Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Top guest favorite

The sunlit sunroom features a sectional couch adorned with plush pillows, positioned beside large wall-to-wall windows that provide views of the peaceful wooded surroundings. Natural wood paneling and a ceiling fan contribute to a warm, inviting atmosphere.

Home in Appleton

5 out of 5 average rating, 110 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, full mason fireplace, vaulted ceilings, large deck and hot tub. Enjoy the backyard with a spacious deck, 7 person hot tub and outdoor fire pit. Five min. from Airport, Downtown, 25 min. to Lambeau and 20 min. to EAA. Includes coffee and breakfast.

Superhost

An aerial view captures the open-concept living space of the rustic cabin, featuring wooden beams and repurposed oak flooring. Bright light streams in from numerous windows, highlighting decorative rugs and cozy furnishings. A ceiling fan and antler accents complement the inviting atmosphere.

Guest suite in Winneconne

4.81 out of 5 average rating, 226 reviews

Lake Winneconne Area Cottage "CabinSong" tradition

Northwoods-ish rustic cabin: 750 sq.ft., open-concept, lotsa windows, repurposed oak floor, 3/4 bth, equipped kitchen, dining/fun bar, two decks, E &W. 1 Qn, 1 dbl bed, qn. hide-a-bed, 1 twin. Optional: qn or twin air-bed. Desk, dresser, views , cable TV, wifi, stereo, heat/AC. Access to Lake Winneconne public boat ramp, 200 yrds! On-site & off-st. parking trailers. Quiet neighborhood; 3 mi. from Winneconne; easy access to Oshkosh, Green Bay, Fox Cities. Fun, not fussy seasonal decor.

Guest favorite

A spacious gathering space is depicted, featuring a sloped metal roof and a combination of large windows and door. Vibrant red chairs are arranged under the covered porch, set against a backdrop of a gravel pathway and green fields. Decorative stones frame the entrance.

Farm stay in New London

4.96 out of 5 average rating, 184 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

A vibrant display of autumn foliage is captured in the image, featuring a mix of golden and orange leaves on trees. A grassy area is visible in the foreground, scattered with fallen leaves, while a chair is positioned for enjoy the natural setting.

Guest suite in Fremont

4.98 out of 5 average rating, 87 reviews

Mother in law suite without the mother in law

Private 1 bdrm. apartment with full bath, kitchen, living room, and outdoor private patio. LR has sofa bed. Parking onsite. Owners live in attached house and will be as available as you need, or not if you are looking for privacy. Our home and the attached apt. are located on 3 acres surrounded by trees. We are 20 minutes to Appleton and Oshkosh and about 50 minutes to Green Bay. We are also 7 miles from downtown Fremont and the Wolf River known for it's fishing and boating activities.

Top guest favorite

A secluded cabin is surrounded by snow-covered trees, with large windows reflecting the winter scene. A bright red fat tire bike rests in the foreground, contrasting against the white snow. The structure's wooden exterior shows signs of weathering, blending into the serene natural setting.

Cabin in New London

4.99 out of 5 average rating, 88 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.

Guest favorite

A modern coffee maker is positioned on a white marble surface, alongside a wooden tray. The tray holds assorted coffee and tea packets, sugar, and creamers, along with a bottle of water, providing convenient beverage options for guests.

Apartment in Downtown Neenah

4.86 out of 5 average rating, 157 reviews

Cozy and Simple Downtown Space

Enjoy this great space in a quiet safe neighborhood. One car allowed at the property! The space has comfortable beds, provided hygiene products, a smart TV and snacks + beverages. Wake up and enjoy coffee provided by us. Shops and restaurants within walking distance! Visit The Plaza downtown with ice skating, fire pits, a coffee shop and more. Great for a couples getaway. Luxury for a great price! A portion of the proceeds from bookings go to housing evacuees, refugees and veterans.

Top guest favorite

A wooden dock extends into the river, featuring a single bench positioned at the end. The water reflects the vibrant blue sky and fluffy white clouds. Surrounding green trees and distant houses can be seen along the shore.

Apartment in Winneconne

4.98 out of 5 average rating, 50 reviews

Boathouse Bungalow

The Boathouse Bungalow is the uniquely perfect getaway located on the river in Winneconne, WI. This bright one bedroom apartment is located on the backside of a large and historical boathouse just a few blocks from the downtown area and features a permanent dock for use. Located in a no-wake zone, the dock is perfect for fishing or tying up a boat overnight. Also close to walking and snowmobile paths, the Boathouse Bungalow is the ultimate retreat for exploring!

Guest favorite

Two horses are seen grazing in a grassy field at sunset. A white horse is positioned in the foreground, while a smaller brown horse grazes nearby. The sun is setting behind trees in the background, casting a warm glow over the landscape.

Farm stay in Omro

4.9 out of 5 average rating, 79 reviews

Comfy Cabin on 170 Beautiful Acres - Come Explore!

The cabin rests on 180 acres of scenic farm wildlife habitat. The property includes an 1800s-era barn & blacksmith shop, a host of wild & domestic animals, miles of private canal with access to the Wolf & Fox Rivers, a hiking trail, garden, orchard, and much more! The farm has been the pride of our family for 6 generations. A converted grainary, the cabin features a full bed, pullout couch, full kitchen, full bathroom, high-speed satellite Wifi and smart-TV.

Top guest favorite

A modern kitchen area features a stone countertop with a toaster and a paper towel holder. Above, glass and ceramic dishware are arranged on shelves. Natural light filters through a nearby window, illuminating the space.

Home in Appleton

4.95 out of 5 average rating, 180 reviews

Modern, Freshly Renovated House - Great Location

-Historic residential district near downtown, Lawrence University, the Performing Arts Center, Mile of Music and more - great location but still VERY quiet area. -30 minutes to Green Bay and Oshkosh -3 season porch -New deck overlooking wooded backyard -Safe, well established neighborhood with tree-lined streets and beautiful parks -Need more space or traveling with friends? Click Visit our profile to see our additional 5★ Appleton properties

Guest favorite

A light-filled kitchen is visible through a doorway, featuring white cabinetry and a wooden countertop. A window allows natural light to illuminate the space. Decorative shelves on one side display colorful glass items and personal touches, enhancing the room's character.

Apartment in Oshkosh

4.86 out of 5 average rating, 214 reviews

No Cleaning Fees! 2 Bedroom Apartment By The Lake

We’re transparent with our pricing, that’s why we don’t have cleaning fees! The price you see is the price you pay (local taxes still apply). Come stay near the heart of Oshkosh - you’ll be on the second floor with views of Lake Winnebago. If you need anything during your stay we live on-site and are only a message away. Don’t worry though, the units are completely separated so you’ll have all the privacy you desire during your stay.

Guest favorite

A coffee station features a coffee maker, neatly arranged mugs hanging on a rack, and a decorative framed piece on the wall. A tray displays assorted packets and a jar, creating a functional and inviting space for beverage preparation.

Home in Appleton

4.94 out of 5 average rating, 441 reviews

Clean and cozy home close to downtown Appleton

The 1920’s home is located near downtown Appleton. The Airbnb is on a major vein of the city. Visitors can walk or take a short ride to events downtown. Enjoy things like the Fox River Mall, Mile of Music, Octoberfest, the summer farmers market, or shows at the PAC. Lambeau Field - 33 miles away EAA in Oshkosh - 21 miles away Milwaukee - 107 miles away The Appleton International Airport is less than 5 miles away from the Airbnb.

Guest favorite

A child interacts with goats through a wire fence, with the goats reaching out to nibble food from the child's hand. The setting is surrounded by trees, suggesting a natural and tranquil environment.

Cabin in Winneconne

4.98 out of 5 average rating, 261 reviews

Barndominium with 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 and chickens 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!

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Popular amenities for Winchester vacation rentals

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Other great vacation rentals in Winchester

A spacious farmhouse is framed by large trees, surrounded by a lush green lawn. The exterior showcases multiple levels with a balcony, and flower beds are visible along the base. The peaceful setting reflects a country atmosphere, ideal for relaxation.

Home in Winneconne

5 out of 5 average rating, 3 reviews

Charming country farm house

LuRating, 5 stars10 months ago

A lovely farm house with a well maintained, very nice yard. Comfy beds. Lots of space. Completely spotless. Loved the quiet location. Peggy was very friendly!

Top guest favorite

A spacious yard features well-maintained green grass, bordered by tall trees and a stone fire pit. Two wooden chairs are positioned nearby, inviting relaxation. A clear view of the surrounding area and nearby roadway is visible, enhancing the outdoor experience.

Private room in Greenville

4.89 out of 5 average rating, 163 reviews

Peaceful pad with Sleep Number bed

EmmanuelRating, 5 stars1 month ago

Host was helpful and accommodating

Top guest favorite

A fire pit made of stone is surrounded by four white chairs on a grassy lawn. In the background, a cottage features large windows, with trees and other homes visible nearby.

Cottage in Fremont

4.94 out of 5 average rating, 67 reviews

Lake Poygan Retreat: The Bell Cottage

JosephRating, 5 starstoday

Amazing and beautiful place. Quiet and peaceful area with a feel of home. Great place to relax by the water and enjoy the sounds of nature with the advantages of comfort

The spacious sleeping area features a king bed dressed in soft yellow and white bedding. Natural light filters through large windows, framed by light drapes. A wooden nightstand houses a lamp, and a comfortable chair adds to the inviting atmosphere.

Home in Downtown Neenah

4.8 out of 5 average rating, 5 reviews

Cozy Boho Home in Neenah

Vandan PankajbhaiRating, 5 stars2 weeks ago

It was a nice place to stay. I would definitely like to stay again if I get the chance.

A concrete patio is showcased with comfortable seating arrangements including chairs and a circular table. Potted plants with colorful blooms are arranged along the edges, and a view of a spacious green lawn and neighboring homes is visible in the background.

Home in Neenah

5 out of 5 average rating, 5 reviews

Spacious modern country home with easy EAA access

CJRating, 5 stars10 months ago

We two seniors with our grandchildren came to attend EAA AirVenture, my 11 years young granddaughter selected this place from pictures, and was she right? The place is beautifully located in a very quiet neighborhood of Clayton. Excellent landscape, single level house with 3 rooms, 2 baths and large living and well stocked kitchen. She had even kept milk in the fridge and lots of chilled water bottles. Rooms, furniture, fixers, beds, bathrooms all are world class. The place is just 30 minutes drive North of Oshkosh, so no maddening crowds or constant aircraft thunders. Very near to beautiful town of Neenah, with excellent restaurants, beautiful glass museum, kayaking. Highly recommended

Guest favorite

A set of wooden stairs leads down from a log home to a grassy area by the river. The surrounding trees create a natural setting, and a small patch of water is visible at the bottom of the steps. Items are partially obscured by trees in the background.

Place to stay in New London

4.88 out of 5 average rating, 17 reviews

Guest Suite @ The River House

PaulRating, 5 stars1 week ago

Host kindly accommodated us with some miscommunication in the booking process. Accommodations were accurately described. Could have elaborated on the incredible opportunity to kayak in a largely undeveloped river backwater system. Caught a meal of walleyes off the dock while watching eagles, egrets and lots of other birds. Host provided an anniversary treat for us which was appreciated. We will look to do this again when the opportunity presents.

Guest favorite

A compact bathroom is featured with a light grey vanity that includes multiple drawers. A white sink is set into the countertop. Natural light filters in from the window, which frames a view of the outdoors. Copper piping is visible along the wall.

Cabin in Winneconne

5 out of 5 average rating, 5 reviews

The Big Blue Jay

JoselineRating, 5 stars2 weeks ago

We stayed for one night cause we had a long drive the next day, but overall this was a really nice, clean and comfortable place to stay.

Home in Winneconne

5 out of 5 average rating, 3 reviews

Near lakes and restuarants

JarynRating, 5 stars4 months ago

Loved this stay! Would highly recommend! Karin was extremely helpful and incredibly sweet. The house was so beautifully decorated and very clean! Loved it! Will be staying again if we come back to the area.

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Vacation rentals in Winchester

Top-rated vacation rentals in Winchester

Vacation rentals for every style

Popular amenities for Winchester vacation rentals

Other great vacation rentals in Winchester

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