Hotels in Chesterton

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Check prices for these dates

Tonight
May 17 - May 18
Tomorrow
May 18 - May 19
Next weekend
May 23 - May 25
In two weeks
May 30 - Jun 1

Where to stay in Chesterton?

Best Western Indian Oak
Lobby

Best Western Indian Oak

2.5 star property
8.6 out of 10, Excellent, (1005)
$100 nightly
The price is $112
May 18 - May 19
Total includes taxes and fees
Best Western Indian Oak
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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Our prices for hotels in Chesterton are cheapest in February

See average prices and weather for all months

Price trends for hotels in Chesterton

Pricing is based on two traveler single night rates
May
$140
Average price during May is $140
Jun
$157
Average price during June is $157
Jul
$165
Average price during July is $165
Aug
$163
Average price during August is $163
Sep
$137
Average price during September is $137
Oct
$135
Average price during October is $135
Nov
$117
Average price during November is $117
Dec
$124
Average price during December is $124
Jan
$112
Average price during January is $112
Feb
$102
Average price during February is $102
Mar
$110
Average price during March is $110
Apr
$111
Average price during April is $111
Currently viewing crowd sizes and weather for May.

May

trending_flatModerate crowds
High 65°F / low 52°F. Sunny most days.
65°
weather_sun
May, Moderate crowds, average high temperature 65 degrees Fahrenheit, average low temperature 52 degrees Fahrenheit. Sunny most days.
52°
74°
weather_sun
June, High crowds, average high temperature 74 degrees Fahrenheit, average low temperature 61 degrees Fahrenheit. Sunny most days.
61°
79°
weather_sun
July, High crowds, average high temperature 79 degrees Fahrenheit, average low temperature 66 degrees Fahrenheit. Sunny most days.
66°
78°
weather_sun
August, High crowds, average high temperature 78 degrees Fahrenheit, average low temperature 65 degrees Fahrenheit. Sunny most days.
65°
73°
weather_sun
September, High crowds, average high temperature 73 degrees Fahrenheit, average low temperature 60 degrees Fahrenheit. Sunny most days.
60°
61°
weather_sun
October, Moderate crowds, average high temperature 61 degrees Fahrenheit, average low temperature 49 degrees Fahrenheit. Sunny most days.
49°
47°
weather_partly_sunny
November, Moderate crowds, average high temperature 47 degrees Fahrenheit, average low temperature 37 degrees Fahrenheit. Partly sunny.
37°
38°
weather_cloudy
December, Low crowds, average high temperature 38 degrees Fahrenheit, average low temperature 29 degrees Fahrenheit. Cloudy most days.
29°
31°
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January, Low crowds, average high temperature 31 degrees Fahrenheit, average low temperature 21 degrees Fahrenheit. Snow likely.
21°
33°
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February, Low crowds, average high temperature 33 degrees Fahrenheit, average low temperature 22 degrees Fahrenheit. Snow likely.
22°
44°
weather_cloudy
March, Moderate crowds, average high temperature 44 degrees Fahrenheit, average low temperature 32 degrees Fahrenheit. Cloudy most days.
32°
54°
weather_sun
April, Low crowds, average high temperature 54 degrees Fahrenheit, average low temperature 41 degrees Fahrenheit. Sunny most days.
41°
Monthly weather averages (˚F)
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Top landmarks in Chesterton

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

Indiana Dunes State Park

Indiana Dunes State Park is 3.2 mi (5.2 km) from central Chesterton, why not stop by during your stay. Chesterton has other activities you might want to enjoy such as Indiana Dunes National Park.

See properties in Indiana Dunes State Park
Indiana Dunes State Park

Learn more about Chesterton

Chesterton is well-known for its top attractions such as Indiana Dunes National Park and Lake Michigan. Visitors to this beachside city speak highly of the restaurants whereas sights include Indiana Dunes Visitor Center and Bailly Homestead - American Indians and Fur Traders.

See all hotels in Chesterton
Indiana Dunes State Park which includes a sandy beach and general coastal views as well as a family
Photo by Indiana Office of Tourism Development
Open Photo by Indiana Office of Tourism Development
A tranquil hotel pool encircled by beautiful arches, enhancing the ambiance for leisure and relaxation.

Summer Getaway Sale

Save 25% or more on select hotels, and earn 50% more rewards on all properties. Book by May 26 and travel by Sep 30, 2025. See terms*
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Frequently asked questions

What hotels do travelers recommend in Chesterton?
Spring House Inn, Hilton Garden Inn Chesterton and Furness Mansion are all accommodations that are popular with guests.
Where can I get free parking with my stay in Chesterton?
These hotels offer the perk of free parking: Riley’s Railhouse Bed & Breakfast and Gray Goose Inn.
Can I book refundable hotels in Chesterton?
If you’re looking for the flexibility to change your plans to Chesterton, most accommodations offer refundable* rates you can book. You can find these properties by searching our site and using the “fully refundable” filter to narrow the results down.
Where can I stay with my pet in Chesterton?
Your animal companion is welcome at these pet-friendly hotels: Hilton Garden Inn Chesterton, Furness Mansion, and Fairbridge Inn Express Chesterton.
Which Chesterton hotels do our guests like for their central location?
Our guests rave about the location of these properties: Spring House Inn and Best Western Indian Oak.
Where can I stay in Chesterton if I'm looking for a budget-friendly accommodation?
Two inexpensive options worth considering are Spring House Inn and Comfort Inn & Suites Porter near Indiana Dunes.
Where can I stay in Chesterton if I want a vacation home instead of a hotel?
If you want a good alternative to a hotel, look over our selection of 29 vacation homes. You can also consider one of the 9 apartments or 8 cottages.
Where can I stay if I'm visiting Chesterton with my kids?
Your kids are welcome at Best Western Indian Oak, Hilton Garden Inn Chesterton and Comfort Inn & Suites Porter near Indiana Dunes. You can also check out 5 options available on our site.
What will the weather in Chesterton be like during my visit?
July and August are typically the warmest months in Chesterton when the average temp is 70°F. January and February are the coldest months when the average temperature is 31°F. June and May are the months with the most rain.
Why should I book my Chesterton hotel with Hotels.com?
There are lots of reasons to book your Chesterton trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

Terms and conditions

*Book by 5/26/2025 11:59 pm in hotel property local time. Stay between 4/17/2025-9/30/2025. Member Prices are available to Hotels.com® app users and One Key members. Limited availability, blackout periods may apply.

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