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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Chesterton vacation rentals

A beach with a parking lot and a building with a sloped roof.

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, (131 reviews)
"Very cozy, comfortable, and relaxing we’ll stay there again"
United States
Vanski M.
The price is ￥19,015
￥24,876 total
includes taxes & fees
Sep 2 - Sep 3
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
A beach with sand dunes and grass.

2. 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, (20 reviews)
"Awesome place to stay and plenty to do"
United States
Cody
The price is ￥31,798
￥40,625 total
includes taxes & fees
Sep 2 - Sep 3
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.

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 ￥17,430
￥61,041 total
includes taxes & fees
Sep 3 - Sep 4
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
A patio with a table and chairs, a bicycle, and a string of lights against a twilight sky.

4. 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 ￥18,376
￥41,699 total
includes taxes & fees
Sep 2 - Sep 3
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
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
8.4 out of 10, Very Good, (22 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 ￥20,613
￥26,666 total
includes taxes & fees
Sep 2 - Sep 3
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
A modern living room with a grey sofa set, a fireplace, and large windows.

6. 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.
Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes
A modern kitchen with a central island, wooden dining table, and chairs. There is a ceiling fan, a microwave, and a refrigerator.

7. NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
7.8 out of 10, Good, (13 reviews)
"Very tranquil and private stay. The house was clean and comfortable, the fire pit was very nice,. CLose to town, and close to the beach. We loved it."
United States
Jeff S.
The price is ￥25,454
￥63,293 total
includes taxes & fees
Sep 2 - Sep 3
NEW! Beautiful Riverfront Home on 10 Acres!
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.

8. 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 ￥38,509
￥91,809 total
includes taxes & fees
Sep 27 - Sep 28
Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
A two-story house with a stone chimney, a brick exterior, and a front porch with a bench.

9. 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
The price is ￥47,458
￥96,939 total
includes taxes & fees
Sep 27 - Sep 28
Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
A hotel lobby with a dining area, a reception desk, and a seating area with chairs and a table.

10. 2 Full Bed | Non-Smoking

2 Full Bed | Non-Smoking
Portage
10.0 out of 10, Exceptional, (62 reviews)
"Surprised by how quickly they brought room service! Enjoyed having breakfast right in our room one morning before heading out."
United States
Anonymous traveler
The price is ￥13,272
￥16,735 total
includes taxes & fees
Sep 3 - Sep 4
2 Full Bed | Non-Smoking
A compact kitchen with wooden cabinets, a dining table with chairs, a TV mounted on the wall, and a clock.

11. Premium King Bed|Portage

Premium King Bed|Portage
Portage
10.0 out of 10, Exceptional, (63 reviews)
"Three nights of hassle-free comfort with fast check-in processes. Really liked the helpful front desk staff!"
United States
Anonymous traveler
The price is ￥14,268
￥18,059 total
includes taxes & fees
Sep 14 - Sep 15
Premium King Bed|Portage
A staircase leading to a second floor in a building with a rustic interior, wooden beams, and a vintage poster on the wall.

12. 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 ￥39,149
￥50,111 total
includes taxes & fees
Sep 7 - Sep 8
Cozy loft inside a vintage store on an animal rescue farm in Westville, IN
A hot tub with water, a wooden deck, and a chair.

13. 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
9.6 out of 10, Exceptional, (10 reviews)
"Nice place close to the beach."
United States
Zdenek M.
The price is ￥17,434
￥39,787 total
includes taxes & fees
Sep 3 - Sep 4
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
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, (38 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 ￥31,798
￥40,267 total
includes taxes & fees
Sep 30 - Oct 1
No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.
A hotel lobby with a dining area, a reception desk, and a seating area with chairs and a table.

15. Premium King Room with Jetted Tub

Premium King Room with Jetted Tub
Portage
10.0 out of 10, Exceptional, (84 reviews)
"So comfortable, slept like a baby!"
United States
Anonymous traveler
The price is ￥29,364
￥37,024 total
includes taxes & fees
Sep 14 - Sep 15
Premium King Room with Jetted Tub
A beach with a pier extending into the water, a lighthouse in the distance, and the sun setting over the horizon.

16. The Boutique at Midtown Central / Hot Tub / Pet Friendly

The Boutique at Midtown Central / Hot Tub / Pet Friendly
Michigan City
9.6 out of 10, Exceptional, (19 reviews)
"Cute and cozy"
United States
angel R.
The price is ￥21,106
￥50,284 total
includes taxes & fees
Sep 2 - Sep 3
The Boutique at Midtown Central / Hot Tub / Pet Friendly
An outdoor garden pathway leading to a gazebo with a vine-covered archway.

17. 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, (6 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 ￥35,234
￥45,191 total
includes taxes & fees
Sep 2 - Sep 3
Renovated 1971 Airstream on an 80 acre animal rescue farm in Westville IN
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.

18. 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 ￥29,337
￥64,892 total
includes taxes & fees
Sep 9 - Sep 10
Black Cabin Getaway in Beautiful Woods I Valpo University | Flint Lake | Dunes
A lighthouse at sunset with rough sea waves.

19. Treehouse Bungalow- Quaint and Cozy Getaway!

Treehouse Bungalow- Quaint and Cozy Getaway!
Michigan City
8.6 out of 10, Excellent, (59 reviews)
"Very cute and comfortable. "
United States
Jacqueline C.
The price is ￥22,866
￥69,279 total
includes taxes & fees
Sep 2 - Sep 3
Treehouse Bungalow- Quaint and Cozy Getaway!
A modern kitchen with stainless steel appliances, wooden cabinets, and built-in shelves.

20. Newely Remodeled Studio!

Newely Remodeled Studio!
Michigan City
9.2 out of 10, Wonderful, (24 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.
The price is ￥12,943
￥24,339 total
includes taxes & fees
Sep 15 - Sep 16
Newely Remodeled Studio!
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

10/10 Excellent
"Clean rooms"
Patience 1-night trip
Posted 6 hours ago
Blue Chip Casino Hotel and Spa

Find out more about Chesterton

Search for holiday rentals in Chesterton on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterton using one of the methods below:

  • View our selection of featured holiday rentals in Chesterton
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Look no further and take a look at our great range of rental properties in Chesterton!

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?

Indiana Dunes National Park and Lake Michigan 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 Indiana Dunes Visitor Center.

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.