Pet-friendly holiday rentals in Ashland County

4.97 out of 5 average rating, 160 reviews

Park Place - Updated Home Close to Downtown

Enjoy our freshly renovated, boho themed home near the heart of downtown Ironwood, MI featuring 2 bedrooms (1 King, 2 Queen & 1 Twin bed) & 1 bath with a beautiful soaker tub. Great starting point for any local activity. Walking, biking, ATV & snowmobile trails only a few minutes away in any direction. Self check in, but always available for help. As loving pet owners, we do allow up to 2 well-behaved dogs. Group event? Book the house next door too (up to 13 guests): airbnb.com/h/greenhaveniwd

4.98 out of 5 average rating, 134 reviews

Trail Riders Haven-Heated Garage-1 Block ATV Trail

Ultimate fall getaway! Cozy 4-bedroom home is just 1 block from heart-pounding ATV trails! Leave straight from the driveway - your choice MI or WI fun adventures! Spacious interior & OVERSIZED garage- a perfect getaway for outdoor enthusiasts. Ample room for trailers. Step inside and find comfort at its best! Fully equipped kitchen-ready, delightful coffee bar. You'll rest easy on dreamy pillowtop beds with cozy duvet covers, creating a heavenly retreat. BBQ grill! A/C, Ping Pong Table, Poker

4.98 out of 5 average rating, 189 reviews

On the Trail-Cedar Sauna & Close to Ski & Trails

Our happy, extremely private little house sits on 2 lots & backs to the Iron Belle Trail! Minutes to Trails, Lakes & more. Updated floor to ceiling bringing a Light & Bright AZ-modern farmhouse vibe. Slate appliances inc a dishwater! farm sink, butcher-block countertops, coffee/Nespresso bar converted from orig owners 1894 stove, restored wood floors, 3 season porch w/ 1970's console & vinyls for your evening dance. Large deck & fire pit awaits your bottle of wine or cup of coffee.

4.98 out of 5 average rating, 331 reviews

Cabin in Bayfield

The Copper Squirrel of Little Sand Bay DogsWelcome

A mature forest and a beautiful pond are what you'll see when you arrive at this cozy, secluded, full log cabin. The cabin was recently completely renovated (Mar/April 2025)from log to log and is stocked with everything you'll need for your stay. It has all new appliances, furniture, fixtures, bathroom, cabinetry. 💚 It is the perfect homebase to relax after a long day of hiking Frog Bay, Houghton Falls, Lost Creek Falls, Meyers Beach, or shopping in nearby Bayfield, Washburn, or Cornucopia.

Superhost

Apartment in Bayfield

4.8 out of 5 average rating, 292 reviews

One Minute Walk to Lake Superior. Brookside #3

Amazing location! No cleaning fee! This Condo sleeps 4, King bed & Queen air matress. Full kitchen, balcony, AC, CableTV, Strong WiFi, fire pit wood povided. Restaurant, bar and pool in July-Sept.Bayfield is a 2.3 mile hike or bike on the Brownstone Trail. Bikes provided. Brookside is 5 minutes from Mt Ashwabay, Big Top, Bayview beach and multiple hiking trails. Ride a ferry ride to Madeline or cruise the Apostles. Sail, fish, kayak, golf, ski. $40 pet fee per stay. 🙂 No smoking allowed.

4.96 out of 5 average rating, 537 reviews

Cabin in Ironwood

The Shell Cabin at Rockhound Hideaway

An outdoor enthusiasts dream awaits at Rockhound Hideaway's Shell Cabin, with opportunities for hiking, biking, fishing, boating and everything in between. Take in the views from your back deck, relax around the bonfire, enjoy walk to Lake Superior, hike or snowshoes the North Country Trail to waterfalls or take a day trip to the Porkies. Don't forget to visit Downtown Ironwood and experience its charm for yourself. Amazing star gazing and Northern Lights potential! 420 Friendly for 21&up.

4.96 out of 5 average rating, 274 reviews

Home in Ramsay

TINY Home - BIG Adventures - Hike/Bike/Ride

Couples retreat! Self check in to our Tiny Home with a door code and let the Big adventures begin! Only minutes from Indianhead, Blackjack, Big Powderhorn & Mt. Zion ski hills. A bit further away, but worth the drive, are Whitecap Mountain and Porcupine Mountains. Also, close to ABR x-c skiing, the Iron Belle Trail, and Lake Superior. Winter Hikes are beautiful in the U.P. Bring your fur babies along for a winter hike to the Porkies, Lake of the Clouds or Black River Scenic Byway.

4.97 out of 5 average rating, 246 reviews

Tiny home in Saxon

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.

4.85 out of 5 average rating, 130 reviews

Black River Road Retreat

Private home on 40 acres surrounded by woods and wetlands on the Black River Rd. National Scenic Byway. It's a secluded place with lots of peace and quiet to be had. This is a perfect base for exploring the Northwoods with Copper Peak just 1 mile north, and 5 waterfalls on the 5 mile drive to Black River Harbor. It's a great place to get away and into Nature. There's a big yard with ample parking, playset and space for trailers. Trails in the back yard with a nice fire pit too!

4.95 out of 5 average rating, 265 reviews

Chalet in Bessemer

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

4.99 out of 5 average rating, 267 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!