Photo by Susan Ross

Find a Bed and Breakfast in Chesterton from CA $100

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10
No exact matches found, but these alternatives could be just right

Recommended hotels in Chesterton

A modern building with large windows and balconies, a wooden deck, and a calm lake.

1. Best Western Indian Oak

Best Western Indian Oak
2.5 star property
Chesterton
8.6 out of 10, Excellent, (1,005 reviews)
"The staff was friendly and room was clean."
United States
Alyssa
The price is CA $126
CA $141 total
includes taxes & fees
Nov 16 - Nov 17
Best Western Indian Oak
A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.

2. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
3.0 star property
Chesterton
8.8 out of 10, Excellent, (1,007 reviews)
"Excellent hotel, friendly staff"
United States
Cheryl
The price is CA $180
CA $202 total
includes taxes & fees
Dec 4 - Dec 5
Hilton Garden Inn Chesterton
A spacious dining area with high ceilings and large windows, featuring wooden tables and chairs.

3. Spring House Inn

Spring House Inn
2.5 star property
Chesterton
8.8 out of 10, Excellent, (1,010 reviews)
"Good breakfast, staff was very helpful, there was a good restaurant on site."
United States
Michael
The price is CA $128
CA $151 total
includes taxes & fees
Nov 17 - Nov 18
Spring House Inn
A modern bathroom with a large mirror, a bathtub, and a sink.

4. Waterbird Lakeside Inn

Waterbird Lakeside Inn
2.0 star property
Chesterton
8.2 out of 10, Very good, (1,002 reviews)
"Loved the balcony overlooking the lake."
United States
Marsha
The price is CA $133
CA $149 total
includes taxes & fees
Nov 10 - Nov 11
Waterbird Lakeside Inn
A modern dining area with multiple tables and chairs, a kitchen area with blue cabinets, and a reception desk in the background.

5. 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
7.8 out of 10, Good, (874 reviews)
"Had a great weekend. Staff was great, room was clean, facility was great for a budget."
United States
Albie
The price is CA $107
CA $120 total
includes taxes & fees
Dec 8 - Dec 9
Quality Inn Chesterton near Indiana Dunes National Park I-94
A reception area with a counter, a vending machine, and a view of the outside through glass doors.

6. Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes
2.5 star property
Chesterton
7.8 out of 10, Good, (1,002 reviews)
"Good one night stay. Nice to have breakfast there before we headed out."
United States
Julie Van
The price is CA $115
CA $129 total
includes taxes & fees
Dec 1 - Dec 2
Comfort Inn & Suites Porter near Indiana Dunes
A large house surrounded by dense forest with a beach and ocean in the background.

7. Furness Mansion

Furness Mansion
2.0 star property
Chesterton
9.0 out of 10, Wonderful, (118 reviews)
"Staff was extremely helpful and responded promptly. The room was very clean, and inviting. Great location for the beaches or short trips to Michigan."
United States
Bryan
The price is CA $188
CA $210 total
includes taxes & fees
Nov 10 - Nov 11
Furness Mansion
A patio with a table and chairs, a bicycle, and a string of lights against a twilight sky.

8. The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly

The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Porter
9.4 out of 10, Exceptional, (11 reviews)
"We enjoyed our stay. Very inviting and comfortable accommodations. Would stay again and would recommend!"
United States
Amanda E.
The price is CA $111
CA $287 total
includes taxes & fees
Nov 10 - Nov 11
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
A beach with a parking lot and buildings in the background.

9. Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Chesterton
8.8 out of 10, Excellent, (141 reviews)
"Perfect for location to walk to local winery or brewery for a little fancy and fancy-free!We’d recommend"
United States
Laura H.
The price is CA $168
CA $207 total
includes taxes & fees
Nov 10 - Nov 11
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
A hotel lobby with a red carpet, a bookshelf with books, a potted plant, a table with chairs, a small table with a vase, and a door with a red mat.

10. Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton
2.0 star property
Chesterton
6.8 out of 10, (397 reviews)
"Stayed here several times over the years. Always clean so we keep coming back. Recently updated furniture is an improvement."
United States
Daniel
The price is CA $114
CA $128 total
includes taxes & fees
Nov 19 - Nov 20
Fairbridge Inn Express Chesterton
A beach with sand dunes and grass.

11. 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
9.0 out of 10, Wonderful, (22 reviews)
"Awesome place to stay and plenty to do"
United States
Cody
The price is CA $281
CA $342 total
includes taxes & fees
Nov 29 - Nov 30
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
A beach with a sunset, waves, and sparse vegetation.

12. Tower Haus w/Private Hot Tub

Tower Haus w/Private Hot Tub
Chesterton
9.8 out of 10, Exceptional, (38 reviews)
"Great place to stay! It was really clean! Highly recommend!"
United States
Joshua N.
The price is CA $155
CA $360 total
includes taxes & fees
Nov 10 - Nov 11
Tower Haus w/Private Hot Tub
A living room with a dark blue door, a grey sofa, a blue sofa, a coffee table, and a floor lamp.

13. Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes

Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
Chesterton
9.6 out of 10, Exceptional, (76 reviews)
"Great location, walking distance to downtown Chesterton which had an excellent ice cream shop and other restaurants. Easy driving distance to different parts of Indiana Dunes National Park. Host had great communication before and throughout the visit and the house had all the amenities we needed."
United States
Ammari Capito F.
The price is CA $140
CA $496 total
includes taxes & fees
Nov 24 - Nov 25
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
A living room with a flat-screen TV, a wooden console table, a green armchair, a leather sofa, and a ceiling fan.

14. Dunes Homestead - Near Dunes + Lake + Dog Friendly

Dunes Homestead - Near Dunes + Lake + Dog Friendly
Porter
9.8 out of 10, Exceptional, (37 reviews)
"Everything was as described, and had everything we needed!"
United States
Chrissy B.
The price is CA $197
CA $430 total
includes taxes & fees
Nov 13 - Nov 14
Dunes Homestead - Near Dunes + Lake + Dog Friendly
A sandy beach path leading to the sea with grassy dunes on either side.

15. Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
Chesterton
9.4 out of 10, Exceptional, (50 reviews)
"Fantastic stay!"
United States
Steven F.
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
A wooden deck with a glass-top table and chairs, surrounded by lush greenery.

16. Indiana Dunes National Park

Indiana Dunes National Park
Porter
9.4 out of 10, Exceptional, (3 reviews)
"Clean accommodations, everything was as advertised for our 1 night stay. The album collection was a bonus."
United States
Heather F.
The price is CA $242
CA $343 total
includes taxes & fees
Nov 11 - Nov 12
Indiana Dunes National Park
A beach with sand dunes and grass.

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

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
8.6 out of 10, Excellent, (23 reviews)
"Camper is small, but cozy and worked well for my son and I to spend a few days relaxing! Hosts are very friendly, responsive, and helpful and we loved spending time in the pool."
United States
Melissa P.
The price is CA $182
CA $223 total
includes taxes & fees
Nov 23 - Nov 24
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
A bedroom with two beds, a ceiling fan, a TV on a dresser, and a window with blinds.

18. Full House booking of a history building close to the Dunes

Full House booking of a history building close to the Dunes
Chesterton
9.4 out of 10, Exceptional, (6 reviews)
"We are happy with the property. clean property, quite spacious and large enough to accommodate large group, quite close to Dunes."
United States
Mahesh K.
The price is CA $2,518
CA $3,057 total
includes taxes & fees
Nov 11 - Nov 12
Full House booking of a history building close to the Dunes
Pool

19. Country Inn & Suites by Radisson, Portage, IN

Country Inn & Suites by Radisson, Portage, IN
3.0 star property
Portage
8.4 out of 10, Very good, (1,003 reviews)
"Nice breakfast, and a wonderful, kid-friendly pool that is particularly good for very young children."
United States
Rachel
The price is CA $190
CA $213 total
includes taxes & fees
Dec 6 - Dec 7
Country Inn & Suites by Radisson, Portage, IN
A dining area with high ceilings, wooden beams, and large windows with a view of the outdoors.

20. The Brewery Lodge Hotel

The Brewery Lodge Hotel
3.5 star property
Michigan City
9.0 out of 10, Wonderful, (926 reviews)
"Was a great stay. Would highly recommend."
United States
Andrew
The price is CA $100
CA $148 total
includes taxes & fees
Nov 11 - Nov 12
The Brewery Lodge Hotel
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.
View all properties

Learn more about Chesterton

Nestled along Lake Michigan's shore, this small town offers scenic trails through Indiana Dunes National Park for hiking and birdwatching. Coffee shops and local restaurants line the historic downtown, while nearby beaches provide perfect spots for summer swimming and sunset views.

See all hotels in Chesterton
A wooden staircase leading up a sandy hill with dense green forest in the background.
Photo by Susan Ross
Open Photo by Susan Ross

Top reviews in Chesterton

A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton

10/10 Excellent

Clean rooms. Helpful staff. Food at the bar was very good.
Canada
Scott
Reviewed July 26, 2026
Hilton Garden Inn Chesterton

Frequently Asked Questions

Searching for B&Bs in Chesterton?

Whether you're on a romantic trip and want to stay somewhere quiet and intimate, or you're traveling solo and hoping to make some connections, B&Bs can be a great choice for many types of vacationers. If your ideal vacation to Chesterton includes spending lots of time outside, Indiana Dunes Visitor Center and Indiana Dunes National Park are good spots to enjoy the scenery.

Are you thinking about a B&B for your stay?

B&Bs all have a unique charm. Whether it's a cozy reading space or a sunlit breakfast nook, the little details are what make bed and breakfasts a fun place to get away.

What are the best B&Bs in Chesterton?

Here is a B&B that guests like in the area: Valparaiso Inn Bed & Breakfast: 5 rooms. 9.7 mi (15.6 km) from the heart of Chesterton. Enjoy the free full breakfast and private yard.

When is the best time to book my B&B in Chesterton?

When you're planning your stay in Chesterton, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Chesterton are January, December, November, and February, with each month seeing an average of 6 inches of snowfall.

What is there to do in Chesterton?

Travelers looking to spend some time in nature enjoy Chesterton for its beaches and lakeside setting. Spend some time exploring Lake Michigan and Indiana Dunes Visitor Center if you're hoping to see some of the area's natural features. You might put Lustron House and Bailly Homestead - American Indians and Fur Traders on your list if you want to see more of the area.

How can I get to and around Chesterton?

You can plan your excursions in and around Chesterton ahead of time with these transportation options. Fly into Chicago Midway Airport (MDW), which is located 37 mi (59.6 km) away from the heart of the city. You can also search for flights into Chicago O'Hare Intl. Airport (ORD), which is 50.2 mi (80.7 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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