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Holiday rentals in Ashland

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Ashland

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

Garden House
Tiny house · 3 guests · 1 bed · 1 bathroom

Garden House

Applegate Cottage, the gateway to Bayfield, WI
SUPERHOST
Entire cottage · 4 guests · 2 beds · 2 bathrooms

Applegate Cottage, the gateway to Bayfield, WIApplegate Cottage is an adorable cottage right on Highway 13 in Herbster, WI - the gateway to the abundant orchards and wineries of Bayfield, and the Apostle Islands - all just half an hour away. A very short walk to beautiful Lake Superior, located on the Lake Superior Circle Tour. Enjoy kayaking, or explore the sea/ice caves. One hour from the infamous Birkie Trail. There is absolutely no better place to enjoy any season of the year!

The Garland City Downtown Apartment
SUPERHOST
Entire flat · 5 guests · 3 beds · 1 bathroom

The Garland City Downtown Apartment1920s, craftsman and art-deco-inspired apartment 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. Whatever you do, at the end of your day you’ll find cozy comfort at The Garland City Downtown Apartment.

Holiday rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Ashland holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Ashland

SUPERHOST
  1. Entire house
  2. Ashland
Northern WI, Chequamegon Bay.
SUPERHOST
  1. Entire apartment
  2. Bayfield
One Minute Walk to Lake Superior. Brookside #3
SUPERHOST
  1. Entire cabin
  2. Herbster
Stunning Bark Point Home on Superior's South Shore
SUPERHOST
  1. Entire guest house
  2. Ashland
Norrsken Scandinavian Cottage
  1. Entire townhouse
  2. La Pointe
Treehouse on Madeline Island 2A
  1. Entire cottage
  2. Bayfield
A Restful Place in Bayfield Wisconsin
SUPERHOST
  1. Entire house
  2. Ashland
Ashland Charm on Saint Claire
SUPERHOST
  1. Entire guest house
  2. Cornucopia
Waterfront Lake Superior's South Shore, "Sky Fire"
SUPERHOST
  1. Entire cabin
  2. Washburn
Artists Secluded Country Home
SUPERHOST
  1. Entire guest suite
  2. Bayfield
Huron Suite
SUPERHOST
  1. Entire cottage
  2. Herbster
Lake Superior's Cranberry River Cottage- The Wren
SUPERHOST
  1. Entire loft
  2. Bayfield
Garden Loft in the Woods

Nearby destinations