A wooden staircase ascending a sandy hill with sparse vegetation.

Chesterton Holiday Rentals

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Check prices for these dates

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

Our top choices for Chesterton holiday 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 HK$1,325
HK$1,668 total
includes taxes & fees
11 Aug - 12 Aug
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Smart TV, fireplace, table football, 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 HK$2,209
HK$5,538 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 HK$1,261
HK$3,467 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 HK$1,011
HK$1,308 total
includes taxes & fees
26 Jul - 27 Jul
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 HK$1,246
HK$3,099 total
includes taxes & fees
20 Jul - 21 Jul
NEW! Beautiful Riverfront Home on 10 Acres!
Living area

Pleasant Townhome/Chesterton/Indiana Dunes/close to Chicago

Pleasant Townhome/Chesterton/Indiana Dunes/close to Chicago
Chesterton
The price is HK$2,547
HK$4,846 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 HK$1,929
HK$2,201 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 HK$1,254
HK$2,432 total
includes taxes & fees
11 Aug - 12 Aug
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
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 HK$2,328
HK$4,755 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 HK$2,743
HK$4,389 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.
The price is HK$6,772
HK$8,664 total
includes taxes & fees
21 Jul - 22 Jul
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 price is HK$1,764
HK$2,204 total
includes taxes & fees
5 Aug - 6 Aug
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.
The price is HK$13,967
HK$17,873 total
includes taxes & fees
10 Aug - 11 Aug
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
9.0 out of 10, Wonderful, (2 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 HK$1,728
HK$2,217 total
includes taxes & fees
16 Jul - 17 Jul
Renovated 1971 Airstream on an 80 acre animal rescue farm in Westville IN
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 HK$1,795
HK$4,373 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 HK$1,615
HK$4,021 total
includes taxes & fees
20 Jul - 21 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 HK$1,568
HK$2,809 total
includes taxes & fees
10 Aug - 11 Aug
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 HK$1,873
HK$3,534 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 HK$1,312
HK$3,023 total
includes taxes & fees
21 Jul - 22 Jul
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 HK$1,205
HK$2,767 total
includes taxes & fees
21 Jul - 22 Jul
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

The Blue Heron Inn

The Blue Heron Inn

8/10 Good
"We had a relaxing stay at the Blue Heron. They have a nice breakfast in a cute breakfast area. The dockside bar and restaurant was very good and convenient with excellent service. We also tried out the onsite steakhouse (T-bones), great food and drinks. One of the best things about our stay was the view from our balcony. We had an upper floor facing the lake. The sunset was beautiful. The check-in staff was very nice and helpful. My one disappointment with our stay was we were charged a different price than what the original confirmation stated. "
Rose 2-night trip
Posted 10 hours ago
The Blue Heron Inn

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
  • Use the map to find apartments and other holiday homes in the Chesterton neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesterton while they last

Look no further and take a look at our great range of rental properties in Chesterton!

Frequently asked questions

Are there holiday rentals in Chesterton?

Yes, there are holiday rentals close to the most popular sights in Chesterton, or you can select a more secluded option if you're looking for a relaxing stay. 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 are some of the best holiday rentals that Chesterton has to offer?

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park: This highly rated holiday home rental in Chesterton offers a patio, a private garden and a BBQ 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 holiday with amenities such as a selection of books.

How many holiday rentals are there in Chesterton?

Choose from 36 Expedia holiday rentals in Chesterton for a memorable holiday.

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 holiday rentals like in Chesterton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterton. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for family gatherings.