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Upfront pricingWe are not like the others - we include taxes and fees
Our top choices for Chesterton guest houses
1. Beacons' Nest – Valpo U, Downtown & Dunes
Beacons' Nest – Valpo U, Downtown & DunesValparaiso
9.6 out of 10, Exceptional, (4 reviews)
9.6/10
Exceptional
(4 reviews)
"Cute, cozy and comfortable!!"
"Cute, cozy and comfortable!!"
Shelly N.
$258 nightly
The price is $289
$289 total
Nov 23 - Nov 24
Total with taxes and fees
2. Luxury Guesthouse in private wooded setting in Grand Beach New Buffalo
Luxury Guesthouse in private wooded setting in Grand Beach New BuffaloNew Buffalo
8.0 out of 10, Very good, (18 reviews)
8.0/10
Very good
(18 reviews)
"Great place to post up for a night, everything we needed and more. "
"Great place to post up for a night, everything we needed and more. "Andrew N.
$363 nightly
The price is $363
$363 total
Nov 9 - Nov 10
Total with taxes and fees
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.
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.
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.
Photo by Susan Ross
Open Photo by Susan Ross
Top reviews in Chesterton
Hilton Garden Inn Chesterton
Hilton Garden Inn ChestertonChesterton
10/10 Excellent
Nice decor, clean room.
Nice decor, clean room.
anne
Spring House Inn
Spring House InnChesterton
10/10 Excellent
It was very beautiful and quiet
It was very beautiful and quiet
Melissa
Best Western Indian Oak
Best Western Indian OakChesterton
10/10 Excellent
Great location with plenty to do in the area. The purpose of our trip was to visit Indiana Dunes NP, which is very close to the hotel. The hotel is located on a lake which added to its appeal. The general areas of the property were well kept and clean as was our room and bathroom. The breakfast was a typical hotel breakfast. I would definitely recommend this hotel when traveling to the area, and I would stay here again.
Great location with plenty to do in the area. The purpose of our trip was to visit Indiana Dunes NP, which is very close to the hotel. The hotel is located on a lake which added to its appeal. The general areas of the property were well kept and clean as was our room and bathroom. The breakfast was a typical hotel breakfast. I would definitely recommend this hotel when traveling to the area, and I would stay here again.
Edward
Waterbird Lakeside Inn
Waterbird Lakeside InnChesterton
10/10 Excellent
Great hotel… clean, quiet and friendly staff. Our room had a balcony that was right on the lake with a relaxing view.
Great hotel… clean, quiet and friendly staff. Our room had a balcony that was right on the lake with a relaxing view.
Philip
Quality Inn Chesterton near Indiana Dunes National Park I-94
Quality Inn Chesterton near Indiana Dunes National Park I-94Chesterton
10/10 Excellent
Judith at the front desk was very helpful in giving us advice on where to go and what to see. We had a nice conversation and a great day!
Judith at the front desk was very helpful in giving us advice on where to go and what to see. We had a nice conversation and a great day!
Jerry
Comfort Inn & Suites Porter near Indiana Dunes
Comfort Inn & Suites Porter near Indiana DunesChesterton
10/10 Excellent
Very nice and clean! Loved the room decor and cute swimming pool! Very cozy rooms!!
Very nice and clean! Loved the room decor and cute swimming pool! Very cozy rooms!!
Anonymous traveler
Fairbridge Inn Express Chesterton
Fairbridge Inn Express ChestertonChesterton
10/10 Excellent
I always go there to recharge
I always go there to recharge
Rosa
Four Winds Casino Resort – New Buffalo
Four Winds Casino Resort – New BuffaloNew Buffalo
10/10 Excellent
The room was spacious, bed was comfortable. Nice casino and hotel.
The room was spacious, bed was comfortable. Nice casino and hotel.
Angela
Holiday Inn Express & Suites Michigan City by IHG
Holiday Inn Express & Suites Michigan City by IHGMichigan City
10/10 Excellent
Short stay before going to Chicago. Very pleasant staff and a good breakfast.
Short stay before going to Chicago. Very pleasant staff and a good breakfast.
Anonymous traveler
Bridge Inn
Bridge InnMichigan City
10/10 Excellent
We stayed in suite 23. Its an upper level room but the stairs were quite manageable. We received a text when our room was ready which was before check in time. The room was very cozy and clean. This suite has a jetted tub 😀. The property manager Pete was very nice. We were only in the area 1 night but I waa amazed at all the things to do in the area. We definitely want to go back for a longer visit in the summer. They have a website that you can contact separately that will save you money on...
We stayed in suite 23. Its an upper level room but the stairs were quite manageable. We received a text when our room was ready which was before check in time. The room was very cozy and clean. This suite has a jetted tub 😀. The property manager Pete was very nice. We were only in the area 1 night but I waa amazed at all the things to do in the area. We definitely want to go back for a longer visit in the summer. They have a website that you can contact separately that will save you money on...
Joyce
Home2 Suites by Hilton Michigan City
Home2 Suites by Hilton Michigan CityMichigan City
10/10 Excellent
Excellent service and clean.
Excellent service and clean.
Melina
Hampton Inn Crown Point
Hampton Inn Crown PointCrown Point
10/10 Excellent
The hotel is bright, shinny and new.
The hotel is bright, shinny and new.
Ronald
Hampton Inn & Suites Valparaiso
Hampton Inn & Suites ValparaisoValparaiso
10/10 Excellent
Eight 1981 VHS grads used Hampton Inn & Suites as our home base for a reunion weekend. The staff was very pleasant and accommodating, the breakfast was very good and plentiful, and the rooms were exceptionally quiet and comfortable. The beds and pillows were so nice that my body was convinced that it rested at home. It was a lovely weekend. Thank you for the “Vail of Paradise” hospitality.
Eight 1981 VHS grads used Hampton Inn & Suites as our home base for a reunion weekend. The staff was very pleasant and accommodating, the breakfast was very good and plentiful, and the rooms were exceptionally quiet and comfortable. The beds and pillows were so nice that my body was convinced that it rested at home. It was a lovely weekend. Thank you for the “Vail of Paradise” hospitality.
Susan
Holiday Inn Express & Suites La Porte by IHG
Holiday Inn Express & Suites La Porte by IHGLa Porte
10/10 Excellent
Staff super friendly. Room comfortable and quiet.
Staff super friendly. Room comfortable and quiet.
Carole
The Brewery Lodge Hotel
The Brewery Lodge HotelMichigan City
10/10 Excellent
Our stay was just great, and the facility was wonderful. However we had serious problems with the Hotels.com website. The website and booking process were deceptive and difficult. Our efforts to communicate with hotels.com did not get results and we were not able to find out why our credit card was charged more than advertised. We will go to the Brewery Lodge Hotel again but we won't be booking through Hotels.com. Final score 5+ for the Brewery Lodge Hotel 0 minus for Hotels.com.
Our stay was just great, and the facility was wonderful. However we had serious problems with the Hotels.com website. The website and booking process were deceptive and difficult. Our efforts to communicate with hotels.com did not get results and we were not able to find out why our credit card was charged more than advertised. We will go to the Brewery Lodge Hotel again but we won't be booking through Hotels.com. Final score 5+ for the Brewery Lodge Hotel 0 minus for Hotels.com.
Anonymous traveler
Frequently Asked Questions
What are the most popular guest houses in Chesterton according to reviews?
Chesterton “Golf View Estate” is an exceptional choice for travelers seeking a memorable stay in Chesterton, boasting an outstanding review score of 10.0. This guest house is great for those who love to cook and enjoy quality family time, featuring a fully equipped kitchen with everything from a microwave to a blender and a dining table, making meal prep and family meals a breeze. The spacious layout encourages relaxation after a day of exploring the beautiful Great Lake Beaches and the scenic Trails of the Dunes, ensuring your group can unwind in comfort.
What is the nightly rate for a guest house in Chesterton?
Rates for Chesterton guest houses vary, but travelers can find great-value prices from $289 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Chesterton guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a Chesterton guest house and a B&B?
A guest house in Chesterton is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.