House holiday rentals in Chesterton

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.

4.92 out of 5 average rating, 111 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! 🌞🏖️🌳

A spacious living area showcases a light-colored sectional sofa adorned with plush pillows. Large windows allow natural light to fill the room, revealing wooden flooring and eye-catching artwork on the walls. A dining table is visible in the background, complemented by a minimalist plant.

4.98 out of 5 average rating, 307 reviews

House of Zen: Peaceful Modern Cabin on Tryon Farm

The House of Zen is an architect designed home situated in the woods, part of a sustainable farm community on 170 acres. Only an hour drive from Chicago, and close to Indiana Dunes National Park, it is the ultimate escape. The perfect getaway for couples, creatives and nature lovers who want some peace, quiet and space. Explore the farm trails & enjoy the wildlife and soothing sounds. Note: We have a 3 night minimum stay during summer, but open up 2 night stays 1-2 weeks before if possible.

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, 346 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. ✌️

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, 134 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.

4.84 out of 5 average rating, 109 reviews

A spacious living room is visible, featuring a burgundy sofa and a brown recliner. A wooden coffee table sits in front, adorned with a small floral arrangement. The dining area is adjacent, showcasing a rectangular table surrounded by six chairs. Light-colored walls enhance the room's brightness.

Home in Portage

Indiana Dunes, Beach, Chicago, Shopping Center

Near Indiana Dunes, Lake Michigan and Chicago when you stay at our centrally-located townhome. For family fun we’re is located a few minutes away from the shopping center, plenty of restaurants, main chain stores and more. Enjoy the convenience a parking garage& driveway, outdoor patio, dishwasher and washer & dryer. home has 4 beds 2 bedrooms. One bedroom has a Queen bed, second bedroom has a Queen bed and a Full bed. The Living room has a sofa bed. Shovel in the garage for when it snows.

A modern living space features two green sofas and light grey chairs surrounding a round wooden coffee table. A patterned accent wall adds color, while the open layout reveals a fully equipped kitchen in the background. Soft lighting enhances the inviting atmosphere.

4.98 out of 5 average rating, 143 reviews

Michigan City Getaway w/Games, Firepit, 75"TVs

Welcome to The Bolka Dot House! This family friendly house is newly renovated with a designer interior, beautiful furnishings, three bedrooms (King/Queen/Full), two living rooms, a fully equipped kitchen, a full and half bathroom, and a three seasons room! The house is located within 10 minutes of the Washington Park Beach, Blue Chip Casino and Spa, Lighthouse Place Premium Outlets, Shady Creek Winery, Uptown Arts District, various local and chain restaurants, coffee shops, and breweries.

The modern tree-house structure is illuminated by warm lighting, showcasing large windows that reflect the surrounding trees. A screened porch with seating is visible, extending from the main building, creating a connection with nature.

4.95 out of 5 average rating, 298 reviews

TRYON FARM MID-MODERN SPA IN THE WOODS

Come, enjoy our Tryon Farm modern spa. A Sustainable luxurious open concept tree-house in the woods. Minutes from the beach with an outdoor sauna, Hottub, shower, and Mr. Steam. Perfect for two or a family/group adventure. A true destination with Yoga studio, Mirror by LuLu lemon and wellness elements. The house is a perfect balance of art and nature and luxury and spiritual. Treat yourself to a farm to table, hand made, locally sourced chef services for an extra special experience.

4.97 out of 5 average rating, 232 reviews

Visit LakeMichigan Beach-Brewery-Casino-OutletMall

Explore the beautiful Indiana Dunes National and State Parks. Book your stay at this cozy, newly renovated 2 bedroom home centrally-located for all your adventures. Within 2 miles of beach, restaurants, brewery, winery, casino, concert venue, spa, botanical garden, splashpad, zoo, boat tours, kayak rental. Explore all the south shore of Lake Michigan has to offer then kick back at your home away from home. Only a half mile walk to the Southshore commuter train to Chicago! So COZY. 💙

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.

4.88 out of 5 average rating, 117 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.

A modern two-story home constructed from wood is nestled among trees in a wooded area. Large windows allow natural light to brighten the interior. A deck is visible at the back, surrounded by a carpet of fallen leaves and greenery.

4.96 out of 5 average rating, 416 reviews

Dunefarmhouse Modern Country Escape

Experience nature and design in an unforgettable way! This thoughtfully curated home is located within a unique green community surrounded by 200+ acres of woods, prairies and meadows - yet minutes to the beach, great restaurants, wineries and activities in harbor country. A unique and immerse art experience awaits every guest. Dunefarmhouse was featured in TimeOut magazine in 2019-2020, as a "Top 10 Airbnb rental in the Midwest" and part of "Perfect Midwest Getaways."

4.96 out of 5 average rating, 229 reviews

The open living area features large floor-to-ceiling windows framing views of the surrounding woods. A sleek two-tone sofa and modern armchairs are arranged near a minimal table. Warm wooden flooring complements the contemporary design, and a staircase leads to the upper level.

Home in Beverly Shores

Secluded Modern Retreat Near Beach - "Sandlot"

Stunning modern home overlooks private sand dunes on 5 wooded acres just a mile away from beautiful Lake Michigan beaches and surrounded by the Indiana Dunes National Park. Relax in our updated open-concept unique home nestled in the dunes. Enjoy the trails in the backyard, the friendly community, and local attractions near by. Just an hour to Chicago by car or the South Shore train is 1/2 mile from the house, with easy rides to Chicago and South Bend.

A welcoming living space features soft lighting from a table lamp beside a wooden accent table. The walls are adorned with decorative panels and wall art, while a circular wreath adds a natural touch. A ceiling fan provides airflow, enhancing comfort in the room.

4.98 out of 5 average rating, 174 reviews

Hotel Whiskey

Fully remodeled and tastefully decorated two bedroom home for short or long term stays. Office space for work travelers. Pet friendly with secure fenced in back yard. Walking distance from downtown with quaint shops, wine bar, craft beer bar, restaurants and bike trails. Whether you're in town for work, visiting family or just looking for a weekend getaway, this house and location are perfect for short or long term stays.

Popular amenities for house rentals in Chesterton

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.89 out of 5 average rating, 139 reviews

A private pool area is framed by a white fence, featuring a clear blue pool surrounded by lounge chairs. Lush greenery and a large tree provide shade, while the serene view of Lake Chapin and distant trees is visible in the background.

Home in Berrien Springs

Lake House Retreat on the water

The exterior of a multi-level house is depicted, featuring a combination of siding and stone accents. Large windows are present, along with balconies on the upper levels. A paved driveway leads to a garage, surrounded by greenery and a clear blue sky.

4.92 out of 5 average rating, 115 reviews

Beautiful home with Beach views in Beachwalk

4.92 out of 5 average rating, 104 reviews

A modern dining area features a wooden table surrounded by sleek black chairs. Behind it, a vibrant mural of South Bend adds color to the space. A cozy living area with a large sectional sofa and ample natural light can be seen through the open layout.

Home in South Bend

Large, Cozy, Theatre, Pool, Walk to ND Restaurants

The charming two-story home features a wide front porch with ample seating and decorative lighting. White railings and a wooden design enhance its appeal. Flanking trees provide some greenery, and the entryway is welcoming with its open doors and stylish decor.

4.96 out of 5 average rating, 184 reviews

5 Bedroom Luxury Home In Heart of Beachwalk Resort

4.94 out of 5 average rating, 164 reviews

A private hot tub is set in a wooden enclosure, surrounded by a serene natural landscape. Steps lead up to the hot tub, offering easy access. Two white Adirondack chairs are positioned nearby, inviting relaxation in the peaceful outdoor setting.

Home in Union Pier

Winter & Holiday Couples getaway Pvt Hot tub

4.85 out of 5 average rating, 197 reviews

A spacious green house features a traditional design with multiple windows on the upper level, bordered by well-maintained landscaping. A large driveway extends in front, accommodating parking for several vehicles, leading to a three-car garage with white doors.

Home in Union Pier

New Buffalo / Union Pier Pool Hot tub 6 Bedroom

4.88 out of 5 average rating, 135 reviews

A stone pathway leads through lush greenery and colorful flowerbeds toward a light-filled, glass-fronted structure. Towering trees create a natural canopy, enhancing the serene atmosphere of the garden setting.

Home in Three Oaks

Harbor Country Charm w Heated Pool Open Til 10/12!

4.91 out of 5 average rating, 309 reviews

A game room features a multi-game table for pool, air hockey, and ping pong, surrounded by comfortable bean bag seating. Bright, geometric lighting enhances the space, while classic arcade machines and a large wall Connect 4 game add fun to the cozy environment.

Home in South Bend

Hot Tub | Backyard Oasis | Game Room | |Coffee Bar

Weekly house rentals

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.

4.91 out of 5 average rating, 11 reviews

Close to the Dunes State Park!

The image displays a collage featuring the bright living room with a Smart TV and a comfortable couch, the charming exterior of the cottage, the modern kitchen showcasing a gas stove, and a tastefully decorated bedroom with a spacious bed and soft linens.

5 out of 5 average rating, 28 reviews

Downtown 2 BR Cottage w/ King Bed

5 out of 5 average rating, 3 reviews

Cozy Studio for ND Football Games & Apple Picking!

The spacious living area features vaulted wooden ceilings and large windows allowing natural light. A white sofa is positioned on a vibrant red rug, complemented by modern chairs. An elegant wooden cabinet is visible, along with a minimalist artwork on the wall.

4.79 out of 5 average rating, 56 reviews

Two Night Min. Close To Association Beach

A modern kitchen features a large central island with dark cabinetry and a white countertop. Natural light floods in through a wide window overlooking greenery. A chandelier hangs from the ceiling, adding a touch of warmth to the bright, airy space.

5 out of 5 average rating, 24 reviews

Indiana Dunes Modern Farmhouse

A serene bedroom features a spacious bed with textured white linens and a colorful striped accent pillow. On either side, bedside tables hold stylish lamps. A coastal-themed artwork hangs above the headboard, complementing soft wall colors.

5 out of 5 average rating, 38 reviews

Family Spot• Dunes, Downtown, Grill & Screen Porch

A bright and functional kitchen area is presented, featuring modern white cabinetry and stainless steel appliances. A round dining table with four chairs occupies the space, complemented by a decorative mirror and a welcoming bouquet of flowers on the table.

4.85 out of 5 average rating, 20 reviews

Home Sweet Home

A charming blue exterior of the home features a welcoming yellow front door. A wooden pathway leads to the entrance, bordered by vibrant flower beds. Two yellow chairs are positioned on the porch, alongside well-kept greenery that enhances the inviting appearance.

4.91 out of 5 average rating, 78 reviews

Michigan City Indiana Dunes Beach National Park

Private house rentals

5 out of 5 average rating, 3 reviews

Home in La Porte

New Carlisle 3BR | Fast Wi-Fi & In-Unit Laundry

4.9 out of 5 average rating, 29 reviews

A spacious living area features high vaulted ceilings and natural wood paneling. Large windows allow natural light to illuminate the room. A stone fireplace serves as the focal point, complemented by a mounted television. Comfortable blue sofas and a dining table enhance the inviting atmosphere.

Home in Stevensville

Cozy cabin for two w/hot tub

5 out of 5 average rating, 3 reviews

Private Space & Group Fun in One

A serene landscape is captured, featuring calm waters that reflect the sun and surrounding trees. The sky displays a mix of clouds and blue hues, while fallen leaves rest on the water's surface, creating a tranquil scene in nature.

5 out of 5 average rating, 9 reviews

The House Near The Lakes

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.

4.9 out of 5 average rating, 72 reviews

Lake Trail Cottage

5 out of 5 average rating, 46 reviews

A spacious living area showcases a natural wood ceiling and a stone fireplace. A sleek coffee table sits in front of a comfortable sofa, with a television mounted on the wall displaying a serene beach scene. A dining table is visible in the background.

Home in Gary

Hoosier Home - 5 min walk to the beach

4.96 out of 5 average rating, 100 reviews

The modern two-story house is surrounded by landscaped grounds, featuring a mix of wood and dark paneling. A spacious deck extends from the upper level, with seating and hanging planters. A pathway leads to the outdoor dining area, bordered by vibrant flower pots.

Home in Gary

Steps from the beach and a mile from National Park

The Glass House is situated amidst vibrant autumn foliage, showcasing a modern design with expansive glass walls and a stone façade. The surrounding lawn features fallen leaves and natural wooden elements, with outdoor seating options visible on the terrace.