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Vacation rentals in Chequamegon Bay

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Top-rated vacation rentals in Chequamegon Bay

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.
$130 per night
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Condo in Ashland
1 bedroom apartment with Lake Superior views!
STELLA South Shore Stay is a gorgeous, one bedroom apartment just two blocks from Lake Superior with beautiful lake views. Located on Main Street in Ashland. Enjoy amenities like memory foam mattresses, high-quality bedding, Wi-Fi, all natural skin care, Duluth Coffee Co. coffee, 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. Also enjoy the many local hikes or the Apostle Islands.
$142 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.
$79 per night
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Other great vacation rentals in Chequamegon Bay

Condo in Bayfield
One Minute Walk to Lake Superior. Brookside #11
$72 per night
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Cabin in Herbster
SOUTH SHORE A-FRAME//Steps from Lake Superior
$196 per night
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Cabin in Bayfield
The Acorn of Little Sand Bay
$194 per night
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Vacation home in Washburn
Historic Hawkes Apartment
$153 per night
Home in Washburn
*New* Contemporary Comforts w/Large Outdoor Space
$193 per night
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Rental unit in Washburn
NEW! Cabin on Lake Superior ~ 11 Mi to Bayfield!
$207 per night
Tiny home in Two Harbors
Superior Hideaway Tiny Home with Private Sauna
$259 per night
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Cabin in Bayfield
Modern Tiny House w/Lake Superior View
$175 per night
Rental unit in Ashland
The Zen Den. Cozy One Bedroom Near Lake Superior
$95 per night
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Cabin in Ashland
Relaxing cabin with fireplace on Lake Superior
$206 per night
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Cabin in Washburn
The Long House
$130 per night
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Cabin in Bayfield
Romantic Tiny House on a Vineyard in Bayfield
$250 per night