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Chesterton Vacation Rentals

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Check prices for these dates

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

Our top choices for Chesterton vacation 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 CA $111
CA $287 total
includes taxes & fees
Dec 6 - Dec 7
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 CA $168
CA $207 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $169
CA $531 total
includes taxes & fees
Nov 24 - Nov 25
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 CA $281
CA $338 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $197
CA $429 total
includes taxes & fees
Nov 13 - Nov 14
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 CA $155
CA $360 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $182
CA $223 total
includes taxes & fees
Nov 23 - Nov 24
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 CA $242
CA $343 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $2,516
CA $3,055 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $129
CA $161 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $122
CA $380 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $139
CA $174 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $129
CA $161 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $176
CA $361 total
includes taxes & fees
Nov 30 - Dec 1
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 CA $146
CA $287 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $121
CA $151 total
includes taxes & fees
Nov 12 - Nov 13
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 CA $177
CA $421 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $304
CA $370 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $132
CA $311 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $140
CA $319 total
includes taxes & fees
Nov 11 - Nov 12
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

A spacious atrium with a stone and wood interior, a sign reading "White Birch Market," and a seating area with chairs.
Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo
New Buffalo

10/10 Excellent

How convenient the hotel was to the casino and the atmosphere in general
Canada
Devin
Reviewed November 8, 2026
Four Winds Casino Resort – New Buffalo

Find out more about Chesterton

Everything you need to know about Chesterton vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterton vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterton vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterton vacation rentals we have selected for you start as low as CA $374 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 vacation 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 vacation.

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 vacation rentals in Chesterton?

Yes, we give you a choice of vacation rentals close to the most popular local attractions in Chesterton, or you can choose a more secluded option if you're looking for relaxation. 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's the top vacation rental that Chesterton has to offer?

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park: This highly rated vacation home rental in Chesterton offers a patio, a private yard, and a barbecue grill 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 vacation with amenities like a selection of books.

How many vacation rentals are there in Chesterton?

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

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 vacation rentals like in Chesterton?

Vacation rentals are private properties you can reserve for a couple days or more in Chesterton. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for a family getaway.