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Family-friendly holiday rentals in Wakefield

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Wakefield

Guests agree: these family-friendly homes 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, 111 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
A single family home features a charming front porch embellished with decorative lattice and potted plants. Snow blankets the ground and roof, contrasting with the beige exterior. A brick chimney rises above, surrounded by trees and neighboring houses under a cloudy sky.
Home in Ironwood
4.94 out of 5 average rating, 121 reviews

Comfy Homebase for your Upper Peninsula Getaway

Centrally located 2 bed, 1.5 bath single family home all to yourself. Terrific floorplan with eat-in kitchen, large living + dining room with fireplace, 2 bedrooms and newly remodeled full bath. Powder Room on lower level. Just a few blocks to charming downtown Ironwood, Iron Belle Trail + close to Miners Park with trails for walking, mountain biking, snowshoeing, x-skiing. Quick access to all that’s amazing about the U.P.! If you love outdoor fun, this is the place to stay, relax + rejuvenate!

Top guest favourite
A scenic winter landscape features a gently sloping hill covered in fresh snow, marked with ski tracks. Trees with bare branches frame the scene, leading up to a cozy building nestled among the trees, accented by a clear blue sky overhead.
Apartment in Wakefield
4.97 out of 5 average rating, 105 reviews

Cute & Cozy 1B/1B Condo w/ Jetted Tub!

My clean, cozy, quiet, and Completely remodeled condo is located at Indianhead/Snowriver Resort. It's a brief walk to the Sky Bar/Jack's Cafe 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 romantic getaway, family trip, after hiking/camping refresh, ski vacation, or peace and quiet on the mountaintop. I provide exceptional communication and top notch responsiveness. You won't be disappointed with your stay!

Top guest favourite
The entrance features a white door adorned with a festive wreath and flanked by windows. A large 'WELCOME' sign, decorative greenery, and a small chair are positioned on the porch, creating an inviting entryway.
Bungalow in Ironwood
4.96 out of 5 average rating, 134 reviews

HOT FIND *Powderhorn Porch* 4B/1BA dwntwn Bungalow

Welcome to the Powderhorn Porch! When you get off the trails or slopes there isn't a better place to come home to than this cozy 4BR/1BA bungalow located in downtown Ironwood just blocks from the trails. Long driveway to hold your vehicles and trailers. Centrally located to all that the Gogebic Range has to offer including 4 ski resorts, snowmobile trails, waterfalls, hiking, Porkies, Lake Superior, Copper Peak, and cute shops & restaurants. This home is perfect for your next trip to the UP!

Top guest favourite
A cozy trailer is nestled among snow-covered trees, showcasing a welcoming entrance with a brown door and a sign that reads 'Sodalite Shasta.' A white exterior contrasts with the winter landscape, while a metal trash can is visible nearby.
Campervan/Motorhome in Ironwood
4.93 out of 5 average rating, 164 reviews

Off grid Shasta trailer at Rockhound Hideaway

An outdoor enthusiasts dream awaits at Rockhound Hideaway's Sodalite Shasta with opportunities for snowshoeing, skiing, hiking, and ending the day with a steamy sauna. This off grid, cozy 14' trailer is situated on a two acre lot with two other rentals and my full time residence on the edge of the Ottawa National Forest. A short walk to Black River Harbor, the North Country Trail & Lake Superior, this is a perfect getaway for those seeking a rustic yet comfortable stay with a campy feel.

Top guest favourite
The exterior of a Swiss-inspired chalet is showcased, surrounded by a winter landscape with snow-covered trees. The building features distinct architectural details, such as wooden shutters and a decorative balcony. A pathway leads to the entrance, creating a welcoming approach.
Chalet in Ironwood
4.95 out of 5 average rating, 168 reviews

Swiss Chalet at Big Powderhorn resort

You will love our Swiss-inspired Chalet in the Alpine Village at the Big Powderhorn Mountain Resort. The 1500 sq feet Chalet is surrounded by 0.6 acres of woods for your privacy and enjoyment of this gorgeous area. You are 5 minutes away from the ski slopes at Big Powderhorn, 15 minutes from Indianhead and Blackjack resorts, Copper Peak, numerous gorgeous waterfalls on Black River and 19 min away from the Black Harbor Pavillion and Lake Superior. This is your all season destination!

Top guest favourite
A sitting area features a futon draped with a cozy blanket, complemented by colorful accent pillows. A spacious bed with a patterned coverlet is positioned nearby, while a countertop with bar stools creates an inviting space for dining or gathering.
Tiny home in Saxon
4.97 out of 5 average rating, 272 reviews

Parker Creek Tiny House

Come stay on our hobby farm with us! We are in a great central location to multiple hiking trails and gorgeous falls. We have had many guests visit the sea caves in Cornucopia, spend the day in Bayfield, or hike the Porcupine Mountains. We also are only a few miles from the ATV trails if you would rather spend the day riding the trails. We have multiple places to mountain bike or kayak. We have more things to do listed in our details section! Feel free to message me with questions.

Top guest favourite
A charming A-frame chalet is surrounded by vibrant autumn foliage. The exterior features a blue metal roof and large windows that allow natural light to fill the interior. A wooden deck extends from the front, providing outdoor seating options, while a small shed is visible to the right.
Chalet in Bessemer
4.95 out of 5 average rating, 282 reviews

Hot Tub • Fireplace • Dog Friendly •Big Powderhorn

My place is located at Big Powderhorn Ski Resort and close to Lake Superior, family-friendly activities, great views, restaurants and dining. You’ll love my place because of the location, the ambiance, the outdoor space, and the neighborhood. My place is good for couples, solo adventurers, and families (with kids). Dog friendly! Outdoor Hot Tub! Wood burning Fireplace with wood supplied! Great cell service! TV, Cable, Roku, WIFI....great entertainment! Washer/Dryer

Top guest favourite
Home in Ironwood
4.99 out of 5 average rating, 295 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!

Top guest favourite
A charming house features a light-colored exterior with red accents around the windows and door. A green roof complements the vibrant flowers in the front garden, while a small porch with seating is visible. Several parked cars are present in the background.
Cottage in Marenisco
4.94 out of 5 average rating, 195 reviews

Whitley House

Get away from it all! Step back and enjoy nature at its finest. The Whitley house is furnished with all the essentials plus some and if you have a special request or need we do everything we can to try to accommodate you. 10 mins from Lake Gogebic County Park and many other fishing spots. A short drive to the Porcupine Mountains and directly off the ATV/snowmobile trail that runs through Marenisco.

Top guest favourite
A charming red farmhouse is set against a snowy landscape, surrounded by trees. The sky is bright with scattered clouds, enhancing the wintry scene. A small outbuilding is visible nearby, while a vintage bicycle is seen resting in the foreground.
Home in Ironwood
4.98 out of 5 average rating, 243 reviews

Our Finnish Farmhouse: 2 miles from ABR Ski Trails

Note: No Smoking, vaping, or cannabis anywhere on property and no pets allowed. Our Finnish Farmhouse is a log home that was first established in 1906. The home was purchased and completely renovated and restored from 2016-2020. The original logs have been restored on the interior of the home and many updates have been made. We are sure you will enjoy your stay with us.

Top guest favourite
An inviting kitchen area features modern cabinetry and a spacious wooden island with seating for three. A black refrigerator and stove are positioned alongside a sink, with decorative fixtures and a window allowing natural light to brighten the space.
Apartment in Wakefield
4.96 out of 5 average rating, 101 reviews

Sun Dance Apartments unit 1

Full condo with one queen bed in the bedroom and pull out couch in the living area. Can sleep 4 comfortably. You also have access to a full kitchen. Enjoy Snow River Ski Resort and snowmobile trails just yards away from the property in the winter or hiking the porcupine mountains and other outdoor activities in the summer! We kindly ask for no pets at this time.

Popular amenities for Wakefield family-friendly rentals

Quick stats about holiday rentals that are family-friendly in Wakefield

  • Total holiday rentals

    Explore 20 holiday rentals in Wakefield

  • Nightly prices starting at

    Wakefield holiday rentals start at $103 SGD per night before taxes and fees

  • Verified guest reviews

    Over 920 verified reviews to help you choose

  • Wifi availability

    20 of Wakefield holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wakefield rentals

  • 4.9 Average rating

    Wakefield stays are highly rated by guests – averaging 4.9 out of 5!