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Pleasant Street Bed and Breakfast

Certificate of Excellence
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329 Pleasant Street, Oconomowoc, WI 53066
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1 room 1 guest
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Pleasant Street Bed and Breakfast
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33 Reviews from our TripAdvisor Community

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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
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    (33)
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    (10)
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Sun Prairie
Level Contributor
88 reviews
22 hotel reviews
common_n_hotel_reviews_1bd8 20 helpful votes
4 of 5 stars Reviewed March 14, 2015

We very much enjoyed our stay in the Oconomowoc suite. It was very comfortable and if you're looking for modern amenities, then the room/B & B is perfect for you. Free wifi, Sonos, Apple TV. We didn't use any of those, but still felt we had a nice stay with a great TV and a fireplace in our room. The... More 

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Lake Mills, Wisconsin
Level Contributor
32 reviews
10 hotel reviews
common_n_hotel_reviews_1bd8 14 helpful votes
4 of 5 stars Reviewed January 31, 2015

My husband and I recently spent a night at the Pleasant Street B&B. We enjoyed the spacious Oconomowoc Suite, especially the full body immersion spa tub. The B&B is located near downtown, making it convenient to visit shops and restaurants and walk around Fowler Lake. Randy was helpful in suggesting places to eat. In spite of numerous upscale amenities, there... More 

Was this review helpful? Yes
RandyandSara, Owner at Pleasant Street Bed and Breakfast, responded to this review

However flattering or constructive, we genuinely appreciate the feedback from all our guests. It’s the only way to stay at the top of our game. While we strive for excellence, we are human and sometimes fall short. Obviously, we have done that and for that we genuinely apologize. We hope that you come back again soon and let us show... More 

Indianapolis, Indiana
Level Contributor
118 reviews
40 hotel reviews
common_n_hotel_reviews_1bd8 40 helpful votes
5 of 5 stars Reviewed January 17, 2015

This is one of the better Bed and Breakfasts we have stayed at, Historic house, renovated extremely well back to the original, with modern amenities. Only 2 rooms, which makes it quiet and ensures good service. Met at the door by Sara, who gave us a brief rundown of the houses history and what had been done so far as... More 

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RandyandSara, Owner at Pleasant Street Bed and Breakfast, responded to this review

We're so glad you enjoyed your stay and appreciate the feedback about the spa tub. From our experience the tub is a bit unique, given that it's a full immersion tub, has a heater, offers chromatherapy and gives a choice of jets or bubbles. The irony of it is that my wife and I have yet to try it ourselves. More 

Beaver Dam, Wisconsin
Level Contributor
4 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed December 20, 2014

Our stay at Pleasant Street Bed and Breakfast was wonderful. The house was historic, our room was luxurious and romantic, the meal was delicious, and the hospitality was warm and welcoming. We opted for the home made truffles which were the best we have ever tasted. This bed and breakfast is easily one of the very best that my wife... More 

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RandyandSara, Owner at Pleasant Street Bed and Breakfast, responded to this review

So glad you loved the truffles. I enjoy making them and eating a few myself. Come back again soon. More 

Roselle, Illinois
Level Contributor
4 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed December 16, 2014 via mobile

My husband and I stayed at Pleasant Street Bed and Breakfast in celebration of our 1 year wedding anniversary and our expectations were beyond exceeded. The owner is very kind, attentive and makes amazing food and drinks! The orange pineapple juice was unparalleled! Very cute town as well. Oconomowoc oozes charm and character. We cannot wait to return!

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RandyandSara, Owner at Pleasant Street Bed and Breakfast, responded to this review

How immensely flattering. We too hope you come back and want you to know that we are extremely grateful for the kind words. More 

mukwonago
Level Contributor
5 reviews
3 hotel reviews
5 of 5 stars Reviewed December 5, 2014

Over the years we have stayed in many very nice B&B's. Pleasant Street Bed and Breakfast has become our number one favorite B&B. Randy and Sara have done everything so well! A very warm greeting started our weekend away with a brief history of their home and a tour. Our room was big yet so cozy and comfortable. We loved... More 

Was this review helpful? Yes
RandyandSara, Owner at Pleasant Street Bed and Breakfast, responded to this review

How immensely flattering. We too hope you come back and want you to know that we are extremely grateful for the kind words. More 

delafield
2 reviews
5 of 5 stars Reviewed November 17, 2014

I blind folded my husband and took him to this bed and breakfast as a birthday present. It was an excellent surprise. The accommodations were superb. I felt like we were sleeping on a cloud. Pillows like lamb's wool! A good wine and tasty artisan cheese with crackers in the afternoon. A dynamite breakfast. Quiche that was outstanding. The hosts... More 

Was this review helpful? Yes
RandyandSara, Owner at Pleasant Street Bed and Breakfast, responded to this review

We're so glad you enjoyed your stay and look forward to hosting you and your family in the future. Quiche is one of our signature dishes. We feature it on our website and we are always happy when guests enjoy it. More 

Cary, North Carolina
Level Contributor
9 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 5 helpful votes
5 of 5 stars Reviewed September 17, 2014

Being Bed and Breakfast owners ourselves, we can't say enough positive things about Pleasant Street Bed and Breakfast. Wish we could have met Sara, but Randy was over the top with service and information. The inn is receiving 5 diamond status and it should!! Immaculate, well located, great stories, fabulous food and the service is the tops. Way to go... More 

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RandyandSara, Owner at Pleasant Street Bed and Breakfast, responded to this review

I can't thank you enough for your kind words. I enjoyed your visit equally as much. So glad the fishing guide was enjoyed. I must admit I was a little jealous myself. More 

Saint Paul, Minnesota
Level Contributor
2 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed August 17, 2014

Could we live there?! The combination of great Innkeepers, a clean yet not fussy, historic yet wireless, understated but exceptional (linens and private baths) make your stay so special....it's everything you need. Ask for Randy's pancakes....

Was this review helpful? Yes 2
RandyandSara, Owner at Pleasant Street Bed and Breakfast, responded to this review

Thank you for the kind praise. Your feedback let's us know we are on track and inspires us to do even more. As for the pancakes, they are one of our favorites too! I believe it was the first recipe we added to our repertoire. More 

Sugar Grove, Illinois
2 reviews
common_n_hotel_reviews_1bd8 3 helpful votes
5 of 5 stars Reviewed July 28, 2014

This review was a bit delayed. Our apologies on that or maybe not. We love staying at Pleasant Street Bed and Breakfast and are afraid it may get too popular for us when we need that quite relaxing get away. Randy and Sara did it again. As business owners ourselves we need that quick getaway to rejuvenate ourselves. We are... More 

Was this review helpful? Yes 3
RandyandSara, Owner at Pleasant Street Bed and Breakfast, responded to this review

We hope every guest wants to come back over and over. In the B&B industry, repeat business is the highest form of flattery. As for our plans of opening a restaurant, It's still something we're kicking around. What we're really hoping for is a limited menu restaurant that caters to our guests. More 

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