Holiday houses in Wakefield

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Top-rated holiday rentals in Wakefield

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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, 118 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.

Superhost
Home in Wakefield
5.0 out of 5 average rating, 3 reviews

Lakeside Oasis on Chaney Lake *In-Floor Heating*

Escape to this stunning Lakeside Oasis on Chaney Lake, where tranquility meets nature. This spacious rental, with its open-concept design, offers plenty of room for everyone. A short walk through the woods takes you to Chaney Lake where you can relax and enjoy the outdoors at all times of the year. In the evenings, gather around the fireplace with loved ones, sharing stories and laughter, or indulge in a home-cooked meal prepared in the kitchen. Notable features include a central air conditionin

Guest favourite
A well-lit living area features large windows showcasing natural scenery. Two comfortable sofas of neutral tones surround a wooden coffee table. Decorative cushions add texture, while a lamp provides soft lighting. Natural light enhances the cozy atmosphere of the space.
Condo in Wakefield
4.89 out of 5 average rating, 36 reviews

Liftside Loft - SI/SO Condo @ Jackson Creek!

Relax by the fireplace or the ensuite sauna in this large family-friendly, SI/SO condo, located on the new Jackson Creek Ski Hill! This 4 bedroom + loft condo has plenty of space to spread out and enjoy your time away. Special features like the cedar-lined sauna, gas fireplace, and private deck with propane grill make this rental a perfect year round getaway! Guests are also within walking distance to the ski lodge restaurants for great food and drinks, ski rentals, and purchasing lift tickets.

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
4.92 out of 5 average rating, 12 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..

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, 61 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!

Guest favourite
A renovated kitchen and dining area showcases wooden cabinetry and a spacious island. A dining table with multiple chairs is set up beside a wall adorned with artwork. Soft lighting enhances the welcoming atmosphere, while large windows bring in natural light.
Home in Ironwood
4.87 out of 5 average rating, 127 reviews

Renovated 19th Century UP Getaway in Ironwood

Enjoy a this late 19th century in this centrally-located and renovated home in Ironwood. 3 Bedroom/ 1.5 bath house in Ironwood, MI within walking distance of restaurants. Access to snow mobile trails across the street. Close to parks and trails. Cook your own meals in or dine locally. Park your trailer with your ATVs in the driveway or keep your equipment in the 2-car garage. Use the house as a launching pad for your UP adventures while you explore the entire UP or Northern WI.

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
4.95 out of 5 average rating, 44 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
Condo in Wakefield
4.97 out of 5 average rating, 214 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!

Guest favourite
The spacious kitchen features a large island with ample counter space and wooden cabinetry. Two pendant lights hang above the island. Natural light illuminates the area, revealing a dining room connected to the kitchen, enhancing the open layout.
Home in Wakefield
4.99 out of 5 average rating, 73 reviews

King Bed Suite-The Copper House

This three-bedroom (5 beds) ranch home is located in the heart of Wakefield. You will enjoy the large kitchen, dining room, and deck for entertaining. Three of the best ski resorts in the area are located only 3-10 miles away. The snowmobile trail/ATV trail is easily accessible from across the street. The beautiful Lake of the Clouds is located 47 miles away in the Porcupine Mountains Wilderness State Park. Copper Peak Ski Jump is only 16 miles away.

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, 45 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
4.75 out of 5 average rating, 8 reviews

Trailside Retreat #1 - ski, snowboard, snowmobile

Vacation goers- this ones for you!! Located just off of ATV/UTV/Snowmobile Trail #2, this beautiful home has been remodeled top to bottom, in U.P. Winter hot-tub perfect to relax after a hard days work on the trails or hills! 5-10 minute drive to near ski resorts. Summertime- have fun in ATV trails, hiking and swimming in waterfalls! Peaceful neighborhood. Air conditioned.

Top Guest favourite
Home in Wakefield
5.0 out of 5 average rating, 6 reviews

Autumn Wind at Sunday Lake

Autumn Wind is a cozy two-bedroom home in Wakefield, Michigan, perfect for fall color trips and Upper Peninsula getaways. Enjoy a queen bedroom, a comfortable bunk room, a fully equipped kitchen, and a welcoming living space with an electric fireplace and smart TV. Close to trails, local shops, and seasonal adventures, it’s an easy place to relax after a day outdoors.

Popular amenities for Wakefield holiday rentals