Pleasant Street Bed and Breakfast

329 E Pleasant Street, Oconomowoc, Wisconsin 53066
Innkeeper(s): Randy and Sara Bangs
  • Introduction

    Pleasant Street Bed and Breakfast

    Opened August 2013 and possesing a perfect 5 star rating on Trip Advisor!

    Welcome to Pleasant Street Bed and Breakfast located in historic Oconomowoc, Wisconsin. 

    We invite you to indulge yourself.  Exult in the pleasures of our nightly wine and cheese reception.  Savor our gourmet multi-course breakfasts and homemade treats.  Unwind in the Oconomowoc Suite spa tub or reconnect by the Wisconsin Suite fireplace.  Rejuvenate yourself on your deluxe pillow-top mattress.  Immerse yourself in your suite’s state-of-the-art amenities (iPad 4, HD television, Sonos stereo system, Apple tv, Keurig coffee-maker and stocked mini-refrigerator). 

    Looking for more … experience the sights and sounds of scenic Fowler Park.  Enjoy an evening cruise on Fowler Lake.  Go fishing on Lac Labelle.  Take a two block stroll and experience the shops, dining and architecture of downtown Oconomowoc.  Drive 10-15 minutes and explore the quaint offerings of downtown Delafield, the beauty of the Kettle Moraine State Park and the magnificence of the Glacial-Drumlin Trail.  Be adventurous and go skydiving or hot-air ballooning.  Get historic and explore Old World Wisconsin, Ten Chimneys or the Les Paul Exhibit.  Unleash your romantic self and book an in-suite couple’s massage.  Challenge yourself and make a reservation at nearby Erin Hills Golf Course, site of the 2017 U.S. Open. Test your sharpshooting skills and go pheasant hunting.  Pamper yourself at the luxurious Craig Bern’s day spa.  

    Whether you come for business, relaxation, intimacy, fun or just an inviting atmosphere, we are here to fulfill your needs.  Our home is your getaway. We look forward to hosting you.

    Randy and Sara Bangs

    Wooden Staircase

    Living Room

  • Insider's Info

    Travelers are always looking for memorable and relaxing experiences. Let’s discover more through the words of our innkeepers. Many thanks to Randy and Sara Bangs for sharing their own secrets with!
    Why do most travelers stay at your inn?

    I think most travelers stay at our inn because we offer unmatched amenities at a very competitive rate and our suites are very large and decorated in a very contemporary manner.

    What are you best known for? What makes your inn unique? What do you love most about your inn?

    After reading our reviews, I think we are best known for giving our guests a very personalized experience that satisfies their individual needs. For some guests I think that’s just an opportunity to feel totally pampered – great food, luxury amenities, amazing sheets and towels, a super comfortable bed and a genuine feeling of warmth and hospitality. For others, it’s a matter of creating a set of experiences that speak to who they are. To be successful, I think you have to customize what you do to every guest you have.

    If someone has never been to your city, what is the #1 reason to come visit?

    Most people would say because of the gorgeous lakes. But I think the #1 reason to visit Oconomowoc is because within a short drive we can satisfy almost any guest’s need for excitement and adventure.

    What’s the best compliment you have ever received about the inn?

    We get lots of compliments about the beauty of the house, the amenities we offer, the décor of the suites, our hospitality, our wine and cheese reception and our gourmet breakfasts. That said, we believe the best compliment is when our guests say they want to return. And so far we have been very lucky because every guest has said that.

    What’s the best kept secret about the area?

    I think our best kept secret is just the natural beauty of the Lake Country region.

    If a traveler is staying at your inn for 4 nights, what should he/she do in the area?

    I would definitely recommend exploring downtown Oconomowoc and nearby Delafield. I would also encourage guests to take advantage of the many beautiful lakes in the area. If visitors were inclined toward outdoor activities, I would recommend hiking, cross country skiing or mountain biking at the Kettle Moraine State Park or biking on Glacial Drumlin Trail. I would also encourage guests to visit Old World Wisconsin, Ten Chimneys and the Les Paul exhibit. Lastly, I would offer to set someone up with one of our special packages where they could hire a fishing guide for the day, rent a boat, kayak or canoe, spend a day at the local spa, go pheasant hunting, be daring and go hot air ballooning or skydiving, or just play 18 holes of golf at Erin Hills (site of the 2017 US Open) or one of the many other area golf courses.

    Is there anything within walking distance of your inn?

    Our B&B is situated on the most popular walk in all of Oconomowoc. It takes you through the heart of downtown, around Fowler Lake, past Fowler Park and next to Lac LaBelle.

    What is your favorite restaurant/food in the area?

    We have several great restaurants in the that we recommend to guests depending on budget, atmosphere, food preferences and proximity to the B&B. As foodies ourselves, we try to match our recommendations to the desires of our guests.

    Any good area guides/websites that travelers could reference?

    The Wisconsin Travel Guide is excellent but our website also tries to highlight many of the area activities.

    How many rooms does your inn have?

    We have two suites.

    Do you accept pets?

    We do not accept pets but we are very fortunate because just one block away there is a business that boards dogs and cats and allows all the animals to interact with one and other.

  • Our Story

    Pleasant Street Bed and Breakfast Sign

    Our foray into Innkeeping is both funny and serendipitous.  It started in the winter of 2009 when Sara and I were given a gift certificate for a free night of lodging in Green Bay.  In planning our trip, we opted to extend our vacation a few days and explore Door County.  There, we stayed at a romantic Inn in Fish Creek. As expected, Door County brought great pleasure and led to an innocuous discussion about how cool it would be to run a luxury Inn or B&B.  I remember discussing how it would enable us to work together and meet interesting people.  We were also allured by the attractiveness of building a business together and leveraging our diverse but complimentary skill-sets.  Undoubtedly, we cited our love for food and hosting others.  

    This fascination manifested itself each time we traveled.  Inevitably, one of us would bring it up and the conversation would take-off.  With each occasion we felt more confident that a B&B was the perfect opportunity.  Yet we did nothing.  We did after all have four teenage boys, a beautiful home that we restored and two jobs that commanded our time.  Given that, how was a bed and breakfast even remotely viable?

    Fast forward to October, 2012.  We had just returned from a B&B weekend in western Wisconsin and feeling rather settled in Oconomowoc set out for an evening stroll around Lac LaBelle and Fowler Lake.  We had walked this route hundreds of times.  Yet, it was a beautiful night and a walk offered fresh air, exercise and time together.  

    As we headed through downtown, we approached the corner of Pleasant and Walnut and noticed this amazing house for sale.  We had seen and admired the home many times.  Innocently, we pulled a flyer.  We had no notion of moving, selling or opening a business.  We were simply curious.

    As we examined the sheet, I remember commenting on the price.  It seemed surprisingly affordable.  Without pause, Sara noted that it would be a great bed and breakfast - a beautiful home in a great location with a nice yard in an attractive community, not far from Milwaukee, Madison or Chicago.  It had all of our bed and breakfast must-haves.

    From there, our minds exploded.  We couldn't think or talk about anything else. 

    The next day, I set-up a showing and loved what I saw.  The house was more impressive on the inside than outside.  I immediately called Sara and set-up a second showing.  Two days later, with little sleep and a spreadsheet full of calculations, we made an offer.  After a brief negotiation, our offer was accepted.

    It was crazy and exciting and scary and stressful and liberating.  We were going to be Innkeepers.

     It changed our lives and for that we are grateful!  

  • Amenities

    Relax on the Porch

    Luxury Amenities

    • Complimentary breakfast in bed option
    • State-of-the-art i-pad 4 for in suite use  
    • Sonos 5 stereo system
    • Gourmet wine and artisanal cheese welcome reception (5:30 p.m., unless other arrangements have been made)
    • Luxurious Kohler spa tub with effervescing bubbles and chromatherapy experience (Oconomowoc Suite)
    • Gorgeous Lopi gas stove/fireplace with three-sided views (Wisconsin Suite)
    • 250 sq ft private walk-out deck (Oconomowoc Suite - 2014)
    • Private outdoor patio with two patio heaters
    • Commercial quality video-conferencing equipment for rental (anticipated service - 2014)
    • 32" high definition television with premium satellite access and Apple TV

    High End Finishes

    • Gourmet multi-course breakfast with flexible breakfast time
    • Shared common areas - the living room and dining room
    • Deluxe king or queen sized bed with pillowtop mattress
    • Ultra-premium bed linens, towels and spa robe
    • In-room refrigerator with complimentary beverages
    • Fresh cookies to tide you over between meals
    • Alarm clock with i-pod/phone docking system
    • Free WiFi
    • In room Keurig coffee machine
    • Aromatherapy soaps and body lotion
    • Casablanca Ceiling Fan
    • A separate sitting area
    • Drink coasters
    • Bathroom nightlight
    • Wine glass and corkscrews    
  • Living Green

    Travel Green

    Some of the steps we've undertaken to be sustainable and meet the Travel Green Wisconsin standards include:

    Locally sourcing food items (Oconomowoc, Delafield, Milwaukee, Madison, etc.) - eggs, honey, milk, handrolled butter, maple syrup, coffee, cheese, many fruits and vegetables, some wine and as many proteins as possible.

    Reusing bed linens when guests are staying multiple nights unless requested otherwise.

    Reducing our consumption of single use items like shampoo bottles, bar soaps, body lotions, etc.

    Recycling most paper, cardboard, plastic and aluminum products

    Composting as much food and yard waste as feasible

    Bulk purchasing of most cleaning products (laundry detergent, window cleaner, toilet bowl cleaner, floor cleaner and laundry softener) and many food products (sugar, flour, dried fruits, nuts, etc.)


  • Dining

    Wine and Cheese Reception

    Our passion for great food doesn't stop at breakfast.  We also love great wine and gourmet cheese.

    > Each night at 5:30 we host a wine and cheese reception by the fireplace in the living room with a cool jazz mix playing softly in the background.  We feature high quality wines and local artisinal cheeses.  Typically, we'll offer two wine choices and a couple of cheeses that have been carefully paired with those wines.  We also serve some fruit slices, nuts and a dry bread/crackers to enhance the experience.

    We're proud that our wines come from a local wine bar.  While our original plan was to serve wines from the Zagat wine club (we are long standing members), the idea of patronizing a local business who offers comparable, if not better, wine seemed alluring.  So, we approached Wine Maniacs about the idea and they jumped right on board.  We're confident you'll find these wines to be exceptional.

    As for the cheese service, we always intended to feature local dairies.  Fortunately, we live in a state that produces many of the finest cheeses in North America and a few of the top dairies happen to be nearby.  The ones we represent are Koepke Farms, right here in Oconomowoc, Sartori in Plymouth, Crave Bros. in Waterloo and Carr Valley in the western Madison suburbs.  They are award winning dairies and offer very diverse products.

    Koepke Farms is an up and coming dairy.  They offer two products that we love, their signature La Belle cheese (named after Lac La Belle) and a fenugreek version of their signature cheese.  Both are amazing! 

    Sartori specializes in more traditional hard italian cheeses.  However, they have a new cheese, BellaVitano, that we love and is quickly becoming a  marketplace favorite.  The BellaVitano line also comes in several varieties.

    Like Sartori, Crave Bros. has an italian orientation but specializes more in soft Italian cheeses.  We incorporate many of these products into our breakfast dishes but serve a few of their farmstead products at our wine and cheese reception.

    Carr Valley is a well accomplished dairy and probably the most recognizable.  In the last five years alone, they have received 400+ medals at national and international competitions.  Understandibly, their product line is broad and offers a wide spectrum of choices that pair nicely with our wines.

    We hope you join us at 5:30.  If that's not possible, please let us know.  We'd be happy to reserve a little for later.

    Bon appetite!

    Wine Bottles


  • Trip Advisor Reviews

    5 reviews of Pleasant Street Bed and Breakfast in Oconomowoc
    Pleasant Street Bed and Breakfast
    TripAdvisor Traveler Rating:
    5.0 of 5 stars
    Based on 5 traveler reviews
    TripAdvisor Popularity Index: #1 of 2 B&Bs in Oconomowoc
    Most Recent Traveler Reviews:
    • Dec 13, 2013: “Beautiful, welcoming and cozy (not meaning small)! This B&B is a wonderful treat in Lake Country....” more
    • Dec 12, 2013: “My wife and I took a week long trip where we stayed at four different B&B's,...” more
    • Dec 10, 2013: “My husband and I stayed two nights for our anniversary getaway! We had a great time!...” more
    • Dec 5, 2013: “I stayed for one night at the B&B while passing through the area on business and...” more
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  • Exterior Photos




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