10/10 Excellent
Willie T.
3 Feb, 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Willie T.
Stayed 3 nights in Jan 2026
Entire home
Trailside #1 Winter Fun Retreat~ Ski, Snowboard, Snowmobile, HotTub, Hiking
Photo gallery for Trailside #1 Winter Fun Retreat~ Ski, Snowboard, Snowmobile, HotTub, Hiking
Reviews
9.8 out of 10
Exceptional
4 bedrooms2 bathroomsSleeps 101300 sq ft
Popular amenities
Explore the area
Wakefield, MI
- Place, Gabbro Falls9 min drive
- Place, Indianhead Mountain9 min drive
- Place, Black River Basin10 min drive
- Airport, Ironwood, MI (IWD-Gogebic County)20 min drive
Rooms & beds
4 bedrooms (sleeps 10)
Bedroom 1
1 King Bed
Bedroom 2
1 Queen Bed
Bedroom 3
2 Double Beds
Bedroom 4
1 King Bed
2 bathrooms
Bathroom 1
Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer
Bathroom 2
Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer
Spaces
Deck or patio
Kitchen
About this property
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.
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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Trailside #3 ~ Winter Fun Retreat! Ski, Snowboard, Snowmobile, Hot Tub, Hiking!
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- Hot tub
- Kitchen
- Washing machine
- Dryer
9.8 out of 10, Exceptional, (27 reviews)
House Rules
Check in after 3:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
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
We should mention
This property does not have any lifts
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.
Wakefield, MI
What's nearby
- Gabbro Falls - 9 min drive - 6.9 km
- Indianhead Mountain - 9 min drive - 5.8 km
- Black River Basin - 10 min drive - 7.3 km
- Gogebic County Forest - 10 min drive - 11.7 km
- Big Powderhorn Mountain Resort - 16 min drive - 16.4 km
Getting around
Restaurants
- Pit Stop - 9 min drive
- Dairy Queen - 9 min drive
- Randall Bakery - 4 min drive
- Korner Kitchen - 5 min drive
- Club 28 - 4 min drive
Frequently asked questions
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
9.8/10
Check-in
9.8/10
Communication
9.6/10
Location
10/10
Listing accuracy
Reviews
10/10 Excellent
Amber A.
17 Oct, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amber A.
Stayed 3 nights in Oct 2025
10/10 Excellent
Verified traveller
8 Aug, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Verified traveller
Stayed 5 nights in Aug 2025
10/10 Excellent
Ann O.
7 Jun, 2025
Liked: Cleanliness, check-in, communication, listing accuracy
Ann O.
Stayed 4 nights in Mar 2025
10/10 Excellent
Amy H.
24 Sept, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amy H.
Stayed 7 nights in Sep 2025
10/10 Excellent
Sammy J.
12 Jul, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Sammy J.
Stayed 4 nights in Jun 2025
10/10 Excellent
Christopher M.
2 Apr, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay for skiing!
Christopher M.
Stayed 3 nights in Feb 2025
10/10 Excellent
Ross G.
28 Mar, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent Ski Lodge
Ross G.
Stayed 3 nights in Mar 2025
10/10 Excellent
Julie F.
18 May, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wakefield stay
Julie F.
Stayed 3 nights in May 2025
10/10 Excellent
Pawel M.
8 Jan, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic stay
Pawel M.
Stayed 4 nights in Jan 2025
10/10 Excellent
Verified traveller
8 Mar, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay
Verified traveller
Stayed 4 nights in Mar 2022
10/10 Excellent
Heather M.
14 Jan, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Property
Heather M.
Stayed 3 nights in Jan 2024
10/10 Excellent
Verified traveller
13 Mar, 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great updated spot near the slopes!
Verified traveller
Stayed 3 nights in Mar 2020
10/10 Excellent
Heather M.
20 Feb, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property/location
Heather M.
Stayed 4 nights in Feb 2024
10/10 Excellent
Scott s.
23 Jul, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Quick summer getaway with family
Scott s.
Stayed 3 nights in Jul 2023
10/10 Excellent
Corey A.
21 Jan, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Snowmobile Trip 2023
Corey A.
Stayed 4 nights in Jan 2023
10/10 Excellent
Ashley H.
21 Jul, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great for families
Ashley H.
Stayed 3 nights in Jul 2024
10/10 Excellent
Jason B.
29 Aug, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
In Wakefield for boat races.
Jason B.
Stayed 7 nights in Jul 2023
10/10 Excellent
Debbie C.
31 May, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing property! Highly recommend
Debbie C.
Stayed 3 nights in May 2024
10/10 Excellent
Alex R.
23 Jan, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Location location location
Alex R.
Stayed 3 nights in Jan 2023
10/10 Excellent
Karen S.
1 Aug, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wakefield
Karen S.
Stayed 4 nights in Jul 2024
10/10 Excellent
Dustin B.
9 Feb, 2018
Very clean and cozy house. Comfortable beds
Dustin B.
Stayed 2 nights in Feb 2018
10/10 Excellent
Curt R.
7 Mar, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Exceeded Expectations
Curt R.
Stayed 6 nights in Feb 2023
10/10 Excellent
Timothy W.
28 Mar, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Spot for Skiing the UP
Timothy W.
Stayed 4 nights in Mar 2023
10/10 Excellent
Dave N.
26 Feb, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Ski Weekend
Dave N.
Stayed 3 nights in Feb 2024
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.
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 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
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
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