
House holiday rentals in Chesterton
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Top-rated house rentals in Chesterton
Guests agree: These houses are highly rated for location, cleanliness and more.

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. Bonus trip: take the Southshore commuter train to Chicago for the day. Here, you can explore all the south shore of Lake Michigan has to offer then kick back at your home away from home. 💙

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.

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! 🌞🏖️🌳

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.

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. ✌️

Lake Michigan Farm Retreat w/ Yoga Shed & Hot Tub
Luxury farm retreat on 7 wooded acres with hot tub, yoga shed, fire pit, fully fenced yard & pond! This home is a five minute drive to the beach, blueberry picking, Burn 'Em Brewing, Shady Creek Winery, next to Tryon Farm or 10 minute drive to downtown, the casino, and the outlet mall, but our guess is that you won't want to leave the property! This designer home has super comfy beds, 800 thread count sheets, a gourmet coffee bar, screened in porch, and even a tiny library in the laundry room

UncleLarrysLakePlace HotTubKayaksPingPong
A tribute to our favorite world traveler-he's the first to stay at our properties and give us the good, bad and ugly so we can fine-tune the ultimate experience for YOU. This newly remodeled lake home boasts 4 sleeping areas, year-round hot tub, game room with a ping pong table and large screen TV, large gathering spaces in and out, new kitchen and your own kayaks to explore the area. Enjoy sunsets and lake views from the hot tub on the expansive deck or while grilling on the Weber gas grill.

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.

✦Cozy Bungalow✦ Central location, 2.4mi to Beach
Relax in our charming & cozy bungalow close to beach, hiking trails, breweries, & conveniences like restaurants & grocery stores. A great getaway year-round. 20 mins to cross-country ski trails at the State Park! 2.4 miles from Lake Michigan to enjoy a day at the beach. 2 miles to Outlet Mall and Casino. 3 miles to Mount Baldy & Indiana Dunes National Park to explore 50mi of dunes, beaches, wetlands, prairies, rivers & forested trails. Perfect hub for a day trip to Michigan or South Bend!

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.

Duplex | Firepit | Game Room | Hot Tub-all year
You've found it – the perfect fun spot for your family beach vacation! Just a road trip away and less than half a mile from the beautiful beaches. Guests rave about the supplied beach accessories! You'll love the quiet, peaceful neighborhood close to the Michigan City's Washington Park beach, downtown, zoo, restaurants, outlet-mall shopping, and more. Grill outside; gather the family around the firepit , roast marshmallows, Smores Board provided. Play games like cornhole and board games.

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!
Popular amenities for Chesterton house rentals
House rentals with a pool

Beautiful home in Beachwalk/Notre Dame weekends

Sauna | Hot Tub | Heated Pool | Beach Walk

5 Bedroom Luxury Home In Heart of Beachwalk Resort

Pool House near the Indiana Dunes

New Hot tub Heated Pool Union Pier

Home near the lake with an inground pool

A Glass House in a Gated Nudist Resort

Cozy Mid-Century Home•Private Pool• Dog-friendly!
Weekly house rentals

Playground Fenced Patio/1.7m to Bch/mall/bewery

Long Lake Retreat

Downtown 2 BR Cottage w/ King Bed

Special February rates, book NOW!

2 bedroom 2 bathroom home away from the noise.

Stylish Home Near Notre Dame

Cozy Haven ~Modern Cottage in woods close to Dunes

Stone's Throw Lake House
Private house rentals

Close to the Dunes State Park!

Cozy cabin for two w/hot tub

The House Near The Lakes

Dunes Retreat with Private Hot Tub

Hoosier Home - 5 min walk to the beach

The Jefferson House

Moonstone Cottage

Parking|12 min walk to beach| Hot tub| & Chef Exp
When is the best time to visit Chesterton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $198 AUD | $217 AUD | $200 AUD | $203 AUD | $255 AUD | $259 AUD | $286 AUD | $281 AUD | $242 AUD | $249 AUD | $220 AUD | $220 AUD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about house rentals in Chesterton

Total holiday rentals
Explore 40 holiday rentals in Chesterton

Nightly prices starting at
Chesterton holiday rentals start at $85 AUD per night before taxes and fees

Verified guest reviews
Over 2,050 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Chesterton holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesterton rentals

4.9 Average rating
Chesterton stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
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- Rentals with outdoor seating Chesterton
- Pet-friendly rentals Chesterton
- Rentals with a fire pit Chesterton
- Family-friendly rentals Chesterton
- Rentals with a washing machine and dryer Chesterton
- Cabin rentals Chesterton
- Rentals with a patio Chesterton
- House rentals Porter County
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Soldier Field
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Warren Dunes State Park
- University of Notre Dame
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Oak Street Beach
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- Washington Park Zoo
- University of Chicago




