A Collection of Luxe Bayfield, Wi Lodging

Enjoy a Luxury Superior Vacation in the Heart of Bayfield with our Lodging Collection

Located in Bayfield, WI, Windseeker Rentals focuses on providing experiences that make every aspect of your stay memorable. From our creatively designed spaces to our high standards of cleanliness, we provide more than just a place to stay. We offer a home away from home where every detail is designed for your comfort.

Experience the Bayfield Collective Difference

  • Curated Design + Cleaning Standards

    Curated Design

    Our in-house design team has left their signature aesthetic on each of our well-appointed Bayfield lodging properties. Our attention to detail is evident and our top-notch housekeeping team is recognized for their elevated standards of cleanliness. Enjoy beautifully designed and curated spaces when you stay with Windseeker Rentals in Bayfield.

  • Eco Luxe Amenities

    We care about the impact we have on the environment and the health of our guests, which is why we have selected some of the safest brands. Our cleaning products and bath amenities are created responsibly, manufactured carefully, and result in minimal impact on the environment. That’s good for your health too, as we have done the homework to ensure your vacation experience is a non-toxic one!

  • #BayfieldLove

    Windseeker Rentals was founded and owned by two entrepreneurial women - each with a deep connection to the waters of Lake Superior and a contagious love for Bayfield. We offer the inside-scoop on some of the best places to visit, eat, explore and more. Our in-house vacation concierge can personally connect you with the best Bayfield experiences. Ask us how to enhance your stay with these services.

  • The Best Sleep of your Life

    We believe your stay should be filled with some serious adventures by day and the best sleep of your life by night (and some luxury pampering in between). Our lodging properties all feature our hand selected lineup of Eco Bath Sheets, Signature Spa Robes and Eco Luxe Recyclable Sheets by Monarch Cypress. Bedding also features exclusive Hotel Collection Down Alternative Comforters and Duvet Covers, and premium down alternative pillows.

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 + Annalisa, Co-founders, Windseeker Rentals LLC

Choose Your Bayfield Lodging Experience

 

About the Bayfield Collective

Founded by Jenna and Annalisa, Windseeker Rentals embodies a deep love for Lake Superior and a commitment to exceptional guest experiences. Our lodging properties are more than just rentals; they are gateways to making lasting memories in the enchanting town of Bayfield.

  • Annalisa developed deep roots and a connection to the Bayfield area through childhood summers spent boating the Apostle Islands with her family. With a background in branding and marketing, her passion has always been to create unique and inspiring experiences through thoughtful real estate development. She helped to develop a 120-year old historic warehouse building in Minneapolis now turned boutique lodging, restaurant, and social club known as the Hewing Hotel. She was involved in development and branding efforts of the Wild Rice Retreat right here in Bayfield.

    After years of branding and developing real estate projects for clients in markets nationwide, Annalisa and her husband have planted their feet as full time Bayfield residents, embracing their lifelong dream of starting a lavender farm and raising their two daughters in the Bayfield community. Together, they have recently completed a full historic rehabilitation in downtown Bayfield that opened late 2023 as the St. James Social, a boutique hotel, social lounge and restaurant at the heart of downtown Bayfield.

  • Born and raised on a 4th generation farm in the Red River Valley of North Dakota, Jenna learned the value of family, commitment and hard work. She earned a Bachelors in Business Management at North Dakota State University, and began her real estate career managing rental properties in Fargo, ND.

    Jenna has experience working in healthcare, startup companies, and non-profit environments, and continuously engages in learning and educational opportunities to best serve the community around her.

    Jenna found the Bayfield area through an interest in sailing and continues to race locally on Lake Superior and around the region. She now resides between Bayfield and Cornucopia and raises chickens and pigs with her husband on their small hobby farm.

    Jenna is also Owner/Broker of Windseeker Realty LLC where she loves to help buyers and sellers with making the most of their investment in the region. Jenna and her husband are also the proud owners of Sweet & Salty in downtown Bayfield with delicious ice cream and homemade popcorn treats to enjoy.

Frequently Asked Questions

  • Windseeker Rentals stands out through our commitment to curated design, luxury eco-friendly amenities, and personalized guest experiences.

  • Contact our in-house vacation concierge to personalize your visit with unique local experiences and services.

  • Choose your experience to get started. CLICK HERE