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Cottage vacation rentals in Wind Point

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Top-rated cottage rentals in Wind Point

Guests agree: these cottages are highly rated for location, cleanliness, and more.

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Top guest favorite
A cozy four-season porch features light wood paneling and large windows offering views of the outdoors. Comfortable seating, including woven chairs, is arranged around a small space, with decorative elements adorning the walls. A small electric fireplace provides warmth and ambiance.
Cottage in Trevor
4.98 out of 5 average rating, 138 reviews

The Lakehouse-3bdr/Lakefront/Wi-Fi

Enjoy your stay at this cozy cottage just steps away from beautiful Cross Lake and 5 minutes from Antioch, IL. This 3bdr, 1bath house features a 4 seasons porch so you can relax and unwind all year. Our large yard provides ample space to enjoy the stunning view. From May-Sept 30th, you will also have access to our shared pier. Enjoy swimming, boating, fishing or other nearby activities: skiing, golfing and ziplining. Beach chairs/toys, fire pit, grill, games and folding chairs are also provided.

Superhost
A cottage exterior is showcased with a well-maintained wooden deck and black railings. A welcoming front door is featured, which is flanked by two windows. The surroundings include a manicured lawn with small flower beds, enhancing the cottage's inviting appearance.
Cottage in Antioch
4.82 out of 5 average rating, 122 reviews

#4: Cute 2 bedroom cottage on the beach!

Relax & make lasting memories at this peaceful 2-bedroom cottage at Turtle Beach Marina. Enjoy the sandy beach on the lake, rent a boat or kayak, & unwind with summer drinks at the beach bar. A restaurant & game room (slots) are right on the property. (Bar & slots open mid-May through October.) Celebrating something special? Add a $75 package: 🌹Romantic Package: rose petals, candles, wine, & chocolates. 🎂 Birthday Package: HBD banner, balloons, 10-inch cake, & candles. Let us know in advance!

Top guest favorite
A charming white cottage sits within a landscaped area, surrounded by a white picket fence. Lush greenery and flowering plants are visible in the foreground, while trees stand in the background under a clear blue sky.
Cottage in Hartland
4.96 out of 5 average rating, 157 reviews

Cozy cottage in the heart of Lake Country

Entire cottage in the heart of Lake Country. Merryhill Cottage is nestled on two acres with mature trees. Included on the two acres- the host's farmhouse, a guest house and barn. The feeling of a country setting but with easy access to Hwys 16, 83 and I 94. Close to shopping, restaurants, parks, hiking, cross country skiing and snowshoeing, lakes, and beaches (10 min. to Delafield and Oconomowoc and 15 min. to Pewaukee.) Perfect for day trips to Madison (54 min.) and Milwaukee (30 min.).

Superhost
A well-maintained cottage is set in a spacious yard surrounded by green grass and large trees. Outdoor seating is arranged near the water, with colorful chairs facing the waterway. The property features steps leading to a wooden deck, enhancing the connection to the scenic surroundings.
Cottage in Fox Lake
4.94 out of 5 average rating, 18 reviews

Lakefront Cottage with Gorgeous Sunsets

Great cottage so close to the water you can fish right off the deck, bring your boat right up to the dock and drive it all over the chain of lakes and out to dinner. Endless things to do on the chain, tons of restaurants, sand bars, fishing, bars, boats, etc. Then, watch the sunset at the beach right outside your door before retreating for the night into the cottage. The yard is fenced in, with a fire pit and is shared with permeant residence and another house I air bnb but is yours to enjoy

Top guest favorite
A tranquil outdoor area features a wooden deck with comfortable seating and a small table. Lush greenery surrounds the space, leading to a serene lake visible in the background under a clear blue sky. A canoe rests on the shore near the water's edge.
Cottage in Burlington
4.98 out of 5 average rating, 90 reviews

The Butterfly Cottage

Your winter get-away is perfect at The Butterfly Cottage on Honey Lake! Relax and enjoy the serenity of the lake and all the natural beauty of the season! This is a cozy cottage on Honey Lake, just 4 miles from downtown Burlington and 13 miles from Lake Geneva. Alpine Valley for skiing and concerts, fishing on Honey Lake or nearby Browns Lake as well as shopping in Lake Geneva are the highlights of the season! There are hiking/walking trails all around as well as rustic roads to explore.

Superhost
A vibrant purple room features a suspended chair swing and St. Andrew's Cross against a backdrop of textured curtains. LED lights add a soft glow, while a television mounted on the wall complements the unique decor, creating an intriguing space for intimate exploration.
Cottage in Riverwest
4.92 out of 5 average rating, 13 reviews

MKE Pleasure Paradyz - BDSM - Adult Themed Cottage

Ignite your senses at The MKE Pleasure Paradyz. Indulge in the erotic arts of St. Andrew's Cross, Tantra couch, and Adult Swing. Have an experience of pleasurable memories. This meticulously designed cottage offers an immersive and sensual experience with elements of Kink, BDSM and Role Play. Every detail, from the pristine cleanliness to the carefully curated ambiance. Seek to explore new dimensions of intimacy or simply unwind, we provide a welcome environment to enhance your desires!

Top guest favorite
A charming orange bungalow is framed by lush greenery. The exterior features large windows and a welcoming front door with a star motif. The overall structure reflects a cozy, cabin-like feel, inviting guests to relax and enjoy the surrounding nature.
Cottage in Twin Lakes
4.94 out of 5 average rating, 67 reviews

Twin Lakes Bungalow

Cute 1930’s bungalow with a cabin feel and many modern updates, just blocks away from Lake Mary in the adorable Twin Lakes Manor neighborhood of Twin Lakes, WI! Relax in this 2 bedroom, one bath cabin with a full tub and shower, fully-stocked kitchen, and a HUGE fully fenced-in backyard you can bring your dogs to! Patio with table and a fire pit surrounded by Adirondack chairs to relax in! 2 kayaks and 2 sets of golf clubs included! You don’t want to miss this adorable and cozy place!

Top guest favorite
Cottage in Lake Geneva
4.94 out of 5 average rating, 157 reviews

Boutique Charming Cottage | Walk to Beach & Cafés!

Kinfolk Cottage is our treasured retreat located in Lake Geneva’s historic Maple Park district. When we’re not gathering here with friends and family, we open our doors to guests. This chic, restored gem blends timeless character with modern comfort. An easy walk to local cafes, boutiques, and the beach, or simply stay in and soak up the cottage charm. Designed for making memories that last a lifetime, Kinfolk Cottage captures the true spirit of classic Lake Geneva living. Welcome!

Top guest favorite
Cottage in Wonder Lake
4.94 out of 5 average rating, 170 reviews

The Cozy Lake House, Dm me ?s Lake Front Property!

Welcome to The Cozy Lake House, your year-round haven for relaxation and celebration! Savor breathtaking sunsets, indulge in boating, watersports, and high-speed internet, and make special memories during holidays, bachelorette party's getaways, birthdays, family reunions, micro weddings, and more. With a fully equipped kitchen, spacious rooms, and the tranquil lakeside setting, every moment here is magical. Reserve your spot now and experience the ultimate in lakeside living!

Top guest favorite
A cozy sunroom features a round dining table surrounded by four white chairs, with yellow placemats set for meals. Natural light floods in through multiple windows, illuminating the space. A door leads outside, enhancing the connection with nature.
Cottage in Burlington
4.91 out of 5 average rating, 76 reviews

Cottage Escape near Private Browns Lake Beach

Families, Creatives, and Professionals: welcome to our comfy cottage! You'll enjoy exclusive access to private Cedar Park beach on Browns Lake, a wooded yard with great privacy, a cozy sunroom, and two desks ideal for a personal creative retreat or remote work. Charming downtown Burlington has shopping and restaurants, and Lake Geneva and Alpine Valley are both 20 minutes away. Activities year-round: swimming, boating, fishing, hiking, snowmobiling, ice fishing, and skiing.

Top guest favorite
A welcoming exterior of a cottage is surrounded by well-maintained green grass. Two bright pink Adirondack chairs are positioned in the front yard, inviting relaxation. The entrance features a porch with a circular decorative element, complemented by neatly arranged shrubs and trees.
Cottage in Lake Geneva
4.98 out of 5 average rating, 195 reviews

Seven Oaks Bed & Breakfast

Come stay at our top rated Bed & Breakfast, located two blocks from the beautiful Lake Geneva. Relax in our California king suites, each contains a spa tub and shower, with heated floors and towel rails in the bathroom. Your complimentary breakfast basket is placed in your fridge prior to arrival, as well as complimentary gift of wine & cheese. Free WIFI is available on the property. No Pets, ADULTS over 21 ONLY.

Guest favorite
Cottage in Spring Grove
4.91 out of 5 average rating, 11 reviews

Lakefront 2BR Nautical Cottage with Hot Tub

Welcome to your perfect lakeside cozy cottage getaway! This newly remodeled 2-bedroom, 1-bath cottage sits just 60 feet from the scenic shoreline of Grass Lake on a shared resort property. Nautically decorated and thoughtfully updated, this cozy cottage offers the best of year-round lake living—whether you're soaking in the hot tub after a day on the water or gathered around the firepit under the stars.

Popular amenities for Wind Point cottage rentals

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