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Trailside #1 Summer fun~ AC, HotTub, ATV, hiking, waterfalls, fishing, boat

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Our happy place
Plenty of space for family and friends!
Welcome to the Trailside Retreat #1!
Cars, Trucks, ATVs, UTVs, Snowmobiles, we have space for all of them!
Relaxing in the woods.

Reviews

9.8 out of 10
Exceptional
4 bedrooms2 bathroomsSleeps 101300 sq ft

Popular amenities

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

Explore the area

Map
Wakefield, MI
  • Indianhead Mountain
    ‪11 min drive‬
  • Black River Basin
    ‪12 min drive‬
  • Big Powderhorn Mountain Resort
    ‪19 min drive‬
  • Ironwood, MI (IWD-Gogebic County)
    ‪24 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 Summer fun~ AC, HotTub, ATV, hiking, waterfalls, fishing, boat

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. 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.

Property manager

Dean Rossey Jr
Premier Host

Languages

English

Add dates for prices

Amenities

Hot tub
Kitchen
Washer
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
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Events

No events allowed
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Pets

No pets allowed
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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

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.
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) - 19 min drive

Restaurants

  • ‪Dairy Queen - ‬9 min drive
  • ‪Randall Bakery - ‬4 min drive
  • ‪Jagger s Ore House - ‬4 min drive
  • ‪Korner Kitchen - ‬5 min drive
  • ‪Jj's Yale Bar - ‬11 min drive

Frequently asked questions

Is Trailside #1 Summer fun~ AC, HotTub, ATV, hiking, waterfalls, fishing, boat pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Trailside #1 Summer fun~ AC, HotTub, ATV, hiking, waterfalls, fishing, boat?

Check-in begins at 3:00 PM.

What time is check-out at Trailside #1 Summer fun~ AC, HotTub, ATV, hiking, waterfalls, fishing, boat?

Checkout is at 10:00 AM.

Where is Trailside #1 Summer fun~ AC, HotTub, ATV, hiking, waterfalls, fishing, boat 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 78 out of 83 reviews
Rating 8 - Good. 3 out of 83 reviews
Rating 6 - Okay. 0 out of 83 reviews
Rating 4 - Poor. 1 out of 83 reviews
Rating 2 - Terrible. 1 out of 83 reviews

10/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.6/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Ann O.

Liked: Cleanliness, check-in, communication, listing accuracy
Everything was clean and comfortable. Very nice stay!
Stayed 4 nights in Mar 2025

10/10 Excellent

Julie F.

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

Wakefield stay

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.
Stayed 3 nights in May 2025

10/10 Excellent

Christopher M.

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

Great stay for skiing!

Very easy in and out, in a great location, we will be renting again
Stayed 3 nights in Feb 2025

10/10 Excellent

Ross G.

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

Excellent Ski Lodge

Wonderful property that is well maintained & very enjoyable to stay at!
Stayed 3 nights in Mar 2025

10/10 Excellent

Pawel M.

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

Fantastic stay

The place was immaculate, and set up with just about anything you might need during your stay. Definitely hope to be back soon.
Stayed 4 nights in Jan 2025

10/10 Excellent

Verified traveller

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

Great stay

Great places had all we needed and a very nice hot tub
Stayed 4 nights in Mar 2022

10/10 Excellent

Karen S.

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

Wakefield

This house worked really well for our utv trip. The house was clean and well stocked. The property manager was very responsive to questions. Definitely recommend!
Stayed 4 nights in Jul 2024

10/10 Excellent

Heather M.

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

Great property/location

Everything was perfect! Highly recommend for a ski vacation! Very clean and the owners were very responsive/informative!
Stayed 4 nights in Feb 2024

10/10 Excellent

Heather M.

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

Great Property

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!
Stayed 3 nights in Jan 2024

10/10 Excellent

Debbie C.

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

Amazing property! Highly recommend

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.
Stayed 3 nights in May 2024

10/10 Excellent

Scott s.

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

Quick summer getaway with family

Very clean remodeled home, worked out great for a long weekend in the UP.
Stayed 3 nights in Jul 2023

10/10 Excellent

Corey A.

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

Snowmobile Trip 2023

Great location, nice place. Will be staying here again if available when we come up.
Stayed 4 nights in Jan 2023

10/10 Excellent

Dave N.

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

Ski Weekend

Really enjoyed our stay. Nicely remodeled house well thought out wet room area upon entrance. The place had new appliances and a well stocked pantry with staples and cookware. Beds were all comfortable and the hot tub was wonderful. No issues with check in or check out and good communication. Great Place!
Stayed 3 nights in Feb 2024

10/10 Excellent

Jason B.

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

In Wakefield for boat races.

Property was great
Stayed 7 nights in Jul 2023

10/10 Excellent

Alex R.

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

Location location location

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.
Stayed 3 nights in Jan 2023

10/10 Excellent

Timothy W., Oak Park

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

Perfect Spot for Skiing the UP

We were really impressed by how well set up and well situated this house was for all our spring skiing needs. Very clean, excellent amenities, and unusually well stocked for anything you might need. Highly recommended!
Stayed 4 nights in Mar 2023

10/10 Excellent

Bill and Michelle H., Wabasha

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

Stay Review

We so enjoyed our stay at your Vrbo. Everything was excellent, very clean, and great Customer Service. Would definitely come here to stay again and would refer to others. Thank you so much! Bill & Michelle Huth
Stayed 4 nights in Aug 2023

10/10 Excellent

brent t.

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

Wakefield house

Great location, well stocked, only thing we couldnt find was a toaster. Highly recommend!
Stayed 4 nights in Feb 2023

10/10 Excellent

Heather R.

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

Snowmobile weekend

Great clean and well stocked place. Hot tube was wonderful! Owner very responsive. Trail connection at the end of the short road.
Stayed 4 nights in Jan 2023

10/10 Excellent

Darcene B.

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

Familyvacay

We had never stayed at a VRBO. This by far exceeded our expectations. This cozy house in a quiet neighborhood couldn’t have been a better experience. This house is so clean and comfortable. It has absolutely everything we needed. We could definitely stay here for a long time and be very content. The service was great also. We had an issue with the dishwasher and our maintenance man responded right away and was there the next morning. He was very friendly and helpful. I could go on and on how great this property is and how well you’ll be taken care of. We loved the quiet, rural neighborhood. It was exactly what we were looking for. The hot tub was definitely the icing on the cake each evening. We will definitely be back here in the future!
Stayed 4 nights in Aug 2024

10/10 Excellent

Heather M.

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

Annual Trip

This is my second year renting Dean's property. We LOVE it! It is the perfect size for 6- 8 people and was very clean. It is 10 minutes from the snow river hills and the hot tub is an excellent reward after a day of skiing. We hope to be able to come every year. Thanks Dean!
Stayed 4 nights in Jan 2023

10/10 Excellent

Roslyn B.

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

AMAZING!!

Dean was the perfect host for our first annual friend's ski trip. He was very friendly! The house was perfect for all of us! The beds were comfortable. The house was clean! We had so much fun getting to know some of the locals in the area! We will be back next year! Thank you for the fantastic hospitality Dean!
Stayed 3 nights in Jan 2022

10/10 Excellent

Shayne H., Winnipeg

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

No snow so we didnt stay

There wasnt enough snow to drive 10 1/2 hours to try sledding so unfortunately we cancelled our trip last minute. I had to fill out the star ratings in order to leave a review or comment but am unable to leave a review on the accomadations as we did not use them. I did contact the host a few times with questions and they responded right away so that was great. Hopefully can get out that way sometime in the future.
Stayed 4 nights in Feb 2024

10/10 Excellent

Cindy P.

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

Family Memorial Celebration of Life

Very welcoming and clean, we felt at home right away. In the area to spend time with extended family for a celebration of life. Also was during the fourth of July events. Three nights of exceptional fireworks, two parades, and many family events. Location is perfect for all and so many summertime outdoor activities nearby.(hiking, swimming, many gorgeous waterfalls, Lake Superior) Felt wonderful to come back to at the end of the day. Beds were very comfortable! House was fully stocked with everything you could possibly need. We will definitely come back.
Stayed 6 nights in Jul 2021

4/10 Poor

Jennifer N.

Liked: Cleanliness, check-in
Disliked: Location

Frightening Neighborhood

We have stayed at many VRBO properties, and this was by far the most disappointing. The house itself is fine. It is as pictured, was clean and had all of the supplies noted in the listing. Our issue was with the neighborhood. When we pulled in, we noticed that the house next door has garbage/old objects piled up on the porch, overgrown yard. The other properties on the street are even more poorly maintained (garbage/junk in front yards, etc). We booked this home for a week with me, my husband and two children (under 10 y/o). When we unloaded our bikes, there was a car that drove by multiple times, scoping out our four nice bikes. It was extremely unnerving. We have NEVER left a property early before. But after a few hours, we knew we could not stay here. We found another property and moved out the next day. After we left, I informed the owner and stated my concerns. He would not refund any money and did not believe that these were my real concerns. I paid full price for two homes for one week. We had to disrupt our entire family and move in, out and in again in 24 hours. I would only do so if I (and my husband) had serious safety concerns. He also stated that I was not used to a rural area. We live in a rural area, and we moved to a rental home 4 miles from this one. I came to this area specifically for the remoteness and nature. My issue is with this particular neighborhood. The yard also was very disappointing. The home is located at the corner at the main road into the neighborhood. People drove back and forth constantly (the same people). The yard (which is small) is adjacent to the poorly-maintained house and the road. There was a string of beer cans hanging in the yard. There was absolutely nowhere outside I felt safe with the children. For a summer outdoor vacation, that is very limiting. If you are using this house for a home base for skiing in the winter, especially with adults, you are probably ok because people tend to keep to themselves when their homes are covered in snow. But in the summer, when people are driving by every few minutes, staring at your belongings and your children, it is less than ideal. And I DEFINITELY would not bring my children here ever again.
Stayed 7 nights in Jul 2021

About the host

Hosted by Dean Rossey Jr

Host profile image
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