Holiday houses in Winchester

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Top-rated holiday rentals in Winchester

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

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Top Guest favourite
Home in Omro
5 out of 5 average rating, 16 reviews

Fox River Fishing & Relaxation

Newly remodeled home on the Fox River. Perfect for a fishing trip, family getaway or time with your friends! This property comes with all the amenities you will need from a fish cleaning station to high speed WIFI, Spectrum TV & beds that were picked out with the utmost comfort in mind! Bring your boat and tie up to the seawall so you can jump in to fish on the Fox River and various lakes. The outdoor space is ideal for relaxation, meals, games and time by the firepit. Enjoy beautiful sunsets!

Top Guest favourite
Home in Appleton
5 out of 5 average rating, 168 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 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, 191 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
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, 128 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, 262 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 favourite
A cozy firepit area is surrounded by eight Adirondack chairs, set against a backdrop of a vibrant sunset over the lake. The scene is framed by smooth pebbles, while a 60-foot dock extends into the water, creating a serene outdoor atmosphere.
Home in Menasha
4.94 out of 5 average rating, 251 reviews

Designer Lakefront Home with Views, Firepit, Dock

Relax at Sunset Oasis, where stunning lake views and sunsets set the tone for your stay. Sip coffee in the chef’s kitchen, paddle out in kayaks, grill lunch, and dine lakeside. In the evening, cozy up by the fireplace or gather around the firepit under the stars. Stream your favorite shows on the smart TV or explore nearby downtowns just minutes away. This stylish, updated luxury lake house is the perfect escape to unwind, reconnect, and create unforgettable memories.

Top Guest favourite
The cottage features a long, metal-roofed exterior with gray siding and contrasting purple shutters. Lush greenery surrounds the home, including decorative flower beds. A paved pathway leads to the entrance, highlighting the spacious yard. Sunlight enhances the bright and welcoming appearance.
Guesthouse in Oshkosh
4.95 out of 5 average rating, 196 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.

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, 69 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.

Top Guest favourite
Home in Kaukauna
4.99 out of 5 average rating, 105 reviews

Modern Comfort & Charm with Historic Flair

Ann's Queen Anne is a historic 2-story home with an updated interior offering comfort, convenience, and style. New furnishings and luxurious features make this an ideal place for a retreat, or a base of operations for exploring the area or attending a Packers game at Lambeau Field. Attention to detail and personal touches will make your stay a unique and special experience. Close to Appleton, Oshkosh, Green Bay, Door County, Manitowoc & Sheboygan/Kohler.

Top Guest favourite
A modern dining area features a large, marbled table surrounded by sleek black chairs. The open kitchen is visible in the background, showcasing dark cabinetry and stainless steel appliances. Natural light brightens the space, enhancing the clean lines and neutral color palette.
Home in Menasha
4.98 out of 5 average rating, 100 reviews

Perfectly Located Cozy 2 Bedroom

*Home away from home, Grocery Store and Gas Station just around the corner, for all of your basic needs. *Enjoy a stylish experience at this centrally-located place. *Quick, Easy access to highway 441 to get you where you need to be. *Green Bay (Packer Games, Resch Center, Titletown District, Epic Event Center) 25 minutes *Fox River Mall 10 minutes *Downtown Appleton 5 minutes (PAC, Mile of Music, Octoberfest) *Oshkosh 20 minutes (EAA, Outlet Mall)

Guest favourite
An open living space features warm wooden beams and a mix of modern and rustic decor. A comfortable sofa and armchair are arranged around a coffee table, while a dining area accommodates six. Natural light enters through large windows, complemented by a vintage map on the wall.
Cabin in Winneconne
4.97 out of 5 average rating, 324 reviews

Barndominium: Goats, Hot Tub, Forest & 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!

Guest favourite
Home in Hortonville
4.96 out of 5 average rating, 23 reviews

The Otter's Den

Welcome to The Otter’s Den! This cozy Hortonville retreat is the perfect home base for your Fox Valley stay. Located within easy walking distance to the famous Black Otter Supper Club, you’re never far from great food and local charm. Enjoy a comfortable, well-appointed space ideal for relaxing after a day of exploring the area. Perfect for couples, friends, family or a quiet getaway.

Popular amenities for Winchester holiday rentals

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