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Check prices for these dates

Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec
In one month
26 Dec - 28 Dec
In two months
23 Jan - 25 Jan

B&B in Chesterton

No exact matches found, but these alternatives could be just right

Recommended hotels in Chesterton

Property entrance
Spring House Inn

Spring House Inn

2.5 star property
Chesterton
8.8 out of 10, Excellent, (1015)
"Love staying here. "
United States
Sally
The price is SAR 334
SAR 393 total
includes taxes & fees
1 Dec - 2 Dec
Spring House Inn
Lobby
Best Western Indian Oak

Best Western Indian Oak

2.5 star property
Chesterton
8.6 out of 10, Excellent, (1015)
"It was very nice, with great access to the national park."
United States
leona ann
The price is SAR 351
SAR 393 total
includes taxes & fees
7 Dec - 8 Dec
Best Western Indian Oak
Lobby
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

3.0 star property
Chesterton
8.8 out of 10, Excellent, (1001)
"We loved staying here. "
United States
Linda
The price is SAR 387
SAR 434 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Chesterton
2 Double Bed, Lake View | Iron/ironing board, free WiFi, bed sheets
Waterbird Lakeside Inn

Waterbird Lakeside Inn

2.0 star property
Chesterton
8.2 out of 10, Very Good, (984)
"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
Lobby
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, (1009)
"My room was clean and comfortable. I would definitely stay here again "
United States
Carolyn
The price is SAR 329
SAR 369 total
includes taxes & fees
7 Dec - 8 Dec
Comfort Inn & Suites Porter near Indiana Dunes
Beach nearby
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)
"Great pool hostess was very helpful"
United States
regina
The price is SAR 219
SAR 330 total
includes taxes & fees
2 Dec - 3 Dec
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Free daily continental breakfast
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, (715)
"Clean room, easy check in"
United States
Billy
The price is SAR 287
SAR 322 total
includes taxes & fees
31 Dec - 1 January 2026
Quality Inn Chesterton near Indiana Dunes National Park I-94
Fridge, microwave, oven, stovetop
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 SAR 203
SAR 1,088 total
includes taxes & fees
1 Dec - 2 Dec
Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes
Property grounds
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 SAR 321
SAR 1,116 total
includes taxes & fees
1 Dec - 2 Dec
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago
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

Porter
8.8 out of 10, Excellent, (16)
"Great place to stay with kids."
United States
Jane H.
The price is SAR 436
SAR 572 total
includes taxes & fees
1 Dec - 2 Dec
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
Superior Suite | Premium bedding, pillowtop beds, individually furnished, desk
Furness Mansion

Furness Mansion

2.0 star property
Chesterton
8.8 out of 10, Excellent, (57)
"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 SAR 608
SAR 681 total
includes taxes & fees
2 Dec - 3 Dec
Furness Mansion
Fridge, microwave, oven, stovetop
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)
"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 SAR 422
SAR 1,502 total
includes taxes & fees
14 Dec - 15 Dec
Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago
Property grounds
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)
"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 SAR 536
SAR 620 total
includes taxes & fees
1 Dec - 2 Dec
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
Living area
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)
"Absolutely lovely stay! Space was cozy and host was phenomenal!Amenities were on point, and the location was convenient for traveling to various points on the Dunes and trails! Would recommend anyone spend time at this rental, and would love to come back again!"
United States
Christopher B.
The price is SAR 658
SAR 1,229 total
includes taxes & fees
1 Dec - 2 Dec
That 70’s Loft- Peace, Love and a Funky Stay!
Beach
Cozy Retreat w/Hot tub Indiana dunes Beaches Trails

Cozy Retreat w/Hot tub Indiana dunes Beaches Trails

Chesterton
10.0 out of 10, Exceptional, (12)
"My husband and I met up with our son from Chicago and loved your beautiful home! It was so clean and comfortable. The house was so well stocked with anything we would need! We were very impressed!"
United States
Kim L.
The price is SAR 439
SAR 1,029 total
includes taxes & fees
8 Dec - 9 Dec
Cozy Retreat w/Hot tub Indiana dunes Beaches Trails
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

Chesterton
8.8 out of 10, Excellent, (90)
"Great location for visiting the Dunes. Having a gas grill available was a nice perk. Was what we needed at a great value. "
United States
Brian L.
The price is SAR 301
SAR 421 total
includes taxes & fees
1 Dec - 2 Dec
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Outdoor dining
Indiana Dunes National Park

Indiana Dunes National Park

Porter
9.0 out of 10, Wonderful, (2)
"Clean accommodations, everything was as advertised for our 1 night stay. The album collection was a bonus."
United States
Heather F.
Indiana Dunes National Park
Outdoor dining
Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes

Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes

Chesterton
9.2 out of 10, Wonderful, (19)
"This is a beautiful place. It has everything that you could possibly need. "
United States
George N.
The price is SAR 413
SAR 1,706 total
includes taxes & fees
1 Dec - 2 Dec
Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes
Exterior
Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton

2.0 star property
Chesterton
6.8 out of 10, (342)
"Staff were lovely "
Canada
Jessica
The price is SAR 334
SAR 374 total
includes taxes & fees
7 Dec - 8 Dec
Fairbridge Inn Express Chesterton
Interior
NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!

Chesterton
8.0 out of 10, Very Good, (9)
"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 SAR 597
SAR 1,466 total
includes taxes & fees
28 Dec - 29 Dec
NEW! Beautiful Riverfront Home on 10 Acres!
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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Top Chesterton Hotel Reviews

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

10/10 Excellent
"Loved the place"
Tomalyn 2-night trip
Posted 2 days ago
Four Winds Casino Resort – New Buffalo

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.