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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!

Outdoor spa tub
Up here we dream about snow.
Welcome to our home!
Large open kitchen.
Dining

Reviews

10 out of 10
Exceptional
4 bedrooms1 bathroomSleeps 81300 sq ft

Popular amenities

  • Parking available
  • Dryer
  • Barbecue grill
  • Washer
  • Kitchen

Explore the area

View in a map
Wakefield, MI
  • Place, Indianhead Mountain
    ‪11 min drive‬
  • Place, Black River Basin
    ‪12 min drive‬
  • Place, Big Powderhorn Mountain Resort
    ‪19 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!

Add dates for prices

Amenities

Hot tub
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 3:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
Pack n play & bedding, high chair available.
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Events

No events allowed
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Pets

No pets allowed, service animals permitted
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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.
Map
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

  • Ironwood, MI (IWD-Gogebic County) - 20 min drive

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

Is Trailside #3 ~ Winter Fun Retreat! Ski, Snowboard, Snowmobile, Hot Tub, Hiking! pet-friendly?

No, only service animals are welcome at the property.

What time is check-in at Trailside #3 ~ Winter Fun Retreat! Ski, Snowboard, Snowmobile, Hot Tub, Hiking!?

Check-in begins at 3:00 PM.

What time is check-out at Trailside #3 ~ Winter Fun Retreat! Ski, Snowboard, Snowmobile, Hot Tub, Hiking!?

Checkout is at 10:00 AM.

Where is Trailside #3 ~ Winter Fun Retreat! Ski, Snowboard, Snowmobile, Hot Tub, Hiking! located?

Situated in a rural location, 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).

About the host

Hosted by Dean Rossey Jr

Host profile image
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.

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.

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

Languages:

English

Premier Host

They consistently provide great experiences for their guests