Holiday rentals 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

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.

LocationValueGetting around

4.99 out of 5 average rating, 118 reviews
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.
Apartment in Wakefield

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.

LocationFamilyCleanliness

4.89 out of 5 average rating, 36 reviews
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.
Apartment in Wakefield

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!

LocationFamilyNearby

4.95 out of 5 average rating, 61 reviews
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

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.

ValueLocationBeach

4.87 out of 5 average rating, 130 reviews
Guest favourite
A game room is featured with a well-maintained pool table at its center, accentuated by green pendant lighting. The space includes a cozy seating area with rustic furnishings and warm, earthy tones visible on the walls.
Home in Wakefield

Chateau Relaxo~Jackson Creek Ski

Bring the whole family (and then some!) to the Chateau Relaxo at Jackson Creek - Snow River! Located just one block from the new high speed lift, this home will have you on the slopes in minutes or kick back and relax next one of our two indoor fireplaces and play a game of pool! If you are visiting in summer, CR is only a short drive to some of the best lakes, rivers, beaches and hiking trails in the US! No matter what brings you to our area, Chateau Relaxo is your adventure base camp!

LocationFamilyView

5.0 out of 5 average rating, 13 reviews
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

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!

FamilyValueCheck-in

4.96 out of 5 average rating, 45 reviews
Top guest favourite
A comfortable living area features a stone fireplace as a focal point. Large windows allow natural light to fill the space. A sectional sofa and wooden coffee table invite relaxation, while a staircase leads to the upper level. Decorative elements subtly enhance the ambiance.
Home in Bessemer

Norse House: Year-Round Retreat

Welcome to Norse House, a beautifully remodeled 3-bedroom, 2-bath home just minutes from Big Powderhorn Mountain in Bessemer, MI! Whether you're here for skiing, snowmobiling, hiking, or simply relaxing with family, this home offers spacious comfort and modern amenities in a quiet, convenient location. Plenty of Room for the Whole Family! ✔ Bedroom 1 (Upstairs): King bed ✔ Bedroom 2 (Upstairs): Queen bunk, Queen bed ✔ Bedroom 3 (Main): Queen bed ✔ Bedroom area 4 (Basement) Full bed

LocationValueHospitality

5.0 out of 5 average rating, 49 reviews
Guest favourite
Apartment in Wakefield

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!

LocationValueKitchen

4.97 out of 5 average rating, 215 reviews
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

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.

LocationValueCheckout

4.97 out of 5 average rating, 74 reviews
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

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).

LocationFamilySkiing

4.87 out of 5 average rating, 46 reviews
Superhost
Home in Wakefield

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.

LocationQuietCleanliness

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

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.

FamilyLocationHot tub

4.75 out of 5 average rating, 8 reviews

Popular amenities for Wakefield holiday rentals