Hero Image

Your Perfect Getaway Starts Here

Find a stay

Check out all our markets!

Book beautiful, fully equipped vacation rentals in Wisconsin & Northern Michigan — where comfort, cleanliness, and convenience meet.

We are only satisfied with the best. From unbeatable locations to astonishing interior design, we consider every detail when it comes to selecting our luxury vacation rentals.

More Than a Stay — It’s a Clear Trail Experience!

At Clear Trail Properties, we believe every trip should feel effortless. That’s why our homes are clean, thoughtfully stocked, and located in stunning destinations across Wisconsin and Northern Michigan. Whether you’re escaping for a weekend or settling in for a longer stay, we’ve got your comfort covered.

Golf Lover?

Want to be minutes from the famous Sand Valley Golf Course?

Is the Lake calling your name?

If the lake is calling you, come stay with us!

Northwoods Adventures

The northwoods of Wisconsin and northern Michigan are breath taking.

What Guests Love About Us

I booked this for my favorite foursome for our trip to Sand Valley. It was very comfortable and worked well for us. I will be booking again next year.

Thomas O.

Brown Bear Cabin, October 2025

Fantastic waterfront home, breathtaking views from the jacuzzi made recovery from our Ragnar Race weekend relaxing. House was very comfy and spacious, was ideal to remote work from on the weekdays and WiFi was excellent. The place had a great north woods feel without the additional 2hrs trek north. Will definitely return. Lots to do in the area, our favorite is 9 mile Forest for trail runs, biking and walks.

Francis B.

Blue Heron Oar'asis, October 2025

Great pet friendly vrbo that is close to the water and walking distance to town.

Amber S.

Lakeview Stay, September 2025

A great place to stay

Everett U.

Diamondback Ranch, September 2025

This place is great for a weekend getaway. Prime location, just a 3-minute drive to downtown or a 5-minute bike ride. Beautiful views and easy access to the water.

Mike S.

Lakeview Stay, September 2025

Hill Hideaway was just as it was described. We were very comfortable there. It was close to everything for us. They thought of everything. We had everything we needed.

Delores B.

Hill Hideaway Cottage Unit 2, September 2025

Great place to stay at. Good area to go walking. Everything is less than 10 min away. Room was comfortable and clean.

Fidencio G.

McIntosh Room #1, September 2025

Very nice and well appointed home. Very good location on Lake Arrowhead property. Would come back and recommend for others.

Paul C.

Brown Bear Cabin, September 2025

.

Makaya K.

Scott Street Unit #2, September 2025

Great location for accessing the whole lake region. Comfortable and roomy. Everything we needed for the stay.

carl k.

Hill Hideaway Cottage Unit 1, September 2025

Trusted by Hundreds of Happy Travelers


  • Immaculately Clean Homes
  • Fully Stocked with Essentials
  • Fast, Friendly Communication
  • Great Locations for Nature, Relaxation & Fun

Interested in Cohosting with us?

Take your second home or investment property to the highest potential! Let us help you manage your home and take all your stresses away. We meet with you for a free consultation to discuss how best to manage your property. We are experts in design, marketing and pricing strategies to help enhance every detail so your property stands out. We've owned short term rentals since 2018 and we can bring our experience and knowledge to you to help make your rental business a success!

Recognized by


Copyright © 2025. All Rights Reserved.
Website by CraftedStays