We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
New! Find and book your ideal hotel on TripAdvisor — and get the lowest prices

Orphan Annie's Schoolhouse Inn

Show Prices
Book on TripAdvisor
Trusted partner. We work with to make your booking as easy as possible.
Secure payments. We use industry-leading practices to keep your information secure.
Enter dates for best prices
powered by PriceFinder
Prices from our online travel partners are not available
Our online travel partners don't provide prices for this accommodation, but we can search other options in Baileys Harbor
Check In Check Out
Show Prices
Management photos
Orphan Annie\\
View Map
{"widget":{"name":"ibex_photo_carousel","template":"ibex_photo_carousel__widget","dust":{"nav_controls":"ibex_photo_carousel__nav_controls"},"divClasses":"prw_rup prw_ibex_photo_carousel","moduleList":["handlers","shims"],"js":{"handlers":"(ta.prwidgets.getjs(this,'handlers'))","shims":"(ta.prwidgets.getjs(this,'shims'))"}},"containerClass":null}
Add Photo Write a Review

12 Reviews from our TripAdvisor Community

Traveler rating
Traveler type
Time of year
Language
Showing 12: English reviews
Saint Peters, Missouri
Level Contributor
1 review
5 of 5 stars Reviewed 1 week ago

We stayed at Orphan Annie's Schoolhouse in 21-26 Aug 16 with another couple. Upon arrival, Calib spent close to an hr with us, given us a great insite into the area, things to do and showed us all the units and how they were decorated. We were in the garden room and our friends were directly across from us in... More 

Helpful?
Thank cruss1869
Charlotte, North Carolina
Level Contributor
4 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed August 18, 2016

This was one of the most relaxing and peaceful experiences we have had in quite a while. Our room was perfect. The location is great because you can easily drive to the surrounding harbors and other "tourist" spots. The owners made us feel right at home and the history of the school is very interesting. Hope to go back again!

Helpful?
Thank southernbred2016
Racine, Wisconsin
Level Contributor
11 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 6 helpful votes
5 of 5 stars Reviewed August 9, 2016

We loved this place. As the name suggests, it's a converted schoolhouse with 7 rooms available. We chose the Upper Deck Suite which was decorated in a beach theme. Kristin and her daughter Ida were kind enough to show us a few of the other rooms which were all just as nice, each with a different theme. Can't say enough... More 

Helpful?
Thank dhbh92
Sherman, Illinois
1 review
5 of 5 stars Reviewed August 5, 2016

We just spent 3 nights at Orphan Annie's and had a great experience. The management was great...Caleb gave us his cell phone number if we needed anything at all. The Inn is very clean and comfortable and we really had a great experience.

Helpful?
Thank vestalfan
san francisco, ca
Level Contributor
4 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 4 helpful votes
5 of 5 stars Reviewed August 3, 2016 via mobile

I booked last minute and everything was fantastic. Clear communication, clean rooms, great location, tons of history and overall an amazing experience. Caleb was very helpful and it made my trip very smooth. I would recommend for anybody visiting door county.

Helpful?
Thank Worldtraveler1970
Bristol, Wisconsin
1 review
5 of 5 stars Reviewed August 1, 2016

We stayed 2 nights in the Upper Deck Suite. We were so pleased to have picked this place! The building having been a school house has so much character and well represents some of the History of Door County. The place was beautiful inside and out.(beautiful grounds and clean and stylish rooms). It was a very peaceful, quiet location but... More 

Helpful?
Thank abelsj99
Chicago, Illinois
Level Contributor
3 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed July 10, 2016

We recently spent a few nights in the Lighthouse Suite. The room is so clean and spacious. It is FAR better than a traditional hotel room. The location is ideal and has easy access to several fun bars, a brewery and good restaurants. And to top it off the previous owners and new owners (all in the family!) are really... More 

Helpful?
Thank JoMarie11
Halstead, Kansas
Level Contributor
342 reviews
45 hotel reviews
common_n_hotel_reviews_1bd8 71 helpful votes
5 of 5 stars Reviewed July 8, 2016 via mobile

Our stay here was excellent and we will definitely be back. It's such a pretty place to stay, also. The rooms are large and very clean and The owners are fantastic. Some great changes have made it an even nicer place to stay, with updated decor and service.

Helpful?
Thank beth ann k
Chicago, Illinois
Level Contributor
12 reviews
12 hotel reviews
common_n_hotel_reviews_1bd8 8 helpful votes
5 of 5 stars Reviewed June 28, 2016

We recently stayed at Orphan Annie's for two nights in the Lighthouse Suite. This was our 4th or 5th time staying here. Loren and Annie have retired as innkeepers but it's nice that it has stayed in the family .The new owners Kristen and Caleb couldn't have been nicer. This was our second time in the Lighthouse suite. It's quite... More 

Helpful?
Thank TChicagah
Kristen_Caleb, Owner at Orphan Annie's Schoolhouse Inn, responded to this review

Dear TChicagah, It was great to meet you and we're just thrilled to have met your expectations for a successful stay! We totally agree that those historic "schoolhouse" windows throw a lot of light! Room darkening shades and/or drapes are on the list for the next round of improvements! We're looking forward to seeing you, again! More 

Columbus, Wisconsin
Level Contributor
29 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed June 13, 2016 via mobile

My wife and I have been here a few times when traveling to Door County. A unique place! It's cool to stay in an historic place like Orphan Annie's! We've loved it every time we've been there and enjoy the different rooms we've stayed in. The owners are friendly, nice, and VERY accommodating. Will go back again!

Helpful?
Thank jllewis4
Kristen_Caleb, Owner at Orphan Annie's Schoolhouse Inn, responded to this review

Dear jllewis4, Thanks for being fellow “old souls” and enjoying the schoolhouse as much as we do! And, it’s easy to be accommodating innkeepers for such nice guests! More 

Questions? Get answers from hotel staff and past guests. Ask a question

14 photos of this hotel

Traveler photos: See what travelers like you saw

Viewed
All Traveler Photos (7)
Viewed
View from Room (7)

Management photos: Courtesy of the property manager

Viewed
All Management Photos (7)
Viewed
Room/Suite (7)
Check In Check Out
Hotels you might also like...
Also consider these accommodations in or near Baileys Harbor
1.5 mi away
Maxwelton Braes Lodge
Maxwelton Braes Lodge
#4 of 7 in Baileys Harbor
4.0 of 5 stars 29 reviews
0.5 mi away
Baileys Harbor Ridges Resort
Baileys Harbor Ridges Resort
#6 of 7 in Baileys Harbor
3.5 of 5 stars 37 reviews
7.5 mi away
The Ashbrooke
The Ashbrooke
#1 of 7 in Egg Harbor
4.5 of 5 stars 317 reviews
Show Prices
Show Prices
Show Prices
6.9 mi away
Edgewater Resort
Edgewater Resort
#1 of 8 in Ephraim
4.5 of 5 stars 623 reviews
7.4 mi away
Newport Resort
Newport Resort
#2 of 7 in Egg Harbor
4.5 of 5 stars 294 reviews
0.2 mi away
Beachfront Inn
Beachfront Inn
#2 of 7 in Baileys Harbor
4.5 of 5 stars 172 reviews
Show Prices
Show Prices
Show Prices
Questions? Get answers from hotel staff and past guests. Ask a question

Amenities

Highlights
  • Free Parking
About the property
  • Non-Smoking Hotel
Room types
  • Suites
  • Non-Smoking Rooms
  • Kitchenette
In your room
  • Air Conditioning
  • Microwave
  • Refrigerator in room
Services
  • Free Parking
Official Description (provided by the hotel)
Learn to relax in class! Our renovated schoolhouse boasts large suites with kitchenettes, private baths, separate entrances, individual decks or patios and a quiet relaxing atmosphere. Set back just one block from downtown, we're within walking distance from everything you need for a great getaway! ... more   less 

Additional Information about Orphan Annie's Schoolhouse Inn

Address: 8091 Guy Street, PO Box 168, Baileys Harbor, WI 54202
Location: United States > Wisconsin > Door County > Baileys Harbor
Number of rooms: 7
Also Known As:
Orphan Annie's Schoolhouse Inn Baileys Harbor, Door County, WI
Is This Your TripAdvisor Listing?
Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.
Claim Your Listing