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
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
4.97 out of 5 average rating, 116 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
Farm stay in New London
4.96 out of 5 average rating, 190 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 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 out of 5 average rating, 20 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!

Top guest favorite
Home in Oshkosh
4.99 out of 5 average rating, 140 reviews

LakeHome! Relaxing! Cozy! Amazing Sunsets!

On the shore of Lake Butte Des Morts Longer stays welcome!!! Awesome Lake view private pier for fishing/relaxing(we do not allow anything to be tied up to pier at any time) Beautiful Sunsets Gas fireplace Shopping/restaurants/etc Near EAA Approx. 40 miles from Lambeau Field fire pit grill Lake view Bedroom,Living Room,Dining area Near by Wiouwash trail for hiking, biking, etc.. Kitchen space for cooking. Washer/dryer Larger 1 bedroom /Queen Sleep Number mattress Off street parking

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
4.99 out of 5 average rating, 127 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 out of 5 average rating, 256 reviews

sauna and hot tub 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 favorite
Home in Oshkosh
4.94 out of 5 average rating, 115 reviews

Leonard's Birdhouse

Welcome to the Leonards Point Bird House! This newly renovated lake home has all amenities needed for a perfect escape in Oshkosh, WI. You will experience lake views from the south side of Lake Butte Des Morts. For a quieter experience (or louder for the kids) there is a detached bunk house with its own bathroom! The Birdhouse is 10 minutes away from highway 41 and multiple stores for easy access to everything you need. Please feel free to reach out with any questions!

Top guest favorite
Home in Menasha
4.94 out of 5 average rating, 250 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 favorite
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, 195 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 favorite
Home in Kaukauna
4.99 out of 5 average rating, 103 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.

Guest favorite
A welcoming living area features a large gray sectional sofa complemented by colorful throw pillows. A round coffee table is positioned in front of the sofa, and a flat-screen TV is mounted on the wall. Natural light enters through two windows, enhancing the cozy ambiance.
Home in Appleton
4.93 out of 5 average rating, 173 reviews

Cozy Home with 2 Queen & 2 twin beds in Downtown

Gorgeous and clean cape cod in downtown Appleton. Walking distance to downtown restaurants, shops, entertainment, Farmer's Market, Mile of Music, and PAC. You will enjoy the entire house with a large fenced in backyard, beautiful landscaping, attached garage, 2 bedroom with queen beds, large spacious upper bedroom, large open kitchen, informal dining, and two relaxing living spaces. Every stay includes complimentary coffee.

Top guest favorite
Cabin in Winneconne
4.97 out of 5 average rating, 321 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!

Popular amenities for Winchester vacation rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Winnebago County
  5. Winchester