Trailside #1 Winter Fun Retreat~ Ski, Snowboard, Snowmobile, HotTub, Hiking
Summary: Nestled just off ATV/UTV/Snowmobile Trail #2, Trailside Retreat #1 is a beautifully remodeled vacation home designed with Upper Peninsula adventurers in mind. Black River Basin, Snowriver Mountain Resort, and Powder Horn all within 5-10 minutes drive time. Whether you're winding down in the spacious 8-person hot tub or sinking into one of our plush, freshly upgraded beds, this home has everything you need to make your stay relaxing, memorable, and uniquely U.P.
Just minutes from breathtaking waterfalls, scenic hiking trails, and thrilling outdoor experiences, our retreat is the perfect home base for any Northwoods escape. So grab your hiking boots, and let the adventure begin!
The Home: - Completely renovated from top to bottom, our home features: - All-new sheetrock walls, laminate flooring, cozy carpet, and updated lighting - Two brand new bathrooms (one includes a Jacuzzi tub) - Remote-controlled electric fireplace - Ski/snowboard gear rack - In-home washer and dryer
Living Room Features: - 75" Smart TV with Blu-ray player, Netflix, Amazon Prime, and Pandora - Complimentary high-speed Wi-Fi - Oversized wraparound couch with electric recliners - 8-person hot tub just steps away
Bedroom Setup: - 2 King pillow-top beds (4 pillows) - 1 Queen pillow-top bed (4 pillows each) - 2 Full beds (4 pillows each) - Dressers/hooks/bench in each room for guest use - Extra pillows and blankets available
Bathrooms: - Tiled Jacuzzi tub in the upstairs bath - Complimentary cotton balls, Q-tips, shampoo, conditioner, and body wash - Towels provided for up to 8 guests - Pump hand soap at all sinks - Modern fixtures and finishes throughout
Fully Equipped Kitchen: - All new stainless-steel appliances - Filtered water from the refrigerator - Drip coffee maker & Keurig (coffee & tea station included) - Dishwasher with cleaning supplies - Microwave, range oven, toaster, toaster oven & waffle maker - Slow cooker (perfect for meals after a long day outdoors) - Dining table with seating for 6 - Generously stocked with pots, pans, dishes, utensils, glassware, and extras like wine openers and beer koozies
Bonus Amenities: - Full-sized washer and dryer in laundry closet - Board games and cards for family fun
Guest Access: Guests have full access to the property, excluding the basement and a small owner's storage closet, both of which remain locked.
Location: Located just outside Wakefield in the peaceful Ramsey neighborhood, Trailside Retreats offers immediate access to Trail #2, which connects Wakefield, Bessemer, Ironwood, and Hurley. Whether by car or recreational vehicle, it’s easy to explore the area.
Getting Around: While a vehicle is needed for most travel in the U.P., the property's trail access allows easy navigation via ATV, UTV, or snowmobile.
Important Notes: - Hot Tub: Use at your own risk. Consult a doctor if pregnant or if you have medical conditions. - Pets: No pets allowed. A $350 fee applies to any undisclosed animals. - Cooling: Home is equipped with air conditioning.
Owner Interaction: Your stay is managed by owners Dean Rossey Jr. and Ellen Rossey, who are available 24/7 to assist you during your visit. Contact information is provided with your VRBO reservation.
Trailside Retreat #1 invites you to unwind, explore, and create unforgettable memories in Michigan’s serene Upper Peninsula.
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
About the area
Wakefield
Wakefield is home to this holiday home. Old Depot Park Museum and Historic Ironwood Theatre are cultural highlights, and some of the area's activities can be experienced at Black River Basin and Indianhead Mountain. Take in the nearby slopes with cross-country skiing and snowboarding, or try out other outdoor activities such as snowmobiling and ice skating.
Big Powderhorn Mountain Resort - 16 min drive - 18.2 km
Getting around
Ironwood, MI (IWD-Gogebic County) - 19 min drive
Restaurants
Randall Bakery - 4 min drive
Keystone Bar - 4 min drive
Dairy Queen - 9 min drive
Korner Kitchen - 5 min drive
Jagger's Ore House - 4 min drive
Frequently asked questions
Is Trailside #1 Winter Fun Retreat~ Ski, Snowboard, Snowmobile, HotTub, Hiking pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Trailside #1 Winter Fun Retreat~ Ski, Snowboard, Snowmobile, HotTub, Hiking?
As of 8 May, 2026, prices found for a 1-night stay for 2 adults at Trailside #1 Winter Fun Retreat~ Ski, Snowboard, Snowmobile, HotTub, Hiking on 11 May, 2026 start from S$319, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Trailside #1 Winter Fun Retreat~ Ski, Snowboard, Snowmobile, HotTub, Hiking?
On-site parking is available at the property.
What time is check-in at Trailside #1 Winter Fun Retreat~ Ski, Snowboard, Snowmobile, HotTub, Hiking?
Check-in begins at 3:00 PM.
What time is check-out at Trailside #1 Winter Fun Retreat~ Ski, Snowboard, Snowmobile, HotTub, Hiking?
Checkout is at 10:00 AM.
Where is Trailside #1 Winter Fun Retreat~ Ski, Snowboard, Snowmobile, HotTub, Hiking located?
Situated in Wakefield, this holiday home is steps from Ottawa National Forest and within 6 mi (10 km) of Black River Basin and Gabbro Falls. Indianhead Mountain and Aspirus Ironwood Hospital are also within 9 miles (15 km).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Awesome Spot! Hot tub full and hot. House was preped and had everything we needed. Only thing i would ask for is the check put list being sent the day prior to check out instead of after we had already checked out.
Jake R.
Stayed 3 nights in Feb 2026
Response from VrboOwner on 9 Feb, 2026
Hey Jake, thanks for the great review and I apologize for not getting you the information in a timely manner. You did great and communicated very well so thank you.
The house was lovely. Newly redone throughout. Stocked kitchen. Comfy. Nice hot tub and deck area. Plenty of room for trucks and trailers. Only issues, oven was a bit finicky and out of gas for grill. We worked through it. Overall great stay.
Perfect getaway location. Close to the softball fields that we came to play in a tournament at. Beautiful house and the hot tub was awesome after days at the field.
Loved this property! It was even nicer than the pics. It was easy check in and out, easy to find and was stocked with all the accessories one could need. Definitely would come to this here again while visiting family.
We stay here every year for a ski trip and it is always very clean! The hot tub is great after a day of skiing and the rental has everything that you'd need!
Heather M.
Stayed 3 nights in Jan 2024
Response from VrboOwner on 15 Jan, 2024
Thank you for your review! It is always a pleasure hosting you and we hope to see you again in the future!
Property was in a very peaceful setting during the summer close to fishing, golf, and a short drive to many other attractions. Modern amenities ensure all the comforts of home for adults and children. I would recommend this place to anyone looking for a peaceful stay in the Western U.P.
This place is the perfect spot to visit snow river, powderhorn, and whitecap. Lots of amenities and the beds were comfortable. Hot tub was in perfect condition. A great place to stay after a long day of snowboarding or skiing.
Alex R.
Stayed 3 nights in Jan 2023
Verified
10/10 Excellent
Dustin B.
9 Feb, 2018
Very clean and cozy house. Comfortable beds
Had a great time at the Wakefield Hotel House. First time using VRBO and had a great experience. Homeowner was very helpful in answering any questions. Only a few miles from Big Snow Resort which was great for skiing.
Dustin B.
Stayed 2 nights in Feb 2018
Response from VrboOwner on 20 Jul, 2023
Dustin thank you for the great review. We are happy you liked the place. Please consider us next time you are in the area. As new owners, we will look to continue make upgrades to the house, making it a more enjoyable experience for our guests.
This home was the absolute best one we've ever rented and we've rented many. It is an updated home with everything you will need. Comfortable, roomy well stocked. We had a mini family reunion and were able to comfortably accommodate numerous people for an evening gathering. We highly recommend this property.
Generously furnished and wonderfully provisioned, this VRBO was everything and more in the way of comfortable accommodations. The entertainment options were outstanding (streaming services and DVD Player). We truly enjoyed the stay.
Curt R.
Stayed 6 nights in Feb 2023
About the host
Hosted by Dean Rossey Jr
Our journey to Trailside Retreat #1 began in 2016, when our family of five first visited Blackjack and Indianhead Mountains. We instantly fell in love with the area—the crisp mountain air, the abundant outdoor activities, and the peaceful escape it offered from our busy lives.
Over the years, these mountains became our favorite family getaway. We knew we wanted more than just seasonal trips; we wanted a place that felt like our own slice of the Northwoods. Somewhere that truly felt like home.
That dream became a reality when we purchased this property. Our vision was simple: create a space where we could build lasting memories with our children and a place they could grow up enjoying year after year. We’ve poured our hearts into making this retreat comfortable, welcoming, and filled with all the things we love most about the U.P.
We hope Trailside Retreat #1 becomes as special to you as it is to us.
Why they chose this property
When we first saw this property, we knew it was the one for us. With four spacious bedrooms, it was the ideal fit for our family of five—plenty of room for us and our three kids to spread out and feel at home.
What truly stood out was how beautifully updated the interior was. From the start, it felt like a turnkey retreat, ready for us to enjoy right away without needing immediate work.
As a licensed contractor, I also saw the incredible potential this home had. While it's already a fantastic space, I’m excited to continue enhancing it over time—adding thoughtful touches and upgrades that will make this great property even better for our family and for our guests.
Trailside Retreat #1 isn’t just a place to stay—it’s a space we’re proud to share and continually invest in.
What makes this property unique
What makes this home truly special is its rare combination of four bedrooms and two full bathrooms, all wrapped in a warm, inviting atmosphere. It offers just the right balance of space and coziness—ideal for families, couples, or friends looking to relax and reconnect.
We genuinely hope that when you stay at our home, you feel the same comfort and peace that we experience every time we walk through the door. Whether you're here for adventure or rest, Trailside Retreat #1 is ready to welcome you.
Thank you for choosing to stay with us.
Warm regards,
Dean and Ellen
Languages:
English
Premier Host
They consistently provide great experiences for their guests