Vacation rentals in Glidden

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Top-rated vacation rentals in Glidden

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Superhost

A yurt is nestled among trees, featuring a circular white top and green walls. A small wooden deck extends from the entrance, providing a welcoming outdoor space. The surrounding area is landscaped with lush greenery and scattered underbrush.

Yurt in Bayfield

4.87 out of 5 average rating, 521 reviews

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.

Top guest favorite

A vibrant living area is visible, featuring a colorful area rug that adds warmth. Two patterned armchairs and a sofa with eclectic cushions surround a wooden coffee table. A large wall mural depicting a tree in vivid hues serves as a focal point, complemented by indoor plants.

Home in Ramsay

4.96 out of 5 average rating, 168 reviews

Happy Hippie Shack! Good U.P. Vibes Hike/Bike/Ride

Hippies Retreat!! Self check in with a door code and let the Good Vibes and Adventures begin! Our place is designed for guests with an open mind, free spirit and great Hippie sense of humor. You will have a Groovy pad to land after exploring the U.P. and are 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.

Guest favorite

The living area features a blend of seating options including a sofa, armchair, and daybed, enhancing comfort. Warm lighting highlights the space, while aviation-themed decor, including a vintage airplane mural, adds character. Natural wood flooring contributes to the cozy atmosphere.

Apartment in Glidden

4.92 out of 5 average rating, 63 reviews

Harry's Hangar Apartment ** Glidden, WI.

This cozy apt is the lower level of a ranch house, off hwy 13 in Glidden. 4 rooms - a big bedrm w/ king & single beds, kitchenette with a table, refrig, dishwasher, microwave, dishes, coffee supplies and elect. skillet. The big bathrm has a large shower, & the "Garage Bar" (Aviation theme) is "Harry's Hangar." Walk downtown to the Bear Crossing Conven. Store, bakery, bars etc. Great location for snowmobiling, one block from snowmobile trail & 4 wheeling. Near Copper Falls, Apostle Islands

Guest favorite

The cabin's exterior is framed by vibrant autumn foliage, showcasing a blend of wood and metal materials. A screened porch is visible at the front, while a natural stone and pebble landscape surrounds the foundation. The expansive yard offers a peaceful retreat atmosphere.

Cabin in Winter

4.94 out of 5 average rating, 33 reviews

Northwoods Cabin

Peaceful retreat in the Wisconsin Northwoods. Well designed and stylish cabin on two wooded acres. Just steps to the Chippewa River. Fully equipped kitchen, 2 full bathrooms and 2 beds on the second floor loft. High speed internet, electric car charger available. ***In winter months, the road/driveway to the cabin are plowed when there is 6+ inches of snow. AWD vehicles are recommended during snow season.*** A shovel is provided in case guests need to shovel path from vehicle to front door.***

Top guest favorite

The modern cabin features a covered deck with ample seating, including bright red Adirondack chairs positioned around a fire pit. Large windows display warm ambient lighting within, while smoke gently rises from the roof, blending with the surrounding woods.

Cabin in Hayward

4.99 out of 5 average rating, 219 reviews

Hayward Haus, Modern Design w/ Classic Experience

Built as a winter or summer escape for a couple or small group, this beautiful four season cabin is a great way to experience the Northwoods of Wisconsin in a modern, well-appointed, aesthetically rich space designed with relaxation in mind This cabin was built in 2021 and host is 13 year "superhost" This is a default "no pets" cabin, however exceptions can be made with permission and a fee. Inquire with host. NEMA 15-40R outlet provided for level 2 EV charging. You bring chord and adapter.

Top guest favorite

The A-frame cabin is nestled among trees, showcasing a vibrant wooden exterior and a sloped metal roof. Sunlight filters through the foliage, creating a serene and inviting setting. The surrounding area features large rocks and a gravel pathway, enhancing the peaceful atmosphere.

Cabin in Hayward

4.98 out of 5 average rating, 119 reviews

Seeley Oaks A-Frame | Quiet, 40 Acres, Near Trails

This is a cabin-in-the-woods experience! The Seeley Oaks A-Frame is our slice of the peaceful Northwoods experience. It's on 40 private, tranquil acres (no neighbors!) with great access to all the Hayward-Cable area has to offer. It's small - intended for two adults, with the option of 2 addtl kids. It's a total of 700 sq ft, with a queen bed in the loft, in-floor heat, full kitchen, and washer and dryer. Less than 2 mi from Highway 63, 8 mi from Cable, and 10 mi from Hayward. IG: @Seeleyoaks

Top guest favorite

A charming red cottage is nestled among tall trees, showcasing a welcoming front with two white Adirondack chairs placed on a natural surface. Decorative flower arrangements hang near the entrance, surrounded by lush greenery and plants.

Guesthouse in Ashland

4.99 out of 5 average rating, 385 reviews

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.

Top guest favorite

A cabin nestled among colorful autumn trees surrounds a tranquil pond. The landscape features a mix of vibrant red, orange, and yellow foliage. The cabin's exterior is visible, with outdoor seating on the porch. Fallen leaves spread across the ground, enhancing the natural setting.

Cabin in Glidden

4.92 out of 5 average rating, 25 reviews

Whole Cabin on the Trails!

Come visit our beautiful cabin in the woods. You will have access to Snowmobile and ATV trails right at the end of the driveway. After a long day on the trails, you can come home to a nice hot shower. We've seen deer and black bears passing through near the pond. You will see plenty of fish in our pond, however they are our pets. NO FISHING is allowed. Dogs welcome; no cats as I am very allergic. I added atv trail map pics for Ashland and Iron counties, but please check for updates.

Top guest favorite

A sitting area features a futon draped with a cozy blanket, complemented by colorful accent pillows. A spacious bed with a patterned coverlet is positioned nearby, while a countertop with bar stools creates an inviting space for dining or gathering.

Tiny home in Saxon

4.97 out of 5 average rating, 247 reviews

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.

Top guest favorite

The bungalow features a light yellow exterior with decorative shutters, surrounded by well-maintained gardens. A welcoming front door with glass panels opens to a path lined with greenery and seasonal flowers. Tall trees provide shade, enhancing the outdoor area.

Home in Ironwood

4.99 out of 5 average rating, 269 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!

Guest favorite

A charming cabin with wooden siding is surrounded by colorful autumn foliage. The exterior features large green windows and a decorative quilt pattern on the front wall, indicating a welcoming atmosphere. A slight lawn leads towards the porch, offering a view of the nearby lakeside.

Tiny home in Lake Nebagamon

4.96 out of 5 average rating, 427 reviews

Berrywood Acres Cabin

Berrywood Acres is located on the eastern shores of Lake Nebagamon. We are known for beautiful sunsets with quiet surroundings and located minutes from the famous Brule River, great hiking trails nearby and a 35 minute drive from Duluth/Superior or a bit further east to the Bayfield/Ashland area. The cabin is simple with all you need for a little RnR. Come relax on the porch and enjoy the view. We look forward to welcoming you to Berrywood Acres Cabin!

Top guest favorite

A charming red farmhouse is set against a backdrop of colorful autumn foliage, featuring green fields and trees. A gazebo is visible in the foreground, complemented by a small red outbuilding. A winding path leads through the landscape, enhancing the rural setting.

Home in Ironwood

4.98 out of 5 average rating, 228 reviews

Our Finnish Farmhouse: Autumn leaves in the U.P.

Note: No Smoking anywhere on property and no pets allowed. Our Finnish Farmhouse is a log home that was first established in 1906. The home was purchased and completely renovated and restored from 2016-2020. The original logs have been restored on the interior of the home and many updates have been made. We are sure you will enjoy your stay with us.