Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Top guest favorite
A serene view of the water at dusk is framed by trees along the riverbank. The calm surface reflects soft colors of the sunset, enhancing the tranquil natural setting.
Home in Appleton
4.96 out of 5 average rating, 126 reviews

Riverfront log cabin in the heart of the valley

◖30 minutes to Oshkosh(EAA) & Green Bay(Lambeau), 10 minutes to Downtown Appleton ◖10 minutes to Kimberly boat launch; travel the Fox River Locks system You will LOVE this property: ◖Outstanding views from the amazing sunsets to the relaxing water & wildlife ◖Newly renovated with many amenities ◖Enjoy the Northwoods setting in the heart of the valley ◖Relax at end of the day sitting around a campfire or by indoor fireplace ◖Tie your boat to dock in front of property ◖Full kitchen/outdoor grill

Top guest favorite
Home in Appleton
5.0 out of 5 average rating, 176 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 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, 219 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!

Guest favorite
The image captures a panoramic view of the GlampGround, featuring multiple barndominium cabins surrounded by lush greenery and open fields. Dense trees form a backdrop, creating a serene atmosphere. The landscape is punctuated by vibrant patches of colorful outdoor seating and recreational spaces.
Cabin in New London
5.0 out of 5 average rating, 17 reviews

Chicken Coop: Irish Acres Farm Charm Glamping

Experience peace and privacy in a handcrafted Amish "Barndo" cabin on our historic 75-acre family farm, established in 1848. Relax, reconnect with nature, and explore the flora and fauna in their natural habitat. As a working and teaching farm, we welcome visitors of all ages and interests. These cabins are part of Irish Acres GlampGround. We are a perfect place for a micro wedding, family reunion, spirit filled retreats, bridal showers and all of your birth to end of life celebrations.

Top guest favorite
The exterior of a cabin is depicted, featuring large windows framed by wood. Warm light emanates from within, revealing a cozy interior with a lamp and seating. Snow covers the ground, and icicles hang from the roof, creating a serene winter scene.
Cabin in New London
4.98 out of 5 average rating, 133 reviews

Secluded Cabin with Sauna

Place yourself in nature. Put down your phone and pick up a book. Clear your mind, focus on your breath, connect with your inner self. Sleep like you’ve never slept before accompanied only by the sound of owls and wind in the pines. The Belden Farm offers land that is a true retreat. Enjoy the privacy and quiet of our cabin in the woods. Extensive, well-maintained trails for hiking, skiing or Fattire biking lead you through towering hardwoods, cathedral white pines, and golden meadows.

Top guest favorite
Cabin in Cascade
5.0 out of 5 average rating, 272 reviews

hot tub and sauna on 5 private acres

Looking for a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your getaway awaits!

Guest favorite
A modern kitchen features sleek white cabinetry and stainless steel appliances. An island with seating is highlighted by elegant pendant lighting. A decorated vase adds a natural touch to the countertop, and natural light enters through the window, illuminating the wooden floor.
Home in Neenah
4.96 out of 5 average rating, 49 reviews

Whole House on Reed Street

Enjoy being close to everything when you stay at this centrally located home. Located only a short 20 minutes away from both EAA Aviation Museum in Oshkosh and 20 minutes from Houdini Plaza in Appleton. Appleton and Oshkosh offer a variety of restaurants, shops, and entertainment. Only 40 minutes from Lambeau Field Green Bay. 1.5 miles from Lake Winnebago. Neenah has parks, a library, farmer's market, shops, and restaurants so you don't need to travel far to enjoy your stay.

Top guest favorite
Guesthouse in Oshkosh
4.96 out of 5 average rating, 201 reviews

Cottage on Lake Winnebago

Furnished Cottage on Lake Winnebago with beautiful sunrises. 1 bedroom with queen bed. There is plenty of space for air mattresses in common areas. 1 queen air mattress available. One bath, full kitchen fully stocked with dining area, bring your own food to prepare. Bring your water toys or boat, launch nearby and dock access in warmer months with great fishing. Winter months, bring your snowmobile, trails nearby. Great ice fishing when lake is frozen and ice is safe.

Guest favorite
A charming outdoor seating area features a round table surrounded by two green metal chairs. A blue bench sits nearby, complementing the inviting entrance of the newly renovated cottage. The building's exterior displays a mix of red and wood tones, with multiple windows ensuring abundant natural light.
Cabin in Larsen
4.92 out of 5 average rating, 13 reviews

Newly Renovated Waterfront

Take it easy at this unique and tranquil getaway. This newly renovated cottage has a Murphy style Queen bed as well as a pull out couch to sleep four. The quartz counters make a perfect gathering space for friends and family. Plenty of room in the yard for your boat or other toys. Lake access is right around the corner for swimming, boating & kayak rentals. Enjoy a little slice of heaven on Lake Poygan with the Wolf River right around the corner! #fishon #boatlife

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, 72 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.

Superhost
A spacious yard is presented, featuring a smooth gravel area surrounded by a winding stone pathway. A fire pit sits at the center, offering a focal point for gatherings. Lush greenery and various trees provide a natural backdrop, enhancing the outdoor experience.
Cabin in Winneconne
4.83 out of 5 average rating, 30 reviews

The Big Blue Jay

Nestled in a semi-secluded setting, this charming blue cabin offers two cozy bedrooms and an open living room and kitchen with vaulted ceilings. Large windows bring in natural light and stunning lake views. A spacious bathroom adds comfort, while the generous yard is perfect for playing, relaxing, or bonfires under the stars. Offering both privacy and convenience, this cozy retreat is ideal for peaceful getaways or adventure-filled weekends by the water.

Guest favorite
Cabin in Winneconne
4.96 out of 5 average rating, 329 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!

Popular amenities for Winchester vacation rentals