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Trailside #3 ~ Winter Fun Retreat! Ski, Snowboard, Snowmobile, Hot Tub, Hiking!

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

9.8 out of 10
Exceptional
4 bedrooms1 bathroomSleeps 81300 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View in a map
Wakefield, MI
  • Place, Gabbro Falls
    ‪9 min drive‬
  • Place, Indianhead Mountain
    ‪9 min drive‬
  • Place, Black River Basin
    ‪10 min drive‬
  • Airport, Ironwood, MI (IWD-Gogebic County)
    ‪20 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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  • Kitchen
  • Washing machine
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9.8 out of 10, Exceptional, (93 reviews)
Trailside #1 Winter Fun Retreat~ Ski, Snowboard, Snowmobile, HotTub, Hiking

House Rules

Check in after 4:00 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.
View more Holiday homes in WakefieldOpens in a new window
Map
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

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

Restaurants

  • ‪Pit Stop - ‬9 min drive
  • ‪Dairy Queen - ‬9 min drive
  • ‪Randall Bakery - ‬4 min drive
  • ‪Korner Kitchen - ‬5 min drive
  • ‪Club 28 - ‬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.

How much does it cost to stay at Trailside #3 ~ Winter Fun Retreat! Ski, Snowboard, Snowmobile, Hot Tub, Hiking!?

As of 28 Mar, 2026, prices found for a 1-night stay for 2 adults at Trailside #3 ~ Winter Fun Retreat! Ski, Snowboard, Snowmobile, Hot Tub, Hiking! on 1 Apr, 2026 start from S$209, 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 #3 ~ Winter Fun Retreat! Ski, Snowboard, Snowmobile, Hot Tub, Hiking!?

On-site parking is available at the property.

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

Check-in begins at 4:00 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).

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 window
Rating 10 - Excellent. 25 out of 29 reviews
Rating 8 - Good. 4 out of 29 reviews
Rating 6 - Okay. 0 out of 29 reviews
Rating 4 - Poor. 0 out of 29 reviews
Rating 2 - Terrible. 0 out of 29 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Bryan S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place! Everything was clean and exactly described. Would definitely stay here again
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

Melissa P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location to visit the local ski hills.
Stayed 4 nights in Dec 2025
Verified

10/10 Excellent

Joe J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent place which was clean and well maintained
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Katie R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean and spacious for us all. Would recommend to all if you need aplace to stay.
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Turner P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home was very clean and stocked with everything we needed. A great place to stay for a snowmobile trip, right off the trail. We will definitely be back!
Stayed 3 nights in Dec 2025
Verified

8/10 Good

F F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean property, everything as advertised.
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Adam T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Dean was a great host, he helped us get our sleds running on a very cold morning without hesitation, we'll be back
Stayed 4 nights in Jan 2026
Verified

10/10 Excellent

Christopher L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

This is a very nice property very clean and comfortable
Stayed 5 nights in Feb 2023
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
Hot tub was nice, very clean with well balanced water. Everything we needed was furnished.
Stayed 5 nights in Sep 2025
Verified

10/10 Excellent

Shannon S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay at Trailside #3! Two families shared the house and everything was perfect - the beds were comfortable, tvs in every room kept the kids happy when the adults wanted to watch football, and it was close proximity to the ski hills. After spending the day skiing, coming back to the hot tub and the ability to cook our own food was a real treat. We will definitely be back! Thanks so much, Dean!
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Tom H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

UP Michigan ski trip

Very nice accommodations, clean, decorated nice. Very close to ski hills, a short drive to hiking and water falls. Comfortable stay for a family of 5! Plan on going back.
Stayed 4 nights in Dec 2024
Verified

10/10 Excellent

Brett H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place

Perfect place for 5 guys in their 40's to ski the nearby hills during the day and relax in the hot tub at night. Everything very clean and the hot tub was big. Will stay again as the kids get older and I bring the family to the U.P.
Stayed 4 nights in Feb 2024
Verified

10/10 Excellent

Stu E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family ski trip

Great property. Close to all the ski areas. Clean and roomy little house. Would definitely recommend.
Stayed 4 nights in Mar 2023
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Snowmobile/Hot tub Vacation

Great location for snowmobiling. Hot tub was new and large. The owner was awesome in responding to questions.
Stayed 4 nights in Jan 2023
Verified

10/10 Excellent

Tony U.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cozy and close to ski hills

We enjoyed our stay here and found all the amenities and items we needed were at the cabin. Hot tub was well maintained and got used a lot. We had a great time enjoying the lake effect snow at the nearby ski hills.
Stayed 3 nights in Jan 2024
Verified

8/10 Good

Tracy R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ski & snowmobile weekend

Spent a long weekend with family. Property is very clean with plenty of amenities. Only downside is the shower is difficult to use if you are taller than 5’4”. Would stay again if coming back to this area.
Stayed 3 nights in Feb 2025
Verified

10/10 Excellent

Shannon B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Solo Adventure

This property is everything I was looking! Clean, relaxing, quiet, comfortable, and safe. It is close to everything the West UP has to offer.
Stayed 5 nights in Jul 2024
Verified

10/10 Excellent

KRISTI S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

4 wheeling getaway

We stayed at this cozy little house to do some four wheeling in the beautiful forest area up North. The hot tub was a welcome delight at the end of the day for our tired muscles. We would definitely stay here again.
Stayed 3 nights in Sep 2023
Verified

10/10 Excellent

Benjamin R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ski Getaway

The property was exactly what we were looking for and the check in process was a breeze. The house is very clean and comfortable as well as adequately stocked with everything you need. We were up north for a ski trip and the location was perfect for getting to Snowriver resort and shopping in Ironwood. We would definitely stay here again!
Stayed 3 nights in Feb 2023
Verified

10/10 Excellent

Corinne M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wakefield

Great space. Close to slipes and snowmobile trails. Loved the hot tub
Stayed 3 nights in Jan 2024
Verified

10/10 Excellent

GiGi B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great as usual

This is our 2nd stay at this property. Its clean, spacious, kitchen is well stocked with necessities and hot tub is perfection after a day of skiing. Dean has great communication and it’s exactly as advertised. Looking forward to next year!
Stayed 3 nights in Jan 2025
Verified

10/10 Excellent

Amanda B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing property, in great condition and very well appointed! Kitchen was thoughtfully stocked, and we were very impressed that the host thought to provide a baby gate for the steps and door knob covers for the basement door. Beds were very comfortable, with nice bedding. The hot tub was a nice treat after a day of hiking. Host went above and beyond after our stay when we realized a beloved stuffy had been accidentally left behind. Communicated promptly and made sure it was mailed back to us right away.
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

Eric A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic house for ski weekend!

Loved the house! Perfect space for everyone. Comfy beds, big screens in every room. Kitchen was well stocked with everything needed to cook a big meal or just grab a snack. Close to Snowriver and Rt 2 so accessibility is good. Very clean and well maintained. Will definitely look to return.
Stayed 3 nights in Jan 2023
Verified

10/10 Excellent

Eric C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay for a ski trip!

4 of us planned a snowmobile trip but due to conditions we were not able to use the trails. We switched last min to a Ski trip and the location could not have been better! We did a day at Snow River and a day at Powederhorn. Both were only 10 min away from the house! The hot tub was the best after a long day!!
Stayed 3 nights in Feb 2024
Verified

10/10 Excellent

Tania W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wakefield House

The property was beautiful! Big beautiful trees in the backyard and the yard was so pretty vibrant green yet. The house itself was beautifully decorated and felt a little like home! It reminded me of my grandparents house in Ironwood. Loved Our Stay! Neighbors were very friendly, it turned out they knew some of my family from Ironwood Michigan. Thank you again for making us feel welcome and for letting us stay on your beautiful property.
Stayed 3 nights in Aug 2023

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

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