Our third trip, an updated review of this Wisconsin destination for a NYE vacation.

We were feeling caged and needed a change of scenery.  A Wisconsin winter getaway over the New Year’s holiday seemed like the perfect escape.  This was our third trip to the Osthoff Resort but our first time staying during the winter months. 

I didn’t know if I would even write this one up, since I had already highlighted this resort in the post I wrote for the Top Destinations for Romantic Weekends in Wisconsin.  I do have a couple things to say about our most recent stay at the Osthoff resort in Elkhart Lake.

New Year's Eve at The Osthoff Resort

Elkhart Lake, WI

Elkhart Lake has a full calendar of events throughout the year and it’s only an 1 hour 45 min drive from Sun Prairie, WI.  Road America is located here and is one of the biggest draws for hosting international car racing events and a racing school.  

The Victorian homes around town, the stately street lights and paved walkways along the lake give you a peak into another time and a different place.  The downtown area has some neat shops and restaurants, the main strip is in walking distance from The Osthoff Resort.  In the summer you can rent bikes, let the wind blow through your hair, while you cycle through the quaint village. 

Swimming Pool at the Osthoff

Many of the shops are not operating as usual so take the extra time to google that up.   On this trip we picked up a couple trinkets from the gift shop at the Elkhart Outfitter .  Buy some tasty wine & cheese from the Vintage Elkhart Lake, we did that on our 13th year anniversary trip.  Be sure to order online they are currently only offering curbside pick-up.

the osthoff Resort review
3 Bedroom Woodland Deluxe

We booked the 3 Bedroom Woodland Deluxe for four nights.  My husband’s brother and his wife and kids came and met us.  The rooms could certainly use an update, particularly the pull out couches in living room area.  It’s a bit stiff and dated but at the same time the bones of this place are good.  It has timeless charm with it’s horseshoe shape that flows you either way straight to the lake.  

In the summer you can rent watersport equipment such as Paddle Boats, Swans, Kayaks and Canoes.  There is a beach side ice cream shop, a stage for live music, and a grill with all your favorite apps and sandwich items.  

This time around the girls felt special because they held a room key in their new clutches.  Of all the amenities they care about, an indoor pool is at the top of their list.   The game room was a total rip off with half the machines were not functioning.  When I mentioned it to the front desk staff they penciled it down and said the machines are owned by someone else.  

Make sure to bring your own paper towels and know that the kitchen is minimally stocked with basic cookware if you are planning on eating some meals in the room. I brought k-cups but they have a coffee pot. I premade a lasagna but there was no baking sheet in the room for cheese bread. Bring cooking oil, the kitchen has dish towels, a couple packs of dishwasher powder ,a few trash bags, salt and pepper.

KD Ranch Carriage Ride

Winter Activities

During the winter there are still some really neat activities you can get into.  We found out you can do a dog sledding adventure with The Siberian Outpost but we were too late to get in.   We went night sledding down the big hill at the High School.  The hill had two areas to choose from for take off a deep slope and the sleds went fast.   It was lit by overhead lamps.  The perfect ambiance for an evening sledding.

I booked another special outing for us when our family joined us for the last part of our trip. I knew it would be fun for our nieces.  On New Year’s Day we got picked up KD Ranch in a horse and carriage.  The girls were delighted, my youngest niece kept asking when we would get to the castle.

Aspira Spa

Meditation, Yoga, Massage Therapy….these days you have to do, what you got to do, to arm yourself with several layers of wellness.  Guard your sanity.  Therapeutic Massage has benefits that go far beyond your muscular tension.  It reduces anxiety, provides stress relief and breaks down muscular adhesions (knots).

I held a Massage Therapy license for many years, and believed in the practice enough to open up my own day spa establishment. If we are vacationing and a couple’s massage is an offering, we are getting it! On New Year’s Eve we did just that, we booked the 80-minute couple’s massage at @aspiraspa 

The service was flowy and light, it felt nice but didn’t have the depth that I really like. The preferred amount of pressure should always be addressed before the treatment starts with options to upgrade to deep tissue, aromatherapy etc. 


Communicating the various options that the spa sells ensures the service meets the client’s expectations.  I mentioned my knots and tension and wanting to focus on the neck muscles but we were only given the option of Swedish massage or relaxation.

ImpressiveThe Elk Room at the Osthoff Resort

The Elk room is at the center of this grandiose resort.  

It transitions from coffee shop in the morning to hotel lounge in the evening and there is always a flow of energy as new guests check in.  It has a look out spot and a balcony with a picture perfect lake view.  The barista isn’t particularly friendly before 2pm, but the lattes are on point and the Bloody’s come fully dressed.  

One afternoon when the kids could stand the chlorine stinging their eyes no more and they ran out of quarters to donate to the arcade games, we found ourselves with prime seating in the Elk room. 

An afternoon drink , sweeping views of the freshly snow covered lake, comfy seating next to the massive fireplace, overall this resort still does it for me.   

Soon it will be due for new furnishings but it’s exterior is crispy, classic with architectural peaks.  The rooms are like condos and offer privacy, but a short elevator ride and you can walk down and be in the middle of the scene.  They had live music in the lounge on New Years Eve.

NYE at the Osthoff Resort