Holiday houses in Ashland County

4.95 out of 5 average rating, 110 reviews

Bungalow in Ironwood

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!

4.96 out of 5 average rating, 517 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.

4.99 out of 5 average rating, 368 reviews

Guesthouse in Ashland

Norrsken Scandinavian Cottage

The guest cottage is painted to resemble a Scandinavian retreat. Complete with separate bedroom, extra fold-out sofa queen bed, kitchenette, wood burning stove, WiFi (the best we can find but not great!!!) and large television (DirecTV), it is a great getaway for a couple or a family. Owners live on property if you need anything. If you are a bit adventurous, we can put up a tent right next to Lake Superior. The entire property is smoke free. For a quiet stay, no snowmobiles or ATVs.

4.97 out of 5 average rating, 221 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.

4.79 out of 5 average rating, 159 reviews

Condo in Bayfield

One Minute Walk to Lake Superior. Brookside #10

Amazing location! This Comfy Studio Condo sleeps 4, King bed & Queen sofa sleeper. kitchen, balcony, AC, CableTV, Strong WiFi, BBQ, fire pit, jet-tub/shower. Walk to the restaurant, bar, marina and pool. The pool opens in July. Brookside is 2.3 miles from Bayfield. Hike or bike the Brownstone trail along the lake. Ride the ferry to Madeline or cruise the Apostles. Sail, fish, kayak, golf, orchards, ski. Mt Ashwabay, Big top , Bayview beach plus many trails within minutes.

4.9 out of 5 average rating, 116 reviews

Condo in Ashland

Main Street apt 2 blocks from Lake Superior!

STELLA South Shore Stay is a new, gorgeous, one bedroom apartment just two blocks from Lake Superior, located on Main Street in Ashland, WI. Enjoy amenities like memory foam mattresses, high-quality bedding, Wi-Fi, all natural skin care, and much more. Walk to Lake Superior in minutes, get a coffee at the Black Cat or a pastry at the bakery, or enjoy the many restaurants and shops on Main Street. You can also enjoy the many local hikes or check out the Apostle Islands.

4.98 out of 5 average rating, 158 reviews

Chalet in Bayfield

The Acorn of Little Sand Bay Dog Friendly

Modern, rustic, Aframe cabin in the woods with beautiful, simple décor, fully equipped kitchen, new appliances, glass stove top, airfryer oven, filtered H2O/ice maker. Enjoy a luxurious bathroom, heated tile floor, walk-in shower, shampoo/conditioner/bodywash provided. King-size bed in the loft area. Smart TV, wifi. Books, games, bluetooth speaker The woodstove heats the cabin perfectly in the colder months. All wood provided. There is also a minisplit heat/ac unit.

4.94 out of 5 average rating, 435 reviews

Yurt in Bayfield

Twisting Twig Gardens and Orchard Yurt

Our yurt offers a sweet retreat in the woods about 10 miles outside of Bayfield. We are located on a small working organic farm with vegetable gardens, apple trees, and rustic accommodations. We are close to great outdoor recreation near Lake Superior and are about 6 miles from Meyers Beach in the Apostle Islands National Lakeshore. Our property is located on 40 acres and is very remote. We are on the edge of thousands of acres of county land. The perfect escape!

4.99 out of 5 average rating, 247 reviews

Home in Ironwood

"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!

4.95 out of 5 average rating, 349 reviews

Yurt in Bayfield

Bayfield Rustic Yurt 2 (Terra Cotta)

Nestled in the middle of the Bayfield County Forest, this rustic, minimally maintained yurt has direct access to miles of non-motorized rec trails (mountain bike, cross-country ski and hiking). Enjoy panoramic views of Lake Superior including; Pike's Bay, four of the Apostle Islands (Madeline, Basswood, Stockton and Michigan) and the Upper Peninsula of Michigan. Come prepared to relax, unwind and explore the wonders of the north woods.

4.96 out of 5 average rating, 114 reviews

Cabin in Bayfield

Romantic Vineyard Cabin, Sauna, Plunge Pool

Come and celebrate all that Bayfield has to offer at this quiet vineyard and forest getaway, just 2 miles from downtown. Located in Bayfield's charming Fruit Loop, you'll be surrounded by vines, forest, orchards, and berry farms. The Scandinavian cabin, forest facing sauna with plunge pool, and vineyard sit within 5 acres of woods, secluded from roads and neighbors. The cabin has an occupancy limit of 2 adults and one dog.

4.96 out of 5 average rating, 189 reviews

Apartment in Ashland

The Garland City Downtown Apartment

1920s, craftsman and art-deco-inspired apartment, furnished with antiques, located in the heart of Ashland’s Main Street Historic District. Ditch the car and walk to local amenities like the grocery store, brewpub, bars, restaurants, shops, library, and movie theater. View Ashland’s downtown murals. The Lake Superior waterfront is steps away...where you can stroll the shoreline path or bicycle the 9-mile town loop.

Holiday rentals for every style

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Chalets

Adventure-ready homes with après-ski style

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Ashland County holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Ashland County

4.96 out of 5 average rating, 57 reviews

Farm stay in Ashland

Cozy Farm Retreat - minutes to Ashland

TonyaRating, 5 stars1 week ago

Fantastic Friendly Hosts! Beautiful and Unique! We will be back again!

4.85 out of 5 average rating, 78 reviews

Home in Montreal

Cozy Home (Hurley, WI/Ironwood, MI area)

CherrieRating, 5 stars5 days ago

We came up with our side by side and it was perfect location. The home was clean and comfortable and everything we needed. Next time we come up we will stay here again.

4.94 out of 5 average rating, 47 reviews

Cabin in Washburn

White Wings Cottage

KauriRating, 5 stars1 week ago

This place was absolutely incredible. It is so cozy and homey with everything you need! The views and beachfront are unbeatable! The grill, fire pits, kayak/paddle board all accessible to us made us not want to leave. It is so peaceful and well kept. The hosts went out of their way to recommend great food/drinks, check in on us, and even about the Strawberry moon that was rising one night. Could not recommend more!

4.89 out of 5 average rating, 27 reviews

Home in Highbridge

Copper Falls Cabin

KenRating, 5 stars2 weeks ago

The house was recently upgraded and very clean and tastefully decorated. The ping-pong table was a nice touch. We had a lot of fun with that when the weather turned sour. Rebecca answered my messages immediately and showed concern we were pleased with our stay. The property was the most private of anyplace we ever stayed. It was quiet and relaxing. We would definitely stay there again.

4.9 out of 5 average rating, 39 reviews

Cabin in Ironwood

Tuna Shack

KristinaRating, 5 stars1 week ago

Our two night stay at the Tuna Shack was very enjoyable! Aysha provided lots of extras making us feel right at home with a large selection of bathroom products, S’more supplies and a well stocked kitchen. The cottage was clean and tidy upon our arrival. There were yard games and board games that kept the kids busy and there are lots of beautiful areas to explore in close proximity. We would book here again if ever back in the area.

Home in Washburn

4.74 out of 5 average rating, 361 reviews

The Red Onion House near Bayfield

KellyRating, 5 stars8 months ago

The host was extremely pro-active with communication, gave suggestions for local things to do and the home was comfortable. We overlooked the fact that there is not a television, but there is WiFi so we played a lot of cards and listened to music.

5 out of 5 average rating, 12 reviews

Cabin in Ironwood

*HOT TUB* 6 Mile Hideaway

EmmaRating, 5 stars1 month ago

Hannah’s place was gorgeous, comfortable, functional and clean. The location was amazing for nature lovers although we were just as happy relaxing at the house! I definitely plan to return in the future because we had such a great experience.