Chesterton Holiday Rentals from AU$145: Search Short-Term Rentals

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Our top choices for Chesterton holiday rentals

A beach with a parking lot and buildings in the background.

1. Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

Chesterton

Vanski M.

includes taxes & fees

25 Oct - 26 Oct

A patio with a table and chairs, a bicycle, and a string of lights against a twilight sky.

2. The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly

Porter

Amanda E.

includes taxes & fees

4 Nov - 5 Nov

3. The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

Porter

Cody

includes taxes & fees

19 Oct - 20 Oct

A living room with a dark blue door, a grey sofa, a blue sofa, a coffee table, and a floor lamp.

4. Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes

Chesterton

Briana R.

includes taxes & fees

29 Oct - 30 Oct

5. The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

Porter

Melissa P.

includes taxes & fees

19 Oct - 20 Oct

A modern kitchen with a central island, wooden dining table, and chairs. There is a ceiling fan, a microwave, and a refrigerator.

6. NEW! Beautiful Riverfront Home on 10 Acres!

Chesterton

Maria jose S.

includes taxes & fees

9 Nov - 10 Nov

A bedroom with two beds, a ceiling fan, a TV on a dresser, and a window with blinds.

7. Full House booking of a history building close to the Dunes

Chesterton

Deborah S.

includes taxes & fees

15 Nov - 16 Nov

A hotel lobby with a dining area, a reception desk, and a seating area with chairs and a table.

8. King Bed | Non-Smoking

Portage

Luis

includes taxes & fees

18 Oct - 19 Oct

9. Premium King Bed|Portage

Portage

Dave

includes taxes & fees

16 Oct - 17 Oct

A spacious living room with a white sofa, two leather chairs, a wooden coffee table, and large windows offering a view of the outdoors.

10. Black Cabin Getaway in Beautiful Woods I Valpo University | Flint Lake | Dunes

Valparaiso

Amy H.

includes taxes & fees

19 Oct - 20 Oct

A hot tub with water, a wooden deck, and a chair.

11. Charming 1-bedroom apt in house by creek with AC, in delightful Portage

Portage

Michael T.

12. Premium King Room with Jetted Tub

Portage

Anonymous traveller

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with white cabinetry, stainless steel appliances, and a marble countertop.

13. No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.

Michigan City

Crystal K.

includes taxes & fees

27 Oct - 28 Oct

A compact kitchen with a stove, microwave, and a dining area with a glass table and chairs.

14. Downtown Getaway 2

Michigan City

Sandi B.

includes taxes & fees

27 Oct - 28 Oct

A staircase leading to a second floor in a building with a rustic interior, wooden beams, and a vintage poster on the wall.

15. Cozy loft inside a vintage store on an animal rescue farm in Westville, IN

Westville

Jean G.

includes taxes & fees

18 Oct - 19 Oct

A hotel lobby with a dining area, a reception desk, and a computer station.

16. King Bed | Non-Smoking

Portage

Anonymous traveller

includes taxes & fees

16 Oct - 17 Oct

A modern kitchen with stainless steel appliances, wooden cabinets, and built-in shelves.

17. Newely Remodeled Studio!

Michigan City

JoC S.

includes taxes & fees

27 Oct - 28 Oct

A hot tub with a control panel, a wooden wall, and a stone-like exterior.

18. BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

Michigan City

Katie K.

includes taxes & fees

27 Oct - 28 Oct

A hotel room with two beds, a desk, a TV, and a seating area with a sofa and chairs.

19. Portage|Suite - Two Double

Portage

Anonymous traveller

includes taxes & fees

16 Oct - 17 Oct

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Top Chesterton Hotel Reviews

Pine Lake Resort and Banquets

8/10 Good

"For a small waterfront Town feel, you pay for what you get compared to other hotels in the area its nice/clean and kid friendly, I was on the 1st floor and my room opened up to this villa type area on the way to the pool area it was an adventure almost like you were in a different country, yes, I would go back and will go back. I give The Pine Lake Resort 8 of 10"

Spring House Inn

8/10 Good

"The hotel itself was great for my family of 4. No complaints about the cleanliness or staff. Pool was clean and working, a tad cold, but not a big issue. The only issue i had was with the smell. Walking into the main lobby the strong smell of fragrance greeted me. And the room itself had a perfume smell to it as well. To normal people it may not be a problem, however im highly sensitive to fragrances and often times will get a migraine from strong smells like that. Fortunately I didnt get one while staying there which amazed me. But maybe the hotel can keep in mind that some people do have a sensitivity to fragrance and it may deter them from wanting to stay again."

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

10/10 Excellent

"The rental was great and the Lake view was lovely! The filtered water was appreciated. We enjoyed the kuerig, nicely updated bathrooms, ample TP, and found the kitchen well stocked. The sunsets were beautiful :)"

Fairbridge Inn Express Chesterton

10/10 Excellent

"Debbie was the most beautiful and warm hearted person we have met in town. From the very moment we were looking to park our trailer she step out and guided us through. She gave us a warm welcome and guided us through everything. She would make sure we are situated in. Will be back soon!!"

Find out more about Chesterton

Everything you need to know about Chesterton holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterton holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterton holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Chesterton holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterton. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterton holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterton holiday rentals we have selected for you start as low as AU$145 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesterton rentals

At Expedia, we put the best Chesterton holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chesterton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterton holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there holiday rentals in Chesterton?

Yes, there are holiday rentals close to the most popular sights in Chesterton, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Chesterton is known for its shops and beaches. While you're here, grab a bite or have a drink at the restaurants.

What are some of the best holiday rentals that Chesterton has to offer?

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park: This highly rated holiday home rental in Chesterton offers a patio, a private garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of books.

How many holiday rentals are there in Chesterton?

Choose from 32 Expedia holiday rentals in Chesterton for a memorable holiday.

What can I see and do in Chesterton?

Lake Michigan and Indiana Dunes Visitor Center are a couple of scenic spots to enjoy the outdoors, whereas Chesterton Art Center is one of the cultural attractions. Other places in town to visit include Lustron House and Bailly Homestead - American Indians and Fur Traders.

What are holiday rentals like in Chesterton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterton. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for family gatherings.

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Check prices for these dates

Our top choices for Chesterton holiday rentals

1. Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

2. The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly

3. The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

4. Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes

5. The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

6. NEW! Beautiful Riverfront Home on 10 Acres!

7. Full House booking of a history building close to the Dunes

8. King Bed | Non-Smoking

9. Premium King Bed|Portage

10. Black Cabin Getaway in Beautiful Woods I Valpo University | Flint Lake | Dunes

11. Charming 1-bedroom apt in house by creek with AC, in delightful Portage

12. Premium King Room with Jetted Tub

13. No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.

14. Downtown Getaway 2

15. Cozy loft inside a vintage store on an animal rescue farm in Westville, IN

16. King Bed | Non-Smoking

17. Newely Remodeled Studio!

18. BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

19. Portage|Suite - Two Double

Find holiday rentals that suit your style

Top Chesterton Hotel Reviews

Pine Lake Resort and Banquets

Holiday Inn Express & Suites New Buffalo by IHG

Spring House Inn

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

Econo Lodge Portage

Blue Chip Casino Hotel and Spa

Furness Mansion

Fairbridge Inn Express Chesterton

Quality Inn Chesterton near Indiana Dunes National Park I-94

Find out more about Chesterton

Frequently asked questions

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