Vacation rentals in Chesterton

4.99 out of 5 average rating, 509 reviews

A charming, rustic cabin is nestled among vibrant autumn foliage, showcasing a wooden exterior and a sloped metal roof. The cabin is partially obscured by trees, with golden leaves creating a warm frame around the structure, signaling a serene woodland retreat.

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.

4.98 out of 5 average rating, 102 reviews

A clear, geodesic dome is set on a paved patio surrounded by a grassy area and decorative plants. The backdrop features a tranquil lake and lush trees, illuminated by a colorful sunset sky.

Guesthouse in Valparaiso

Unique Dome Retreat by Indiana Dunes w/ Lake View

Escape to our Valparaiso Lakeside Retreat with king bed, lake views, unique dome experience, fire pit, grill & hot tub, all near Indiana Dunes National Park, Valparaiso University & 4 local parks! Experience a nature getaway at our newly renovated lake guest house on the ground level of our home with keyless entry & unique outdoor amenities, ideal for friend groups, small families, business travelers & couples. 10 min - downtown Valparaiso. Book now to experience this unique tranquil retreat.

A multi-level house is set on a grassy area, featuring a stairway leading to a deck adorned with flower pots. Vibrant red canopies provide shade, and bicycles are stationed nearby, creating an inviting environment. The exterior showcases a mix of wooden and painted surfaces.

4.82 out of 5 average rating, 332 reviews

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. ✌️

Superhost

The front of a charming house is presented, featuring a welcoming porch with decorative railings. Lush greenery surrounds the entrance, and a bright yellow door enhances the facade. The roof is sloped, and large windows allow for ample natural light.

4.9 out of 5 average rating, 131 reviews

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, 199 reviews

A spacious living area features a soft sofa and an accent chair, enhanced by a large blue area rug. A striking mural of rolling hills adorns one wall, complemented by modern kitchen appliances and dining space in the background.

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.

4.95 out of 5 average rating, 213 reviews

A private cottage is surrounded by lush greenery and features a wooden deck adorned with several blue planters. Steps lead up to the entrance, which is framed by large windows allowing natural light to fill the interior.

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.

4.97 out of 5 average rating, 273 reviews

A modern house is situated amidst lush greenery. A wooden walkway leads to the entrance, framed by trees and underbrush. Large windows reflect natural light, blending the structure harmoniously with its surroundings while offering a glimpse of the cozy interior.

Cabin in Michigan City

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!

4.96 out of 5 average rating, 190 reviews

A serene sunset casts warm hues of orange and gold over a calm body of water, with a distant city skyline silhouetted against the horizon. The smooth water surface reflects the colors of the sky, creating a tranquil 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, 197 reviews

The cottage exterior showcases a single-story structure with a light grey facade and a newly roofed design. Large windows allow natural light to enter, framed by a lush green landscape. A welcoming entryway leads to the home, complemented by garden pots and a gentle pathway.

Cottage in Miller

Neon Dunes Vista Beachfront Cottage

Neon Dunes Cottage is a one bedroom 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.

4.91 out of 5 average rating, 387 reviews

An outdoor space is presented with a patio featuring a round table and four chairs under a red umbrella. A fire pit is positioned nearby, with a pile of branches placed in the foreground. The area is enclosed by a wooden fence with decorative artwork visible.

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.

4.96 out of 5 average rating, 396 reviews

An open studio space features a black leather sofa alongside a wooden coffee table on a textured rug. Colorful wall art adds vibrancy, with a light fixture illuminating the area. A chair with a unique design offers additional seating, enhancing the contemporary aesthetic.

Guest suite in Miller

Miller Mermaid Suite-100 yds from the beach!

100 yds from the beach, the cozy MERMAID SWEET awaits you and is well suited for a young family or 2-3 adult friends. This artsy basement open studio space includes a private entrance, kitchenette, unique art & a cozy reading/sleeping nook! Enjoy beautiful sunsets from the upstairs deck. BBQ on the grill. Visit local restaurants, shops & galleries. Hike wooded trails & swim by sandy, dune-grass beaches. . House-trained dogs welcome! Sorry no cats (allergies)

4.89 out of 5 average rating, 799 reviews

The swimming pool area features a vibrant blue pool with a fountain at its center. Surrounding the pool, comfortable loungers are arranged, and hanging flower planters add a touch of greenery. A spacious building is visible in the background, framed by lush trees.

Guesthouse in Porter

'Pool Barn' w/Games & Hot Tub near Indiana Dunes

Heated pool open until mid October!Hot tub open all year! The Pool Barn is only 1 hour from Chicago & less than 10 minutes from large sand beaches & hiking trails of Indiana Dunes National Park & Indiana Dunes State Park. Outside enjoy our Pool, hot tub, grill, firepit, playground, & we are on hike/bike trail. Inside is billiards, ping pong, air hockey, darts, popashot, foosball, board games, large smart tv, 5 beds, couch, & full kitchen. Book today!

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations with great services and amenities

Popular amenities for Chesterton vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Chesterton

A single-story home with a sloped roof is set on a well-maintained lawn. The front porch features steps leading to a central door, flanked by windows. Lush green grass surrounds the house, with trees and open space visible in the background.

5 out of 5 average rating, 9 reviews

Close to the Dunes State Park!

Superhost

A warm living area is highlighted by a comfortable brown sofa and armchairs arranged around a wooden coffee table. A ceiling fan provides airflow, while a TV is positioned next to large windows framed by blue drapes. A wooden fireplace adds a cozy touch.

Townhouse in Chesterton

4.82 out of 5 average rating, 45 reviews

South Shore Escape

The exterior of a modern craftsman-style home is displayed, featuring a combination of wood and stone materials. A spacious balcony extends from the second floor, and large glass windows invite natural light. Surrounding trees create a peaceful forest atmosphere.

Home in Porter

4.82 out of 5 average rating, 226 reviews

Modern Indiana Beach Home Near Lake Michigan

The living room is designed with a plush orange sofa, accented by colorful pillows. Two white armchairs with black frames provide additional seating. A small wooden coffee table is centered between them, complemented by a potted plant in the corner, contributing to a comfortable atmosphere.

5 out of 5 average rating, 3 reviews

Modern Retreat w/Hot Tub| Indiana Dunes| Beaches

4.98 out of 5 average rating, 59 reviews

A rustic cabin exterior is framed by dark wood siding and features a welcoming porch. Two rocking chairs are positioned beside the entrance, adorned with potted flowers. Sunlight streams onto the porch, enhancing the inviting atmosphere.

Cabin in Walkerton

Cabin by the Creek

A spacious deck is shown surrounding a private heated pool, with several lounging and dining areas. Large umbrellas provide shade over tables and chairs, while vibrant greenery and flowers are visible in the background.

4.96 out of 5 average rating, 52 reviews

Pool House near the Indiana Dunes

4.95 out of 5 average rating, 62 reviews

A single-story cottage with light gray siding is accompanied by a neatly landscaped front yard. A welcoming front porch is framed by white railings. A paved driveway leads to a garage on the right, while surrounding trees provide ample shade.

Home in Michigan City

Lake Trail Cottage