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Ashland vacation rentals

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Top-rated vacation rentals in Ashland

Guests agree: these vacation rentals 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 #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.
$62 per night
Townhouse in Bayfield
Cozy Downtown Flat with Historic Waterfront Views
While nestled into this cozy flat enjoy a morning cup of coffee as you watch boats depart from the historic waterfront. Leave the car behind and wander historic streets discovering quaint shops and good eats. Venture a little further and find the start to the 300 acre Big Ravine Preserve trails. End the day at Washington Avenue Beach watching the sun set over the islands. This flat welcomes you in and provides easy access to all the charms Bayfield offers.
$131 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
Prentice Park3 locals recommend

Other great vacation rentals in Ashland

Home in Mason
Marengo River Cabin
$136 per night
Cabin in Bayfield
The Copper Squirrel of Little Sand Bay Dogs OK
$158 per night
Tiny home in Saxon
Parker Creek Tiny House
$86 per night
Home in Ashland
Bungalow (House) on Chequamegon Bay.
$125 per night
Apartment in Washburn
Palma Lodge
$125 per night
Home in Washburn
Up North Oasis | Groups & Dogs in Bayfield Area
$99 per night
Cottage in Brule
The Cottage @ Brule River Barn (No Cleaning Fees)
$121 per night
Condo in Ashland
Main Street apt 2 blocks from Lake Superior!
$113 per night
Cabin in Ashland
Relaxing cabin with fireplace on Lake Superior
$144 per night
Cabin in Bayfield
Romantic Vineyard Cabin, Sauna, Plunge Pool
$211 per night
Vacation home in Washburn
Historic Hawkes Apartment
$127 per night
Apartment in Ashland
Main street view apartment
$104 per night

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