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Holiday houses in Winchester

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Winchester

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

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Guest favourite
A living room is displayed with two leather sofas arranged around a centrally located coffee table. A textured area rug covers the hardwood floor. Natural light enters through a large window, illuminating the minimalist decor and decorative elements on the side tables.
Home in Neenah
4.96 out of 5 average rating, 67 reviews

Cozy Boho Home in Neenah

Newly updated home near the heart of Neenah, WI. This home has been meticulously styled with leather sofas, MCM furniture, a high-end Casper King mattress, aesthetic draperies, new appliances, trendy hardwood flooring, ultra comfort bedding, and so much more! Kitchen is fully equipped with basic essentials such as pots, pans, eatery, Keurig coffee maker, full-size fridge, stove, dishwasher, and microwave. You can also enjoy a main-level laundry room with new washer/dryer units detergent supplied

Top Guest favourite
Home in Appleton
5 out of 5 average rating, 177 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 favourite
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, 73 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 favourite
A rustic log cabin is surrounded by greenery, featuring a charming wraparound porch with steps leading up to it. The exterior displays wooden beams and a welcoming front, while a small fence encloses the area, creating a cozy, nature-integrated ambiance.
Farm stay in New London
4.96 out of 5 average rating, 192 reviews

Irish Acres Farm Charm Glamping: FAIRY CABIN

Irish Acres Farm is host to guest friendly activities. Sit & relax or join in farm chores, hike, fish, meditate. Light a camp fire and enjoy Nature at her finest. Experience the coziness of a rustic "tiny house" off-grid log FAIRY CABIN set beside a 1 acre spring fed pond. My place is good for couples, solo adventurers, & families (with kids). No pets or therapy animals allowed. We strive to be a tech free zone (NO WIFI or TV's). A true authentic connection with Nature and each other.

Top Guest favourite
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, 221 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 favourite
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
4.99 out of 5 average rating, 134 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 favourite
Cabin in Cascade
5 out of 5 average rating, 273 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!

Top Guest favourite
Guesthouse in Oshkosh
4.96 out of 5 average rating, 202 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 favourite
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
4.87 out of 5 average rating, 15 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 favourite
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.

Guest favourite
A blue cabin is nestled among greenery in a spacious yard, with manicured shrubs lining the gravel driveway. Tall trees surround the property, providing a tranquil atmosphere. A neighboring building is visible, contributing to the serene setting of the retreat.
Home in Winneconne
5 out of 5 average rating, 14 reviews

The little blue jay

Welcome to The Little Blue Jay, a cozy blue cabin nestled in a semi-secluded spot by the lake. This peaceful retreat offers two comfy bedrooms, an open living area and kitchen, and large windows with beautiful lake views. Enjoy a spacious bathroom and a generous yard perfect for relaxing, playing, or evening bonfires. Whether you’re seeking a quiet escape or outdoor adventure, The Little Blue Jay is the perfect place to unwind and recharge.

Guest favourite
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 holiday rentals