Entire home
Trailside #3 ~ Winter Fun Retreat! Ski, Snowboard, Snowmobile, Hot Tub, Hiking!
Holiday home in Wakefield with kitchen and patio
Photo gallery for Trailside #3 ~ Winter Fun Retreat! Ski, Snowboard, Snowmobile, Hot Tub, Hiking!





Reviews
10 out of 10
Exceptional
4 bedrooms 1 bathroom Sleeps 8 1300 sq ft
Popular amenities
Explore the area

Wakefield, MI
- Place, Indianhead Mountain11 min drive
- Place, Black River Basin12 min drive
- Place, Big Powderhorn Mountain Resort19 min drive
- Airport, Ironwood, MI (IWD-Gogebic County)24 min drive
Rooms & beds
4 bedrooms (sleeps 8)
Bedroom 1
1 Queen Bed
Bedroom 2
1 King Bed
Bedroom 3
1 Single Bunk Bed
Bedroom 4
1 Queen Bed
1 bathroom
Bathroom 1
Bathtub · Toilet · Shower only
Spaces
Deck or patio
Kitchen
Dining area
About this property
Trailside #3 ~ Winter Fun Retreat! Ski, Snowboard, Snowmobile, Hot Tub, Hiking!
Welcome to Your Ultimate U.P. Retreat – Complete with Hot Tub!
Experience the beauty and adventure of Michigan's Upper Peninsula in this cozy, well-appointed home situated in the heart of Big Snow Country. With an impressive average snowfall of 217 inches per year, it’s a winter wonderland just waiting to be explored. Enjoy easy access to three nearby ski hills and direct trail access—Snowmobile and ORV Trail #2 is just 30 seconds from your doorstep!
In the warmer months, the area transforms into a haven for outdoor enthusiasts. Hike scenic trails, mountain bike through the woods, explore nearby waterfalls, or swim in one of several nearby lakes. Wildlife sightings are common, and the natural beauty is unforgettable year-round.
The Space:
This welcoming retreat features 4 bedrooms, 5 beds, and 1 full bathroom—making it ideal for families, friend groups, or couples looking for a quiet getaway.
- 1 bedroom located on the main floor
- 3 bedrooms and 1 bathroom located upstairs
Please note: A few steps lead into the home, and a staircase is required for second-floor access
Enjoy a fully stocked kitchen equipped with:
-A wide range of pots, pans, and baking dishes
-Spices and cooking essentials
-A complete coffee bar setup
-Large outdoor propane grill for year-round cookouts
The spacious open-concept living and dining area is perfect for entertaining, cooking, relaxing, and staying connected with your group.
Guest Access:
Guests have full access to the entire home. Check-in is a breeze with a smart lock on the front door for self-service entry.
The Neighborhood:
Trailside Retreats is conveniently located just outside Wakefield in the peaceful Ramsey neighborhood, offering easy access to both adventure and relaxation.
Getting Around:
You’ll need a car or truck for general travel around the U.P., but the home's location on Trail #2 makes it perfect for exploring Wakefield, Bessemer, Ironwood, and Hurley by snowmobile or ATV.
Important Notes:
- Hot Tub: Use at your own risk. Please consult a doctor if you are pregnant or have medical conditions.
- Pets: Not allowed. A $350 fee applies for any undisclosed pets.
- Air Conditioning: Yes, the home is fully air-conditioned.
Guest Support:
Owners Dean Rossey Jr. and Ellen Rossey personally manage this home and are available 24/7 throughout your stay. Their contact details can be found in your VRBO reservation.
Come make memories at your U.P. home away from home—Trailside Retreat #2!
Experience the beauty and adventure of Michigan's Upper Peninsula in this cozy, well-appointed home situated in the heart of Big Snow Country. With an impressive average snowfall of 217 inches per year, it’s a winter wonderland just waiting to be explored. Enjoy easy access to three nearby ski hills and direct trail access—Snowmobile and ORV Trail #2 is just 30 seconds from your doorstep!
In the warmer months, the area transforms into a haven for outdoor enthusiasts. Hike scenic trails, mountain bike through the woods, explore nearby waterfalls, or swim in one of several nearby lakes. Wildlife sightings are common, and the natural beauty is unforgettable year-round.
The Space:
This welcoming retreat features 4 bedrooms, 5 beds, and 1 full bathroom—making it ideal for families, friend groups, or couples looking for a quiet getaway.
- 1 bedroom located on the main floor
- 3 bedrooms and 1 bathroom located upstairs
Please note: A few steps lead into the home, and a staircase is required for second-floor access
Enjoy a fully stocked kitchen equipped with:
-A wide range of pots, pans, and baking dishes
-Spices and cooking essentials
-A complete coffee bar setup
-Large outdoor propane grill for year-round cookouts
The spacious open-concept living and dining area is perfect for entertaining, cooking, relaxing, and staying connected with your group.
Guest Access:
Guests have full access to the entire home. Check-in is a breeze with a smart lock on the front door for self-service entry.
The Neighborhood:
Trailside Retreats is conveniently located just outside Wakefield in the peaceful Ramsey neighborhood, offering easy access to both adventure and relaxation.
Getting Around:
You’ll need a car or truck for general travel around the U.P., but the home's location on Trail #2 makes it perfect for exploring Wakefield, Bessemer, Ironwood, and Hurley by snowmobile or ATV.
Important Notes:
- Hot Tub: Use at your own risk. Please consult a doctor if you are pregnant or have medical conditions.
- Pets: Not allowed. A $350 fee applies for any undisclosed pets.
- Air Conditioning: Yes, the home is fully air-conditioned.
Guest Support:
Owners Dean Rossey Jr. and Ellen Rossey personally manage this home and are available 24/7 throughout your stay. Their contact details can be found in your VRBO reservation.
Come make memories at your U.P. home away from home—Trailside Retreat #2!
Add dates for prices
Amenities
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
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9.8 out of 10, (85 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
Pack n play & bedding, high chair available.
Events
No events allowed
Pets
No pets allowed, service animals permitted
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
Located in Wakefield, this holiday home is in a rural area. Black River Basin and Indianhead Mountain are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Interstate Falls and Ottawa National Forest.

Wakefield, MI
What's nearby
- Indianhead Mountain - 11 min drive - 5.8 km
- Gabbro Falls - 11 min drive - 6.9 km
- Black River Basin - 12 min drive - 7.3 km
- Big Powderhorn Mountain Resort - 19 min drive - 16.0 km
- Copper Peak - 34 min drive - 28.6 km
Getting around
Restaurants
- Pit Stop - 9 min drive
- Dairy Queen - 9 min drive
- Club 28 - 5 min drive
- Randall Bakery - 4 min drive
- Korner Kitchen - 5 min drive
Frequently asked questions
About the host
Hosted by Dean Rossey Jr

Our family of five first discovered the magic of Blackjack and Indianhead Mountains back in 2016. From the very first trip, we were hooked—the snow, the scenery, the sense of escape. We knew right away this place was special.
It wasn’t long before we realized we wanted more than just a vacation spot—we wanted a place that truly felt like home. A place we could return to time and again, filled with warmth, comfort, and memories in the making.
That’s when we decided to purchase a home in the area. It was important to us to find a space that not only met our needs today but could grow with us and continue to be a source of joy for our kids as they get older.
Trailside Retreat isn’t just a getaway—it’s a part of our family story, and we hope it becomes part of yours too.
It wasn’t long before we realized we wanted more than just a vacation spot—we wanted a place that truly felt like home. A place we could return to time and again, filled with warmth, comfort, and memories in the making.
That’s when we decided to purchase a home in the area. It was important to us to find a space that not only met our needs today but could grow with us and continue to be a source of joy for our kids as they get older.
Trailside Retreat isn’t just a getaway—it’s a part of our family story, and we hope it becomes part of yours too.
Why they chose this property
The moment we saw this property, we knew it was meant for us. With its four spacious bedrooms, it offered the perfect layout and space we were looking for.
We could instantly envision its potential—with a few thoughtful interior updates, a brand-new deck, and the addition of a hot tub, we knew it would become a guest favorite in no time.
As a licensed contractor, I see opportunities where others may not. While the home already has so much to offer, I look forward to continuously improving it, adding upgrades and personal touches that will transform a great property into an exceptional one.
We could instantly envision its potential—with a few thoughtful interior updates, a brand-new deck, and the addition of a hot tub, we knew it would become a guest favorite in no time.
As a licensed contractor, I see opportunities where others may not. While the home already has so much to offer, I look forward to continuously improving it, adding upgrades and personal touches that will transform a great property into an exceptional one.
What makes this property unique
What makes this home truly special is its unique combination of four bedrooms and a single bathroom—all while maintaining a warm, cozy atmosphere that makes it feel like home from the moment you walk in.
We genuinely hope you enjoy the same comfort and relaxation here that our family experiences every time we visit. Whether you're here for adventure or a quiet escape, our home is ready to welcome you.
Thank you for choosing to stay with us.
Warmly,
Dean and Ellen
We genuinely hope you enjoy the same comfort and relaxation here that our family experiences every time we visit. Whether you're here for adventure or a quiet escape, our home is ready to welcome you.
Thank you for choosing to stay with us.
Warmly,
Dean and Ellen
Languages:
English
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