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Boutique Hotels & Resorts in Chesterton

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Check availability on Chesterton Boutique Hotels

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Recommended hotels in Chesterton

Best Western Indian Oak

Best Western Indian Oak
2.5 star property
Chesterton
8.6 out of 10, Excellent, (1004)
"It was very nice, with great access to the national park."
United States
leona ann
The price is AU$158
includes taxes & fees
23 Dec - 24 Dec
Best Western Indian Oak

Spring House Inn

Spring House Inn
2.5 star property
Chesterton
9.0 out of 10, Wonderful, (1002)
"Beautiful Hotel"
United States
Joseph
The price is AU$141
includes taxes & fees
15 Jan - 16 Jan 2026
Spring House Inn

Waterbird Lakeside Inn

Waterbird Lakeside Inn
2.0 star property
Chesterton
8.2 out of 10, Very good, (989)
"Balcony was a nice extra. Room was clean and bed was comfortable. I’d stay here again if in the area"
United States
Jorge
Waterbird Lakeside Inn

Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
3.0 star property
Chesterton
8.8 out of 10, Excellent, (1004)
"We loved staying here. "
United States
Linda
The price is AU$179
includes taxes & fees
23 Dec - 24 Dec
Hilton Garden Inn Chesterton

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
9.0 out of 10, Wonderful, (12)
"Hosts are easy to communicate with and very nice. The pool barn is not part of the package. You will be able to swim and use the hot tub, however. We enjoyed the hot tub after a day of hiking! Cute town with interesting places to visit. "
United States
Sherri K.
The price is AU$136
includes taxes & fees
29 Dec - 30 Dec
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes
2.5 star property
Chesterton
8.0 out of 10, Very good, (1002)
"Nice and close to the beach."
United States
Alison
The price is AU$153
includes taxes & fees
21 Dec - 22 Dec
Comfort Inn & Suites Porter near Indiana Dunes

Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes

Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes
Chesterton
9.8 out of 10, Exceptional, (63)
"This place was great. It was very spacious, clean, and close to restaurants and grocery stores. The host was very communicative and answered any questions we had very quickly. The house was easy to find and parking was right in front of the house. The neighborhood was quiet and safe."
United States
Christine C.
The price is AU$480
includes taxes & fees
18 Dec - 19 Dec
Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes

Quality Inn Chesterton near Indiana Dunes National Park I-94

Quality Inn Chesterton near Indiana Dunes National Park I-94
2.5 star property
Chesterton
8.0 out of 10, Very good, (718)
"Clean room, easy check in"
United States
Billy
The price is AU$132
includes taxes & fees
7 Jan - 8 Jan 2026
Quality Inn Chesterton near Indiana Dunes National Park I-94

Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago

Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago
Chesterton
8.6 out of 10, Excellent, (7)
"Excellent spot for several people to stay and enjoy the Dunes. Clean, quiet, centrally located to lots of Dunes hotspots. Thanks for the great stay!"
United States
Nick R.
The price is AU$489
includes taxes & fees
18 Dec - 19 Dec
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago

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
8.8 out of 10, Excellent, (16)
"Great place to stay with kids."
United States
Jane H.
The price is AU$233
includes taxes & fees
21 Dec - 22 Dec
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
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.

Top Chesterton Hotel Reviews

Frequently asked questions

What's there to see and do in Chesterton?
The beaches, shopping and lakefront are just some of the things to enjoy while you're in the area. Activities and attractions to experience around Chesterton include Lake Michigan, Lustron House and Chesterton Art Center. You might also like to explore more of the area and take in additional sights like Chellberg Farm, Chicago Street Theatre and Barker Mansion while you're here.
What kind of weather should I plan for when I travel to Chesterton?
Understanding the weather in Chesterton will help you enjoy your stay to the fullest. The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Chesterton are January, December, November and February, with each month seeing an average of 15 cm of snowfall.
What's the best way to get to my boutique hotel in Chesterton?
You have a few options for travelling to and around Chesterton. The nearest major airport is Chicago Midway Airport (MDW), which is located 37 mi (59.6 km) from the heart of the city. If you'd like to explore around the area, you may want a rental car for your journey.

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