Riley's Railhouse

Bed & breakfast · Chesterton

Riley's Railhouse

Bed & breakfast · Chesterton
123 N 4th St, Chesterton, IN 46304

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Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null
Riley's Railhouse by null

Highlights

Nestled in a charming 1914 freight station, this train-themed B&B boasts cozy rooms, a chef's kitchen, and a delightful breakfast experience—perfect for train lovers!  

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123 N 4th St, Chesterton, IN 46304 Get directions

rileysrailhouse.com
@rileysrailhousebnb

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123 N 4th St, Chesterton, IN 46304 Get directions

+1 219 395 9999
rileysrailhouse.com
@rileysrailhousebnb

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Last updated

Mar 8, 2025

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Emma H

Google
We stayed here on the way home from a wedding, we were all tired and sad to be heading home and parting ways with friends from distant places, but Riley’s Railhouse was a fantastic place to stay and the perfect way to end our vacation. I have no strong feelings about trains, but have two little train enthusiasts and we were all welcomed warmly! The owners are really lovely folks, the room we stayed in was beautiful, clean, and comfortable. The building felt rustic but not shabby at all. The setup in the room was thoughtful, lots of materials on trains and train-themed or derived(!) decor (of course) and local attractions. There was a little loft with a mattress and kids’ books about trains complete with nightlight! It was accessible by a ladder bolted to the wall and sturdy enough for even very nervous kids and parents to feel comfortable. ||Our room also had a door leading to a balcony overlooking the train tracks that was perfect when we wanted to see the trains, but two thick velveteen blackout curtains inside the door muffled the noise, in addition to earplugs provided on the bedside table so that we were able to get a good night’s sleep. ||The morning light comes in through skylights and it made our room and the gathering area look really beautiful, a great way to start the day. We also had a window overlooking the gathering/eating area that was high enough up to allow for privacy, but still accessible and delightful for kids to get a better view of the train on the elevated tracks. We were greeted with a delicious breakfast—including gluten free pancakes to accommodate our dietary needs— and good conversation.||Riley’s Railhouse exceeded my expectations (already high due to reviews) and we will definitely go back and bring more extended family! I wish we’d taken more photos, because it’s a beautiful place, but we were enjoying ourselves so much that it didn’t occur to us, which is the surest proof of a great place to stay :)

Kevin D

Google
If you like trains, this is the place to go. Probably 30 trains per day, blaring their horns, literally 30 feet from your room. Perfect for train watchers! Highly recommend the Upper Berth for great train watching. Been there 4 times in 3 years, will visit again. Breakfast also awesome.

Luke

Google
A destination for anyone interested in Trainspotting. Located along a Norfolk Southern mainline with heavy use (60-80 trains per day). Additional road names seen were BNSF, Amtrak, and KC Southern. Covered porch facing the tracks for inclement weather. We stayed in the upper berth, which faces the tracks and has a covered balcony. Other rooms are available, some of which are built in converted train cars. Our room was clean, orderly, and comfortable. Earplugs are provided if you’re unable to sleep through train horns. Breakfast is served by owners at 0900 and was very good - consisted of blueberry pancakes, sausage, fruit, OJ, and coffee. Food allergies were accommodated. Common/dining area is heavily trained themed and has toy wooden trains to keep children occupied. Also many train related books and magazines for all ages. Public park East of the property with picnic tables, drinking fountains, and bathrooms. Located near downtown in the city of Chesterton, which is a small town with a lot dining and dessert options, within walking distance.

Tracy J

Google
Unique experience and very comfortable accommodations. Delicious breakfast with all the extras. Anne and Richard are wonderful, friendly hosts. This is the full train experience with actual trains going by beginning early in the morning until late in the evening. We thought it added to the authenticity of staying at a train depot, but don’t be surprised by the sound.

CinnamonFluff

Google
DON'T DRINK THE OJ. OR EAT ANYTHING PROVIDED HERE!!!!! Whole family got food poisoning, one currently in hospital with an IV.

Paul Hoch

Google
We spent two nights in the caboose suite. It was incredible. You would never guess how luxurious a caboose could be, but as soon as you open the door, it's just the nicest setup. It's a little secluded and you feel like you have a private cabin. Definitely will be back.

EmmKaa

Google
Tho we've never stayed in a room, we enjoy Riley's Rail House often. With roughly 80 trains rolling by in a 24 hour period, train buffs come from the world over to see a conglomeration of all sorts of freight trains and four Amtrak trains. Even those who aren't "real" rail fans will enjoy the sights here. When trains aren't pounding by on the two side-by-side tracks, it's wonderfully peaceful and quaint.

Ira Sena

Google
Coming from a train fan, this place was amazing! We stayed in a renovated caboose right behind the old depot, which was beautifully decorated and very cozy! The nearly constant parade of freight and passenger trains hurtling past did not rouse us from our sleep, but they do run through the night and their horns are loud. Breakfasts were delicious, personally prepared by the owners! And I could spend hours studying all the train-themed antiques inside and outside the depot! The owners have a ton of stories to tell, so plan on a leisurely morning!
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Jay B.

Yelp
We enjoyed a most pleasant experience in Chesterton staying to Riley's Rail House! The accommodations are beautifully unique and our hosts made us feel welcomed. There is so much to do within walking distance and look forward to a return trip. Small town America at its best!!

Ben W.

Yelp
Richard, his wife, their staff, and lovable dog Jack made our stay more than comfortable. They were well prepared and fed us a great breakfast. All four of our kids loved it! If we ever pass by the area again we will make a point to spend the night here again!!
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John H.

Yelp
B&B's and Restaurants are primarily in the hospitality business. Riley's Railhouse is clueless when it comes to hospitality. I observed the owner make his client cry over something that is never an issue in the hospitality industry. The owner's attitude and actions were shameful and not necessary. they were very unprofessional, in fact disgraceful. When he was questioned why he behaved the way he did, it was apparent that the man held perceptions not based on facts and readily available observations. Owner needs help with hospitality and being a decent human. Do not go here, avoid this place.
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Flo H.

Yelp
I highly recommend Riley's Railhouse for everyone looking for a comfortable and enjoyable getaway. The owners have taken care of everything to make sure that you have the best stay. The location in downtown Chesterton is perfect. It's within walking distance to shopping, restaurants, and 2 wineries. We stayed in the New York Central Railway Boxcar which sleeps 4 people. The bed and bedding were so comfortable! Even though there were trains passing by I slept like a baby! They've done an excellent job with soundproofing. Earplugs are also provided. Breakfast the next morning in the lounge was delicious! The food just kept coming. The hospitality shown made it difficult to pack up and leave. Can't speak enough about how much we love this place, looking forward to going back.

Nancy J.

Yelp
What a wonderful find! Last night we spent a night at Riley's Railhouse in Chesterton, IN. So much fun for our grandsons. It's a converted railway station directly on the railroad tracks so we saw at least 7 freighters and 4 Amtrak trains. The kids and their parents stayed in a room that is a converted boxcar. The host and hostess made us feel so welcome and The included breakfast was delicious.

Christopher H.

Yelp
This place was amazing, right next to the Norfolk Southern Chicago District. At the beginning of the week, train service is a little down, but getting near the end of the week, service is booming. I slept in the upper Berth, which has a fold out couch, adult bed that can fit 2, and a kids loft, that can fit 1. The upper Berth also has a balcony looking over the tracks, which also has enough room to fit your tripod if you're into filming trains.The only problem I had was the trains rattling the building as they came by at night, but that's what trains do. Move freight at high speeds. Breakfast was amazing, what I had was French toast with fruit, and it was an average breakfast. There is also a G-Scale layout rounding the lower part of the building where you eat breakfast. There are also 2 dogs on the lower floor. I highly recommend this place for your next trip.
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Kristy S.

Yelp
This place is awesome. I've never stayed here because I live half a mile away, but I've been here twice for parties and it's beautiful. The commons area is well decorated with a train theme and the owners are very accommodating. They have 2 chill dogs that hang out too!
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David B.

Yelp
We have stayed in many B&Bs in many cities, Riley's Railhouse is our favorite. We arrived mid-morning and Richard graciously allowed us to check in early. The accommodation, in our case a "boxcar," was very clean and the decor innovative. The breakfast was delicious and served up with Richard answering our questions about the awesome collection of railroad artifacts in the dining hall. Riley's Railhouse is a unique B&B that railroad buffs like ourselves will enjoy.
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Doug F.

Yelp
Riley's is great! We stayed in a boxcar, which was really cool. Its upper bunk could easily sleep a couple of young children (we don't have kids, but it had two little beds up there). Breakfast the next morning was delicious, and we were seated with a nice couple staying there also, which was a nice touch. This was in the beautifully renovated station. Highly recommended!
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S L.

Yelp
An outstanding find in Chesterton, Indiana. My wife and I visited Riley's Railhouse in July 2012. We we very impressed with the quality of the food offered at this B&B. The rooms are spacious and extremely clean. As well, the owners and staff are some of the nicest people you will meet anywhere. What is more is that the railroad theming is created with impeccable detail. Nearly every corner of the place is decked out with some form of theming. You will find a model railroad and all of the other accoutrements of railroads and the culture associated with them. What a great new establishment that offers guests an opportunity to escape chain hotels. Highest recommendation! Here is a video overview of the B&B: http://www.indianadunes.com/video-podcasts/lodging-series-rileys-railhouse-video/
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Emmalena G.

Yelp
If you are a railroad fan, you absolutely must stay here. The place is decked out in countless historical railroad artifacts in lovely detail. The rooms are immaculate, well- designed, and comfortable. The owners exhibit the greatest of midwestern hospitality. There are a great number of trains that pass through every day (don't worry, they give ear plugs for night). There's some wonderful local restaurants as well. We stayed here with our two young kids in the loft bed, while our in-laws took the box car. Needless to say, we will return next time we are in the area!
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Lori L.

Yelp
I LOVE Riley's Railhouse. It's fun, quaint, comfortable, clean and is filled with character and charm. The food is not only yummy, but the presentation of each item will make you smile and feel so well cared for. I've had the pleasure to check out three restaurants in town, each unique and wonderful in their own way. To top it off the owners are wonderful people too. they are so kind and I just can't wait to tell everyone I know about this wonderful B & B.

David C.

Yelp
Stayed there on the night of 9/22/19 and Anne and Richard could not have been kinder or better hosts. Fascinating place, great upper berth room, and you will leave with a greater appreciation and love for all things trains.
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Mark J.

Yelp
We have enjoyed coming here for a multitude of local events and meetings, too. That's one of the reasons we chose Riley's Railhouse for our wedding and cocktail reception. Can hold 70+ in the main room for small events. The owner and staff are genuine and easy going. Recommend highly. If I didn't live locally, I'd be staying here for travel or a getaway.

Matt A.

Yelp
A perfect getaway. Riley's Railhouse is a short drive from Chicago, but is an absolute must for anyone who loves trains, or has a kid obsessed with trains like my 3 year old. It's right next to working railroad tracks where trains pass frequently and can be viewed easily from inside and out. There's also many restaurants, bars, a couple wineries and a park all within a block or two walk. The inside is impeccably decorated with various train artifacts and 2 working model trains that left both my kids in awe. The owner is a very gracious host, and made sure we had everything we needed during our stay. He has toys for kids to keep them occupied, and also made a fire for us and offered us a couple beers during our stay. We will be back no question.

Doug M.

Yelp
This place is fantastic! The Rileys are the nicest people you would ever want to meet. The inn is simply spectacular. The main room makes you want to come in and sit down and read, enjoy a glass of wine or a cup of tea and some company. For my son and I who love trains, it is heaven. My wife, son and I stayed in the upper berth room which was gorgeous. The breakfast was top notch, beautifully prepared and simply delicious. My only complaint is I wasn't smart enough to book for two nights! We will absolutely be back!