Chesterton Holidays

Photo by City Circus Wandering

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to HK$1,282 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Chesterton

Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is HK$856 per night from 2 Sept to 3 Sept
HK$856
HK$998 total
2 Sept - 3 Sept
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"I feel better breakfast options but everything else was perfect"

Reviewed on 10 Aug 2025

Spring House Inn
Best Western Indian Oak

Best Western Indian Oak

2.5 out of 5
558 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is HK$801 per night from 1 Sept to 2 Sept
HK$801
HK$897 total
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
"Was close to the National Park. Rooms are what you’d expect. Pillows could have been better. Water pressure decent and the breakfast at least didn’t have the powdered eggs that a lot of places put out. Decent value for a place to crash after hiking the Dunes."

Reviewed on 10 Aug 2025

Best Western Indian Oak
Waterbird Lakeside Inn

Waterbird Lakeside Inn

2 out of 5
556 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
8/10 Very Good! (899 reviews)
"Nice and clean place to stay!"

Reviewed on 7 Aug 2025

Get rates
Waterbird Lakeside Inn
See all 1,368 properties in Chesterton
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.

Popular places to visit

Indiana Dunes State Park which includes a sandy beach and general coastal views as well as a family

Indiana Dunes State Park

The southern shores of Lake Michigan consist of a stunning dune landscape, which is ideal for hiking, camping, bird-watching, picnicking and swimming.

Indiana Dunes State Park

Frequently asked questions

How much does a Chesterton holiday package cost?
You can grab a holiday package to this top destination on Expedia. However, how much your holiday to Chesterton costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Chesterton?
If you're looking to book a cheap Chesterton holiday package, consider planning a trip in December, January and February. You'll typically find lower prices on hotels and flights during these months — perfect for a budget-friendly getaway.
How many days is enough for Chesterton?
Typically, a few days is enough for a Chesterton holiday. With a carefully crafted itinerary, you can see all the top attractions like Coffee Creek Watershed Conservancy Preserve, as well as explore some hidden gems along the way.
Is it worth booking a holiday package to Chesterton?
From cool attractions such as Coffee Creek Watershed Conservancy Preserve and Lustron House to its terrific golfing, a Chesterton holiday guarantees an unforgettable adventure. With so much to see and do, find out for yourself why Chesterton is such a good holiday destination.
How to find the best Chesterton package deals?
Landing a cheap Chesterton package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can tweak your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Chesterton package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Chesterton holiday as a package?
An Expedia holiday package could land you significant savings when compared to booking stays and flights individually. Better still, you can personalise your Chesterton trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Chesterton?
If you're considering an impromptu Chesterton holiday, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Chesterton?

  1. Choose when to go: Check your calendar and get packing. Your preferred time of year and the activities on offer will also help you decide when to escape to Chesterton.
  2. Set a budget: Consider expenses such as food, flights and transportation when working out how much to save for your trip to Chesterton. Then, pick a property that matches your budget, whether that's a low-cost stay or a lavish retreat.
  3. Determine how many days away: Start by listing all the activities and sights you'd like to experience in Chesterton. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your airfare and accommodation: After you've nailed down your dates and duration, lock in the right Chesterton holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.