We stayed at the Osthoff for two nights. One just my husband and I - one with our two young sons.
It is an impressive looking resort from the outside and mostly throughout. Could be defined as sprawling - which could mean a lot of walking if you are on an end wing. Not an issue for us.
Customer service was great from the moment we booked. (Gave us a free upgrade since it was our anniversary weekend.)
We stayed in a 1 bedroom woodland deluxe. We were happy with the amount of space a one bedroom gave us - especially with having two young kids. Most of the furnishings are upper end and fitting of the price of the rooms - which tend to be on the high side even in the winter. However, there are some updates they should consider. When staying at nicer, more expensive resorts these days, you usually get a nice flat screen tv. Our room still had to small tube tvs. The living room one is so high up you have to strain your neck while sitting to see it. Same kind in armoire in bedroom. Also, if you have the armoire doors open - you can't open the bathroom door to get out without slamming into it. Poor design.
Our room was handicap accessible so had a roll in shower which was a little dark. The whirlpool tub was nice though along with everything else in the bathroom. Mini kitchen area was nice too.
The pool and hot tub was great. The air was warm in there which was a nice perk. A lot of times the air is so cold you freeze moving around. We enjoyed the hot tub and our son enjoyed the pool.
The arcade was the ripoff you would expect it to be.
My husband and I ate dinner at Lola's which was expensive (also as expected) but good.
The second night we ordered room service - pizzas from Ottos. Average.
Overall, we really enjoyed our stay and would love to try it sometime in the summer when there is more to do.

We really enjoyed this hotel. The grounds were beautiful, even in the winter, and the staff were very welcoming. The village of Elkhart was steps away and fun to explore. Everyone we met was very friendly.

We stayed in a 1 bedroom suite with full kitchen and jacuzzi bath. The room was very nice and well cared for, although a bit dated. The bed was made with a heavy quilt that had seen better days. The TV's were all the old analog style. We had to head for town to catch the Packer game in HD (no HD at the resort at all... not even in the lounges). The kitchen appeared to have been updated recently and was well appointed.

We were surprised at the details that were missed. The bed pillows although plentiful, were all the same; very firm foam. There was not a "pillow menu" the better resorts and hotels now offer. I found a softer pillow from the sofa pillows and put a pillow case on that. The bath tissue was "public restroom" fare.

The resort has 2 restraunts reasonably priced. Otto's food was good, but the kitchen was extremely slow, especially for breakfast. Best to bring something to read while you wait.

A great way to put one in the holiday spirit is to visit the Osthoff Resort on beautiful Elkhart Lake, WI. Numerous vendors from Germany make the trek each year to sell their wares such as nutcrackers, handblown ornaments, and wood carvings.

The resort is splendidly dressed in the trappings of the season and music fills the air. The front desk staff is sensitive to one's needs, and we discovered that our suite was upgraded due to a birthday in our party. The suite was spacious and impeccably clean. The resort offers brunch with Santa on weekends prior to Christmas for the young and young at heart.

We dined in the resort's themed restaurant, Lola's. Hot bread arrived from the kitchen immediately after our seating. The food was savory and there wasn't a morsel left on anyone's plate! Perhaps this was due to the fact that The Osthoff has a cooking school and its chefs are second to none.

I'm 5 months pregnant, so my husband and I decided to find a place to take a quiet get away after Christmas to spend some quality time together before the baby is born. We researched several resorts within 3 hours of Milwaukee, and found the Osthoff had great reviews (especially about the spa), so we decided to make that our destination for our 2 night get away.
We arrived at 1:30pm on Monday, December 26th, and we were able to check into our room right away which was nice. No upgrades were offered, which I'm very surprised because the resort was obviously deserted and empty.
When we got to our room, it was nice, but the TVs were small and old Tube TVs. Even Holiday Inn's have Flat Screen LCD TVs now. We were really disappointed as we had planned to spend a majority of the time in the room relaxing and watching movies. Unfortunately, I also forgot to bring a DVD player. I assumed they would have one, but they did not. When we checked about renting movies through the TV, they were charging up to $15.99 for a movie! So we decided not to rent any movies.
I decided to take a soak in the whirlpool tub in the room, and realized there were no bathrobes. I was surprised a 4 diamond "Spa" resort did not provide bathrobes. I called down to the front desk to see if they could provide one for me, and they said they don't offer bathrobes to their guests. I thought to myself, why couldn't they use a robe from the spa to bring to their guest's room? For some reason this was a big disappointment for me. I really enjoy lounging in a bathrobe and relaxing. Why wouldn't they go above and beyond to provide a simple customer service such as this. So my husband and I thought we'd go down to the spa and gift shop to see if they sold any. This was at 5pm. Unfortunately, both the spa and the gift shop were closed! I was very surprised both were closed so early.
The next morning I called the spa to schedule a "Mother-To-Be" massage. No one answered the phone and it went to voicemail, so I left a message with the room number to call back and what I was looking for. 2 hours later, with no return phone call, we called the front desk to see if the Spa was open and that we hadn't received a call back. The person at the front desk said they'd check and have someone from the spa call us back. 10 minutes later, a young girl calls back and asked if I needed something. I told her I called about booking a "mother to be" massage for today (December 27th) and she said there were no massages available for today. I was surprised seeing as the resort was so empty. She said I could book something for tomorrow. I declined since we were checking out tomorrow. She didn't seem to know what to say after, so I said thank you and hung up. I was disappointed she didn't try to offer another service that perhaps was available. I still wonder if I was called back 2 hours earlier if I would have been able to get in for a massage. I guess I won't be able to experience the great Spa the Osthoff is so known for.
My Husband and I decided to try dinner at Lola's. The atmosphere was nice, but again the service was average. He ordered Veal Ragout and I ordered the Butternut squash Ravioli. His Veal was good but the Gnocchi was burnt. I enjoyed the ravioli. When we were finished, the bus boy took our plates and then the server came with our bill. She never showed us the Dessert tray that we saw all the other servers showing the other tables. I was surprised, and again, disappointed. So we paid the bill and left. We then went to the Elk Lounge and sat for a while. It's a beautiful room.
By the time we got back to our room, I was craving something sweet, so we called down to room service at 9:05pm to see if they would serve us dessert. The person said their services closed at 9pm. I was shocked...5 minutes late and they won't attempt to go above and beyond in service to please a guest at a 4 diamond resort?!

So to summarize, to me it's the little things that make a resort a 4 diamond resort along with top customer service, and those little things added up to a disappointing trip:
1. No robes, and no offer to accommodate our need for one.
2. Lack of spa service response
3. Burnt dish at a fine restaurant
4. No offer for dessert after an expensive dinner at a fine restaurant
5. No ability to provide room service 5 minutes after the 9pm cutoff (What resort stops room service at 9pm anyway?)
6. Small tube TVs from the 80s in the rooms.
7. Movie rental prices - outrageous!
8. Lack of activities to do on the resort grounds during this time.
9. Spa and Gift Shop close very early (5pm!)
10. Overall lack of customer service...most everyone we spoke to that worked here seemed cold and not interested in helping or going above and beyond.

I usually don't expect much, but for the price we paid per night, and the mediocre customer service, I can't say I plan to come back here again. Unfortunately, this will most likely be our first and last time here.