Our family has farmed this land since 1871. My great grandparents, Swan and Johanna Johnson immigrated to America in the 1860's, found this land which was similar to Sweden. They raised their family here. Approximately 65 Swedish families settled in this community, became to be know as the "Swede Hills". We just received the Hoosier Homestead Award from Indiana celebrating the Sesquicentennial Award. We invite you to come...... and experience country life.

4.88 out of 5 average rating, 547 reviews

Cottage in Valparaiso

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 a that leads to Flint lLake.The lake can be acce - Pet free - 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 - Local breweries & award winning restaurants - Biking & hiking trails near by - Wood fire places to enjoy in cold weather only

4.92 out of 5 average rating, 97 reviews

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.

Home in Porter

Blue Birdhouse - Indiana Dunes - No Cleaning Fee

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! 🌞🏖️🌳

4.95 out of 5 average rating, 117 reviews

A cozy seating area within the log cabin features two dark armchairs positioned beside a small wooden table. Large windows allow ample natural light, providing views of the lush greenery outside. The wooden walls and floors enhance the cabin's rustic character.

Cabin in Portage

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

4.8 out of 5 average rating, 297 reviews

A wooden staircase leads to a second-story deck with yellow chairs and flowers. The deck is surrounded by green grass, and the building's exterior features a dark color. Sunlight illuminates the scene, contributing to a serene outdoor setting.

Home in Chesterton

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. ✌️

4.9 out of 5 average rating, 126 reviews

A dining area is showcased with a large wooden table surrounded by eight chairs. Wooden flooring reflects natural light from windows, while a unique pendant light hangs above. Nearby, an open layout leads into a kitchen, enhancing the spacious atmosphere.

Home in Chesterton

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.

5 out of 5 average rating, 180 reviews

A smart home device sits on a countertop beside a wire basket filled with various colored eggs. The countertop features a modern gray surface and white tiled backsplash, providing a clean and functional kitchen space.

Barn in Valparaiso

The Good Farm: Barn BnB on 44 acres near Lake Mich

Enjoy 44 acres just 15 minutes from the beaches of Lake Michigan! With room to sleep 6, guests will enjoy this fully stocked barn apartment with gorgeous views! You'll be near Indiana Dunes National Park, tree-lined hiking/biking trails, wineries, cafes, outlet malls, & antique shops. Roast s'mores in the fire pit, watch chickens free range through the yard or grab a bite to eat downtown Valpo/Chesterton/MC—the perfect getaway for families or friends who want to relax or adventure in nature.

4.93 out of 5 average rating, 202 reviews

A private deck is featured in front of the cottage, with a glass door providing access. Potted plants line the deck, and a grassy area extends beyond, leading to additional buildings in a wooded setting.

Guesthouse in Valparaiso

Private Cottage in Gated Nudist Community

We offer a private cottage on the grounds of Lake O the Woods Club. Cottage has Queen size bed, air conditioning, heater, refrigerator, microwave, TV, coffee maker, work/dining area, private deck and porta-potty. Payment of club daily grounds fee ($30-$60) is mandatory. Pricing on club website. There is no running water in the cottage. Bathrooms, showers, hot tub, sauna and swimming pool are available at the clubhouse and pool area . The cottage is sanitized after every rental.

4.96 out of 5 average rating, 168 reviews

A charming town square is featured, showcasing a clock tower surrounded by benches and vibrant flower planters. The brick paved walkway leads to storefronts under a clear blue sky, providing a welcoming community atmosphere.

Guesthouse in Chesterton

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

4.95 out of 5 average rating, 176 reviews

Cottage in Miller

Neon Dunes Vista Beachfront Cottage

Neon Dunes Cottage is perfect for a romantic getaway. A newly renovated cottage with new kitchen, modern appliances and new bathroom all in a bright airy home. It is located in Indiana Dunes National Park/Miller Beach. Only 1.5 blocks to the beach, you can hike trails nearby and come back to relax in a unique, comfortable setting with ambiance and charm. It's perfect for summer/holidays. Wifi, onsite parking and self check in, allow you to enjoy our wonderful home in privacy and peace.

4.92 out of 5 average rating, 366 reviews

A wide sandy beach extends to the water's edge, with gentle waves lapping at the shore. Clouds create a soft gray backdrop while distant figures walk along the beach. Vegetation is visible in the foreground, indicating the natural landscape surrounding the area.

Guesthouse in Chesterton

"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.

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Popular amenities for Chesterton places to stay

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Chesterton

4.98 out of 5 average rating, 157 reviews

A sandy beach stretches alongside calm waters, with numerous umbrellas and beachgoers scattered across the shore. A large, historic building stands nearby, surrounded by trees and a parking area. The backdrop features rolling dunes and a green, forested landscape.

Home in Chesterton

Hotel Whiskey

5 out of 5 average rating, 9 reviews

A modern two-story home features a combination of white siding and stone accents. Large windows allow for ample natural light, while a snowy landscape surrounds the exterior, creating a calm and serene environment. The front porch is bordered by small evergreen shrubs.

Home in Valparaiso

Serene Retreat in Beauty Creek

4.85 out of 5 average rating, 211 reviews

The modern craftsman-style home is set among lush greenery. A spacious front lawn is visible, bordered by trees. The house features a covered porch with a railing and a mix of stone and wood elements, contributing to its welcoming exterior.

Home in Porter

Modern Indiana Beach Home Near Lake Michigan

4.97 out of 5 average rating, 34 reviews

The cabin exterior is softly illuminated by string lights, creating a welcoming ambiance at night. A central fire pit is surrounded by chairs, with a pathway leading towards the cabin entrance. The scene includes a lush, grassy area and a starry sky overhead.

Cabin in Walkerton

Cabin by the Creek

4.95 out of 5 average rating, 37 reviews

The entrance features a welcoming porch with white railings and steps leading up to the door. A large window allows natural light to enter, while potted flowers add a touch of greenery to the space. Dense trees surround the cottage, providing a serene environment.

Home in Michigan City

Lake Trail Cottage(NO Cleaning Fee!)

4.88 out of 5 average rating, 26 reviews

A serene beach scene is captured at sunset, featuring a wooden boardwalk leading towards a sandy shore. The sky displays soft hues of orange and pink as the sun descends, with silhouettes of people enjoying the tranquil atmosphere along the water's edge.

Home in Portage

Welcome Home

4.89 out of 5 average rating, 89 reviews

A charming street view is displayed, featuring brick buildings with awnings in various colors. Business signs are visible, indicating shops and services, while traffic signals and street signs denote the intersection of Broadway and Calumet Road. A wide sidewalk invites pedestrian activity.

Home in Porter

New Dunes Escape