Holiday rentals with outdoor seating in Ashland County

Cheerful, Charming Retreat

Enjoy a stylish experience at this centrally-located place; it’s a hidden treasure. Enjoy walking to restaurants, and adventure surrounding Hurley’s historic Silver Street while being able to retreat to a place of your own. Conveniently located close to the Iron Horse Trail. Waterfalls, skiing, kayaking, mountain biking are all adventures close by. Start your morning with a cup of coffee in the beautiful three-season porch, and end your day with your favorite drink under the glowing chandelier!

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.

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!

Off grid Shasta trailer at Rockhound Hideaway

An outdoor enthusiasts dream awaits at Rockhound Hideaway's Sodalite Shasta with opportunities for hiking, biking, swimming, boating and everything in between. 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.

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!

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.

"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!

Hippophile Farm Get-a-way Garden Apartment

The space is a newly renovated apartment on the lower level of our home which is located at our private horse farm on Madeline Island. It is light, bright, with a modern and clean look. It has all the things you need to relax and rejuvenate after spending a day exploring Madeline Island. Enjoy the beautiful woods surrounding the apartment or take a walk to our beautiful stables on the property. Bring your horses if you wish, or just come to enjoy the scenery.

Welch Creek Inn

This beautiful and spacious apartment is within walking distance to Mt Zion, which can be seen while relaxing in the front porch. This centrally located space is perfect for exploring all the Gogebic range has to offer. Riding trails are right around the corner. This space can accommodate up to 9 people. First bedroom has queen bed, second bedroom has bunk beds, living room has hideabed couch, and front heated porch has a couch and trundle bed.