Stay two weekday nights (Sunday - Thursday) in February or March for $225! (New reservations only).
The 1st two suite Diamond Collection Property in the world!
1 of only 7 Diamond Collection properties
Among the first B&B’s worldwide
to earn “Diamond” Status in it’s
inagural year of operation!
Welcome to Pleasant Street Bed and Breakfast, one of Wisconsin’s newest B&B’s. Located in historic Oconomowoc, we are three miles off Hwy 94 between Milwaukee and Madison in the heart of Wisconsin’s lake country region.
We invite you to indulge yourself. Exult in the pleasures of our evening wine and cheese reception. Savor our homemade treats. Unwind and reconnect by the Wisconsin Suite fireplace. Soothe yourself in the Oconomowoc Suite full immersion spa tub. Take refuge in the private outdoor patio. Feast on our sumptuous multi-course breakfasts. Sip some of our custom blended coffee. Rejuvenate yourself on your deluxe pillow-top mattress. Explore the sights and sounds at scenic Fowler Park. Enjoy an evening cruise on nearby Lac LaBelle or Fowler Lake. Take a two block stroll and experience the shops, dining and architecture of downtown Oconomowoc. Drive ten minutes and discover the quaint offerings of Delafield.
Whether you come for 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.Check Availability
We are adding a third suite in the very near future. We’d love your help in designing this “dream suite.” To do so, just click on the above link, complete our short survey and your dream suite may soon become a reality.
Current Beach Conditions
Water Temperature = Cold but navigable
Water Quality = Good
Swimming Hours = Next Season
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 … you'll certainly get a lot more value here for a few extra dollars. Pretty much as good as it gets.- Carlson, New Orleans, LA