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Vacation rentals in Ashland

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Top-rated vacation rentals in Ashland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Condo in Bayfield
One Minute Walk to Lake Superior. Brookside #3
Amazing location! No cleaning fee! This Condo sleeps 4, King bed & Queen sofa sleeper. Full kitchen, balcony, AC, CableTV, WiFi, BBQ, fire pit, and bikes. Restaurant, bar and pool in July-Sept.Bayfield is a 2.3 mile hike or bike on the Brownstone Trail. Brookside is 5 minutes from Mt Ashwabay, Big Top, Bayview beach and multiple hiking trails. Ride a ferry ride to Madeline or cruise the Apostles. Sail, fish, kayak, golf, ski. Pool opens in July. $40 pet fee per stay. 🙂 No smoking allowed.
Guest favourite
Guesthouse in Ashland
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.
Guest favourite
Tiny homes in Saxon
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.

Popular amenities for Ashland vacation rentals

Stay near Ashland's top sights

Deep Water Grille16 locals recommend
El Dorado3 locals recommend
Frankie's Pizza4 locals recommend
Super One Foods7 locals recommend
Prentice Park3 locals recommend
Black Cat Coffeehouse11 locals recommend

Other great vacation rentals in Ashland

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Home in Washburn
Up North Oasis | Groups & Dogs in Bayfield Area
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Cabin in Bayfield
The Copper Squirrel of Little Sand Bay Dogs OK
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Home in Ashland
Entire- Cozy Chequamegon Home
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Apartment in Washburn
Palma Lodge
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Home in Ashland
Bungalow (House) on Chequamegon Bay.
Condo in Ashland
Main Street apt 2 blocks from Lake Superior!
Guest favourite
Apartment in Ashland
Main street view apartment
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Cabin in Ashland
Relaxing cabin with fireplace on Lake Superior
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Vacation home in Washburn
Historic Hawkes Apartment
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Cabin in Cornucopia
Romantic Forest Cabin, Sauna, Trail to Beach
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Cottage in Bayfield
Bayfield Fruit Loop Retreat - Main Cottage
Home in Ashland
South Superior Escape

Quick stats about vacation rentals in Ashland

Total rentals

30 properties

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

1.6K reviews

Nightly prices starting at

$54 CAD before taxes and fees

Destinations to explore

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