Vacation rentals in Chesterton

The image captures a serene beach scene at sunset, with soft sand and gentle waves. Tall grasses frame the foreground, leading the eye toward the calm water reflecting the warm hues of the setting sun and a lighthouse silhouette in the distance.

4.9 out of 5 average rating, 371 reviews

Best Deal In Michigan City 1.3 miles to Beach

Quiet for a well deserved nights rest. Plenty of space for 4-8 guests indoors and out. Short drive to the Washington Park beach & zoo Walking distance to south shore train for a quick ride into the heart of Chicago. Less than a mile from uptown arts center and district Short drive to The National Lakeshore, that has great beaches, hiking, and biking trails! Have a day in the sun, and come back to relax, in a quiet backyard patio area equipped with grill & night lighting... Must be 24 to book

4.98 out of 5 average rating, 220 reviews

A cabin-style home is nestled among tall pine trees, featuring a large facade with distinctive tall windows that allow natural light to flood the interior. Colorful chairs are positioned on the screened porch, surrounded by well-maintained greenery and flower beds.

Cottage in Union Pier

"The Pines" in Union Pier: Year-round getaway

Under towering pine trees that feel more like the Northwoods, you're in the heart of Harbor Country. About 1.25 miles from the shore, minutes from New Buffalo & Three Oaks. Newly updated cabin-style home offers rustic feel with luxury comforts & highspeed WiFi, and great indoor & outdoor space. Garage plus add'l parking. Enjoy the area's beaches, restaurants, outdoor activities, breweries & wineries. Southwest Michigan at it's best! Please see policies for pets & children in house rules.

4.96 out of 5 average rating, 79 reviews

A spacious screened-in porch is showcased, featuring ample seating and views of the surrounding greenery. A well-manicured lawn lies in front, complemented by a wooden fence. Sunlight filters through the trees, creating a relaxed outdoor atmosphere.

Home in Sawyer

Here and Now

Beautifully decorated home that has been featured in magazines on Interior Design. Fantastic location right next to the Warren Dunes and walking distance to the lake. Beautiful landscaping from every window. Professionally designed home features an upscale interior with a fun twist and a fabulous screened in porch. The perfect spot to enjoy a getaway in style , look no further. 2 separate buildings on the acre property , this rental is for the front building. Wi fi included but can be weak.

Superhost

Apartment in New Buffalo

4.92 out of 5 average rating, 25 reviews

Charming 2BR/2BA Cottage with Full Kitchen & Patio

The cottages, or townhouses, are situated steps away from the main inn, providing an added sense of privacy while still feeling the vibe of the community. This cottage has two bedrooms (one with a queen bed in the downstairs bedroom + another with 2 twin beds in the upstairs bedroom). Two bathrooms (one upstairs, one downstairs) keep things fresh with a queen sleeper sofa. The upstairs loft space provides extra room for rest. An in-unit washer/dryer and high speed WiFi makes things easy.

4.82 out of 5 average rating, 96 reviews

A spa hot tub sits on a grassy area, designed for relaxation. Surrounding the tub is lush greenery, offering a sense of privacy. The hot tub features a smooth blue surface with built-in jets, inviting for a peaceful soak after outdoor activities.

Home in Three Oaks

Three Oaks Creek House Perfect

3BR, 2 bath contemporary house on Spring Creek--a spawning waterway and spectacular architectural screenhouse (4th BR) at water's edge. Open floorplan, stone fireplace, gourmet kitchen and 4000CDs for spontaneous entertaining. Tempur-Pedic King master BR/office suite with lots of storage and large desk Queen 2nd BR w/standing desk, dresser, books. Full 3d BR w/ 3/4ba en-suite. Wi-fi throughout, Roku, DirecTV with HBO. Spectacular privacy, quiet and tons of specialty ameneties!

5 out of 5 average rating, 110 reviews

Home in Grand Beach

Superhost, hot tub, golf cart, fire pit, large!

Newly renovated 5 bed, 2 bath home in the quaint village of Grand Beach. Golf cart included with rental (in season - May thru mid-Nov). Home is situated on a large lot, high on a sand dune that overlooks the 6th fairway and park area. Enjoy two large decks and year-round eight person hot tub. The property is very private, on secluded street and fully stocked for a great stay. It's a great place to enjoy some down time in an idyllic village in the heart of Michigan's "Harbor Country."

5 out of 5 average rating, 57 reviews

A spacious kitchen is visible through large glass doors. Modern white dining chairs surround a round table, and natural light illuminates the room. The kitchen features a sleek design with ample counter space and built-in shelves, all set against a backdrop of wooded scenery.

Home in Lakeside

Beautiful New Retreat in Lakeside - Walk to Beach

Our sunny Harbor Country home is surrounded by woods at the end of a private street and is walkable to Lake Michigan. 7-day Saturday to Saturday rental only, please. We are a 15-min walk from the Union Pier/Berrien public beach, 5-min drive from New Buffalo & Sawyer, 10-min drive from Three Oaks. There is even a pickleball court outside the front door! Occasional trains only add to the atmosphere. Owners stay on premises in their separate, upstairs studio from time to time.

A serene view of the beach extends to the horizon, where gentle waves meet the sandy shore. Lush greenery frames the foreground, leading to a tranquil expanse of water under a partly cloudy sky.

4.89 out of 5 average rating, 113 reviews

Roomy and Private Getaway for Families & Friends

Perfect for Gatherings, Families, Birthdays, Group Outings: Enjoyment & Tranquility in Nature. Nestled on two acres of picturesque land, the property boasts a fully-equipped six-bedroom house. Conveniently located within a 5-minute drive to popular attractions such as the beach, casino, and outlet mall. Formerly a church, the house has been transformed into an inviting Airbnb rental, featuring a renovated interior, fire pit, gazebo, and many amenities.

Apartment in Michigan City

A sunset over Lake Michigan is captured through silhouetted trees. The sun's reflection glimmers on the water, creating a serene atmosphere. The peaceful scene is framed by a wooden railing, emphasizing the natural beauty of the lakeside setting.

4.94 out of 5 average rating, 136 reviews

Charming apartment in Arts District

Walk to outlet mall, art galleries, parks, restaurants, and Lake Michigan beach. Walk or drive to casino. This is a 2nd-story apartment in Michigan City's historic homes. A full 1,400 sq ft of space! Fully appointed, clean and beautifully decorated. Newly renovated kitchen and bath. WIFI. Access to beautiful back yard patio and deck. Great proximity to attractions. Great for couples, solo adventurers, and families with children.

4.91 out of 5 average rating, 112 reviews

A circle of Adirondack chairs surrounds a central fire pit, positioned on gravel. Potted plants and flowers add greenery, while a backdrop of trees and a storage shed enhance the natural setting of the outdoor space.

Cottage in Three Oaks

Private, Sun-filled Union Pier Cottage

Sunny, private cottage set on a half-acre facing woodlands. Quick drive to everything - beaches, hiking, restaurants, wineries, breweries, etc. High-speed internet available and desk with two monitors. Please be advised: reservation requests from first-time AIRBNB renters will be declined. You must have rented through AIRBNB in the past and received a high rating.

4.92 out of 5 average rating, 104 reviews

A spacious screened-in porch is presented, featuring a wooden floor and exposed beams overhead. Large windows on three sides allow natural light to flow in, offering views of the surrounding neighborhood. Two wicker chairs and a small table are arranged for relaxation.

Townhouse in New Buffalo

Downtown NB! Walk Everywhere! Huge screened porch

If you want to be in middle of everything with ample off street parking walking distance to everything you’ve found it! This is a two story two bedroom two bathroom recently remodeled unit. Perfect for 2-6 Primary has a Queen Twin over twin guest Twin over full guest Full size pull out couch in main level. Recently remodeled 2 Large flat screen tv

4.95 out of 5 average rating, 149 reviews

A charming yellow cottage is framed by a white picket fence and greenery. An American flag decorates the front, while a welcoming pathway leads to the entrance. Large windows with shutters provide light to the interior, complemented by a modest porch and seating.

Cottage in New Buffalo

The Lemonade Cottage, New Buffalo. Walk to beach!

You'll fall in love with this cute and inviting cottage. From the white picket fence to the updated kitchen and bath...you won't be disappointed. Enjoy the beautifully secluded back yard with hot tub, gazebo, grill and fire pit. Walking distance to downtown, shops, bars, restaurants, beach, marina, brewery, Redamaks, StrayDog and much more.

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 and amenities

Popular amenities for Chesterton vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Chesterton's top sights

Chesterton’s European Market20 locals recommend

Lucrezia® Café20 locals recommend

Wagner's Ribs19 locals recommend

Running Vines Winery18 locals recommend

Octave Grill18 locals recommend

Indiana Dunes National Lakeshore Visitor Center12 locals recommend

Other great vacation rentals in Chesterton

Superhost

The exterior view reveals a two-story home with a light blue facade and a vibrant red front door. Outdoor verandas are present on both levels, adorned with hanging plants. A well-maintained garden surrounds the home, featuring various greenery and flowers, and offers a welcoming entry.

5 out of 5 average rating, 4 reviews

Lake Life Livin’- Beach House

Superhost

An inviting backyard features a central fire pit surrounded by several metal chairs. The bi-level house is visible in the background, with large windows reflecting the evening light. A hot tub is seen nearby, framed by trees and a spacious lawn.

Apartment in Bridgman

4.79 out of 5 average rating, 106 reviews

Relax - SW Mi Getaway/Hot Tub-Beaches & Wine Tours

4.95 out of 5 average rating, 123 reviews

A circular arrangement of colorful Adirondack chairs is set in a lush green lawn. The seating area is shaded by surrounding trees, creating a relaxed outdoor space for gatherings. A small table is positioned at the center, enhancing the inviting atmosphere.

Home in Berrien Springs

Great Living Too

An inground swimming pool features clear, blue water surrounded by a spacious deck area. Several lounge chairs are arranged alongside the pool, and pool floats are visible in the water. A secure fence encloses the area, providing safety and privacy.

4.92 out of 5 average rating, 64 reviews

Home near the lake with an inground pool

4.94 out of 5 average rating, 17 reviews

The exterior of the estate is showcased, featuring a combination of natural stone and dark siding. Large glass windows enhance the entryway, framed by a geometric roofline. Lush greenery surrounds the property, with tall trees and well-maintained shrubs providing a serene ambiance.

Vacation home in Baroda

Location location

4.96 out of 5 average rating, 200 reviews

Cottage in Union Pier

Designer Cottage Relax Beach Pool & Spa—Windjammer

4.96 out of 5 average rating, 114 reviews

Home in Union Pier

cozy new buffalo cabin, hot tub, 14m walk to beach