Skip to content

Ashland vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Ashland

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

Rental unit in Ashland
The Zen Den. Cozy One Bedroom Near Lake Superior
Enjoy Ashland at this peaceful, cozy, & centrally-located space. We're down town, just one block from Lake Superior, & directly across the street from local favorites as the Chequamegon Food Co-op, Black Cat Coffee Shop, Ashland Bakery, & the Saturday Farmers Market. A great spot to disconnect & Treat yourself! The Zen Den sits directly above an Arts and Wellness studio that offers Yoga, Meditation, as well as massage/body work. Need to connect? We have a workspace for you with quality wifi!
$110 per night
Condo in Ashland
Main Street apt 2 blocks from Lake Superior!
STELLA South Shore Stay is a new, gorgeous, one bedroom apartment just two blocks from Lake Superior, located on Main Street in Ashland, WI. Enjoy amenities like memory foam mattresses, high-quality bedding, Wi-Fi, all natural skin care, and much more. Walk to Lake Superior in minutes, get a coffee at the Black Cat or a pastry at the bakery, or enjoy the many restaurants and shops on Main Street. You can also enjoy the many local hikes or check out the Apostle Islands.
$116 per night
Rental unit in Ashland
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.
$141 per night

Stay near Ashland's top sights

Deep Water Grille16 locals recommend
El Dorado3 locals recommend
Chequamegon Food Co-Op20 locals recommend
Frankie's Pizza4 locals recommend
Black Cat Coffeehouse11 locals recommend
Super One Foods7 locals recommend

Other great vacation rentals in Ashland

Guesthouse in Ashland
Norrsken Scandinavian Cottage
$145 per night
Rental unit in Ashland
Gichigami Getaway, Cozy Remodeled 2BR 1BA Duplex.
$129 per night
Cabin in Bayfield
Romantic Tiny House on a Vineyard in Bayfield
$257 per night
Condo in Bayfield
One Minute Walk to Lake Superior. Brookside #11
$102 per night
  1. Airbnb
  2. United States
  3. Wisconsin
  4. Ashland County
  5. Ashland