Chesterton Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by City Circus Wandering

Top hotels in Chesterton

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 3.653.039 ₫ per night from 30 Jun to 1 Jul
3.653.039 ₫
4.091.404 ₫ total
30 Jun - 1 Jul
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"location"

Reviewed on 24 Jun 2025

Best Western Indian Oak
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 3.105.305 ₫ per night from 30 Jun to 1 Jul
3.105.305 ₫
3.477.942 ₫ total
30 Jun - 1 Jul
includes taxes & fees
8.8/10 Excellent! (1,011 reviews)
"We really loved that hotel. The property is beautiful and well maintained."

Reviewed on 27 Jun 2025

Spring House Inn
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! (850 reviews)
"The rooms all have lake views. Lots of waterbirds to watch including a family of swans"

Reviewed on 24 Jun 2025

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Waterbird Lakeside Inn
See all 1,352 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.

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.

Popular places to visit

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

Indiana Dunes State Park

4/5(1 review)

You can take time to visit Indiana Dunes State Park during your travels to Chesterton. Wander the beautiful beaches and lakeside in the area.

Indiana Dunes State Park

Coffee Creek Watershed Conservancy Preserve

Explore the great outdoors at Coffee Creek Watershed Conservancy Preserve, a lovely green space in Chesterton. Wander the area's beautiful beaches or simply enjoy one of its cosy cafes.

Coffee Creek Watershed Conservancy Preserve

Lustron House

Find out about the history of Chesterton with a stop at Lustron House. Wander the area's beautiful beaches or simply enjoy one of its cosy cafes.

Lustron House