A wooden staircase ascending a sandy hill with sparse vegetation.

Chesterton Vacation Rentals

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Chesterton vacation rentals

Beach

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.
$139 nightly
The price is $156
Aug 27 - Aug 28
Total with taxes and fees
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Beach

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
$228 nightly
The price is $255
Aug 27 - Aug 28
Total with taxes and fees
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
Living area

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.
$353 nightly
The price is $395
Sep 3 - Sep 4
Total with taxes and fees
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
Exterior

4. The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly

The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Porter
9.2 out of 10, Wonderful, (7 reviews)
"We enjoyed our stay. Very inviting and comfortable accommodations. Would stay again and would recommend!"
United States
Amanda E.
$228 nightly
The price is $255
Sep 22 - Sep 23
Total with taxes and fees
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Beach

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.
$149 nightly
The price is $167
Sep 1 - Sep 2
Total with taxes and fees
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Beach

6. Tower Haus w/Private Hot Tub

Tower Haus w/Private Hot Tub
Chesterton
9.8 out of 10, Exceptional, (34 reviews)
"This is a great setup for visiting the Dunes and also Chicago via South Shore. Host was great and place was very clean and new."
United States
Kevin J.
$400 nightly
The price is $448
Aug 30 - Aug 31
Total with taxes and fees
Tower Haus w/Private Hot Tub
Interior

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.
$353 nightly
The price is $395
Sep 1 - Sep 2
Total with taxes and fees
NEW! Beautiful Riverfront Home on 10 Acres!
Room

8. 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.
$2,015 nightly
The price is $2,257
Sep 7 - Sep 8
Total with taxes and fees
Full House booking of a history building close to the Dunes
Property grounds

9. 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.
$253 nightly
The price is $283
Aug 27 - Aug 28
Total with taxes and fees
Renovated 1971 Airstream on an 80 acre animal rescue farm in Westville IN
Interior

10. 2 Full Bed | Non-Smoking

2 Full Bed | Non-Smoking
Portage
10.0 out of 10, Exceptional, (62 reviews)
"Spacious rooms gave us plenty of space for our things while we were there, enjoyed that feature!"
United States
Anonymous traveler
$95 nightly
The price is $105
Aug 30 - Aug 31
Total with taxes and fees
2 Full Bed | Non-Smoking
Dining

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
$103 nightly
The price is $114
Aug 30 - Aug 31
Total with taxes and fees
Premium King Bed|Portage
Terrace/patio

12. 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.
$214 nightly
The price is $239
Aug 30 - Aug 31
Total with taxes and fees
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
Living area

13. 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.
$344 nightly
The price is $386
Sep 21 - Sep 22
Total with taxes and fees
Black Cabin Getaway in Beautiful Woods I Valpo University | Flint Lake | Dunes
Private kitchen

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.
$238 nightly
The price is $267
Sep 25 - Sep 26
Total with taxes and fees
No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.
Interior

15. 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.
$280 nightly
The price is $314
Aug 27 - Aug 28
Total with taxes and fees
Cozy loft inside a vintage store on an animal rescue farm in Westville, IN
Private kitchen

16. 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.
$136 nightly
The price is $152
Sep 14 - Sep 15
Total with taxes and fees
Newely Remodeled Studio!
Private kitchen

17. Newly Renovated / Dog Friendly / Sleeps 6

Newly Renovated / Dog Friendly / Sleeps 6
Michigan City
10.0 out of 10, Exceptional, (5 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.
$277 nightly
The price is $299
Sep 23 - Sep 24
Total with taxes and fees
Newly Renovated / Dog Friendly / Sleeps 6
Interior

18. 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
$211 nightly
The price is $233
Aug 30 - Aug 31
Total with taxes and fees
Premium King Room with Jetted Tub
Beach

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.
$387 nightly
The price is $434
Sep 1 - Sep 2
Total with taxes and fees
Treehouse Bungalow- Quaint and Cozy Getaway!
Beach

20. Cozy House: 5 min drive to beach-zoo-restaurants-casino-brewery-train to Chicago

Cozy House: 5 min drive to beach-zoo-restaurants-casino-brewery-train to Chicago
Michigan City
9.8 out of 10, Exceptional, (28 reviews)
"It was a cute little place to stay"
United States
Janielle K.
$233 nightly
The price is $261
Sep 8 - Sep 9
Total with taxes and fees
Cozy House: 5 min drive to beach-zoo-restaurants-casino-brewery-train to Chicago
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

Furness Mansion

Furness Mansion

8/10 Good
"This was the first property I had stayed in that had a bidet and a heated towel bin, and a massage chair. Let me start by saying everything was lovely and the “Superior suite” accommodations worked out for my husband, son and myself. However, the advertisement for the accommodations on Expedia is incorrect. It states that there are three beds including a king, full, and sofa bed. In reality, there was only a king with a twin daybed in the same room. There was no sofa bed, and in fact, no sofa. Instead of a sofa, they had a reclining loveseat that was missing a cord or broken. I like attention to detail, and they need to work on the landscaping as the grass had been mowed when it was allowed to get too tall, and there’s a lot of weeds and trees allowed to grow out of control. The neighboring yards looked much better. Some of the flowerbeds however were beautiful."
Eileen 1-night trip
Posted 2 days ago
Furness Mansion

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 $156 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?

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.