Chesterton Holidays

Photo by City Circus Wandering

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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 S$185 per night from 3 Aug to 4 Aug
S$185
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"It reminder me of a german house. Everything was clean but it was old . No elevator but the ckerk was nice enought to give us a room on the main floor. Pool was nice and pool area was clean. Breakfast was ok"

Reviewed on 8 Jul, 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 S$186 per night from 10 Aug to 11 Aug
S$186
10 Aug - 11 Aug
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
"The room was nice and clean. The dining area was too small for the mornings we were there and insufficient kitchen equipment. Highly recommend having two waffle making stations at different locations. Also recommend two toasters. Both of these stations had lines the entire time I wae eating."

Reviewed on 1 Jul, 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
The price is S$172 per night from 3 Aug to 4 Aug
S$172
3 Aug - 4 Aug
includes taxes & fees
8/10 Very Good! (865 reviews)
"As described. Nothin fancy but nice and clean. Great staff! Nice guy"

Reviewed on 7 Jul, 2025

Waterbird Lakeside Inn
See all 1,378 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.

What to do in Chesterton

Red Fox

Indiana Dunes National Park Self-Guided Audio Tour

S$19
per traveller
Indiana Dunes National Park Self-Guided Audio Tour
See all activities in Chesterton

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.