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
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Chesterton vacation rentals

Beach nearby

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
8.8 out of 10, Excellent, (16 reviews)
"Great Stay!"
United States
Erin
The price is AED 621
AED 786 total
includes taxes & fees
2 Aug - 3 Aug
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Smart TV, fireplace, foosball, books

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, (21 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.
The price is AED 1,198
AED 2,802 total
includes taxes & fees
19 Jul - 20 Jul
Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes
Smart TV, fireplace, books

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, (71 reviews)
"Host was welcoming and very responsive "
United States
Shannon B.
The price is AED 591
AED 1,625 total
includes taxes & fees
27 Jul - 28 Jul
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
Beach nearby

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, (122 reviews)
"Hot tub was working great, air conditioning great, quite roomy, with a full kitchen."
United States
Piotr S.
The price is AED 474
AED 613 total
includes taxes & fees
2 Aug - 3 Aug
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Interior

NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
8.0 out of 10, Very Good, (9 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 AED 584
AED 1,452 total
includes taxes & fees
20 Jul - 21 Jul
NEW! Beautiful Riverfront Home on 10 Acres!
Private kitchen

Pleasant Townhome/Chesterton/Indiana Dunes/close to Chicago

Pleasant Townhome/Chesterton/Indiana Dunes/close to Chicago
Chesterton
The price is AED 1,194
AED 2,271 total
includes taxes & fees
20 Jul - 21 Jul
Pleasant Townhome/Chesterton/Indiana Dunes/close to Chicago
Beach

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
Chesterton
9.4 out of 10, Exceptional, (43 reviews)
"We loved the house. It was in a great location to all the dog friendly activities we did! Would definitely recommend staying here. "
United States
Raylynn K.
The price is AED 904
AED 1,031 total
includes taxes & fees
5 Aug - 6 Aug
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
Exterior

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

The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Porter
9.0 out of 10, Wonderful, (4 reviews)
"We enjoyed our stay. Very inviting and comfortable accommodations. Would stay again and would recommend!"
United States
Amanda E.
The price is AED 588
AED 1,140 total
includes taxes & fees
11 Aug - 12 Aug
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
House (4 Bedrooms) | Front of property

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 AED 1,091
AED 2,228 total
includes taxes & fees
5 Aug - 6 Aug
Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
Beach

Tower Haus w/Private Hot Tub

Tower Haus w/Private Hot Tub
Chesterton
9.8 out of 10, Exceptional, (29 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.
The price is AED 1,304
AED 2,082 total
includes taxes & fees
11 Aug - 12 Aug
Tower Haus w/Private Hot Tub
Property grounds

Heart of Indiana Dunes National Park with Hot Tub

Heart of Indiana Dunes National Park with Hot Tub
Chesterton
10.0 out of 10, Exceptional, (8 reviews)
"The house was beautiful and had so much charm. The amount of activities available was great. Highly recommend and we will definitely be back!"
United States
Becky G.
Heart of Indiana Dunes National Park with Hot Tub
Beach nearby

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, (18 reviews)
"Awesome place to stay and plenty to do"
United States
Cody
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
6 bedrooms, desk, free WiFi

Full House booking of a history building close to the Dunes

Full House booking of a history building close to the Dunes
Chesterton
9.0 out of 10, Wonderful, (4 reviews)
"Beautiful historic building. "
United States
Deborah S.
Full House booking of a history building close to the Dunes
Property grounds

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
9.4 out of 10, Exceptional, (3 reviews)
"A perfect getaway to clear the noise in your head"
United States
Edward
The price is AED 810
AED 1,039 total
includes taxes & fees
23 Jul - 24 Jul
Renovated 1971 Airstream on an 80 acre animal rescue farm in Westville IN
House (4 Bedrooms) | Interior

Group-friendly Michigan City Home Near Beach!

Group-friendly Michigan City Home Near Beach!
3.0 star property
Michigan City
10.0 out of 10, Exceptional, (2 reviews)
"This was exactly what we needed for our little family getaway. The only thing was there was very little parking and make sure to not park in the alley right next to the house as the neighbor will ask you to move. "
United States
Hannah
The price is AED 841
AED 2,049 total
includes taxes & fees
5 Aug - 6 Aug
Group-friendly Michigan City Home Near Beach!
Beach nearby

Treehouse Bungalow- Quaint and Cozy Getaway!

Treehouse Bungalow- Quaint and Cozy Getaway!
Michigan City
8.6 out of 10, Excellent, (55 reviews)
"Very cute and comfortable. "
United States
Jacqueline C.
The price is AED 757
AED 1,885 total
includes taxes & fees
19 Jul - 20 Jul
Treehouse Bungalow- Quaint and Cozy Getaway!
Property grounds

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, (133 reviews)
"Great spot. So close to the beach and the hot tub was amazing!"
United States
Sean B.
The price is AED 735
AED 1,316 total
includes taxes & fees
19 Jul - 20 Jul
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Beach nearby

The Boutique at Midtown Central / Hot Tub / Pet Friendly

The Boutique at Midtown Central / Hot Tub / Pet Friendly
Michigan City
9.8 out of 10, Exceptional, (16 reviews)
"Cute and cozy"
United States
angel R.
The price is AED 870
AED 1,648 total
includes taxes & fees
22 Jul - 23 Jul
The Boutique at Midtown Central / Hot Tub / Pet Friendly
Smart TV, books

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
9.2 out of 10, Wonderful, (45 reviews)
"Our stay was comfortable and the host was very communicative through the entire process. "
United States
Elizabeth G.
The price is AED 563
AED 1,334 total
includes taxes & fees
11 Aug - 12 Aug
Black Cabin Getaway in Beautiful Woods I Valpo University | Flint Lake | Dunes
1 bedroom, iron/ironing board, free WiFi, bed sheets

Classic One-Bedroom apartment with King Bed

Classic One-Bedroom apartment with King Bed
La Porte
The price is AED 637
AED 1,377 total
includes taxes & fees
16 Aug - 17 Aug
Classic One-Bedroom apartment with King Bed
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

Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes

10/10 Excellent
"Very nice stay at this hotel. The breakfast was "minimal" continental style. Would have liked to see some additional fruit choices besides apples. Bananas or oranges would have been nice options. The pool and hot tub area was nice. The floor is very slippery when wet so be careful! Overall this was a great location for us and visiting the Dunes areas."
melissa 2-night trip
Posted 12 hours ago
Comfort Inn & Suites Porter near Indiana Dunes

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 36 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 Indiana Dunes State Park and Lustron House.

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.