A collection of unique vacation rentals in Bayfield, Wisconsin

BOOK BY PHONE: (715) 513-6540

Apostle Islands

Rated Best Places to go in 2025

Stay in Bayfield, WI

  • White Pine Chalet

    Most Booked

    Sleeps 4+

    Wood fireplace

    Access to beach & trails

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  • Lakeshore Retreat

    Most Booked

    Sleeps 9+

    Perfect for Large Groups

    Private sand beach

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  • Apostle Pines #4

    Most Booked

    Sleeps 4

    Lake Superior views

    Perfect for 2-4 guests

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  • Northwoods Chalet

    Sleeps 2-4

    Gas fireplace

    Modern style stay

    Access to beach & trails

    Perfect for two guests

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  • Bayfield Guest House

    6 suites

    Hotel-style stay

    Downtown Bayfield

    Jacuzzis available in 4 rooms

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  • Hemlock Chalet

    Sleeps 4

    Gas Fireplace

    Prairie views

    Access to beach & trails

    Modern aesthetic

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Stay & Explore the Shore

  • Howl Adventure Center

    All guests who book through Windseeker Rentals get 10% off all rental gear with Howl Adventure Center. They have everything you need for a day in the woods like:

    - Nordic Ski’s

    - Snow Shoes

    - Mountain Bikes

    - Fat Tire Bikes

    After a day out on the trails, enjoy trailside and beer at Howl.

  • Tour the Apostle Islands

    This is the best way to see Wisconsin’s “Crown Jewels”. Tour the lighthouses, sea caves and some of the 21 islands that makes up the Apostle Islands National Lakeshore. All tours start within minutes of every Windseeker Rentals in downtown Bayfield.

  • Dogsledding with Wolfsong

    Ranked #1 Sightseeing Tour in Bayfield, Wisconsin, on TripAdvisor! Get to know the dogs, harness them up, and drive your own team or ride with us. This hands-on trip includes a hot, hearty lunch served on the trail.

Create a Getaway You’ll Never Forget

Windseeker Rentals has everything you need to enjoy a comfortable getaway. Bayfield, WI has everything to make it truly unforgettable.

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Bayfield, WI is 4hrs from Minneapolis. 7hrs from Chicago.

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One visit to Bayfield, Wisconsin and we are certain you’ll be hooked. Windseeker Rentals provides an unparalleled vacation experience through our curated collection of properties. Whether it’s your very first or hundredth time coming to this special community, we can’t wait to welcome you!

- Jenna, Co-founder + Owner/Broker, Windseeker Rentals LLC