We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

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.

0 of 0 items showing

1 of 3 pages

Home in Chesterton

4.8 out of 5 average rating, 255 reviews

South Shore Studio Apartment {National Park}

I have to warn u 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 11 -8 generely some music playing and musicians are welcome !! if you happen to book on a sunday i host open mic in my Barn every sunday ..... pretty relaxed. Upon arriving turn into the driveway just passed my house and then right into the yard apartment is upstairs the door is open keys inside. ✌️

Home in Michigan City

4.94 out of 5 average rating, 427 reviews

Small Clean Home Near Beach, Casino, Outlet Mall

This cozy, clean home is located 2.9 miles to Beach, Outlet Mall, and Casino. Quiet neighborhood. Well maintained property. Perfect for a couple or business traveler. It is not child proof. It is not suitable for small children. There are open stairs that cannot be blocked. We do not accept pets. I have an autoimmune disease. I am allergic to pet dander We request drivers license of each guest f Per Airbnb guidelines I am disclosing we have cameras on exterior north/east of home with audio

Home in Portage

4.93 out of 5 average rating, 182 reviews

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.

Home in Michigan City

4.98 out of 5 average rating, 258 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, 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 during our high season (mid May-mid September), and open 2 night stays 1-2 weeks prior if we have a couple open days.

Home in Valparaiso

4.95 out of 5 average rating, 123 reviews

Lakefront House, Pontoon, Deck, Fire Pit & More!

Pontoon INCLUDED in all rentals starting May 2025! No extra fees for unlimited use of private pontoon, pier, paddle boards and more!! Rental price of our lakefront house includes the pontoon, deck, yard and endless activities!! Take the pontoon for a cruise, fish, swim, paddle board, kayak, watch the wildlife or have a bonfire!! Travel 15 minutes to the Indiana Dunes or 10 minutes to downtown Valpo. You will also be able to cook delicious meals on the propane grill & fully stocked kitchen

Home in Chesterton

4.9 out of 5 average rating, 114 reviews

Downtown Chesterton 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.

Home in Michigan City

4.95 out of 5 average rating, 267 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.

Home in Michigan City

4.96 out of 5 average rating, 167 reviews

5 Bedroom Luxury Home In Heart of Beachwalk Resort

Beautiful home in the heart of Beachwalk, across the street from Lake Kai, pools, basketball & tennis courts and 2 blocks to Lake Michigan. This home is bursting with charm. Front porch runs the width of the house. Dining area opens up to family room with a lovely fireplace. Stunning master bedroom w/walk-in closet and beautiful new bathroom with all the finishes. 3 more bedrooms upstairs, one with full bathroom attached and the other 2 sharing bathroom. 5th bedroom on the lower level.

Home in Michigan City

4.92 out of 5 average rating, 222 reviews

Casinos, Shopping, Pets, and Parking a Plenty!

1 mile from BLUE CHIP CASINO - with its new SPORTS BOOK and is where the away team stays for NOTRE DAME FOOTBALL, 2 miles from the outlet mall, 7 blocks to the beach, and plenty of parking! 3 bedrooms (4 beds) and 1 bathroom. This is a great place regardless of the season and though in the city; it backs up to woods with lovely walking trails. The home also has hi speed internet/WiFi and HD cable television. Simple, practical home in a safe neighborhood - and it’s a bargain!

Home in Michigan City

4.96 out of 5 average rating, 127 reviews

Midcentury marvel steps from beach! Pups

Year-round beach fun an hour from Chicago!Welcome to Barefoot Bungalow, a mid-century marvel with modern amenities. Your group will love the game room with pool table, ping pong. Private dog-friendly fenced backyard with grill, patio & firepit. Short stroll to Stop 7 to beach (Beachwalk boardwalk, wagon provided). Quiet relaxation far from the madding crowds. So many excellent restaurants, shopping, brew pubs, wineries, hiking, biking. Off-street parking, Wave bus

Home in De Motte

4.95 out of 5 average rating, 228 reviews

Country Cottage

Looking for week-end get away? Traveling through Northwest Indiana on I-65 and looking for a quiet place to stay for the night? Situated on 6 acres and with convenient (2 mile) access to I-65, our cozy Country Cottage is a great choice! Enjoy the cottage feel of this recently renovated (new cabinets, flooring, appliances) and charmingly decorated home, located in close proximity to local attractions! Our 650 square foot cottage is ideal for 1 - 4 guests.

Home in Beverly Shores

4.96 out of 5 average rating, 209 reviews

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.

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

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Chesterton house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Michigan City

4.84 out of 5 average rating, 51 reviews

Vip! 4BD 5 min to Lake, W pool heater.

Home in Schererville

4.92 out of 5 average rating, 26 reviews

Cozy house in Schererville

Home in Berrien Springs

4.9 out of 5 average rating, 103 reviews

Lake House Retreat with a Pool

Home in Chesterton

4.98 out of 5 average rating, 40 reviews

Pool House near the Indiana Dunes

Home in Union Pier

4.96 out of 5 average rating, 136 reviews

Winter retreat PVT hot tub & Fireplace Union Pier

Home in Michigan City

4.97 out of 5 average rating, 59 reviews

Home near the lake with an inground pool

Home in Gary

4.81 out of 5 average rating, 226 reviews

Oasis , Near Beach, Hard Rock and Dunes

Home in New Buffalo

4.92 out of 5 average rating, 302 reviews

Farmesque with a splash of modern

Weekly house rentals

Home in Chesterton

4.84 out of 5 average rating, 63 reviews

Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home

Home in Chesterton

4.83 out of 5 average rating, 89 reviews

National Park Nature Lover's Paradise

Home in Porter

4.87 out of 5 average rating, 77 reviews

New Dunes Escape

Home in Valparaiso

4.95 out of 5 average rating, 57 reviews

Secluded 3400sq ft home jet tub close to amenities

Home in Porter

4.98 out of 5 average rating, 47 reviews

Dunes Woodland

Home in Chesterton

4.89 out of 5 average rating, 65 reviews

Blue Birdhouse by the Beach - No Cleaning Fee

Home in Chesterton

5 out of 5 average rating, 17 reviews

Heart of Indiana Dunes National Park • Hot Tub

Home in Portage

4.91 out of 5 average rating, 70 reviews

Indiana Dunes, Beach, Chicago, Shopping Center

Private house rentals

Home in Porter

4.97 out of 5 average rating, 38 reviews

National Park / Lake Michigan Neighbor

Home in Porter

4.91 out of 5 average rating, 35 reviews

The Waverly Retreat

Home in Michigan City

4.99 out of 5 average rating, 91 reviews

5 min to beach-zoo-brewery-casino-restaurants

Home in Chesterton

4.83 out of 5 average rating, 12 reviews

Luxurious;Balcony/Patio/Fenced backyard/ Beach

Home in Chesterton

4.94 out of 5 average rating, 47 reviews

4 Season House

Home in Michigan City

4.92 out of 5 average rating, 62 reviews

Roomy & Cozy 3 Bd 2Ba just mins from Indiana Dunes

Home in Chesterton

5 out of 5 average rating, 16 reviews

INDIANA DUNES/LAKE MICHIGAN/CHESTERTON HOUSE

Home in Valparaiso

4.92 out of 5 average rating, 50 reviews

Wooded Lake Home, 15 min. IN Dunes, 7=DT, 50=CHI.

Quick stats about house rentals in Chesterton

Total rentals
40 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore