Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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

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Top guest favorite
Home in Appleton
5.0 out of 5 average rating, 184 reviews

Appleton Wooded Oasis - Hot Tub-6 Star Hospitality

Relax and enjoy in a beautiful scenic home conveniently located in a quiet wooded neighborhood in Appleton. It has all the elements of being your get away from home. Nearly 3,000 sq. ft. Guests have access to all living areas, modern kitchen, wood fireplace, vaulted ceilings, spacious sunroom, large deck and therapeutic hot tub. Enjoy the scenic backyard with a large deck, 7 person hot tub and fire pit. Five minutes from airport, vibrant downtown, 25 min. to Lambeau. Includes breakfast.

Top guest favorite
A modern executive home is presented, featuring a stone facade and a spacious driveway. The front yard is well-manicured, with green grass, decorative shrubs, and a tree. The roof is gently sloped, and two garage doors are visible on the left side.
Home in Greenville
4.95 out of 5 average rating, 75 reviews

Home away from home

Located less than 2 miles from the Appleton airport, and 32 miles from Lambeau, this executive home sits on a quiet cul de sac. There are 3 bedrooms on the main floor, two with queen sized beds and there is a bathroom in between them. The master suite sits on the opposite end of the house. In the basement is a rec room and a 4th bedroom and 1/2 bath. There’s a beautiful yard and deck and big fire pit. A great place to stay for EAA or Packers games (take a shuttle bus for about $30 each).

Top guest favorite
A serene sunset view over the lake is captured, with the sun reflecting off the water's surface. A dock with a bench is positioned in the foreground, providing a peaceful setting to enjoy the evening's colors. Silhouettes of birds are seen perched nearby.
Home in Winneconne
4.91 out of 5 average rating, 75 reviews

Reel in the Fun: @ Lakeside Getaways Lake Poygan

Make some memories at this unique and family-friendly place. This is a great lakeside home close to some of the best fishing spots on the lake. The lake has a sandy bottom where the kids can enjoy swimming or kayaking. Fish off the dock or bring your boat and enjoy the whole lake. It is only a 4 minute drive to the boat landing and bait shop. Launch your boat once and leave it on the boat lift. Boat to many waterfront restaurants or drive to many nearby restaurants and supper clubs.

Top guest favorite
Home in Oshkosh
5.0 out of 5 average rating, 84 reviews

Fenced Yard; Waterfront; Dock, Cozy & Refreshing

Take it easy at this unique and tranquil getaway. Located on Sawyer Creek; enjoy peaceful views in a quiet neighborhood. Privacy is yours with a fenced in yard & attached 2 car garage. Comfortable 2 bedrooms with Queen beds & a fully stocked kitchen, outdoor grill, 55 in Smart TV and dedicated desk area. Propane firepit, patio table & 2 kayaks, washer & dryer. Close to Wiowash Trail, resturants, UW-Oshkosh and Oshkosh Corp headquarters. EAA grounds is a short 12 minute drive. Dog friendly.

Top guest favorite
The bedroom features a spacious bed covered with a multicolored quilt. A wooden dresser and a vintage mirror are positioned nearby, with warm lighting creating a cozy atmosphere. Soft colors adorn the walls, complementing the overall calming effect of the room.
Home in Winneconne
5.0 out of 5 average rating, 26 reviews

Near lakes and restuarants

Welcome to our lovely 2 bed, 1 bath "cottage" in Winneconne! This charming home combines comfort and convenience in a safe and vibrant community. Relax and enjoy restful nights at our home, and prepare meals in the fully equipped kitchen. The bathroom is stocked with fresh towels and other essentials. Located near boat landings, you'll have easy access to the river and lakes. You'll love the walkable neighborhood, just blocks from restaurants and bars. Book now and enjoy a relaxing getaway!

Guest favorite
The living room features a spacious layout with an L-shaped sectional sofa and a circular ottoman. A brick fireplace serves as a focal point, with a decorative mantel above. Natural light is welcomed through nearby openings, enhancing the warm and inviting atmosphere.
Home in Appleton
4.89 out of 5 average rating, 117 reviews

Spacious Home, Fireside Charm

Embrace the warmth of your home away from home, where comfort and convenience blend seamlessly. Stroll the streets of this family-friendly neighborhood, sip hot chocolate by the wood fireplace or enjoy a bath in your spacious en-suite bathroom. Boasting facilities such as laundry, a home office, garage, and a well-equipped kitchen, this home is tailored for both leisure and business travelers. Experience a true sense of belonging in a space designed to encourage relaxation and connection.

Top guest favorite
Home in Oshkosh
4.94 out of 5 average rating, 126 reviews

Birdhouse | Lakefront • Private Dock • Bunkhouse

Welcome to the Birdhouse, a private lakefront getaway on Lake Butte des Morts in Oshkosh! Enjoy your own dock, waterfront yard, lake views, and a separate one-bedroom/one-bath bunkhouse just steps from the main home. With 3 bedrooms and 3 bathrooms across the property, the Birdhouse is great for families, multiple couples or groups who want to vacation together while still having their own space! Come home to a beautifully renovated house that's just minutes from Oshkosh and Hwy 41 :)

Top guest favorite
A log home with a wooden exterior is surrounded by lush greenery. The front porch is adorned with a small blue umbrella and features a set of steps leading to the entrance. Gravel driveway and flower beds enhance the welcoming ambiance of the property.
Home in Oshkosh
4.88 out of 5 average rating, 223 reviews

Go and Go

Cozy 2 bedroom Log home. Can sleep 4-6. Across the street from Lake Winnebago. Short walk to park, zoo and boat landing. 6.5 miles to EAA grounds. Off street parking. Close to shopping, restaurants and downtown Oshkosh. Great rental for Air Show, Book now and bring your boat, jet ski, trailer, and fishing gear or just go sightseeing, dining and relaxing. Full kitchen, New Bath. Very comfortable with a great location. Perfect place to stay for family with students at UWO. Book now!

Top guest favorite
A modern living room features a comfortable gray sofa adorned with patterned cushions. A large area rug with a chevron design anchors the space. A wall clock and artwork complement the decor, with a glimpse of the kitchen area visible in the background.
Apartment in Winneconne
4.99 out of 5 average rating, 76 reviews

Boathouse Bungalow

Enjoy a unique getaway in our historic “Boathouse Bungalow” on the Wolf River. The location could not be more perfect when visiting the scenic Fox River Valley; close to walking paths, snowmobile trails and within walking distance to downtown Winneconne. The permanent dock is in a no-wake zone, great for fishing, tying up boats or just relaxing. Located 12 miles to Oshkosh, 23 to Appleton and 48 to Lambeau. A wonderful retreat for making lasting memories.

Guest favorite
An expansive recreational space within the barn features wooden beams and high ceilings. A table tennis setup is positioned in the center, with comfortable seating arranged nearby. Large windows allow natural light to fill the area, highlighting the rustic decor and open layout.
Home in Appleton
4.92 out of 5 average rating, 104 reviews

Renovated Farmhouse w/ Game Barn & Firepit

Discover the allure of this completely renovated 4-bedroom farmhouse located in Appleton, Wisconsin. Situated on a generous acre of land, this distinctive property features a restored barn now serving as a game room, ideal for family entertainment. Enjoy the evenings gathered around the smokeless firepit, and unwind in the expansive indoor and outdoor spaces. This property offers an excellent setting for a memorable retreat.

Guest favorite
Cabin in Winneconne
4.96 out of 5 average rating, 337 reviews

Goat Retreat: Petting Zoo, Barn, Hot Tub & River

The Cloverland Barndominium is a thoughtfully renovated 100-year-old barn sitting on 5+ private acres of forest to explore next to a river. You'll share the land with friendly goats that you can watch from right outside your window! Outside you'll enjoy walking the trails, feeding the animals, taking the canoe down the river, making a fire in the fire pit, and exploring the forest. Escape the busy world and reset!

Top guest favorite
A wooden dock extends into a calm lake, surrounded by gentle water reflections and a soft, cloudy sky. Tree foliage frames the top of the image, creating a serene natural environment.
Home in Neenah
5.0 out of 5 average rating, 59 reviews

Rickers Bay Lake house

Your modern lakefront getaway is just a few clicks away. Whether you're seeking to unwind by the waters edge, embark on exciting aquatic adventures, or simply create unforgettable memories with your friends and or family, this lake house retreat promises an amazing experience. Book your stay now and allow yourself to be swept away by the absolute magic of lakeside living.

Popular amenities for Winchester vacation rentals