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“Amazing Bed & Breakfast Not Sure I want to Share!!!” 5 of 5 stars
Review of Pleasant Street Bed and Breakfast

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Pleasant Street Bed and Breakfast
4.0 of 5 Bed and Breakfast   |   329 Pleasant Street, Oconomowoc, WI 53066   |  
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Ranked #1 of 2 Oconomowoc B&B and Inns
Sugar Grove, Illinois
2 reviews
3 helpful votes 3 helpful votes
“Amazing Bed & Breakfast Not Sure I want to Share!!!”
5 of 5 stars Reviewed January 6, 2014

My Husband and I have stayed at many Bed and Breakfast's over the last 25 years. Most have been good and some not so good. A few, we had to go back again, they were so enjoyable. We choose Bed and Breakfasts for their unique ambiance and hospitality. We looked for three days for the perfect getaway for our anniversary. Finally we found the perfect romantic retreat in Oconomowoc, Wi. The pictures on the website appeared to be a tastefully restored turn of the century home with all the amenities that we had hoped for. Upon our arrival, we were delighted to see the exterior of this historic home, capturing the essence of it's era. When we stepped in and received a warm greeting from Randy, we knew we were at the perfect inn. The tour that followed showed us the passion that the Innkeepers have in maintaining the elegance that a century old house deserves. The dining room is stunning for those of us that appreciate true hand made craftsmanship in architectural woodwork. Our third floor room, the Wisconsin Suite, was warm, cozy and private. The amenities were perfect. You have to come with a big appetite; the breakfasts were outstanding and the evening wine and cheese were a perfect start of the evening. Randy and Sara's dining suggestions were spot on, they have a great knowledge of the local restaurants. In closing, we hope that all who read this will kindly not overbook the inn so that we can continue to visit and become regular guests.

  • Stayed December 2013, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
RandyandSara, Owner at Pleasant Street Bed and Breakfast, responded to this review, January 8, 2014
We're flattered that so many of our guests have commented about our breakfasts and appreciated our restaurant recommendations. As a house full of foodies, we take our meals very seriously. To that end, it may not seem surprising that we have often considered opening a small restaurant and even explored a restaurant license for the B&B.
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33 reviews from our community

Traveler rating
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Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    5 of 5 stars
  • Rooms
    5 of 5 stars
  • Service
    5 of 5 stars
  • Value
    5 of 5 stars
  • Cleanliness
    5 of 5 stars
Traveler tips help you choose the right room.   Room tips (4)
Date | Rating
  • English first
  • Any
English first
Racine, Wisconsin
Reviewer
3 reviews 3 reviews
Reviews in 2 cities Reviews in 2 cities
5 of 5 stars Reviewed December 13, 2013

Beautiful, welcoming and cozy (not meaning small)! This B&B is a wonderful treat in Lake Country. The hosts are friendly, the food is great and the rooms are gorgeous. A great alternative to a hotel! Definitely give it a try.

  • Stayed November 2013, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
RandyandSara, Owner at Pleasant Street Bed and Breakfast, responded to this review, April 2, 2014
Sara's decorating was amazing. We get compliments from almost everyone who has seen the rooms. They are so fresh and contemporary, yet they offer interesting touches and a real sense of warmth.
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Berlin, Wisconsin
Reviewer
4 reviews 4 reviews
4 hotel reviews
Reviews in 4 cities Reviews in 4 cities
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed December 12, 2013

My wife and I took a week long trip where we stayed at four different B&B's, in three different states. All of the B&B's we stayed at had very high ratings from previous guests. Both my wife and I felt that our stay with Randy and Sara at their B&B was the highlight of our entire trip as far as the B&B's go. All the B&B's we stayed at were very nice, but Randy and Sara's was still a notch above the rest of them. Beautiful home! Absolutely WONDERFUL hosts! AND their breakfast was amazing!!! Best breakfast we had on our entire trip!! The food, juice, and coffee we had for breakfast far exceeded anything we had in the other B&B's we stayed at. If you are traveling in this area of Wisconsin, DO NOT pass this place buy! Or you will miss an absolutely wonderful experience.

  • Stayed November 2013, traveled as a couple
    • 5 of 5 stars Value
    • 4 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
RandyandSara, Owner at Pleasant Street Bed and Breakfast, responded to this review, April 2, 2014
When we opened, we set a high bar for ourselves. We wanted to be one of the best B&B's in the world. While we still have a ways to go, we are flattered that your experience was so favorable. Thank you!
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Streator, Illinois
1 review
5 of 5 stars Reviewed December 10, 2013

My husband and I stayed two nights for our anniversary getaway! We had a great time! Randy was so hospitable and friendly from the first moment we met. We were shown to our room, which was the Oconomowoc suite. All of the features/amenities of the room were explained to us in detail. We immediately felt right at home. We were reminded of the wine/cheese reception at 530p and that did not disappoint either. We were asked which types of wine we preferred and every effort was made to accommodate us. It was during our wine/cheese reception that we got to meet Randy's wife Sara and enjoy getting to know one another. {Randy was willing to make dinner reservations for us as well, but we decided to order pizza so that we could enjoy the room :) }
Breakfast the first day was downstairs in the dining room where music from a jazz vocalist named Kurt Elling was playing (so relaxing)...we were served yogurt with homemade granola, banana pancakes and scrambled eggs with ricotta cheese...Yum!!
After our day together which included shopping in Delafield and dinner at Union House Restaurant (its a bit pricey, but the French onion soup is amazing...and were normally not big fans of that soup) we came back to the house grabbed some delicious homemade chocolate chip cookies that were waiting for us in the dining room and arranged for breakfast in bed the next morning. That next morning we had homemade waffles, yogurt with fruit and thick sliced bacon with coffee and juice.....Our bed was so comfortable as well and the immersion tub was so romantic and relaxing. We will definitely be back and have recommended Pleasant Street B&B to our friends as well. Thank you both for your kindness, patience, and generosity.

  • Stayed November 2013, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
RandyandSara, Owner at Pleasant Street Bed and Breakfast, responded to this review, December 12, 2013
Thank you for your amazing comments. The feelings were definitely mutual. We hope you come back again soon!
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McKinney, Texas
1 review
5 of 5 stars Reviewed December 5, 2013

I stayed for one night at the B&B while passing through the area on business and couldn't have been more pleased with my stay. I was warmly greeted by Randy upon arrival who showed me around the house and then showed me all the features of the room (wifi, ipad 4 <to borrow>, apple TV, Direct TV, Sonos music, fireplace, and the list goes on). The room was very comfortable and the shower even had good water pressure - something a frequent traveler really appreciates.

And then the food! The wine and cheese reception was wonderful. Both the cheese (a local Gouda with a little something extra in it) and the wine were delicious plus the owners were really easy and pleasant to chat with. In the morning I was able to smell the coffee even from my room on the top floor. On the menu was a fruit bowl of kiwi, mandarin oranges, and pineapple in a mint syrup, pumpkin pancakes, and warm cinnamon pears.

Finally, the location of the B&B is perfect. It really is just a short walk to all the restaurants and shops. At a loss of where to eat? The owners are full of suggestions.

So happy that I stumbled across this gem. It was certainly a refreshing change from my typical stay at hotel chains.

  • Stayed November 2013, traveled on business
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
RandyandSara, Owner at Pleasant Street Bed and Breakfast, responded to this review, December 6, 2013
Thank you for the wonderful review and for allowing us to host you. We love what we do and we're so pleased that our passion for creating a "Relaxed. Intimate. Inviting." atmosphere translate to the experience you had. We hope you come again.
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Madison, Wisconsin
2 reviews
Reviews in 2 cities Reviews in 2 cities
5 of 5 stars Reviewed September 30, 2013

Our stay was very pleasant. The B&B just opened and everything is nice and new. The decorations are very fitting. The owners could not have bent over backwards more for us. They made sure we were totally happy. It is fun to see owners who are actually excited to be running a B&B.

  • Stayed September 2013, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
RandyandSara, Owner at Pleasant Street Bed and Breakfast, responded to this review, April 2, 2014
Staying at a B&B is an experience. It should be more than just a nice bed and a great breakfast. It should reflect what you value and make you want to return over and over again. That's our goal every time a guests makes a reservation.
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Additional Information about Pleasant Street Bed and Breakfast

Address: 329 Pleasant Street, Oconomowoc, WI 53066
Phone Number:
Location: United States > Wisconsin > Oconomowoc
Amenities:
Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Room Service Suites
Hotel Style:
Ranked #1 of 2 B&Bs / Inns in Oconomowoc
Price Range (Based on Average Rates): $$
Hotel Class:4 star — Pleasant Street Bed and Breakfast 4*
Number of rooms: 2
Official Description (provided by the hotel):
Top rated B&B in WI (Trip Advisor score 99.9/100.0). 1St two suite "Diamond Collection" property in the history of Bed and Breakfast . Com. Located two blocks from downtown in the historic lakeside community of Oconomowoc. Within two hours of Milwaukee, Madison, Chicago and Green Bay. Just two miles off I94 and within 10 miles of Delafield, Pewaukee and Hartland. Intimate rooms in historic 1910 Arts and Crafts home. Exquisite accommodations, gourmet breakfast, nightly wine and cheese reception and a service orientation that caters to each customer's need. An ideal place for a honeymoon, romantic getaway, visit with family, lake vacation or that all important business trip. All guest rooms feature a king or queen sized pillow-top bed, luxurious linens, private bathroom, iPad 4, Sonos stereo system, stocked mini-refrigerator, free wifi, HD television and Keurig coffee-maker. Choose between a beautiful gas fireplace or a full-immersion Kohler spa tub. ... more   less 
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