Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Top guest favorite
The A-frame cabin is framed by lush greenery and colorful landscaping. A welcoming pathway leads to the entrance, featuring a spacious deck. The cabin's dark exterior contrasts with the surrounding trees, creating a serene and private atmosphere.
Cabin in Elkhart Lake
4.99 out of 5 average rating, 331 reviews

Elkhart A-Frame, Wooded Retreat near Road America

The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

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, 111 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
A modern living area features a striking brick fireplace as a focal point. Natural light floods in through large windows, illuminating the hardwood floor. A comfortable gray couch is positioned beside a black chair, with a TV visible across the room.
Home in Appleton
5 out of 5 average rating, 152 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.

Guest favorite
Apartment in Appleton
4.87 out of 5 average rating, 134 reviews

Historical Haven Downtown Appleton

History meets style in this perfectly located downtown spacious 2 bdrm 2 story (2nd n 3rd story) apartment with a full kitchen. The 2nd floor bdrm has a queen bed with a BIFOLD BARN door, the 3rd floor bdrm is its own private oasis boasting a queen bed, a desk, closet and futon. Cozy, updated, historical and has beautiful surroundings. A few blocks to amazing restaurants, Mile of Music venues, Performing Arts Center, The Expo Center, Lawrence University, parks, river trails, and shopping.

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
4.87 out of 5 average rating, 203 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 favorite
A cozy living space features two green sofas and a comfortable armchair, arranged around a wooden coffee table. A television is positioned against the wall, and family photos are displayed in frames. Soft carpet covers the floor, contributing to a warm atmosphere.
Apartment in Appleton
4.98 out of 5 average rating, 163 reviews

Homey lower level apartment with private entrance

This living space is in the lower level of our ranch home, which is located in a lovely and safe neighborhood. The furnishings in this area are mostly antique pieces that came from special family members. You may also use the screen porch and patio for relaxing in the spring/summer. You will have a private entrance through the garage so you can come and go as you like. The kitchen is furnished so you may cook. There are also many restaurants close by. Ask us if you need anything!

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, 120 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 spacious living area features a large sectional sofa with colorful throw pillows, complemented by a cozy armchair. Natural light filters through the expansive windows, enhancing the warm atmosphere. A coffee table sits at the center, surrounded by decorative elements and an entertainment unit.
Home in Kimberly
4.93 out of 5 average rating, 107 reviews

Cheerfully cozy 3BR residential home

Updated & clean spacious open concept side by side duplex home features: 3 bedrooms 1.5 bathrooms (upper & lower level) Brand new kitchen The home is away from: Downtown Appleton & Lawrence university- 3 miles 15 minute drive to fox river mall 30 minute drive to EAA (Oshkosh) 30 minute drive to lambeau field ( Greenbay) Our home will comfortably fit 7 occupants. ( 1 Queen, 1 full and a bunk bed with a twin over full beds.) A cozy and fun home you’ll surly enjoy!

Top guest favorite
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, 242 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 setting sun casts warm hues across the water, creating a serene view. Waves gently crash against a rocky shoreline, with water splashing over smooth stones. The sky exhibits a blend of oranges and blues, reflecting the tranquil atmosphere by the lake.
Home in Hilbert
4.89 out of 5 average rating, 136 reviews

Coffee on the Lake, Firepit, 35 min to Green Bay

Large 3-story home directly on northeastern Lake Winnebago, 1.5 hours N of Milwaukee and Madison airports, 3 hours N of Chicago. Stunning views. Just steps to lake. Open main area. Large driveway. Games/books/cards/coloring/ping-pong. Two steps into house. Main floor bedroom includes walk-in shower. Flat yard with fire pit facing lake. Sunflowers provided for bird feeders. No pier available but boat launch < 1 mile at Calumet County Park. Seven miles to High Cli

Top guest favorite
Home in Oshkosh
4.99 out of 5 average rating, 138 reviews

Cozy Relaxing Lake Home with spectacular sunsets!

On the shore of Lake Butte Des Morts Longer stays welcome!!! Awesome Lake view Beautiful Sunsets Gas fireplace Shopping/restaurants/etc… Approx. 40 miles from Lambeau Field pier/summer,sorry nothing can be tied up to pier at any time solo fire pit grill Lake view Bedroom,Living Room,Dining area Near by Wiouwash trail for hiking, biking, etc.. Near EAA Kitchen space for cooking. Washer/dryer Larger 1 bedroom /Queen Sleep Number mattress Off street parking

Top guest favorite
The inviting living area features a plush sofa with a tropical print and a comfortable armchair. A wooden coffee table centers the space, with a view of the kitchen visible in the background. Natural light filters through large windows, illuminating the wooden ceiling and floor.
Home in Oshkosh
4.9 out of 5 average rating, 106 reviews

Shorehaven Lakehouse

Welcome to the Shorehaven Lake House! Perfect for a couples retreat, an outing for the entire family, or those in town for any of Oshkosh and the surrounding cities many events! Have the ultimate Wisconsin getaway by escaping to this beautifully renovated Lake Butte des Morts home that comfortably sleeps 6. This home provides beautiful sunsets and sunrises over the lake and a quiet neighborhood for your escape! Please let us know if you have any questions!

Popular amenities for Winchester vacation rentals

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