A wooden staircase ascending a sandy hill with sparse vegetation.

Chesterton Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Chesterton vacation 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, (138 reviews)
"Very cozy, comfortable, and relaxing we’ll stay there again"
United States
Vanski M.
$139 nightly
The price is $156
Oct 13 - Oct 14
Total with taxes and fees
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, (10 reviews)
"We enjoyed our stay. Very inviting and comfortable accommodations. Would stay again and would recommend!"
United States
Amanda E.
$224 nightly
The price is $251
Nov 4 - Nov 5
Total with taxes and fees
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
A beach with sand dunes and grass.

3. 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
$225 nightly
The price is $252
Oct 13 - Oct 14
Total with taxes and fees
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
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

Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
Chesterton
9.6 out of 10, Exceptional, (75 reviews)
"Very nice space, with plenty of room and a great location. "
United States
Briana R.
$339 nightly
The price is $380
Oct 12 - Oct 13
Total with taxes and fees
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
A beach with sand dunes and grass.

5. 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.
$149 nightly
The price is $167
Oct 12 - Oct 13
Total with taxes and fees
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
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!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
7.8 out of 10, Good, (13 reviews)
"A nice house, everything is fine, you just have to take into account that there are many mosquitoes and flies"
United States
Maria jose S.
$352 nightly
The price is $394
Nov 1 - Nov 2
Total with taxes and fees
NEW! Beautiful Riverfront Home on 10 Acres!
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

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.
$2,036 nightly
The price is $2,280
Oct 12 - Oct 13
Total with taxes and fees
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.

8. 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
$91 nightly
The price is $101
Oct 12 - Oct 13
Total with taxes and fees
King Bed | Non-Smoking
A hotel lobby with a dining area, a reception desk, and a seating area with chairs and a table.

9. 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 traveler
$99 nightly
The price is $109
Oct 12 - Oct 13
Total with taxes and fees
Premium King Bed|Portage
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

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.
$274 nightly
The price is $307
Oct 19 - Oct 20
Total with taxes and fees
Black Cabin Getaway in Beautiful Woods I Valpo University | Flint Lake | Dunes
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

Charming 1-bedroom apt in house by creek with AC, in delightful Portage
Portage
9.8 out of 10, Exceptional, (11 reviews)
"This was a very comfortable space for our Indiana Dunes area trip. It was the perfect place to relax after busy days at the area attractions. Our host was very kind and messaged us after we arrived to make sure we had everything we needed for our stay and again a couple of days later for the same."
United States
Michael T.
$268 nightly
The price is $300
Oct 31 - Nov 1
Total with taxes and fees
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
A hotel lobby with a dining area, a reception desk, and a seating area with chairs and a table.

12. 2 Full Bed | Non-Smoking

2 Full Bed | Non-Smoking
Portage
9.6 out of 10, Exceptional, (66 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
$91 nightly
The price is $101
Oct 12 - Oct 13
Total with taxes and fees
2 Full Bed | Non-Smoking
A hotel lobby with a dining area, a reception desk, and a seating area with chairs and a table.

13. Premium King Room with Jetted Tub

Premium King Room with Jetted Tub
Portage
10.0 out of 10, Exceptional, (84 reviews)
"Nice hot tub and friendly staff made our stay enjoyable."
United States
Anonymous traveler
$202 nightly
The price is $224
Nov 1 - Nov 2
Total with taxes and fees
Premium King Room with Jetted Tub
A modern kitchen with white cabinetry, stainless steel appliances, and a marble countertop.

14. 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, (48 reviews)
"Very cute house in a great location. Very convenient to The Dunes beaches and hiking."
United States
Crystal K.
$219 nightly
The price is $245
Oct 12 - Oct 13
Total with taxes and fees
No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.
A compact kitchen with a stove, microwave, and a dining area with a glass table and chairs.

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.
$193 nightly
The price is $216
Oct 12 - Oct 13
Total with taxes and fees
Downtown Getaway 2
A staircase leading to a second floor in a building with a rustic interior, wooden beams, and a vintage poster on the wall.

16. 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, (18 reviews)
"Close to Indiana dunes. Had a great stay!"
United States
Jean G.
$280 nightly
The price is $314
Oct 12 - Oct 13
Total with taxes and fees
Cozy loft inside a vintage store on an animal rescue farm in Westville, IN
A hotel lobby with a dining area, a reception desk, and a computer station.

17. King Bed | Non-Smoking

King Bed | Non-Smoking
Portage
10.0 out of 10, Exceptional, (83 reviews)
"Loved how peaceful it was. Perfect place to recharge after our daily outings."
United States
Anonymous traveler
$110 nightly
The price is $122
Oct 12 - Oct 13
Total with taxes and fees
King Bed | Non-Smoking
A modern kitchen with stainless steel appliances, wooden cabinets, and built-in shelves.

18. Newely Remodeled Studio!

Newely Remodeled Studio!
Michigan City
9.0 out of 10, Wonderful, (26 reviews)
"It was amazing and close by the dunes for our National Park and hiking day. Nice area with lots of restaurants around, and the place was super clean and cozy!"
United States
JoC S.
$150 nightly
The price is $167
Oct 18 - Oct 19
Total with taxes and fees
Newely Remodeled Studio!
A hot tub with a control panel, a wooden wall, and a stone-like exterior.

19. 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, (141 reviews)
"Such a beautiful location, easy access to the the beach, and the view was gorgeous. Also, the entertainment options in the Miami were incredible. Will absolutely visit again."
United States
Katie K.
$235 nightly
The price is $263
Oct 13 - Oct 14
Total with taxes and fees
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
A hotel room with two beds, a desk, a TV, and a seating area with a sofa and chairs.

20. Portage|Suite - Two Double

Portage|Suite - Two Double
Portage
10.0 out of 10, Exceptional, (48 reviews)
"Spacious area for two people, felt cozy yet roomy enough for comfort while hanging out together."
United States
Anonymous traveler
$110 nightly
The price is $122
Oct 12 - Oct 13
Total with taxes and fees
Portage|Suite - Two Double
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

Spring House Inn

Spring House Inn

10/10 Excellent
"The room was large with comfortable beds. We enjoyed the view of the forest from our balcony."
Carol 1-night trip
Posted 5 hours ago
Spring House Inn

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Chesterton in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $101 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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.