TOP 30 Holiday rentals in Sister Bay, Wisconsin

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The Yacht Club at Sister Bay is a luxurious lodging institution located at 10673 Regatta Way in the charming town of Sister Bay, Wisconsin, United States. Nestled along the beautiful shores of Lake Michigan, this upscale establishment offers guests a unique and unforgettable experience in a stunning waterfront setting. With elegant accommodations, top-notch amenities, and personalized service, The Yacht Club at Sister Bay is the perfect destination for a relaxing getaway or special event. Whether you're looking to unwind in style or explore the natural beauty of Door County, this premier institution is sure to exceed your expectations.

Little Sister Condo is a charming real estate and travel agency located in the picturesque town of Sister Bay, Wisconsin. Situated at 2715 Little Sister Hill Road, this institution offers a variety of cozy and well-appointed condos for sale or rent, perfect for those looking to experience the beauty of Door County. Whether you're in search of a vacation rental or a permanent residence, Little Sister Condo is here to help you find your dream home away from home. With personalized service and local expertise, this agency is dedicated to making your real estate or travel experience a seamless and enjoyable one. Visit Little Sister Condo today and start your journey towards finding the perfect place to call your own.

Lundquist Realty & Vacation Rentals of Door County, LLC is a premier real estate and vacation rental agency located in the picturesque town of Sister Bay, Wisconsin. With a prime location in the heart of Door County, this agency offers a wide range of services to help clients find their dream vacation rental or purchase their perfect home. Whether you are looking for a cozy cottage by the lake or a luxurious waterfront property, Lundquist Realty & Vacation Rentals has something for everyone. Their experienced team of agents are dedicated to providing exceptional service and helping clients make the most of their time in this beautiful area. Visit them at 10579 Country Walk Lane to start planning your next Door County getaway.

The Shore View Condominiums at Sister Bay, WI is a luxurious waterfront property located at 10612 Shore View Place in the charming town of Sister Bay, Wisconsin. Nestled along the picturesque shores of Lake Michigan, this upscale condominium complex offers stunning views of the water and easy access to the town's shops, restaurants, and attractions. Each unit is beautifully appointed with modern amenities and spacious living areas, making it the perfect retreat for vacationers looking to relax and unwind. Whether you're looking to enjoy a day on the beach, explore the nearby hiking trails, or simply take in the breathtaking sunsets from your private balcony, The Shore View Condominiums at Sister Bay, WI offers the perfect blend of comfort and luxury for your next getaway.

Cottage and Bay is a premier real estate and travel agency located in the picturesque town of Sister Bay, Wisconsin. Situated at 10200 Wisconsin 57, our agency specializes in helping clients find their dream vacation rentals, waterfront cottages, or investment properties in the stunning Bay area. With a team of experienced and knowledgeable agents, Cottage and Bay is dedicated to providing exceptional service and personalized attention to each client. Whether you are looking to purchase a vacation home or plan your next getaway, let Cottage and Bay be your trusted partner in all your real estate and travel needs.

Blue Harbor Lodge is a charming home rental located at 1314 Appleport Road in Sister Bay, Wisconsin. As a real estate and travel agency, we specialize in providing guests with a cozy and comfortable stay in the heart of this picturesque town. Our lodge offers a peaceful retreat with stunning views of the harbor, making it the perfect destination for a relaxing getaway. Whether you are looking for a weekend escape or a longer vacation, Blue Harbor Lodge is the ideal choice for your next trip to Sister Bay. Book your stay with us today and experience the beauty of Door County.

Sister Bay Beach Condos is a charming waterfront retreat located at 572-500 Mill Road in Sister Bay, Wisconsin. These cozy and modern condos offer stunning views of Lake Michigan and easy access to the sandy beach just steps away. Guests can relax and unwind in the comfortable accommodations, equipped with all the amenities needed for a perfect getaway. Whether you're looking to soak up the sun on the beach, explore the quaint town of Sister Bay, or simply enjoy a peaceful retreat by the water, Sister Bay Beach Condos is the ideal destination for your next vacation.

Kinsey Bay Lakehouse is a premier real estate and travel agency located at 1354 Kinsey Bay Lane in the charming town of Sister Bay, Wisconsin, United States. Specializing in lakefront properties and vacation rentals, our agency offers a wide range of options for those looking to experience the beauty of the area. Whether you are seeking a peaceful retreat or a fun-filled family vacation, Kinsey Bay Lakehouse is dedicated to helping you find the perfect property to suit your needs. Our team of knowledgeable agents are ready to assist you in making your dream getaway a reality.

Sunset Shore Cottages in Sister Bay, Wisconsin offer waterfront VRBO vacation rentals with stunning views of the lake. The Shore Cottage can comfortably accommodate up to 16 people with 6 bedrooms and 3.5 baths, a full kitchen, and laundry facilities. Guests can enjoy a wood-burning fireplace, forced air heating, and a four-season front porch with beautiful lake views. The large wood deck is perfect for gas grill cooking and watching the sunset. The Garden Cottage can accommodate up to 6 people with 2 double beds, a screened sleeping porch, and a queen size sleeper sofa. Both cottages provide a peaceful retreat within walking distance to downtown Sister Bay. Affordable seasonal rentals in the heart of Door County, Wisconsin.

The Sister Bay Getaway is a charming lodging located at 2373 Parkview Drive in the picturesque town of Sister Bay, Wisconsin. This cozy retreat offers a peaceful and relaxing atmosphere for guests looking to escape the hustle and bustle of everyday life. With comfortable accommodations and friendly staff, The Sister Bay Getaway is the perfect destination for a weekend getaway or a longer vacation. Explore the beauty of Door County and make unforgettable memories at this lovely institution.

Kayak Door County-Sister Bay is a travel agency located at 2457 South Bay Shore Drive in Sister Bay, Wisconsin. They offer a variety of kayaking tours and rentals for visitors looking to explore the beautiful waters of Door County. Whether you're a beginner or experienced paddler, their knowledgeable guides will ensure you have a safe and enjoyable experience on the water. With stunning views and abundant wildlife, Kayak Door County-Sister Bay is the perfect destination for outdoor enthusiasts looking to immerse themselves in nature.

Northern Door County Boat Rental is your ultimate destination for experiencing the beauty of Door County from the water. Located at 9448 Spruce Street in Fish Creek, Wisconsin, our institution offers a variety of boat tours and rentals to suit your schedule and preferences. Discover the stunning landscapes of Door County with our scenic boat tours, or take control and be your own captain with our boat rentals. With morning, mid-day, and evening time slots available, as well as full day and multi-day rentals, you can explore the Bay at your own pace. Pack a cooler, gather your family, and embark on an unforgettable adventure that will create lasting memories.

Sister Bay Village Hall is a charming park located at 10693 Wisconsin 42 in Sister Bay, Wisconsin. This institution serves as a gathering place for the local community, offering a serene and picturesque setting for events, celebrations, and leisure activities. With its lush green spaces, beautiful landscaping, and convenient location, Sister Bay Village Hall is the perfect spot for residents and visitors alike to relax and enjoy the natural beauty of Wisconsin. Whether you're looking for a peaceful retreat or a place to socialize with friends and family, this park has something for everyone.

Welcome to Country House Resort, located at 2468 Sunnyside Road in Sister Bay, Wisconsin, United States. Our resort offers stunning views of Sister Bay, with 46 rooms and suites that cater to a variety of needs and tastes. Whether you're on a honeymoon, romantic getaway, girl's weekend, or golf trip, we have the perfect accommodations for you. Our resort features 1,100 feet of shoreline, 27 wooded acres, an oversized outdoor whirlpool, heated outdoor swimming pool, kayaks, multi-speed bikes, nature trail with benches, free Wi-Fi, shoreline dock, tennis and pickleball court, and more. During certain seasons, we offer a buffet breakfast, and during quieter times, a Grab N Go breakfast is provided.

The Scandinavian Lodge is a charming lodging facility located in Sister Bay, Wisconsin. Situated at 10506 Wisconsin 57, this cozy retreat offers comfortable accommodations for visitors looking to experience the beauty of Door County. As a real estate agency, the Scandinavian Lodge also provides opportunities for guests to invest in their own piece of this picturesque region. With its Scandinavian-inspired decor and welcoming atmosphere, the Scandinavian Lodge is the perfect place to relax and unwind during your stay in Wisconsin.

SwedeInn is a charming lodging institution located at 10631 Bluffside Road in Sister Bay, Wisconsin. Our newly remodeled private rooms provide a comfortable and relaxing atmosphere for your vacation getaway. Conveniently situated in downtown Sister Bay, SwedeInn is within walking distance to restaurants, bars, shops, the beach, and other attractions. Leave your car behind and explore all that Sister Bay has to offer during your stay at SwedeInn.

Escape to our spacious and secluded vacation home located at 2210 Scandia Road in Sister Bay, Wisconsin. This stunning property, managed by our real estate and travel agency, offers the perfect retreat for those seeking peace and tranquility. Nestled in a secluded area, surrounded by nature, this vacation home provides ample space for relaxation and rejuvenation. With modern amenities and a serene atmosphere, our property is the ideal destination for a peaceful getaway. Book your stay with us today and experience the beauty of Sister Bay in utmost comfort and privacy.

Timberline Cottage, located on Timberline Road in Ellison Bay, Wisconsin, is a charming vacation home perfect for those looking to escape the hustle and bustle of everyday life. Nestled on the tip of Door County, this nostalgic cottage offers a peaceful retreat with easy access to nearby towns such as Sister Bay, Baileys Harbor, and Washington Island. With stunning views, crystal clear water, and nature all around, Timberline Cottage provides a unique and unforgettable experience for guests. The fully screened porch allows guests to enjoy the beauty of the woods without any interruptions from bugs or rain, making it the perfect spot for morning coffee or evening cocktails.

Green Gables Door County is a charming lodging institution located at 10355 Bella Vista Lane South in Sister Bay, Wisconsin. Surrounded by the natural beauty of Door County, this peaceful retreat offers comfortable accommodations and a warm, welcoming atmosphere. Guests can relax in cozy rooms, enjoy delicious meals at the on-site restaurant, and explore the nearby attractions such as Peninsula State Park and local wineries. Whether you're looking for a romantic getaway or a family vacation, Green Gables Door County is the perfect destination for a memorable stay in the heart of the Midwest.

Segway the Door Tours is a travel agency located at 3903 Wisconsin 42 in Fish Creek, Wisconsin. Dive into local history and culture on a Segway tour led by knowledgeable guides, creating an enriching journey beyond the ordinary. Explore Peninsula State Park, a gem of Door County, and discover hidden treasures and breathtaking vistas along the iconic Skyline Road. Foster connections with friends and family on a guided Segway adventure, gliding from Fish Creek Marina down Millionaire Row and finishing up at Sunset Beach Park. Experience wonder at Cave Point, Whitefish Dunes, Ellison Bluff, Ridges Road, Egg Harbor, Sturgeon Bay, Washington Island, and Sister Bay, all while gliding on a Segway. Embark on a one-of-a-kind journey that blends the thrill of Segway exploration with the richness of artistic discovery, uncovering the vibrant tapestry of public art in towns across Northeast Wisconsin. Give the gift of gliding with Segway the Door Tours today!

Located in Sturgeon Bay, Wisconsin, the Peninsula Kayak Company offers a unique travel experience for those looking to explore the natural beauty of Door County. Situated along the stunning Niagara Escarpment rock formations at Cave Point Park, visitors can immerse themselves in the tranquil waters of Lake Michigan with views of Whitefish Dunes State Park. One of the highlights of the company's tours is getting up close and personal with the largest rock formation in the area, towering over 200 feet above the Ephraim shoreline. For a more peaceful experience, guests can paddle down the quiet creek at Logan Creek, home to a variety of wildlife.