Holiday rentals in Ashland

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Top-rated holiday rentals in Ashland

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Guest favourite

Home in Ashland

4.87 out of 5 average rating, 208 reviews

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.

13–20 Aug

€ 194 per night

Superhost

Apartment in Bayfield

4.79 out of 5 average rating, 314 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 , BBQ, fire pit, and bikes. 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 club Brewery.

17–24 Nov

€ 119 per night

Guest favourite

Guest house in Ashland

4.99 out of 5 average rating, 308 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.

5–12 Dec

€ 189 per night

Guest favourite

Yurt in Bayfield

4.9 out of 5 average rating, 140 reviews

Turtle Yurts - Yurt 2

1 Bedroom, 1 Bath, Sleeps 2 Nestled among the north woods, this yurt has everything you need for a comfortable and unique getaway. The design is a contemporary twist on the traditional yurt, featuring classic yurt elements such as lattice walls and radial rafters, along with modern amenities. The yurt sleeps up to two guests with a queen-size bed sitting under a clear dome to watch the sky above. There is a sitting area, as well as a bathroom, complete with shower and flush toilet.

19–26 Sep

€ 161 per night

Guest favourite

Home in Ashland

4.88 out of 5 average rating, 121 reviews

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.

15–22 Sep

€ 159 per night

Guest favourite

Tiny home in Saxon

5.0 out of 5 average rating, 131 reviews

Parker Creek Tiny House

Come stay on our hobby farm with us! We have a great location only a few miles from ATV trails. There are a lot of great hiking trails and falls to visit in the area. We custom designed and built this home in 2020. We have a queen bed with an adjustable head and futon. It has in floor heating and a mini split to stay toasty warm in winter and cool in the summer. It has a washer and dryer, dishwasher, refrigerator and freezer, propane stove and oven, and microwave.

15–22 Feb

€ 125 per night

Guest favourite

Yurt in Bayfield

4.94 out of 5 average rating, 400 reviews

Twisting Twig Gardens and Orchard Rustic Yurt

Our yurt 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!

14–21 Nov

€ 118 per night

Guest favourite

Cottage in Herbster

4.99 out of 5 average rating, 138 reviews

Applegate Cottage - South Shore of Lake Superior

Applegate cottage is an adorable cottage located just a short walk from the beautiful beach in Herbster, Wisconsin on the Lake Superior Scenic Byway. Whether you like hiking, biking, kayaking, skiing or just relaxing, there’s something nearby for everyone. Bayfield County has orchards, wineries, the Apostle Islands, sea caves, boutique shopping, waterfalls, great restaurants and so much more! Best of all…the sunsets! And, every season brings it’s own beauty!

4–11 Nov

€ 154 per night

Superhost

Yurt in Bayfield

4.96 out of 5 average rating, 287 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.

14–21 Sep

€ 88 per night

Guest favourite

Flat in Ashland

4.95 out of 5 average rating, 150 reviews

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.

22–29 Sep

€ 182 per night

Guest favourite

Flat in Ashland

4.84 out of 5 average rating, 102 reviews

Main street view apartment

The apartment is on the edge of the business district. A short walk to all the attractions. A quick two block to Lake Superior, or a block from the local brewery. Local bakery also only a few blocks away, as well as all of Ashland's local businesses. As you enter or exit the town, it is only one block off of US Highway 2.and makes finding your destination much easier.

18–25 Nov

€ 82 per night

Guest favourite

Home in Mason

4.94 out of 5 average rating, 236 reviews

Marengo River Cabin

Quiet, simple cabin with modern amenities overlooking the Marengo River on a dead end dirt road. Enjoy a peaceful getaway in the Northwoods. Many nearby hiking trails including Copper Falls State Park, St. Peter’s Dome, Swedish Settlement and more. Adjacent to 400 acres of public land with groomed cross country ski and snowshoe trails.

11–18 Dec

€ 181 per night