Photo by Ruslian

Find Chesterton Bed And Breakfast

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jan 23 - Jan 25
In two weeks
Jan 30 - Feb 1
In one month
Feb 13 - Feb 15
In two months
Mar 13 - Mar 15
No exact matches found, but these alternatives could be just right

Recommended hotels in Chesterton

Property entrance
Spring House Inn

Spring House Inn

Spring House Inn
2.5 star property
Chesterton
8.8 out of 10, Excellent, (1,001 reviews)
"Beautiful Hotel"
United States
Joseph
The price is ￥12,473
￥14,759 total
includes taxes & fees
Jan 13 - Jan 14
Spring House Inn
Exterior
Best Western Indian Oak

Best Western Indian Oak

Best Western Indian Oak
2.5 star property
Chesterton
8.6 out of 10, Excellent, (1,002 reviews)
"The room's clean and comfy, the staff super helpful, thank you!"
United States
Dmytro
The price is ￥14,761
￥16,532 total
includes taxes & fees
Jan 18 - Jan 19
Best Western Indian Oak
Lobby
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
3.0 star property
Chesterton
8.8 out of 10, Excellent, (1,010 reviews)
"The room is very clean, and the bed is very comfy. We ate at the restaurant as well, and the food and staff were great!"
United States
Maureen
The price is ￥17,608
￥19,720 total
includes taxes & fees
Feb 1 - Feb 2
Hilton Garden Inn Chesterton
Suite, 1 King Bed, Accessible, Non Smoking (Roll-In Shower) | Desk, iron/ironing board, cribs/infant beds, rollaway beds
Comfort Inn & Suites Porter 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, (1,002 reviews)
"Nice and close to the beach."
United States
Alison
The price is ￥14,280
￥15,994 total
includes taxes & fees
Feb 1 - Feb 2
Comfort Inn & Suites Porter near Indiana Dunes
Room, 1 King Bed, Lake View | Iron/ironing board, free WiFi, bed sheets
Waterbird Lakeside Inn

Waterbird Lakeside Inn

Waterbird Lakeside Inn
2.0 star property
Chesterton
8.2 out of 10, Very Good, (993 reviews)
"I enjoyed the stay. It was quiet and convenient to everything "
United States
Marcia
Waterbird Lakeside Inn
Beach nearby
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

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 reviews)
"Every aspect of my booking & stay was convenient & seamless; from the reasonable price, online reservation process, host communication, beautiful grounds, to the abundant amenities offered there was nothing I or my family wanted for. Don & Kim are accommodating, professional & experienced hosts and it showed. Thank you for the wonderful experience I recommend their multiple spaces to anyone & would stay with them again without hesitation! "
United States
esther Amber C.
The price is ￥9,237
￥13,884 total
includes taxes & fees
Jan 13 - Jan 14
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Lobby
Quality Inn Chesterton near Indiana Dunes National Park I-94

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, (720 reviews)
"Good stay"
Canada
Taesung
The price is ￥12,306
￥13,782 total
includes taxes & fees
Feb 1 - Feb 2
Quality Inn Chesterton near Indiana Dunes National Park I-94
Property grounds
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago

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

Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago
Chesterton
9.0 out of 10, Wonderful, (10 reviews)
"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 ￥16,342
￥50,666 total
includes taxes & fees
Jan 13 - Jan 14
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago
Smart TV, books
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

Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes
Chesterton
9.8 out of 10, Exceptional, (64 reviews)
"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 ￥11,842
￥49,868 total
includes taxes & fees
Jan 15 - Jan 16
Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes
Front of property
Furness Mansion

Furness Mansion

Furness Mansion
2.0 star property
Chesterton
8.8 out of 10, Excellent, (58 reviews)
"This was a lovely place to stay...such a nice surprise as we booked at the last minute. We would stay here again for sure! The owner was very accomodating, and the hotel is beautiful...perfectly described as a boutique hotel. Loved it."
United States
Nicole
The price is ￥25,578
￥28,647 total
includes taxes & fees
Jan 13 - Jan 14
Furness Mansion
Property grounds
Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago

Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago

Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago
Chesterton
9.4 out of 10, Exceptional, (3 reviews)
"I enjoyed my short stay and visit to The Indiana National Dunes. The Host was friendly and she put special effort into setting the place up for my stay. I 100% would rent again from this host and would recommend "
United States
T J.
The price is ￥17,763
￥62,337 total
includes taxes & fees
Jan 13 - Jan 14
Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago
Dining
That 70’s Loft- Peace, Love and a Funky Stay!

That 70’s Loft- Peace, Love and a Funky Stay!

That 70’s Loft- Peace, Love and a Funky Stay!
2.0 star property
Chesterton
10.0 out of 10, Exceptional, (6 reviews)
"Perfect location! The loft had everything we needed and Reina is an exceptional host. "
United States
Melissa H.
The price is ￥27,710
￥51,019 total
includes taxes & fees
Jan 13 - Jan 14
That 70’s Loft- Peace, Love and a Funky Stay!
On the beach, sun loungers, beach towels
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
Porter Beach
10.0 out of 10, Exceptional, (133 reviews)
"Loved the cabin, in a beautiful place.William is an excellent host."
United States
Lee Anna E.
The price is ￥24,157
￥41,026 total
includes taxes & fees
Jan 25 - Jan 26
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
Beach
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park

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, (31 reviews)
"We stayed 2 nights at Blue Birdhouse and it was perfect for us! Bonus, big fenced back yard for the pups! "
United States
Carolyn F.
The price is ￥22,547
￥26,084 total
includes taxes & fees
Jan 13 - Jan 14
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
Exterior detail
2 miles from Dunes National Park. A Unique Boutique Hotel.

2 miles from Dunes National Park. A Unique Boutique Hotel.

2 miles from Dunes National Park. A Unique Boutique Hotel.
Chesterton
9.0 out of 10, Wonderful, (4 reviews)
"Beautiful historic building. "
United States
Deborah S.
The price is ￥177,626
￥247,394 total
includes taxes & fees
Jan 13 - Jan 14
2 miles from Dunes National Park. A Unique Boutique Hotel.
Interior
NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
8.0 out of 10, Very Good, (9 reviews)
"Very tranquil and private stay. The house was clean and comfortable, the fire pit was very nice,. CLose to town, and close to the beach. We loved it."
United States
Jeff S.
The price is ￥25,105
￥61,717 total
includes taxes & fees
Jan 13 - Jan 14
NEW! Beautiful Riverfront Home on 10 Acres!
Outdoor dining
Indiana Dunes National Park

Indiana Dunes National Park

Indiana Dunes National Park
Porter
9.0 out of 10, Wonderful, (2 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 ￥21,607
￥33,392 total
includes taxes & fees
Jan 13 - Jan 14
Indiana Dunes National Park
Beach nearby
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

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
9.0 out of 10, Wonderful, (92 reviews)
"Great stay on every level "
United States
Tom M.
The price is ￥11,684
￥16,623 total
includes taxes & fees
Feb 1 - Feb 2
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Standard Room, 1 King Bed | 1 bedroom, premium bedding, desk, iron/ironing board
Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton
2.0 star property
Chesterton
6.8 out of 10, (343 reviews)
"Staff were lovely "
Canada
Jessica
The price is ￥12,631
￥14,147 total
includes taxes & fees
Jan 13 - Jan 14
Fairbridge Inn Express Chesterton
Beach nearby
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

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 reviews)
"Great place to stay with kids."
United States
Jane H.
The price is ￥31,973
￥40,409 total
includes taxes & fees
Jan 13 - Jan 14
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterton Hotel Reviews

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

10/10 Excellent
"Nice hotel, clean rooms and friendly staff "
JAY 2-night trip
Posted 6 hours ago
Four Winds Casino Resort – New Buffalo

Find out more about Chesterton

Chesterton B&B information

Number of reviews
6,499
Accommodation
1 B&B
Lowest Price
￥13,782
Highest Price
￥247,394

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 Chellberg Farm 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.

Explore a world of travel with Expedia