Places to stay in Ashland County

4.96 out of 5 average rating, 515 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, 366 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, 217 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.

4.81 out of 5 average rating, 281 reviews

Condo in Bayfield

One Minute Walk to Lake Superior. Brookside #3

Amazing location! No cleaning fee! This Condo sleeps 4, King bed & Queen sofa sleeper. Full kitchen, balcony, AC, CableTV, WiFi, BBQ and fire pit wood povided. Restaurant, bar and pool in July-Sept.Bayfield is a 2.3 mile hike or bike on the Brownstone Trail. 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.

4.9 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.

4.99 out of 5 average rating, 245 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, 346 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, 111 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.

4.95 out of 5 average rating, 198 reviews

Cabin in Washburn

The Long House

My place is close to Lake Superior and the Apostle Islands It is located 2 miles north of Washburn or 10 miles south of Bayfield. Peaceful country setting, the long house is a freshly remodeled mobile home. Sorry, no pets. I have increased the number of guests to six . There are 4 double beds in the cabin. If you are booking with more than 4 guests, please allow for this. Thanks you! Open June 1 - mid October

4.86 out of 5 average rating, 232 reviews

Cabin in La Pointe

7 Pines La Pointe on Madeline Island

NEED ISLAND SERENITY? Instant Book 7 Pines La Pointe on Madeline Island today! Come see how this 2 bedroom/2 bath cabin offers tranquility and peace in one of the more far away desired destinations in all of the country. Beautiful high peaked windows and glass doors, with a very large deck located in a forest of trees on the picturesque/historic Madeline Island, allow guests the feeling of going back in time.

4.82 out of 5 average rating, 250 reviews

Home in Ironwood

Cheerful 2 bedroom home away from home

Your family will be close to everything when you stay at this centrally-located place. Super easy to find right off US2. Close to any and all adventures in the area. There are 2 separate bedrooms and a pull out bed in the couch if needed. Fully stocked kitchen, extra blankets and pillows, games and a kids version of pool, air hockey, and foosball table in the basement.

Vacation rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Apartments

Convenient locations with everyday essentials

Popular amenities for Ashland County places to stay

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Ashland County

4.93 out of 5 average rating, 45 reviews

Cabin in Washburn

White Wings Cottage

TimRating, 5 stars2 weeks ago

We loved it. My wife needed a getaway and always wanted to see the Apostle Islands, and this turned out to be the perfect choice. Of course the weather was less than cooperative (40°, 40 mph winds and spotty showers mostly), but on the morning we checked out it was clear and calm and let us know why we need to come back. Just beautiful. It is very clean and well staged (my wife's word) - and has THE WORLD'S MOST COMFORTABLE BED!!! That in itself is a reason to come back. Best. Sleep. Ever. We want one! The internet is a little slow but had the weather been better we'd have never known that. There is so much to do and see in the area that TVs need not exist. We are contemplating a fall return. My wife didn't get to do the one thing she most wanted - a boat tour of the Islands (too windy) - so we have yet another excuse to go back. And we're looking forward to it!

4.9 out of 5 average rating, 21 reviews

Cabin in Montreal

Dog Friendly • On the ATV Route • Fireplace

AlyssaRating, 5 stars10 months ago

Cozy, quiet cabin in the trees. Loved the closeness of the water. Had a bonfire every night. Tracy is super prepared and responsive. Great place!

5 out of 5 average rating, 19 reviews

Home in Ashland

A Cozy Getaway in Ashland

KeithRating, 5 stars1 week ago

We found the place to be well updated and clean. The outdoor deck with the beautiful flowering trees was a very nice bonus. It was located in the downtown and if you just walked one block you had a beautiful view of the Ashland Bay. It was an excellent place for us to stay while we fished the bay for smallmouth bass and we had an awesome fishing trip!!!

4.89 out of 5 average rating, 37 reviews

Cabin in Ironwood

Tuna Shack

JoshRating, 5 stars3 months ago

Nice quiet place😁

4.96 out of 5 average rating, 27 reviews

Cabin in Park Falls

Bolo's Landing (last home on peninsula)

KeyvanRating, 5 stars7 months ago

What a beautiful cabin on a secluded lake! I timed it perfectly to catch the magnificent foliage in full colour. Brian was incredibly helpful and proactive throughout my stay. Kayaking on the lake was a highlight, especially with a bald eagle soaring overhead for quite a while. The cabin itself was cosy and quick to warm up, making it the perfect retreat. Dawn’s muffins were excellent—highly recommended! Though my stay was brief, it was truly memorable. Thank you!

4.95 out of 5 average rating, 41 reviews

Home in Ashland

Adventure Homebase

JeanineRating, 5 stars2 weeks ago

This home is a true beauty! The owner has created a lovely oasis with a keen sense of style. Everything was so homey and comfortable. We especially loved cooking in the well-appointed kitchen - top notch! The upstairs great room made us feel like we were in a light and bright treehouse despite being in the woods. It was hard to believe we were just minutes from downtown Ashland. Thank you, thank you for sharing such an amazing home with us (and will you come decorate our house, pretty please?)!!

4.95 out of 5 average rating, 63 reviews

Cottage in Upson

Stunning 3 bed, 2 bath private lake front cottage.

LauraRating, 5 stars4 months ago

This home’s location could not be better—it is nestled in the trees right on the lake and just steps aways from the ski hill allowing you to ski in and ski out! It was down a winding and hilly road that was easy to find with Marks instructions; I was grateful for the all wheel drive on our vehicle to get us there :) The house itself is also very impressive—it was beautiful, well constructed, clean and well stocked. Mark and his brother were super responsive and very friendly. We had a great stay!