Welcome to Woodside Cottages in Bayfield, WI!

Book A Romantic Winter Getaway at Woodside Cottages!

Enjoy an exhilarating day exploring Bayfield-area trails: hike, snowmobile, fat bike, snowshoe and XC ski. Then return to one of our cozy cabins with Jacuzzi tubs and fireplaces to snuggle up and relax!

CLICK HERE to view our convenient, up-to-date online reservation calendar to check availability by dates or cottage and book the perfect Winter getaway today!

Winter Cabin Rentals in Bayfield, Wisconsin

Cozy, Romantic Cabins with Jacuzzi Tubs

We offer year-round lodging in Bayfield, Wisconsin providing comfortable vacation cottages with Jacuzzi tubs, fireplaces, kitchenettes, internet and A/C, a special place to call “home” while you visit Bayfield.

We have furnished our cabin rentals with your comfort in mind, from basic to luxurious amenities for our guests. We offer our accommodations to our Bayfield visitors as an extension of our home, and we want you to relax and enjoy your Cottage as our guest while you spend your days exploring Bayfield, Lake Superior, Madeline Island and the Apostle Islands!

Our private cottages are some of the best places to stay in Bayfield, Wisconsin. Woodside Cottages is a 1-mile drive into downtown Bayfield or 1 1/2-mile hike on the beautiful Brownstone Trail which runs along the brownstone cliffs of Lake Superior on an old railroad bed with views of Madeline Island and the Apostle Islands National Lakeshore.

In and around town, enjoy the treats and cuisines unique to Bayfield, quaint shops and art galleries, catch the ferry to Madeline Island, tour the Apostle Islands, learn about Bayfield and its maritime heritage, visit the beautiful fruit farms and orchards, and participate in the many year-round recreational activities available.

A stay at Woodside Cottages in the Spring brings the chance to welcome a new season with blooming flowers overlooking the shores of Lake Superior. Summer offers Bayfield visitors the traditional family vacation, and Fall produces freshly harvested fruits from Bayfield County orchards worth celebrating. And Winter? Book a stay in one of our cozy, romantic Jacuzzi cabin suites and enjoy the perfect Northern Wisconsin Winter getaway!

We look forward to hosting you at Woodside Cottages of Bayfield ~

Come stay with us and experience Bayfield!

Your hosts,

Jonathan and Laura

  • No pets allowed on property or inside Cottages
  • High-Season Rates are in effect mid-May – Oct and during Ice Caves when open/accessible
  • All rates are subject to WI sales tax (5.5%) and lodging tax (6.5%)

Cottages & Rates

(Click on Cottage for more info & photos)

Cottage 1  2-3 guests, max 4
High-season $179/night

Low-season $159/night

Cottage 2  1-2 guests, max 3
High-season $159/night

Low-season $99/night

Cottage 3, 4, 5  1-2 guests, max 2

Low-season $169/night

Cottage 6  1-2 guests, max 3
High-season $149/night

Low-season $99/night

Cottage 7, 8  1-4 guests, max 4
High-season $179, 1-2 guests, use 1 BR only
$209, 2-4 guests, use 2 BRs
Low-season $149(1BR) – $179(2BR)/night

Cottage 9  1-4 guests, max 4
High-season $199, 1-2 guests, use 1 BR only
$229, 2-4 guests, use 2 BRs
Low-season $169(1BR) – $199(2BR)/night

Cottage 10, 11  1-4 guests, max 4
High-season $179, 1-2 guests, use 1 BR only
$199, 2-4 guests, use 2 BRs
Low-season $149(1BR) – $179(2BR)/night

Cottage 12  3-6 guests, max 6
High-season $269, 2-4 guests, use 2 BRs/2 BAs
$339, 3-6 guests, use 3 BRs/2 BAs
Low-season $199(2BR) – $269(3BR)/night

Cottage 14  1-2 guests, max 2
High-season $199/night

Low-season $189/night

Lodging Promotions

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Gift Certificates

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Woodside Cottages of Bayfield, Inc.
84790 State Hwy 13 (For US Mail: PO Box 494)
Bayfield, WI 54814
Phone: (715) 779-5600

Questions? Contact Us!

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