Pleasant Street Bed and Breakfast

I have stayed here twice and will be staying here for a third time while I am in Oconomowoc for work. The hosts are so friendly and accommodating. The amenities are outstanding and the breakfasts can’t be beat! Truly a treasure and a great experience!

Randy and Sara have outdone themselves. What an amazing retreat close to the city! They’ve thought of everything. This B&B is meticulously cared for with great attention paid to the smallest details. The location is close to everything. Evenings include complimentary wine and cheese, and breakfast was just perfect. We’ve stayed at a lot of B&Bs and nothing has compared to this place. We couldn’t have asked for anything more. Cleanliness, comfort, amenities, location, hosts, etc. All perfect!
Thanks for the great hospitality and amazing stay. Book now before this place books up!

Love this place! I’ve never been spoiled so much! Breakfast every morning, whether it be in your room or in the dining room. Something different and unique every day, ok to me that alone is pretty amazing, Randy the inn keeper makes the BEST german pancakes. I cannot stress that enough. Most people see bed and breakfasts as a weekend getaway. But we paid the same prices as we would at any hotel and received the best service, ever. Literally, Randy and Sarah are extremely attentive and know the true meaning of customer service and fine cuisine. Sadly they don’t have a restaurant. But a couple nights resting in the comfiest bed, with wine and cheese in the evening? I don’t think I’d mind spoiling myself rotten in order to have the best breakfast in town.

Great new B&B in Oconomowoc and the only lodging option within the downtown area which allows you to easily walk anywhere. The older but fully updated house is great with beautiful woodwork and décor is very well done with very comfortable rooms — I could see this being a good fit for either couples looking for a getaway trip or even a business traveler such as myself who wants to be downtown and enjoys great accommodations and food. I’ve stayed a number of times out by the highway at the Hilton Garden Inn and Staybridge Suites which are new and fairly nice for what they are but for a few extra dollars you can get a very high end B&B in downtown Oconomowoc and easily one of the best breakfasts you’ll find.
Start with a nice wine & cheese reception in the living room at 5:30 after you arrive and then be prepared for excellent gourmet breakfasts every morning. The first day was a beet and potato hash with perfectly cooked eggs on top. The second day was a ham & swiss omelet with veggies and it was truly one of the better omelets I’ve ever eaten — and Randy woke up EARLY to serve me breakfast at 5:15 AM before I had to get on the road to work (and it was –15 degrees outside, I’m sure he would have preferred staying in a warm, comfy bed just as I wished I could do). Breakfasts also include freshly squeezed juice, high end coffee, or you can also make excellent coffee in your room with the Keurig machine if you’re so inclined.
If you enjoy the B&B experience then Pleasant Street Bed & Breakfast is excellent all around and by far your best B&B option in the local Oconomowoc-​Delafield area. Randy and Sara just opened this gem a few months ago but are clearly doing everything right and anyone in the area should consider this as an option both for those looking for a romantic B&B getaway or even those considering a local hotel because you’ll certainly get a lot more value here for a few extra dollars. Pretty much as good as it gets.