Holiday rentals in Glidden

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Top-rated holiday rentals in Glidden

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Guest favourite
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.
Flat in Glidden
4.92 out of 5 average rating, 66 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

Top guest favourite
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
4.95 out of 5 average rating, 38 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 favourite
Cabin in Hayward
4.98 out of 5 average rating, 129 reviews

Seeley Oaks A-Frame | Couples Winter Getaway

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 favourite
A charming cabin with gray siding is nestled among snow-covered trees, illuminated by a warm light from the front door. A shoveling shovel is positioned by the entrance, and the surrounding area is blanketed in fresh snow, creating a serene winter atmosphere.
Cabin in Ironwood
4.96 out of 5 average rating, 559 reviews

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.

Guest favourite
A studio space features a spacious bed and a queen sofa sleeper, accented by neutral-colored walls. Natural light enters through a nearby window, illuminating the cozy sitting area with its black couch. A small dining table and kitchenette are seen in the background.
Apartment in Bayfield
4.8 out of 5 average rating, 380 reviews

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.

Top guest favourite
An outdoor seating area showcases comfortable green adirondack chairs arranged around a stone firepit, with a fire actively burning. A wooden structure is visible in the background, surrounded by lush greenery and tall trees, creating a serene natural setting.
Chalet in Hayward
4.97 out of 5 average rating, 99 reviews

Sylvan Chalet, Modern, Lakefront, Close to Trails

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. Cabin is brand new as of January 2024. Host is 14 year "superhost" This is a default "no pets" cabin, however certain sizes and breeds are allowed by permission only. We have a NEMA 15-40R outlet for level 2 EV charging. You bring chord and adapter

Top guest favourite
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
4.94 out of 5 average rating, 32 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 favourite
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, 267 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 favourite
Cottage in Ironwood
4.98 out of 5 average rating, 175 reviews

Bakery Bunkhouse - Sweet Amenities & Nature !

Yooper Delights Baking Co. is now a family style home with beds for 7 ppl, a large, fully stocked kitchen, Scandinavian cottage design with 2 sleeping lofts plus a queen sleeper on main level, oak dining table for 8, Swedish gas fireplace, patio doors to back yard with firepit, gas grill & relaxing patio for outdoor dining & watching our visiting deer! We are located 2 miles from town, on outskirts, semi rural & peaceful , close to trails & Lake Superior!

Superhost
A rustic red yurt is surrounded by a forest of trees. A large wooden deck offers a welcoming entrance and is equipped with a sturdy railing. Natural ground covers and underbrush can be seen nearby, creating a serene and natural setting.
Yurt in Bayfield
4.95 out of 5 average rating, 377 reviews

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.

Guest favourite
A charming two-story cabin features blue siding and a welcoming front porch, surrounded by greenery. A small garden area is visible, with a few potted plants enhancing the entrance. Large windows invite natural light, and a single-car garage is present on the side.
Home in Mason
4.94 out of 5 average rating, 283 reviews

Marengo River Bluff Cabin

Quiet, simple cabin with modern comforts overlooking the Marengo River at the end of a secluded dirt road. Enjoy the back deck with river views and a peaceful Northwoods setting. Pets welcome. Nearby hiking includes Copper Falls State Park, St. Peter’s Dome, Swedish Settlement, and more. The cabin borders 400 acres of public land with groomed cross-country ski and snowshoe trails for year-round exploration and relaxation.

Top guest favourite
A single-story home with a red exterior is set against a clear blue sky. Steps lead to a covered front porch, surrounded by greenery. A driveway is visible on the side, and a small garden area is positioned along the base of the home.
Home in Ironwood
4.94 out of 5 average rating, 120 reviews

Hot Tub • King Bed • "The Bear Den"

Come be our guest! We welcome you to relax and enjoy all the comforts of our cozy home. Minutes from 5 Downhill and several great Nordic ski areas. Close to countless waterfalls, Lake Superior and Copper Peak. Enjoy your stay during all Michigan seasons; summer adventures, crisp fall colors & cozy winter nights in the HOT TUB.

Popular amenities for Glidden holiday rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Ashland County
  5. Glidden