Holiday rentals in Chesterton

The open living area showcases a cozy seating arrangement with a brown sofa and modern chairs. A ceiling fan hangs above, and the space is illuminated by warm light from the nearby kitchen. A large TV is mounted on the wall opposite the seating area.

4.96 out of 5 average rating, 125 reviews

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. 😁

LocationFamilyKitchen

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.

4.89 out of 5 average rating, 135 reviews

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! 🌞🏖️🌳

ValueLocationWalkability

4.95 out of 5 average rating, 296 reviews

A welcoming living area is presented, featuring a light grey sectional sofa paired with plush armchairs. A dark coffee table sits at the center, complemented by a textured area rug. Natural light filters through the nearby window, adding warmth to the space.

Home in Portage

Newly Renovated with Finished Basement

This beautiful house is located near Lake Michigan in Northwest Indiana, less than 10 minutes from the expressway and toll road. There is a stainless steel kitchen, spa bathroom, finished basement and bar with sleeping capacity to accommodate two families. This is a smart home with Ring db, lights and thermostat controlled by your voice. We are less than an hour drive from downtown Chicago, and there are many great beaches nearby. Shopping and great dining options are also within a close drive.

LocationValueCheck-in

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.

4.83 out of 5 average rating, 428 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. ✌️

FamilyLocationDecor

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, 149 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.

LocationValueNearby

A spacious living area features a large flat-screen TV mounted on the wall. Comfortable gray sofas with vibrant red accent pillows are arranged around a marble coffee table. Natural light brightens the space, which includes a glimpse of the dining area and staircase in the background.

4.8 out of 5 average rating, 103 reviews

Roomy Retreat–Family&Friends|2 King Beds|Game Room

🏡Welcome to Your No-Train-Noise, Pet-Friendly Stay in Chesterton! Property Highlights: 🛏️4 Bedrooms | 🛁 3 Bathrooms | 🛋️ 3 Living Areas with Smart TVs 🍸Bar in the Basement 🍽️Outdoor Dining 🚶‍♂️Minutes from historic Chesterton Downtown 🌲 4 miles to Indiana Dunes National Park & the beach 🍳 Fully Stocked Kitchen 👶 High Chair & Crib included Get ready for endless adventures along the sandy shores and tree-lined trails of Indiana Dunes. Enjoy every moment of your stay

ValueFamilyTV

Guest house in Chesterton

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.

"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.

LocationFamilyBathroom

4.92 out of 5 average rating, 421 reviews

A modern kitchen space is presented, featuring a large dining table accompanied by black chairs. White cabinetry and light countertops provide a bright appearance, while decorative elements like a shelving unit and fixtures enhance the welcoming aesthetic. Natural light is allowed in through a nearby window.

4.86 out of 5 average rating, 146 reviews

New Dunes Escape

Your family will be close to everything when you stay at this centrally-located place. Located just 3 minutes from the entrance of the Indiana Dunes National Park, 45 minutes from Chicago, 45 minutes from New Buffalo, MI , and 3 minutes from the Dunes Park South Shore Station, this completely remodeled home is the perfect place for a get-away. With free wifi, firepit with firewood, and a 4-seasons room, this house is the perfect place to relax after a great day swimming or hiking.

ValueFamilyTV

4.96 out of 5 average rating, 80 reviews

A cozy porch area is featured, furnished with a wicker seating arrangement that includes two chairs and a loveseat. A coffee table sits in the center, and large windows allow natural light to fill the space, creating a bright and inviting atmosphere.

Flat in Chesterton

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!

FamilyValueQuiet

A spacious dining area features a large wooden table surrounded by vibrant blue chairs. Large windows showcase views of the lush wooded surroundings, allowing natural light to illuminate the room. A unique light fixture adds a modern touch to the retro decor.

4.98 out of 5 average rating, 100 reviews

Retro 1950s Estate w Hot Tub Near Indiana Dunes

Welcome to the Retro Bird Retreat a 1950s architect-designed estate, sleeping 12 guests on 3 private wooded acres, just 10 minutes from Indiana Dunes National Park. NO cleaning fees. Hot tub greenhouse, speakeasy basement bar, games garage, 5 themed rooms, 2 fire pits, and more entertainment than you can handle in a weekend. Built for large Multi-generational families, group, work retreats & anyone who wants to disappear into a retro world. Book Today!

ValueLocationAccess

5.0 out of 5 average rating, 41 reviews

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.

FamilyLocationComfort

Guest house in Chesterton

A well-maintained garden area features vibrant flowers and greenery surrounding a gated patio. Potted plants and colorful blooms add a touch of nature, while a green umbrella provides shade over the outdoor seating area visible behind the gate.

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.

FamilyLocationHospitality

4.97 out of 5 average rating, 104 reviews

Popular amenities for Chesterton holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Chesterton

4.92 out of 5 average rating, 61 reviews

Townhouse in Chesterton

The Book Nook 2 BDRM

FamilyValueAmenities

4.8 out of 5 average rating, 25 reviews

Porter Beach home minutes to Dune State park

FamilyLocationBeach

5.0 out of 5 average rating, 9 reviews

Chesterton 3 Bedroom Home Away From Home

LocationFamilyHiking

5.0 out of 5 average rating, 16 reviews

Charming Old Town Retreat in the Heart of Duneland

LocationFamilyParks

4.76 out of 5 average rating, 66 reviews

Townhouse in Chesterton

South Shore Escape

ValueLocationHospitality

5.0 out of 5 average rating, 32 reviews

Flat in Portage

Trailside Retreat

ValueLocationOutdoor spaces

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.

4.81 out of 5 average rating, 21 reviews

Close to the Dunes State Park!

LocationValueHospitality

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.