House vacation rentals in Chesterton

Find and book unique houses on Airbnb

Top-rated house rentals in Chesterton

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Union Pier

4.95 out of 5 average rating, 183 reviews

Barn & Beach New Buffalo / Union Pier

So excited to introduce this lovely modern cottage located at ground zero in Union Pier ! , location is just the best !! 2100 sq ft , 4 bed , 2 bath , hot tub . 6 blocks to Townline beach , Timothy’s, Red Arrow Road house , Whistle stop , 1 block to Seeds Brewery ,Union Pier Social , Black Currant Bakery , 2 grocery stores & beach rental store . Bike path directly across street , plenty of bikes to use ! (Guest home also available for large groups , there’s room for 25 people with both homes ).

Guest favorite

Home in Michigan City

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

Superhost

Home in Three Oaks

4.89 out of 5 average rating, 105 reviews

The Lucky Charm House -Walk to it all! Cute, cute

Cute as can be, super comfy, 3 blocks to downtown 3 Oaks. Walk to Acorn Theatre, Journeyman & shopping in an eclectic quintessential small town 90 mins from Chgo. Hike local trails, beach it up at Warren Dunes State Pk, bike ride country roads -Explore Harbor Country. Wonderful dining, brew pubs and wineries to explore. Open living space w/large DR. Primary BR +bth w/shower. 2nd BR w/full bed +single bunk. Large back porch +fenced yard. 2 large TV’s, Wifi/cable. Daybed front porch.

Top guest favorite

Home in Niles

4.97 out of 5 average rating, 180 reviews

Riverwalk Retreat on Main, fully updated Victorian

Beautiful 5 bedroom, 2 bath Victorian home in the heart of Niles, MI Recently remodeled with queen bedroom on main floor! 2 blocks from Riverwalk park All bedrooms and living room/game room have mounted flat screen smart tvs Private back yard with fire pit and corn hole, front and back porch 3-min. walking distance over the river to charming restaurants and shops on Main Street 10 miles from University of Notre Dame, and nearby wineries and breweries 30 min. to St. Joseph and New Buffalo, MI

Guest favorite

Home in Stevensville

4.94 out of 5 average rating, 118 reviews

Clean, dog & budget-friendly--great for families!

Clean single-family home w/3 bedrooms, 2 bathrooms, 2 living spaces, full kitchen and cooking/eating essentials. Quiet neighborhood, 1 mile from Lincoln Township Beach (Lake Michigan), 8 miles to Silver Beach and Lions Park Beach in St. Joseph, MI, 8 miles to Warren Dunes State Park and Beach, in the heart of wine/beer country. A small gas grill and firepit + wood, and chairs and a patio table on back patio. Owner lives next door and will be available to answer questions about the area.

Guest favorite

Home in Culver

4.84 out of 5 average rating, 198 reviews

Perfect spot: 3 FULL baths, 4 bedrooms

All photos are 2025. 4 large bedrooms, 3 FULL bathrooms all separate from bedrooms. Easy walk to academy, Lake Max, ALL restaurants & stores within 2 blocks. Big yard/large deck w/ grill. Washer/dryer, DISH, WiFi. 1 bedroom, 1 full bath downstairs, no stairs for either for older or special needs. 1-night weekday rental ONLY allowed in winter. Central Air + additional room units if someone wants even cooler for sleeping. Annual leader in return rentals in Culver for a reason. Affordable.

Top guest favorite

Home in Three Oaks

4.97 out of 5 average rating, 110 reviews

Three Oaks Getaway-5 BR 2.5 BA-8 Mins to Beach!

Explore Michigan's charming Harbor Country while staying in our relaxing private home in Three Oaks--a short three minute drive to downtown local boutiques, restaurants, and event venues including Journeyman Distillery, The Acorn Theater, Blissful Barn and Froehlich's. This home is just a ten minute drive from the beautiful beaches of Lake Michigan, ten minutes to the casino and thirty-five minutes to Notre Dame. Enjoy all the area has to offer and come back to your cozy, private home.

Top guest favorite

Home in Grand Beach

5 out of 5 average rating, 111 reviews

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."

Guest favorite

Home in Momence

4.96 out of 5 average rating, 167 reviews

Riverfront Oasis: Parks+ Kayaks+Relaxation Await!

Escape to this beautifully renovated 3-bedroom home with stunning Kankakee River views! Relax on the spacious deck or riverside patio while enjoying wildlife and peaceful scenery. Steps from Conrad Park and Island Park, you can stroll to local restaurants and shops. With all the comforts of home and just 50 miles from Chicago, it’s perfect for a getaway. Need more room? Book the cozy cabin next door tha hosts 4 more people! Your riverside retreat awaits—reserve your stay today!

Guest favorite

Home in Three Oaks

4.96 out of 5 average rating, 135 reviews

The Heartwood House<3 : DT Three Oaks w/Game Room

Newly renovated 1920's Bungalow loaded with character. Spacious interior with a mix of modern and vintage furnishings that will leave you relaxed and rested. Large private backyard with grill and firepit to enjoy starry Three Oaks nights. Only 4 blocks from Journeyman Distillery and close to all of the restaurants and shops in downtown. Perfect place to stay for a wedding or getaway near wineries, breweries and beaches. Come see the village that everyone is talking about!

Guest favorite

Home in Michigan City

4.96 out of 5 average rating, 395 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."

Guest favorite

Home in Michigan City

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.