Pleasant Street B&B

Check Availability | 262-567-8525

A Luxury B&B in Historic Oconomowoc, Wisconsin

The 1st two suite Diamond Collection Property in the world!

1 of only 7 Diamond Collection properties
in Wisconsin.

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.

Luxury you can expect …

  • Gourmet multi-course breakfasts with evening wine and cheese reception and fresh baked treats
  • Deluxe king or queen sized beds with pillowtop mattresses and ultra-premium linens
  • Private bathrooms with glass enclosed showers, aromatherapy soaps/lotions and micro-cotton towels
  • Free WiFi with in suite i-pad 4, Sonos 5 stereo system and alarm clock with i-pod/phone docking system
  • In-room Keurig coffee machine and refrigerator with complimentary beverages
  • 32-40″ high definition flat screen television with premium satellite access and Apple TV
  • Luxurious Kohler spa tub with effervescing bubbles and chromatherapy experience (Oconomowoc Suite)
  • Gorgeous Lopi gas stove/fireplace with three-sided views (Wisconsin Suite)
  • Private outdoor patio with heaters
  • Large desk and chair
  • Off street parking
  • Flexible breakfast times and complimentary breakfast in suite option

Check Availability!

Tell us about your “dream suite”

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.