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Orphan Annie's Schoolhouse Inn

8097 School St., Baileys Harbor, WI
Hotel amenities
Orphan Annie's Schoolhouse Inn
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15 reviews from our community

    Trip type
Traveller rating
    8
    1
    1
    3
    2
Date Rating
Pewaukee, Wisconsin
Reviewer
3 reviews 3 reviews
Reviews in 2 cities Reviews in 2 cities
5 of 5 stars Reviewed 8 October 2012

I could not have been more pleased with our stay at this inn! From contacting Loren about the room and details to the incredibly clean rooms and grounds. Loren and his wife were very very nice and happy to help you in any way. A lot of charm to this old school house turned inn. Yes the floors are squeaky,... More

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Milwaukee, Wisconsin
Senior Reviewer
6 reviews 6 reviews
Reviews in 4 cities Reviews in 4 cities
5 of 5 stars Reviewed 7 October 2012

I just arrived home from my first stay here. I was slightly hesitant upon my arrival after reading the reviews. I will say that as a WEEKLY business traveler for 5 years I have never seen a cleaner room! We stayed in the Homestead Suite. It was super quiet at night. Baileys Harbor is on the quieter side of the... More

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Chicago, Illinois
Senior Reviewer
6 reviews 6 reviews
4 hotel reviews
Reviews in 5 cities Reviews in 5 cities
1 helpful vote 1 helpful vote
3 of 5 stars Reviewed 5 September 2012

Only complaints were the horribly squeaky floors and the worn out bed. You roll to the middle of the bed. Also the bed is advertised as "Queen size". It is a full size bed, not a queen size. The room (Upper Deck) was nicely decorated and comfortably furnished. We weren't given any "rules" and the owners seemed fine. One telling... More

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Milwaukee, Wisconsin
1 review
1 helpful vote 1 helpful vote
1 of 5 stars Reviewed 21 July 2012

We found Orphan Annie's at Bailey's Harbor and wanted to reserve for mid July 2013 for a dance festival in Door County. We talked to the innkeepers on Sunday, July 15, 2012 and reserved a room and wrote a check for 1/2 of the amount. We were given the "rules" of no more that 2 guests for only 1 hour... More

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Chicago
Top Contributor
67 reviews 67 reviews
25 hotel reviews
Reviews in 33 cities Reviews in 33 cities
63 helpful votes 63 helpful votes
5 of 5 stars Reviewed 14 July 2012

If you don't need a lake view, this is a lovely place to stay. It's one block out of the center of town, so you can walk to the lake in minutes. The old converted school house is on a park and very quiet. The rooms are large and comforable, each with porches. They don't serve breakfast, but they have... More

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Madison, Wisconsin
1 review
2 helpful votes 2 helpful votes
1 of 5 stars Reviewed 10 July 2012

My warning system went on alert immediately as there were notes with rules pasted all over the room, including cleaning the shower stall every day. Some friends of ours live in the area and wanted to see the room. Oh my lord, you think we were having a bachelor party the way Loren reacted. We were lectured and scolded as... More

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Geneva, Illinois
Senior Contributor
23 reviews 23 reviews
9 hotel reviews
Reviews in 15 cities Reviews in 15 cities
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed 18 November 2011

We recently stayed here for the second time, and confirmed that it's indeed a wonderful choice. A very unique place, my wife and I stayed in the Library room (was actually the library when the building was a school) which is more like a suite. It has a small kitchen area, walk-in closet and lots of space. It's decorated with... More

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Port Washington, Wisconsin
1 review
5 of 5 stars Reviewed 26 August 2011

This inn is a jewel Door Co. My husband and I were thrilled with the space, the hospitality of our hosts Loren and Annie (refrain from reading the bad reviews, please). This inn is aplace for quiet, for a different vacation experience then ordinary lodging. We found it hard to leave, and will certainly return! The deck with the porch... More

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Preston, USA
1 review
5 of 5 stars Reviewed 13 August 2010

Orphan Annie's Schoolhouse Inn is one of the most unique places we've ever stayed. The rooms, decorated in charming "cottage chic" style, are clean, comfortable and "just like home". The grounds at Orphan Annie's are beautiful with abundant, colorful flowers and places to relax outdoors to enjoy the surroundings and the cool breeze off Lake Michigan. The pictures on the... More

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Wisconsin
2 reviews
5 of 5 stars Reviewed 13 August 2009

First, let's dispose of the complaints that you can't bring visitors to the property. Loren makes it clear when you book that it's not allowed; it's not a complicated concept. This is not a motel; it's a small, quiet, privately owned inn. Loren and Annie don't want their other guests disturbed. Now for the heart of the issue: this place... More

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The Rushes
Great value on a similar hotel
Baileys Harbor, Door County
4.5 of 5 stars 18 Reviews
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Additional Information about Orphan Annie's Schoolhouse Inn

Address: 8097 School St., Baileys Harbor, WI
Region: United States > Wisconsin > Door County > Baileys Harbor
Hotel Style:
Ranked #2 of 8 B&Bs / Inns in Baileys Harbor

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