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
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Chesterton holiday rentals

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

1. 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, (11 reviews)
"We enjoyed our stay. Very inviting and comfortable accommodations. Would stay again and would recommend!"
United States
Amanda E.
The price is NZ$362
includes taxes & fees
6 Dec - 7 Dec
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
A beach with a parking lot and buildings in the background.

2. 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, (141 reviews)
"Perfect for location to walk to local winery or brewery for a little fancy and fancy-free!We’d recommend"
United States
Laura H.
The price is NZ$265
includes taxes & fees
10 Nov - 11 Nov
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
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, (77 reviews)
"Great location, walking distance to downtown Chesterton which had an excellent ice cream shop and other restaurants. Easy driving distance to different parts of Indiana Dunes National Park. Host had great communication before and throughout the visit and the house had all the amenities we needed."
United States
Ammari Capito F.
The price is NZ$617
includes taxes & fees
24 Nov - 25 Nov
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
A beach with sand dunes and grass.

4. 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$430
includes taxes & fees
10 Nov - 11 Nov
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
A living room with a flat-screen TV, a wooden console table, a green armchair, a leather sofa, and a ceiling fan.

5. Dunes Homestead - Near Dunes + Lake + Dog Friendly

Dunes Homestead - Near Dunes + Lake + Dog Friendly
Porter
9.8 out of 10, Exceptional, (37 reviews)
"Everything was as described, and had everything we needed!"
United States
Chrissy B.
The price is NZ$540
includes taxes & fees
13 Nov - 14 Nov
Dunes Homestead - Near Dunes + Lake + Dog Friendly
A beach with a sunset, waves, and sparse vegetation.

6. Tower Haus w/Private Hot Tub

Tower Haus w/Private Hot Tub
Chesterton
9.8 out of 10, Exceptional, (38 reviews)
"Great place to stay! It was really clean! Highly recommend!"
United States
Joshua N.
The price is NZ$440
includes taxes & fees
10 Nov - 11 Nov
Tower Haus w/Private Hot Tub
A beach with sand dunes and grass.

7. 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)
"Camper is small, but cozy and worked well for my son and I to spend a few days relaxing! Hosts are very friendly, responsive, and helpful and we loved spending time in the pool."
United States
Melissa P.
The price is NZ$285
includes taxes & fees
23 Nov - 24 Nov
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
A wooden deck with a glass-top table and chairs, surrounded by lush greenery.

8. Indiana Dunes National Park

Indiana Dunes National Park
Porter
9.4 out of 10, Exceptional, (3 reviews)
"Clean accommodations, everything was as advertised for our 1 night stay. The album collection was a bonus."
United States
Heather F.
The price is NZ$432
includes taxes & fees
11 Nov - 12 Nov
Indiana Dunes National Park
A bedroom with two beds, a ceiling fan, a TV on a dresser, and a window with blinds.

9. 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)
"We are happy with the property. clean property, quite spacious and large enough to accommodate large group, quite close to Dunes."
United States
Mahesh K.
The price is NZ$3,782
includes taxes & fees
10 Dec - 11 Dec
Full House booking of a history building close to the Dunes
A hotel lobby with a dining area, a reception desk, and a seating area with chairs and a table.

10. King Bed | Non-Smoking

King Bed | Non-Smoking
Portage
10.0 out of 10, Exceptional, (68 reviews)
"The place is not clean and it smells really bad. It did not look anything like the pictures."
United States
Luis
The price is NZ$204
includes taxes & fees
10 Nov - 11 Nov
King Bed | Non-Smoking
A spacious living room with a white sofa, two leather chairs, a wooden coffee table, and large windows offering a view of the outdoors.

11. 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)
"It was wonderful, peaceful and pet friendly"
United States
Bryan D.
The price is NZ$480
includes taxes & fees
10 Nov - 11 Nov
Black Cabin Getaway in Beautiful Woods I Valpo University | Flint Lake | Dunes
A hotel lobby with a dining area, a reception desk, and a seating area with chairs and a table.

12. Premium King Bed|Portage

Premium King Bed|Portage
Portage
10.0 out of 10, Exceptional, (65 reviews)
"Sketchy property location, not clearly marked on the street (kind of hard to find), unnecessary poor communication regarding check-in procedures, (just like a regular front desk experience but they make it complicated) The room was ok, bed was fine, staff was very helpful, property condition was just ok."
United States
Dave
The price is NZ$220
includes taxes & fees
10 Nov - 11 Nov
Premium King Bed|Portage
A hotel lobby with a dining area, a reception desk, and a seating area with chairs and a table.

13. 2 Full Bed | Non-Smoking

2 Full Bed | Non-Smoking
Portage
9.6 out of 10, Exceptional, (67 reviews)
"This was one of the worst places I have stayed in! The place was in sad need of repairs and although it said no smoking the lobby smelled strongly of smoke, The whole place seemed unclean. I would not recommend it nor will i ever stay there again."
United States
Jacki
The price is NZ$204
includes taxes & fees
10 Nov - 11 Nov
2 Full Bed | Non-Smoking
A hot tub with water, a wooden deck, and a chair.

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

Charming 1-bedroom apt in house by creek with AC, in delightful Portage
Portage
9.8 out of 10, Exceptional, (11 reviews)
"Nice place close to the beach."
United States
Zdenek M.
The price is NZ$453
includes taxes & fees
30 Nov - 1 Dec
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
A living room with a sofa, armchair, coffee table, and a lamp.

15. Downtown Getaway 2

Downtown Getaway 2
Michigan City
9.2 out of 10, Wonderful, (40 reviews)
"Clean property, easy parking, nice area"
United States
Sandi B.
The price is NZ$365
includes taxes & fees
10 Nov - 11 Nov
Downtown Getaway 2
A hotel lobby with a dining area, seating, a reception desk, and a fire extinguisher.

16. Full Bed Accessible|Portage

Full Bed Accessible|Portage
Portage
10.0 out of 10, Exceptional, (82 reviews)
"Spotless bathrooms with enough towels were greatly appreciated, cleanliness makes such a difference!"
United States
Anonymous traveller
The price is NZ$192
includes taxes & fees
10 Nov - 11 Nov
Full Bed Accessible|Portage
A lighthouse at sunset with rough sea waves.

17. Treehouse Bungalow- Quaint and Cozy Getaway!

Treehouse Bungalow- Quaint and Cozy Getaway!
Michigan City
8.6 out of 10, Excellent, (62 reviews)
"We loved our accommodations and the host is wonderful!"
United States
Unspecified U.
The price is NZ$534
includes taxes & fees
10 Nov - 11 Nov
Treehouse Bungalow- Quaint and Cozy Getaway!
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, (52 reviews)
"Very cute house in a great location. Very convenient to The Dunes beaches and hiking."
United States
Crystal K.
The price is NZ$467
includes taxes & fees
10 Nov - 11 Nov
No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.
A modern kitchen with white cabinets, a stainless steel refrigerator, granite countertops, and a brick accent wall.

19. 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$396
includes taxes & fees
10 Nov - 11 Nov
Newly Renovated / Dog Friendly / Sleeps 6
A lighthouse by the sea with a pier extending into the water.

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

BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Michigan City
9.2 out of 10, Wonderful, (144 reviews)
"Its was ok"
United States
Amber C.
The price is NZ$406
includes taxes & fees
10 Nov - 11 Nov
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
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

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

8/10 Good
"N/a"
Emily 1-night trip
Posted 1 hour ago
Blue Chip Casino Hotel and Spa

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$265 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 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.