Holiday rentals in Ashland County

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Top-rated holiday rentals in Ashland County

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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.

4–11 May

$152 SGD per night

Guest favourite

Home in Ramsay

4.97 out of 5 average rating, 119 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.

14–21 Oct

$179 SGD 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.

22–29 Oct

$143 SGD per night

Guest favourite

Cabin in Ironwood

4.95 out of 5 average rating, 418 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.

27 Apr – 4 May

$114 SGD 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.

1–8 Nov

$251 SGD per night

Guest favourite

Home in Ironwood

4.99 out of 5 average rating, 215 reviews

The House Next Door, In-Town Two Story House

The House Next Door has a Northwoods feel while being in town and close to your likely destination. Just four blocks from downtown Ironwood, and in the heart of all the outdoor adventure the Gogebic Range has to offer. You'll love the warm cozy feel, and the ability to mingle in the open concept lr/dr/kitchen downstairs, or retreat upstairs for a quiet, peaceful setting. Individuals, couples, families, and up to eight friends would enjoy my place, provided you can live with one bathroom.

24–31 Aug

$186 SGD per night

Guest favourite

Yurt in Bayfield

4.9 out of 5 average rating, 143 reviews

Turtle Yurts - Yurt 3

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.

3–10 May

$178 SGD 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.

14–21 May

$195 SGD 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.

13–20 Jan

$156 SGD per night

Guest favourite

Home in Ironwood

4.99 out of 5 average rating, 185 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!

14–21 Dec

$179 SGD per night

Guest favourite

Bungalow in Ironwood

4.86 out of 5 average rating, 213 reviews

Quaint and Colorful Bungalow

My place is close to the main East-West Highway, but in a quiet neighborhood. It is near cross country ski trails, snowmobile trails, hiking trails, yet there are restaurants and dining within walking distance. You’ll love my place because of the neighborhood and the colorful coziness. It is easy to access from the road, or from the backyard. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets).

15–22 Jun

$147 SGD 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.

8–15 Sep

$119 SGD per night