Holiday houses in Wakefield

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Top-rated holiday rentals in Wakefield

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
The exterior of Sasquatch Lodge features wood siding and a welcoming entrance with a staircase leading up to two balconies. A large mural of Sasquatch is displayed prominently above the entrance. Surrounding greenery enhances the sense of privacy and connection to nature.
Home in Wakefield
4.99 out of 5 average rating, 117 reviews

Sasquatch Lodge Vacation Home

PERFECT FOR MULTIPLE COUPLES OR FAMILIES This is not your Grandpas Cabin turned Airbnb. Sasquatch Lodge was purposely designed to maximize 3500 square feet of space, providing plenty of room and privacy for our guests. 4 Bedrooms, each with private bath, boasting comfortable, quality bedding, paper goods, shower supplies, linens and towels. We have carefully curated a whimsical sasquatch theme that you will adore and have fun trying to find them all! Just a couple blocks from Indianhead Mt.

Top Guest favourite
Home in Ironwood
4.99 out of 5 average rating, 220 reviews

Cozy Home onTrail|Sauna|PetsI Lakes Trails Falls

Welcome to Little House on The Trail!—perfectly located near the Porcupine Mountains, Lake Superior, waterfalls and hiking trails. This spotless, thoughtfully designed home blends vintage charm with modern comfort, featuring a fully stocked kitchen & coffee bar. Unwind in the cedar sauna or gather around the firepit. Pets ok, spacious, and packed with amenities, it’s the perfect Northwoods getaway year-round. ⭐ Guests consistently say this is the best Airbnb they’ve stayed in—come see why!

Guest favourite
A cozy living area is furnished with a plush sofa and armchair, complemented by a wooden side table and lamp. Natural light filters through two windows adorned with light curtains, while a large wall-mounted TV is positioned above a low wooden console. A decorative area rug adds warmth.
Apartment in Wakefield
4.91 out of 5 average rating, 11 reviews

Sunday Lake Retreat

We are located in the quaint little town of Wakefield Michigan. It offers a bakery, knit and gift shop, four restaurants, a bank, pharmacy, and grocery store all within walking distance ...This retreat is in close proximity to 4 ski hills, gorgeous waterfalls and lakes..30 minute drive to Lake Superior and close to Porcupine Mountains and Copper Peak. Many miles of groomed snowmobile and ATV trails which start one block away.., ample trailer parking ..Clean! Sorry no pets and no smoking..

Top Guest favourite
A cozy living area is revealed, featuring two light tan sofas and a single recliner, arranged around a plush area rug. Wooden walls and ceiling create a natural ambiance. Large windows allow for ample natural light, enhancing the inviting atmosphere of the space.
Home in Wakefield
5 out of 5 average rating, 27 reviews

Howta Lodge w/ Sauna on UTV/Snowmobile Trail #8

Welcome to Howta Lodge, this brand new home is nestled in the serene woods, offering the perfect retreat for your getaway with three bedrooms plus a loft! Immerse yourself in nature's tranquility while enjoying modern comforts. Unwind in the private sauna after a day of adventure on ATV and snowmobile trails. The trails are right next to the property, trail UP8. No need for trailering before riding! Come create lasting memories in this idyllic woodland escape that is only miles from town!

Guest favourite
An aerial view captures the winter landscape surrounding the condo units, blanketed in fresh snow. The buildings are set back from a frozen pond, with evergreen trees visible in the background. A ski lift stands nearby, indicating access to the slopes.
Condo in Wakefield
4.95 out of 5 average rating, 57 reviews

Ski In & Ski Out

Hike, bike, ski, snowshoe, sightsee…we can go on! This stunning ski-in/ski-out condo offers unparalleled access to Jackson Creek Summit part of the Snowriver Mountain Resort. Situated on the top of the hill, this peaceful residence ensures you can hit the slopes as soon as you step out the back patio door. The perfect retreat for access to many area destinations including Porcupine Mtns, waterfalls, ski hills (Jackson Creek, Black River Basin, Big Powderhorn, Whitecap) and much more!

Top Guest favourite
A log cabin exterior is displayed with a green metal roof. The spacious covered deck features wooden railings and chairs, inviting relaxation in a natural setting. Surrounding trees offer shade, and the ground is covered with brown leaves and grass, enhancing the cabin's rustic charm.
Cabin in Wakefield
4.97 out of 5 average rating, 36 reviews

North Woods Cabin

Escape to this charming 3-bedroom log cabin, located near UTV/snowmobile trails and just minutes from ski hills. Perfect for outdoor adventure or a peaceful getaway. Enjoy mornings on the spacious covered deck. The circle driveway makes parking and trailer access a breeze. Inside has modern updates blended with rustic charm, a fully stocked kitchen, and comfy spaces to relax after a day on the trails. Bedrooms offer one king bed, one queen, and two twin bunk beds. Plus, pet friendly!

Guest favourite
A comfortable seating area features a circular sofa arranged around a small coffee table. A television is positioned across from the sofa, and natural light streams in through a large window, illuminating the blue carpet and creating a cozy atmosphere.
Apartment in Bessemer
4.93 out of 5 average rating, 107 reviews

Powdermill Place | Updated Condo

Our freshly renovated, boho ski themed condo near the heart of Big Powderhorn Mountain in Bessemer, MI is a perfect place for your Gogebic County getaway. We offer everything you need for a comfortable and enjoyable visit. Take a quick 1 minute car ride to have a full day of skiing, eating and enjoying time with family & friends. With your own private place, you can come and go as you please. Our spacious condo is set up for two with a great king bed in a lofted bedroom.

Top Guest favourite
Home in Ironwood
4.99 out of 5 average rating, 337 reviews

"Bakery Bungalow" -Sweet Accommodations & Nature !

Completely remodeled from head to toe! Located within half mile of trail system, 2 miles from historic downtown shops, on the outskirt of town (Ironwood Township=great drinking water) minutes from Big Powderhorn Mountain & Copper Peak, walking distance to Gogebic College & Mount Zion, 17 miles from Lake Superior, large private wooded yard with fire pit in summer, private parking, 1 stall garage if needed in winter. A light Bakery breakfast included with your stay!

Guest favourite
Condo in Wakefield
4.97 out of 5 average rating, 210 reviews

Cozy & Clean 2B/2B Condo w/ Jetted Tub!

My clean, cozy, and quiet condo is located at Snow River/Indianhead Resort. It's a brief walk to Jack's Café on site for food, drink, and the best views from the top of the ski hill in the Upper Peninsula. My condo is the perfect place for your ski vacation, romantic getaway, family trip, after hiking/camping refresh, or peace and quiet on the mountaintop. I provide exceptional communication and top notch responsiveness. You won't be disappointed with your stay!

Superhost
Home in Wakefield
5 out of 5 average rating, 11 reviews

Trailside Retreat#3- ski, snowboard, snowmobile

Welcome to your UP Retreat complete with hot tub! This beautiful home sits in the heart of big snow country, that has an annual snow falls averaging around 217 inches a year. You are only a short drive to 3 different ski hills and only 30 seconds away from Snowmobile and ORV Trail #2! The summer months are good for hiking, mt. biking, ATV trails, waterfalls, swimming and plenty of wildlife to see and multiple lakes close by to visit! Air conditioned.

Guest favourite
A spacious living area features a sectional couch in a soft green hue, accompanied by light-colored throw pillows. A coffee table is centered on a neutral-toned area rug. Adjacent, a dining table set for meals is visible, showcasing elegant dishes and comfortable chairs.
Home in Wakefield
4.87 out of 5 average rating, 38 reviews

5B/2Ba | Trails & Slopes Near | Dog Friendly

Welcome to Hancock Hideaway—your year-round escape in Michigan’s beautiful Upper Peninsula! This spacious, pet-friendly home sleeps up to 8 guests with 3 cozy bedrooms, 5 beds, and a comfy pull-out couch. Relax on the large deck after a day on the slopes at Snowriver (5 miles), hitting the snowmobile trails (½ mile away), or soaking up the sun at Sunday Lake (just down the road).

Superhost
Home in Wakefield
5 out of 5 average rating, 4 reviews

Winter Chill at Sunday Lake

Winter Chill is a cozy two-bedroom home in Wakefield, Michigan, designed for comfort and easy Upper Peninsula getaways. Enjoy a queen bedroom, a twin-over-full bunk room, a fully equipped kitchen, and a welcoming living space with a 65-inch smart TV and electric fireplace. Close to ski hills, trails, and local favorites, with private parking and nearby trailer parking available.

Popular amenities for Wakefield holiday rentals

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  1. Airbnb
  2. United States
  3. Michigan
  4. Gogebic County
  5. Wakefield