A wooden staircase ascending a sandy hill with sparse vegetation.

Chesterton Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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

Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Chesterton
8.8 out of 10, Excellent, (137 reviews)
"Very cozy, comfortable, and relaxing we’ll stay there again"
United States
Vanski M.
The price is NZ$274
includes taxes & fees
27 Sept - 28 Sept
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
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

The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Porter
9.4 out of 10, Exceptional, (8 reviews)
"We enjoyed our stay. Very inviting and comfortable accommodations. Would stay again and would recommend!"
United States
Amanda E.
The price is NZ$459
includes taxes & fees
26 Oct - 27 Oct
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
A living room with a dark blue door, a grey sofa, a blue sofa, a coffee table, and a floor lamp.

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

Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
Chesterton
9.6 out of 10, Exceptional, (74 reviews)
"Very nice space, with plenty of room and a great location. "
United States
Briana R.
The price is NZ$674
includes taxes & fees
6 Oct - 7 Oct
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
A beach with sand dunes and grass.

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

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
8.6 out of 10, Excellent, (23 reviews)
"Communication were great. The hosts we close so anything that we needed it got taken care of right away. Close to great food and lake"
United States
Jerrell G.
The price is NZ$281
includes taxes & fees
28 Sept - 29 Sept
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
A beach with sand dunes and grass.

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

The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
Porter
9.0 out of 10, Wonderful, (22 reviews)
"Awesome place to stay and plenty to do"
United States
Cody
The price is NZ$443
includes taxes & fees
27 Sept - 28 Sept
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
A sandy beach path leading to the sea with grassy dunes on either side.

6. Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
Chesterton
9.4 out of 10, Exceptional, (47 reviews)
"Fantastic stay!"
United States
Steven F.
The price is NZ$431
includes taxes & fees
8 Oct - 9 Oct
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
A beach with a sunset, waves, and sparse vegetation.

7. Tower Haus w/Private Hot Tub

Tower Haus w/Private Hot Tub
Chesterton
9.8 out of 10, Exceptional, (37 reviews)
"Great place to stay! It was really clean! Highly recommend!"
United States
Joshua N.
The price is NZ$635
includes taxes & fees
27 Sept - 28 Sept
Tower Haus w/Private Hot Tub
A two-story house with a stone chimney, a brick exterior, and a front porch with a bench.

8. Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park

Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
3.0 star property
Chesterton
Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
A modern living room with a grey sofa set, a fireplace, and large windows.

9. Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes

Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes
Chesterton
9.2 out of 10, Wonderful, (22 reviews)
"I really enjoyed my stay even though I did not venture out but the house was like a dreamy oasis. "
United States
Kendall C.
The price is NZ$1,260
includes taxes & fees
27 Sept - 28 Sept
Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes
A spacious living room with a gray sofa, a wooden coffee table, and a colorful striped rug. There is a dining area with a white table and chairs, and large windows offering a view of the outdoors.

10. Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park

Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
Chesterton
9.4 out of 10, Exceptional, (26 reviews)
"This place was so roomy, clean, and comfortable. Plenty of room to relax and enjoy family company. "
United States
Kile B.
The price is NZ$1,084
includes taxes & fees
27 Sept - 28 Sept
Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
A beach with a parking lot and a building with arched windows.

11. 1:00 pm Check-In & Out! - 1 mile to Dunes - Roomy-Sleeps 16 - 🎮Game Room Loft🏓

1:00 pm Check-In & Out! - 1 mile to Dunes - Roomy-Sleeps 16 - 🎮Game Room Loft🏓
Porter
10.0 out of 10, Exceptional, (101 reviews)
"Our family enjoyed our stay very much, especially with having the clean well-kept accommodations and so close to our favorite Lake Michigan beaches. This is a very comfortable home for family to relax and enjoy their home away from home."
United States
Aleta F.
The price is NZ$1,418
includes taxes & fees
13 Oct - 14 Oct
1:00 pm Check-In & Out! - 1 mile to Dunes - Roomy-Sleeps 16 - 🎮Game Room Loft🏓
A bedroom with two beds, a ceiling fan, a TV on a dresser, and a window with blinds.

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

Full House booking of a history building close to the Dunes
Chesterton
9.4 out of 10, Exceptional, (6 reviews)
"Beautiful historic building. "
United States
Deborah S.
The price is NZ$3,835
includes taxes & fees
6 Oct - 7 Oct
Full House booking of a history building close to the Dunes
An outdoor garden pathway leading to a gazebo with a vine-covered archway.

13. Renovated 1971 Airstream on an 80 acre animal rescue farm in Westville IN

Renovated 1971 Airstream on an 80 acre animal rescue farm in Westville IN
Westville
9.8 out of 10, Exceptional, (8 reviews)
"What a unique and lovely stay! The airstream was thoughtfully renovated and the property was beautiful. Lots of trails to walk and animals to talk to. "
United States
Stef K.
The price is NZ$494
includes taxes & fees
27 Sept - 28 Sept
Renovated 1971 Airstream on an 80 acre animal rescue farm in Westville IN
A hotel lobby with a dining area, a reception desk, and a seating area with chairs and a table.

14. 2 Full Bed | Non-Smoking

2 Full Bed | Non-Smoking
Portage
9.8 out of 10, Exceptional, (65 reviews)
"Room was spacious with a nice layout, perfect for our group. Enjoyed the tea and coffee maker too. Free parking made it easy to explore the area without hassle."
United States
Anonymous traveller
The price is NZ$181
includes taxes & fees
5 Oct - 6 Oct
2 Full Bed | Non-Smoking
A hotel lobby with a dining area, a reception desk, and a seating area with chairs and a table.

15. Premium King Bed|Portage

Premium King Bed|Portage
Portage
10.0 out of 10, Exceptional, (63 reviews)
"A solid choice if you're in town. Felt welcomed by friendly staff at the 24-hour front desk who assisted us promptly when we arrived late at night."
United States
Anonymous traveller
The price is NZ$195
includes taxes & fees
27 Sept - 28 Sept
Premium King Bed|Portage
A modern kitchen with white cabinets, a stainless steel refrigerator, granite countertops, and a brick accent wall.

16. Newly Renovated / Dog Friendly / Sleeps 6

Newly Renovated / Dog Friendly / Sleeps 6
Michigan City
10.0 out of 10, Exceptional, (6 reviews)
"Lovely place, well stocked, clean, safe, comfortable and spacious. Location close to restaurants and outlet mall. Host was wonderful."
United States
Billie Farrar f.
The price is NZ$444
includes taxes & fees
30 Sept - 1 Oct
Newly Renovated / Dog Friendly / Sleeps 6
A spacious living room with a white sofa, two leather armchairs, a wooden coffee table, and a ceiling fan. Large windows offer views of a wooden deck and greenery.

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

Black Cabin Getaway in Beautiful Woods I Valpo University | Flint Lake | Dunes
Valparaiso
9.0 out of 10, Wonderful, (48 reviews)
"Quiet area. We enjoyed having a fenced in yard for our dog. Close to the State and National parks. We really enjoyed the hiking in the area."
United States
Amy H.
The price is NZ$528
includes taxes & fees
6 Oct - 7 Oct
Black Cabin Getaway in Beautiful Woods I Valpo University | Flint Lake | Dunes
A modern kitchen with white cabinetry, stainless steel appliances, and a marble countertop.

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

No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.
Michigan City
9.8 out of 10, Exceptional, (44 reviews)
"The home is beautiful and very clean. It is in an excellent location, close to IN Dunes National Park. We had a very nice stay and will definitely stay here again if we are in the area."
United States
Judy H.
The price is NZ$411
includes taxes & fees
12 Oct - 13 Oct
No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.
A staircase leading to a second floor in a building with a rustic interior, wooden beams, and a vintage poster on the wall.

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

Cozy loft inside a vintage store on an animal rescue farm in Westville, IN
Westville
10.0 out of 10, Exceptional, (17 reviews)
"Close to Indiana dunes. Had a great stay!"
United States
Jean G.
The price is NZ$548
includes taxes & fees
27 Sept - 28 Sept
Cozy loft inside a vintage store on an animal rescue farm in Westville, IN
A lighthouse at sunset with rough sea waves.

20. Treehouse Bungalow- Quaint and Cozy Getaway!

Treehouse Bungalow- Quaint and Cozy Getaway!
Michigan City
8.6 out of 10, Excellent, (60 reviews)
"Very cute and comfortable. "
United States
Jacqueline C.
The price is NZ$576
includes taxes & fees
27 Sept - 28 Sept
Treehouse Bungalow- Quaint and Cozy Getaway!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesterton Hotel Reviews

Comfort Inn Hammond I-94

Comfort Inn Hammond I-94

8/10 Good
"Very clean. Good place for a crash and dash we did not get a chance to check out the breakfast as it ended at nine."
Ron 1-night trip
Posted 14 hours ago
Comfort Inn Hammond I-94

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 favorite 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 depends 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 NZ$181 per night. Entering your travel dates in the search wizard you might find 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 Bailly Homestead - American Indians and Fur Traders and Indiana Dunes National Park.

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.