Holiday houses in Ashland

4.87 out of 5 average rating, 235 reviews

Home in Ashland

Entire- Cozy Chequamegon Home

Escape suburbia at our quaint farm style house about a mile from Lake Superior and about 1/2 mile from Northland College. Guests describe our home as cozy & reminiscent of visiting their favorite coffee shop. The house offers 4 bedrooms, 1 full bathroom on the second floor & a half bath on the main floor. A portable crib is available for infants (30 1b max). Please note that we are in the process of having baseboards milled by a local crafts person who is also installing them when we are closed.

4.87 out of 5 average rating, 503 reviews

Yurt in Bayfield

Bayfield Rustic Yurt 1 (Evergreen)

Explore thousands of acres of the Bayfield County Forest and enjoy endless miles of exceptionally maintained non-motorized recreational trails. The yurt has direct access to CAMBA mountain bike trails and Mt. Ashwabay ski trails. The landscape is also spectacular. Take in the panoramic views of Lake Superior and the Onion River valley. This is a rustic, minimally maintained yurt set in the middle of the county forest, so come prepared to relax, unwind and explore the wonders of the north woods.

4.97 out of 5 average rating, 167 reviews

Guest suite in Brule

The Bee's Balm

You'll find us tucked in the quiet woods of northern WI near the Brule River. We're remote enough to experience star-filled skies & fireflies, but not far from many premier attractions. Your space is a self-contained apartment on the lower level of our 2.5 story home. It features a private entry, queen-sized bed, kitchenette, lower level private deck, access our beautiful grounds & more! We're a family of artists who love to travel & to introduce others to our beautiful part of the world.

4.8 out of 5 average rating, 361 reviews

Condo in Bayfield

One Minute Walk to Lake Superior. Brookside #11

Amazing location! This Comfy Studio Condo sleeps 4, Whirlpool tub/shower,King bed & Queen sofa sleeper. Strong Wifi, balcony, AC, CableTV and fire pit wood provided. 1 minute walk to the marina. Bayfield is 2.3 mi from Brookside. Hike or bike the Brownstone trail along the lake. Take the ferry to Madeline, cruise the apostles, Sail, fish, kayak, golf, orchards, ski and more!! The pool and restraunt opens July 1st. 5 minutes from Bayview beach, Mt Ashwabay, Big top and Adventure Brewery.

4.99 out of 5 average rating, 367 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.

4.87 out of 5 average rating, 149 reviews

Tent in Ironwood

Off grid glamping at a Rockhound Hideaway

A perfect glamping retreat awaits you at Rockhound Hideaway's Agate Grove Bell Tent. Situated on a private two acre lot with two other rentals and my private residence in the Ottawa National Forest, steps from the Black River, North Country Trail and a one mile walk to the Lake Superior Shore, this is an ideal getaway for those seeking the adventure of camping with the comforts of home. Fall asleep to the sound nature and wake up to deer passing by as you enjoy your morning coffee.

4.97 out of 5 average rating, 219 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.

4.93 out of 5 average rating, 109 reviews

Dome in Bayfield

Twisting Twig Gardens and Orchard Geodesic Dome

Our rustic glamping dome 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!

4.87 out of 5 average rating, 156 reviews

Home in Ashland

Bungalow (House) on Chequamegon Bay.

This newly renovated fully furnished home is located within one block from beautiful Chequamegon Bay, Ashland's Oredock Pier, walking and bike trail, boat ramp, and beach. Grab a pole and head down to fish off the Ashland Oredock pier, or pack up for picnic at the beach, launch your boat, kayak or canoe. Take a walk, bike, or run on the walking trails. It is short walk to a few local restaurants and the downtown area. Access snowmobile trails. No pets are 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.

4.96 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.

4.96 out of 5 average rating, 108 reviews

Cottage in Ashland

Cozy remodeled cottage in heart of Ashland

Cozy little cottage in quiet neighborhood in Ashland. Only five blocks from Chequamegon Bay. Completely remodeled in 2019. Home features two cozy bedrooms with queen sized beds. All new furniture and appliances. Nice deck with backyard to enjoy your morning coffee or evening meals. Downstairs area with large sectional sofa for kids, teenagers and Dad to get away by themselves!

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Other great holiday rentals in Ashland

4.96 out of 5 average rating, 57 reviews

Farm stay in Ashland

Cozy Farm Retreat - minutes to Ashland

TonyaRating, 5 stars6 days ago

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

4.94 out of 5 average rating, 47 reviews

Cabin in Washburn

White Wings Cottage

KauriRating, 5 stars5 days 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!

5 out of 5 average rating, 49 reviews

Home in Iron River

Guest House

JessicaRating, 5 stars2 days ago

Wonderful place to stay while up in the North Woods, only 30 minutes to Ashland and 50 to Bay Field. Iron River had restaurants that were actually pretty good and I am overall very happy with the stay. Perfect place for the four of us.

5 out of 5 average rating, 39 reviews

Cabin in Ashland

Relaxing cabin with fireplace on Lake Superior

CassidyRating, 5 stars2 months ago

Cottage 5 was perfect for a cozy and quiet getaway. Very spacious and clean, also had pretty much everything you would need. Plus the ice cream gift, was a great treat! Thank you!!

4.86 out of 5 average rating, 65 reviews

Home in Ashland

Hidden Vines - Walkable To Murals - Dog-Friendly

IanRating, 5 stars1 month ago

Perfect stay! Cute, clean and cozy home!

4.92 out of 5 average rating, 48 reviews

Cabin in Wakefield

Superior Sunset Cabin

BrunoRating, 5 stars3 weeks ago

Absolutely amazing! We went on a road trip with two friends and spent two nights at Dreamwood. Our goal was to find a secluded place—and this was exactly it. It was a rare and unforgettable experience! Everything was perfect: we found ourselves completely alone, surrounded by nature—an ideal setting to disconnect, recharge, and take our time. The cabin is located right in the Porkies, so hiking trails are just a short drive away. There’s also private access to a quiet beach and the views are absolutely breathtaking—especially at sunset. Tom and Sol were lovely and available when needed. We’ll definitely be back!

4.92 out of 5 average rating, 61 reviews

Cabin in Mason

Ridgeline - Your gateway to the Northwoods

AshleighRating, 5 stars2 days ago

The cabin was beautiful and so cozy and check in was a breeze! Will definitely stay here again. Thank you!!