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Pleasant Street Bed and Breakfast

329 Pleasant Street , Oconomowoc, WI 53066 USA (Show map)

Check Dates Diamond Collection

Professionally Inspected & Certified Diamond Collection


Highest rated B&B in WI (Trip Advisor). Perfect 5 star rating on Trip Advisor, Yelp, ILoveInns , Google+ and BedandBreakfast . Historic 1910 home with exquisite architectural detail and chic upscale design. Wisconsin's most state-of-the-art B&B featuring apple t.v., i-pad 4, free wifi, stocked mini-fridge, Keurig coffee machine and Sonos stereo system. Complimentary breakfast in bed. Gourmet food. Nightly wine & cheese reception. Business friendly. WI travel green certified. Situated in historic downtown Oconomowoc and within 4 blocks of two beautiful lakes. Close to Delafield, the Kettle Moraine State Park, the Glacial Drumlin Trail, Old World Wisconsin, Ten Chimneys and Johnson Creek outlet mall. Special packages cover romance, honeymoon, babymoon, anniversary, hot air ballooning, skydiving, pheasant hunting, fishing, lake retreats, foodie getaways, etc. "Relaxed. Intimate. Inviting."



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  • Guest room5
  • Service5
  • Value5
  • Cleanliness5
  • Onsite Dining5

Score Breakdown based on
6 Reviews

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A Wonderful Stay

5 on May 09, 2015

My boyfriend and I stayed here right before Christmas, and had a wonderful time. The walk to downtown was very short, and the shops were very cute and decorated. A lake is also nearby which was fun to walk around. The breakfasts were phenomenal, and we got to eat them in our room in bed as we watched our favorite show on the complementary iPad. The free wine and cheese was a very nice touch as well. --Allison Schedin

Spectacular B&B!

5 on February 20, 2015

Our stay at the Pleasant Street B&B could not have been any better! It was the perfect place to surprise my love for his birthday. The accommodations were excellent, the food was fabulous and fresh and Randy offered excellent customer service and hospitality. We would definitely stay there again and again! Thank you for everything Randy!

Fantastic Find

5 on December 20, 2014

I stumbled across this B&B and am so grateful for doing so. Our stay was phenomenal with a romantic, well appointed room, terrific food (the truffles are a must), and warm hospitality. I had no idea such a fantastic place was so close to home. We shall return again and again and my wife and I highly recommend this B&B.


5 on November 29, 2014

Beautiful setting to relax and get away. Not a worry in the world. Karen & Terry

We will be back

5 on October 27, 2014

We have stayed at many B&B's, and there are very few we would go back to. We will be back to this one!!!


5 on October 29, 2013

Beautiful home and generous hosts. WE had a wonderful experience and will happily return!

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Rooms & Rates

Oconomowoc Suite

One of two suites within Pleasant Street Bed and Breakfast, the Oconomowoc Suite sits in what was once the master bedroom. It offers a rich romantic decor in a spacious environment with a deluxe queen sized brass bed that lures you into a great night of sleep. For those needing a little extra to relax and unwind, this amazing suite has an exclusive spa room that features a full body immersion tub with effervescent bubbles that caress you like champagne and chromatherapy that infuses the water with soothing mood lighting.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $110 - $190

Nightly Rate: $110 - $190

Wisconsin Suite

For a completely different experience, we invite you to stay in the stunning Wisconsin Suite. It offers a very sophisticated and contemporary ambiance with lots of natural light, distinguishing architectural lines and an open floor plan. The suite offers more than 500 square feet of living space and is accessible via a private staircase. It features a beautiful king-sized bed with a luxurious pillow-top mattress. And for added romance, there's a gorgeous cast iron gas fireplace that affords amber views from three sides.

  • Maximum Capacity: 4
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $110 - $175

Nightly Rate: $110 - $175

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Location Type

Historic City, Downtown, Lakefront, Oceanfront, Suburban


Milwaukee, WI (MKE-General Mitchell Intl.) 35 miles

Directions to property:

Convenient to Milwaukee or Madison off I94. Follow directions to downtown Oconomowoc. First driveway on the left going North on the downtown roundabout. 1 1/2 blocks from City Hall. Across the street from Fowler Lake.

Area Attractions

Antique Shopping, Art Galleries, Beach, Gourmet/Fine Dining, Historical interests, Lake, Live Music, Movie Theater, Museum, National/State parks, Nature area, Professional/college sports, Hot Air Ballooning, Pheasant Hunting, Sky diving, Spa services, Golfing, Outlet Stores, Performing Theater, Picnic area, Ski area

Inn Details

Establishment type

Bed and Breakfast

On-site amenities

BBQ grill, Board games, CD player, Computer, Copier, DVD Player, Fax Machine, Piano, Telephone, VCR, Washer/dryer , i-pad 4, Sonos 5 stereo system, Apple t.v., Stocked refrigerator, Nightly wine and cheese reception, Complimentary breakfast in bed

Room amenities

Air conditioning, Alarm clock, Amenities Basket, Bath robes, Ceiling fans, Coffee/Tea facilities, Desk, Fireplace, Fridge, Hairdryer, Hot tub/whirlpool tub, Internet Service, Ironing Board, Radio, Satellite/Cable TV, TV, Turndown Service, Videos, Wi-Fi, Wired internet

On-site activities

Bicycle rental, Bicycle riding trails, Bicycles, Bird watching, Boating, Canoeing, Cross-country ski trails, Downhill Skiing, Fishing, Golfing, Hiking trails, Horseback riding, Hunting, Kayaking, Mountain Bike trails, Sailing, Shopping, Sight-seeing, Ski rentals, Snow shoe rental, Snow shoe trails, Swimming, Tennis courts, Water sports

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  • Check In:: Flexible
  • Check Out:: 11:00
  • Open All Year Round: Yes
  • Smoking Allowed: No
  • Drinking Allowed: Yes
  • Alcohol Provided Yes
  • Suitable For Children: Yes With parental supervision
  • Childcare Provided: No
  • Guest Pets Allowed: No
  • Disabled Access No

Terms and Conditions

  • Minimum Stay: Two night minimum with a Friday or Saturday night stay. Otherwise, no.
  • Accepted payments AMEX, VISA, Discover, Mastercard, Diners club, Personal checks, Travelers checks, Cash
  • Cancellations: WEEKENDS (Reservations that include a Friday or Saturday night stay) Rooms cancelled more than 14 days of a guest's scheduled arrival will receive a complete refund, less a $25 administrative fee. Rooms cancelled less than 14 days of a guest's scheduled arrival will be charged 50% of the daily rate. If the room can be subsequently rented, a credit less a $25 administrative fee will be given toward a future stay. WEEKDAYS (Reservations that do not include a Friday or Saturday night stay) There is no cancellation fee if 24 hours notice is provided.



Randy and Sara Bangs

Languages spoken


Resident Pets


About the innkeepers

All sports, cooking, fine wine, yoga, travel, photography, architecture, art, NPR, antiques, music, education, community service, small business, marketing, healthcare.

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  • Time Served: Flexible
  • Serving Location: Back Patio, Dining Room, Guest room

Special meal options

Low fat , Restrictive , Vegetarian , Gluten Free, Low Calorie

Signature Dish

German Pancakes


329 Pleasant Street , Oconomowoc, WI 53066 USA (Show map)

Property highlights

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