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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.

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 the 2-person tent right next to Lake Superior. Fall asleep to the sound of the waves. The entire property is smoke free.
$145 per night
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.
$156 per night
Apartment 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.
$156 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
Super One Foods7 locals recommend
Black Cat Coffeehouse11 locals recommend

Other great vacation rentals in Ashland

Home in Ashland
Bungalow (House) on Chequamegon Bay.
$122 per night
Home in Ashland
Entire- Cozy Chequamegon Home
$119 per night
Apartment in Washburn
Palma Lodge
$131 per night
Home in Washburn
The Red Onion House near Bayfield
$180 per night
Cabin in Washburn
The Long House
$135 per night
Cabin in Bayfield
The Copper Squirrel of Little Sand Bay
$212 per night
Condo in Ashland
Main Street apt 2 blocks from Lake Superior!
$113 per night
Apartment in Ashland
The Zen Den. Cozy One Bedroom Near Lake Superior
$111 per night
Apartment in Ashland
Main street view apartment
$104 per night
Bungalow in Ashland
Ashland Green Bungalow: Vintage Style w/ lake view
$219 per night
Tiny home in Saxon
Parker Creek Tiny House
$110 per night
Cottage in Ashland
Cozy remodeled cottage in heart of Ashland
$230 per night
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